Happy anniversary to me! A year ago today was my last day in corporate.

In the last year, I’ve filled seven journals, and an eighth is well underway. I wrote at least five pens dry. Contrast this with my previous years’ two-journal max. I guess I had a lot to say to myself in the last 12 months.

As this anniversary approached, I started reading back through the year, beginning in September 2025, right around the breakdown that led me to quit.

It was painful. I felt a deep sadness for the woman who wrote those entries. She was desperate to please others. She was angry about where her ambition had landed her, and she aimed that anger at a roster of characters, past and present. Her self-worth deteriorated with each day she stayed in a role that didn’t square with the passions and values she knew were hers.

I wanted to comfort her after every story of waking up screaming from near-daily nightmares. Her nighttime dreams replayed her waking life: suffocation, destruction, desire for affection, frantic and chronic lateness, mutation, being submerged in ghastly, unsanitary conditions.

She had been handed a map to “the ideal life” and followed it dutifully, dropping her inner compass along the way, deep into the woods. She was doing her best to navigate. In reality, she was dangerously far from safety.

Here are some snippets from my journals:

“I am in the unfathomable and inglorious messy middle between what was — marriage, Seattle, lucrative career, fitness and health, community and friendships nearby — and whatever will be next.

I am giving myself one year of freedom. … No pets, no husband, no job, no girlfriend, no uterus, no home, no plan. And I’m full of everything else - hope, curiosity, audacity, authenticity, and revival. I’m 21 again in spirit, but I have the learnings, strength, reality, and fuck ’em of a 49-year-old. It’s not a second chance. It’s my first chance at ‘right now.’

Now that I don’t have any large forces demanding things from me, the only impetus to act on is my free will, which I don’t have a lot of experience listening to. I feel like a puppet master has been at the top, conducting me for years, and now they’ve left me to unravel.”

Around December, the clouds started to lift. When I went to sleep, I dreamt of impossible leaps, far greater than anyone could make safely, knowing I’d made them before and it hadn’t ended well. But in these dreams, people were watching, and I chose an easier course. Analyzing those dreams, I wrote: “Is that bailing, or is that self-preservation?” Eureka!

Things got better from there.

Looking back, I can name the mindset shifts that put my true self at the center of my life. People-pleasing and financial success now get negotiated around my passions, values, and talents - instead of the other way around.

What Changed This Year

I traded an ingrained definition of success for my own barometers: energy and joy. To retrain my inner compass, I built a Lovable app called Fill My Cup. Every day, I logged how I spent my time and whether each activity and person filled me up or drained me. Every week, I got a report with “Do More of This” on one side and “Do Less of This” on the other. I planned around the first list. Where I couldn’t eliminate the second, I reframed it. For example, if a conversation with a loved one drained me, and I had no intention of cutting them out of my life, I reframed our interactions around gratitude and empathy instead of annoyance.

I abandoned external validation for my own measures of success. Title and salary used to be my success metrics. Now I measure:

• Energy and joy

• Admiration for the people I surround myself with

• Alignment of my work with my talents and passions

• Positive impact on my values

I’ll be honest: the promotions and raises I never got still sting. But the more time I spend outside the corporate world, the clearer it is that most people see a title as a measure of political savvy, not craft. I’m now more proud than ashamed of the reasons I never became a VP:

• I spoke truth to power.

• I prioritized my team’s effectiveness and my customers’ happiness over the bottom line.

• I acted, foremost, with personal integrity.

• I always gave my best effort.

From my journals:

“I feel like my entire career has been for other people. Thank God I got paid well for it. And does that make it all worth it? I wasn’t wrong to follow the money, but doing so contributed to my dis-ease with everything in my life and clouded my judgment about what I truly needed for myself.”

“My drive is to prove how great I am. Yet, the person whose praise I want, I will never, ever receive. The dissonance between these two things have driven me to this suffocating place - rolling around in the most violent tidal wave. This torture is my motivation. Self-masochism. Mutilating, yet comforting.”

On the day I gave notice, I wrote:

“Even as [my boss] asked me to forget my company and everyone there, and just tell him what I need, I didn’t know. I couldn’t say. I lost all memory of what it felt like to want something for myself. I just wanted to be left alone.”

Today, I know I’m okay. The ocean is pretty, not a tidal wave trying to kill me. I am who I am, and who I am has unique intelligence and talent. I no longer need to make someone love me. They will or they won’t, and it isn’t my job to spend my precious energy changing someone’s heart. They will find their way, and so will I.

I traded “do hard things” for “let it come to you.” I still love doing hard things. So much. Both mantras can be true. The difference now is that when I’m chasing something and it feels forced, I hand the universe the reins instead of doubling down on my type-A playbook of goals, strategy and checklists. I used to shy away from the word faith because it felt too religious. Now I trust that my path is already written, and that walking it requires me to act, constantly, as my true self. “Letting it come to you” isn’t sitting back and waiting for magic. It’s showing up as yourself and trusting the timing.

That trust gets tested. My bank account goes into the red every month. I have faith I’m not headed for ruin, because financial management is one of my talents. As long as I act with authenticity and integrity, there is no version of this where I go broke by my own doing.

I redefined productivity. Quiet time is every bit as productive as task time. The forced 9-to-5 is not built for creative work. Some of the most lucrative creative ideas never come to fruition because they’re never given room to tangle, breathe, stretch and grow. Meditating, wandering, making bad art and writing unrealistic business plans are as productive as revenue-driving work. That empty space is where I hand the universe the reins. I am and always will be action-oriented and goal-minded, so I make peace with “unproductive” time by treating it as movement driven by curiosity instead of fear.

I stopped investing my talents in other people’s dreams and started investing in my own. Art Camp (the business, not just the play dates with my aunt) started forming ages ago. Early in my sabbatical, I wrote at length about wanting to create with a co-creator and a community, and about knowing I thrive as The Producer, not The Artist. My business skills are a superpower in the arts, not a betrayal of them.

More insights from my journals:

“I think I’ve always known that my forte is in something in the arts, but not being The Artist. Something in the business or production of it all.”

“I feel an energy, a certainty, that I am meant to be at the intersection of art and science, that I am meant to be the Producer more than the Creator.”

This is likely what led me to product leadership. I wasn’t the engineer building the product, the salesperson selling it, or the marketer crafting the persona. Product is where art and science meet in the technology business.

The next role I’m growing into is being my own boss.

Earlier this year, I worked on a creative project that seemed like the ideal expression of me as a Producer. It checked every box: passions, values, talents. But I wasn’t the boss. My ideas had to clear someone else’s bar before they could happen, and the frustration was far too familiar. It mirrored every great product idea from my career that never saw daylight because of someone else’s vision, goals or ego. When I finally convinced my partner to execute my idea, it succeeded on every measure. I was elated. I was also pissed at myself. How many times would I give my best ideas and instincts away before I used them to build my own vision?

That question to myself was a turning point.

A short while later, I had the chance to angel-invest in a company and founder that excited me. Few angel investments ever pay off, but I had a strong feeling this one would net something for my future self. I was one email away from investing. My vision for Art Camp was coming together, but it still felt fuzzy and far away. So I stopped and asked myself: What if I spent this $5,000 on my own dream instead of someone else’s? Do I believe in myself as much as I believe in them?

That question stopped me cold.

I took the dare. I kept the $5,000 and invested it in Art Camp.

Becoming What I Already Am

This post is not a declaration that I’ve figured it all out. It’s a celebration of how far I’ve come.

The stories from a year ago feel like a dream now. What strikes me most is that I’ve always known my passions, my values and my talents. They’ve barely changed since I was a little girl. They are my true essence. What drove me into the exhaustion and desperation of this time last year was the effort I spent doubting them and “fixing” them to fit “the ideal life.” That was the demon. I never let my passions, values and talents sit at the center of my decisions. I put people-pleasing, financial success and the ideal-life roadmap there instead, and I saw everything else through self-doubt.

I can describe my perfect life clearly. And all year, I’ve been saying that I feel uneasy because I’m not tethered to anything. So why am I not simply living that ideal life? It turns out I am tethered: to my family. I live in a city instead of the mountains. I have to seek out movement in nature instead of waking up inside Planet Earth’s “best of” cycling and mountain destinations. I’ve made peace with the fact that this part of my ideal life doesn’t need to happen right now. I’m giving the universe the reins on this one. It’ll come to me when the time is right.

This weekend, with Halloween’s spooks and spirits for company, I’ll celebrate turning one: one year of choosing myself, and my first chance at “right now.”

Live with Love. Be Unexpected. 😘

I made something! The Art Camp World shop on Etsy is officially open. Take a look here.

I never meant to sell art. Hell, I never meant to really make art for the world to see. This all started as a way to hold on to a trip-of-a-lifetime.

From January through April this year, I traveled through Costa Rica, California, Singapore, Cambodia, Vietnam, Thailand, the Philippines, Bali and Sri Lanka. I brought a sketchbook, a few colored pens and pencils, and a travel watercolor set. I wasn’t trying to become a “real” artist. I just thought that sketching would be a romantic way to remember places in a way my phone couldn’t capture.

What I found was that an hour with a sketch gave me permission to actually look - at the infinite shades of green on a hillside in Sri Lanka, the blues in the sea near the Philippines, and shadows in rocks and trees that I hadn’t noticed before.

My camera roll reminds me where I’ve been, my sketchbook reminds me what I was really paying attention to.

Then there were the people. Almost every time I sat down to draw, someone stopped and asked for a peek. They told me about their town, their own trip, the relative who used to paint. Sometimes, to my shock, they wanted to page through my whole sketchbook. They saw things that I didn’t and made me love the sketches and places even more. Each page holds a place and the people around me when I drew it.

When I got home, I didn’t want those pages to live on a shelf. I wanted them out in the world, doing what they did on the road: starting conversations. So I turned them into prints.

The shop opens with 16 sketches (with many more to come).

Many Lessons Learned

I assumed putting a few prints online would be easy. The tools (social media, Canva) and systems (Etsy, and Gelato, my print-on-demand provider) are all out there, ready to use. Separately, many are brilliant. Fitting them together is another story. Here’s the learning curve from the inside.

1. There are too many tools, and AI has made it wilder. Video, audio, scheduling, captions, keywords, titles… every week brings ten new AI tools promising to do all of it, and few clear winners. Analyzing them all has become a part-time job. I’m trying to keep this as human as possible while being smart with my time and money.

2. Photoshop is a product mystery. Its the #1 tool in its market for what it does, and one of the least intuitive pieces of software out there. It assumes expert-level literacy in color theory, masking, and vector paths. I’m learning it all one YouTube tutorial and one AI conversation at a time.

3. “Museum quality” is a whole education. Paper, color, resolution, scanning, and why colored pencil looks perfect on screen and a little different on paper are things I’ve never given much thought to before this project started. Getting the texture of small sketches to survive the trip to print took more more trial and error than I expected.

4. Great customer experience when you don’t control customer service. Gelato prints and ships my orders, which makes a one-person shop possible, but customer obsession was one of my hallmarks as a product leader, and I won’t let it go. It feels like any gains I’ve made with AI tools, I’ve lost arguing with support bots. Reaching a human is nearly impossible, and that’s on purpose. (There’s a business idea in here somewhere, but I’m a little busy with something else right now.)

5. I launched it like a product. Before opening the shop to everyone today, I ran a friends-and-family soft launch: real people, real orders, the whole experience tested end to end. This alpha test caught glitches in my branded packaging I never would have found alone. Thank you, early buyers. You were my QA department, and you didn’t even get cool swag.

6. Building a brand means taming my own brain. I did the unglamorous work of writing a messaging pillars doc, designing a logo, picking brand colors, defining a brand voice (playful and bold), and creating a social media schedule. My brain always wants to try something new. That’s a superpower, and also one that will drive a new brand straight into a ditch. Consistency is the least exciting thing I’m doing, and probably the most important.

Where Art Camp World is going

The shop is the first piece of something bigger.

“Art Camp” isn’t my phrase. It belongs to my Aunt Betsy, a lifelong NYC artist and former art professor, who has used it for years to describe the play, curiosity, and real conversation that show up when people make art together.

Art Camp World is built on three ideas: know yourself, know your world, know each other. Here’s the roadmap, product-person style:

1. Now: a shop of my own travel sketches.

2. Next: a shop that sells work from other artists, so they can make art instead of wrestling tools and systems to make a living.

3. Later: Art Camp, a physical artist residency and retreat, with room to stay, studio space, and workshops. Come as you are, make what you make, and talk about it.

If you read my earlier post about becoming an Artrepreneur, this is that word in practice: using everything I learned building products to help art reach the people who’ll love it.

Come to Art Camp World!

• Visit the shop here. If a sketch speaks to you, bring it home. If you love it, leave a review and/or like the shop (this helps more than you know).

• Keep a travel sketchbook? Send me a page, or tag @art.camp.world on Instagram.

• Share this post with the friend who always doodles on the napkin.

Wherever you come from, and wherever you’re going, there is art to make and people who want to talk about it.

Visit the Shop

Live with Love. Be Unexpected 😘

The expiration date on my “one year sabbatical” is a few weeks away. I’m not doing the things I expected to be doing at this time, and honestly, I stopped feeling like this was a “sabbatical” a few months ago. That word implies a return to where I came from, and I know now that I am not going back to that place.

Calling this a ‘sabbatical’ has felt easy - it puts this chapter in a box that’s simple to explain. But I’ve taken a distinct turn: from ”I’m on a one-year break from my corporate career” to “I’ve left my corporate career to become a creative entrepreneur.”

Let It Come To You

During my travels this year, I let myself enjoy each place without pressure to make something bigger of it. I wasn’t searching. I was doing my best to let it come to me (whatever “it” may be).

What came: deep conversations with people from all over the world, making and discovering art, being active - biking, snorkeling, running, hiking. The clarity I had about the joy these things brought came with a question:

What would a life built around these things actually look like?

I started making lists of business ideas (it’s just what I do) and creative projects - and the one thing that never strayed too far from the center of my thoughts was this concept of Art Camp that my aunts and I have played around with for many years.

What is Art Camp?

“Art Camp” is a term my Aunt Betsy - a former art professor and lifelong artist in New York City - coined years ago, for the playfulness and real conversation that shows up when people make art in community. Many times over the years we’ve made art side by side - stopping to see what the other’s working on, commenting, brainstorming, expanding each other’s ideas. Between the music playing on the speaker, the paint hitting canvas, and supplies moving in and out of drawers, she’ll quietly say, “Art Camp!” and we glance at each other with a knowing grin.

I very much envision Art Camp as a physical place one day, and I’m in the early stages of building this (stay tuned!). But Art Camp is also a feeling, it is something that follows me wherever I go.

During my travels, Art Camp took the shape of a travel sketchbook. I’m not a trained artist, but I can frame a scene, observe the lines, perspectives, and shadows - and, with enough patience, which was heightened in my relaxing travel state - I could bring a scene to life with a pen and a few random colored pencils. Beyond the joy of simply creating, I noticed that my sketches prompted questions, comments, and conversations from strangers.

In other words, art connected me to myself, to others, and to my world.

This felt like a thesis for my life, more than a sabbatical takeaway.

What this means for me today is that I’ve turned my energy away from getting back into a corporate role, and pointed all of my energy at dreaming, building, and launching this thesis instead.

Sketchbook Inspiration

I’ve built and launched dozens of software products in the last couple decades as a product leader. A business grounded in human connection and tangible art is new territory for me - and while I unpack that gift, I’m leaning into the connection I felt in my travel sketches. I’m making them available as fine art prints, and helping other artists do the same with their artwork. (more on this soon)

Courage

Throughout this past year, I’ve heard more than anything else from others, that I’m brave. Leaving my job was brave. Traveling solo was brave. Not knee-jerking back to a corporate job is brave. Moving out of my apartment and into another temporary home is brave. And building a business in an area where I have few connections is also brave.

None of this feels like courage to me. It feels like the most natural next thing that needs to happen. It is not easy, and I’m trying to make sure it feels fun along the way. I indeed have moments of panic about “what if this doesn’t work out.” And all I can tell myself when I get into that spiral is that I always make it work out.

My 25-year corporate career gave me so much - financial stability that enables me to “be brave” right now, skills and experience of building and launching products, and a network of supportive colleagues.

Being an Artrepreneur

To do research for building my own Art Camp, and to continue to feed my creative practice, I started applying for artist residencies around the world - places to make art, get outside every day, and work in community with other creative people.

In this process, I built a personal portfolio website (cortneyjacobsen.com), where I struggled to call myself an “Artist” - not because I don’t believe that I am one, but because I am more. I considered “Solopreneur,” the label some independent consultants reach for, but that’s not it either. I want to build with others, not alone.

The term “Artrepreneur” popped into my head, and it is sticking.

I define it as: an artist or creative professional who uses business skills, marketing, and commercial strategies to build a sustainable, self-managed career from their work.

This is what I do. Sketching is my art. Painting and writing and collage are my art. Building businesses and launching and selling products is also my art.

I’m filled with so much hope and conviction about this next chapter and can’t wait to continue to report to you about the building of Art Camp.

Stay tuned here! and Follow @art.camp.world on Instagram for news and updates.

Live with Love. Be Unexpected 😘

I’ve come to accept that life is a series of starting-over moments. This used to frustrate me because I understood it to mean that I had wasted a bunch of time on a lost cause and that my life plan needed a reboot. Just two weeks ago, in my last Substack article, I wrote these exact words - “I’ve spent some time over the last several weeks feeling like I need to start this sabbatical all over” - in reference to feeling like life had spun out of control when it was “supposed” to be quiet and calm.

But in the last few weeks, my POV on “starting over” has shifted.

We are always starting over. Each day, we gather new information and experiences, many of which are unanticipated. For me, some of these surprises have felt like a failure - a thing that didn’t go according to my plan because I did something wrong and now I need to fix it. As I write this, I realize the ego-centricity in this thinking. As a goal-oriented individual, I react quickly and decisively to new information in order to bring a situation back on track.

Resisting a natural tendency

When I took this sabbatical, one of my goals was to stop responding in a panic when things were not going according to my master plan. Instead, I was determined to give myself to the universe. Que sera sera, and all of that.

In my tech career, we talk about the sunk cost fallacy - a bias to continue along a path simply because we have invested in it (often, substantially … say, for example, a 25-year career, or a 10-year marriage) even when the path is no longer logical. Resisting the bias takes conscious effort. It means constantly reassessing a situation and taking action based on where we are in the present moment, not based on where we were when we started on the path, or the sacrifices we made along the way. The real resistance is choosing to start anew if the current path is no longer in our best interest. And holy hell, starting anew is fucking scary - not to mention, terribly inconvenient - so most people just stay the course and give themselves to the fallacy: “I’ve invested so much so far! Things are bound to pay off eventually.”

Unfortunately, most of the time, just sticking with something you start doesn’t get you what you set out for in the first place because either (1) the circumstances have changed, or (2) what you set out for has changed.

Either way - the only way out is the most uncomfortable choice: abandon ship and start over. This feels nearly impossible to do, until you do it. Doing it is liberating - but this doesn’t change that it is still fucking scary.

To be guided by belief

A precious learning from my sabbatical has come from acting against the bias of the sunk cost fallacy, and surviving. Even though there are carcasses along the path that I have abandoned, and it is undeniable that I will never get those losses back, the knowledge that I acquired stays with me. Therefore, nothing is a waste of time, and “starting over” is simply letting go of an old modicum of success and re-starting with a different approach and more information on board.

Here I am now - starting over. Again. For the first time in my life, things are very far from being on a course. My grand plan doesn’t extend more than a few months, which is a contrast to the 5-year plan I’ve lived for the last few decades. My goals are not fully formed. My vision for the future morphs in and out and between different shapes. But I’m also filled with gratitude about where I am, inspiration about my ideas and visions of the future, and - dare I say - patience to let it all unfold. And though I feel untethered from a specific course of action - one I may have called a “goal” a year ago - I have conviction that I am on a path of truth, authenticity, and integrity.

I was chatting about this with a friend recently and she said, “It sounds like you believe in yourself.”

And I thought, “Wow! Is THAT what it feels like?” In a way, I didn’t have those words because I hadn’t felt exactly this way before.

The scary part is happening now

Now that I’ve taken the leap to start over, it doesn’t feel so scary anymore to defy sunk cost logic. Setting new goals and charting a new path is becoming an invigorating project! The scary part right now is letting go of the woman who built those old plans in the first place: she was ROI-obsessed, facts-driven, ego-centric, and addicted to progress and production. I’m building someone else in her place - a woman who trusts intuition, who lets an idea sit and take its own shape instead of rushing it toward a deadline, who speaks her inner truth instead of hunting for the ‘right’ answer.

I think the sunk cost fallacy is impossible to fully defy without letting go of a fixed identity. The plans and goals that I made were not based on facts alone - they were formed from my intertwined and complicated preferences, constraints, expectations, and values. If I absorb new data, but refuse to release control on pieces of my identity, then I would obsess over what I left behind instead of focusing on what’s actually in front of me.

And if I can repeat myself: holy hell, identity transformation is fucking scary, not to mention, terribly inconvenient. But it’s also necessary to let go, to stop performing certainty, and to start anchoring to that belief in myself.

Live with Love. Be Unexpected. 😘

I saw The Odyssey this weekend. I walked in with an open mind and open heart. I know Christopher Nolan’s work well and I am an enormous fan. I did not walk into that theater expecting a relaxing Saturday night. I did not expect soft material. I expected intensity, and I like intensity.

I left in total overwhelm.

Not because the film failed. It succeeded completely at what it set out to do. It shocked, it awed, it took my money, and here I am writing about it, which means I'm doing exactly what the marketing department hoped I'd do. But somewhere between the previews and the credits, a question started forming that had nothing to do with Greek mythology: must we be so extreme these days? And why? To get a reaction? A raving summer blockbuster review? To simply feel something, because the absurdity we're swimming in every day has gone numb on us?

The feature hadn’t even started and I was already exhausted. One trailer after another depicting violence, killing, horror, thrill — all turned up to the extreme, past the point where it meant anything. My aunt leaned over to me and said, “Holy shit. All this and the movie hasn’t even started yet.” I was comforted to hear that she felt exactly what I was thinking.

By the time the film itself arrived, I saw that the emotional extremes I felt during the trailers were the perfectly curated warm-up. In a couple sequences — one involving a gargantuan monster, and another involving pigs that I won’t get into here — I found myself thinking that if someone wandered into that theater mid-scene, they’d assume they’d taken a wrong turn into a horror movie. Real fright. Real gore. Not an epic. Not an on-screen honor to classic mythology.

The Odyssey did everything it was built to do. What it didn't do was honor the story it was telling. Afterward, my aunt said the thing that's stayed with me since: she felt like she was watching something from a different time — not "back then," but "in the future." It was too extreme and too visually futuristic to carry the depth and intellect of a historic tale. Truly, I think we were both a little stunned from it all.

I keep coming back to that. Because I don't think this is really about one movie, or even about Hollywood, though I'll admit the thought crossed my mind that an entertainment industry still grossly and overwhelmingly run by white men might have some interest in turning the volume up past the point where anyone else's voice can be heard. Just sayin’.

In an incredibly trite “life imitates art” commentary, what I felt coming out of The Odyssey reflects what I feel in my life right now. In my real life, and in the lives of my many loved ones, we are living at the extremes. It seems like nearly everyone is unsettled in some way, going through something major — not just one hard thing, but a pile-on of really hard career changes, moves, marriages ending, marriages beginning, houses collapsing, lifelong friends dying, health issues disrupting us and demanding that we push more, try harder, hold on another day.

We are all being asked, all at once, to leap into versions of ourselves we don't know yet and are not ready for.

And I wonder — with that much real change already asking everything of us, is it healthy to also be marinating in a manufactured world of extremes? Where do we protect the reserves? If there are any, that is?

It would be easy to blame the usual suspects. Our phones, controlling us like puppets. AI, giving us permission to stop thinking for ourselves. Social media, forcing a one-upmanship that has everyone reaching past the edge of comfort just to be seen. All of that might be true. But every epic story (of which life is one, isn’t it?) has a villain and it makes less sense to name it than it does to learn how to defeat it.

We still have our consciousness, and we still have choice. Which is just another way of saying we still have our humanity. And I want that to be our superpower. With it, we have the extreme privilege to choose human connection over violence, over competition, over horror, every single time something asks us to pick.

I know, I know… That choice doesn’t make headlines. It’s not a summer blockbuster.

I'm not asking for a world without Christopher Nolan movies. Never. I'm asking whether that monster needed to be quite so big, quite so cannibalistic, quite so grotesque, to land the same emotional gut-punch. My guess is no. My guess is the quieter version would have hit equally well because it would have allowed our creative brains to fill in gaps in a way that would be allowed to be personal to each of us, rather than shove extremities (which can also be triggers) down our throats.

I'm in month ten of a twelve-month sabbatical, and I continue my quest for stillness, reflection, and a time-out. But we live in a world that hands out sharp edges and extremes at every turn, which are requiring me to fight daily and intentionally for the ability to hear myself think.

I’ve spent some time over the last several weeks feeling like I need to start this sabbatical all over. That things have become so noisy and extreme during a time that was meant to be quiet and simple. But now — in my belief that everything happens for a reason, and my continual quest to understand what the universe is trying to teach me — I think that this current chaos might be trying to help me.

I’ve been told by coaches, psychics, therapists, friends, and family that I plan too much. Although this planning has provided me with many amazing things (like, the ability to take a year off from full-time work, for example), it has been too rigid to allow space for a so-called cosmic interference.

The thing that I think the universe is saying to me — clearly in an extreme bellow rather than a delicate whisper — is that sometimes the noise and the chaos does not allow us to plan ahead, and there is a gift in relenting that control. As much as I want to spend my time dreaming and scheming the plot of my hero’s journey where I come out of corporate burnout to find myself living a happily-ever-after, I can’t plan that dream ending. At least not right now. One day at time it has to be. And I need to accept — and dare I say, enjoy — that.

Universe, I promise to learn and live this lesson, but I do have one request: Can you please take it down a notch?

Can you fill less of the highs and the lows for us so that we can hear your kind whispers and find your easter eggs? The thing is, I know you are looking out for me, but your constant screaming makes me mistake volume for meaning, and what my human nature really needs right now is an intensity in the form of quiet and stillness and peace. Please and Thank You.

Live with Love. Be Unexpected. 😘

Before leaving for Europe, and planning to be there through August, I made arrangements for someone to apartment-sit, leaving me with the ability to start moving into my next home - a place with an art studio, a yard, and biking trails nearby, just a bit outside NYC - sooner than planned.

But as I am learning, plans often change due to circumstances we don’t control. When I landed at Newark airport from Lisbon, I received a text message that this next home would be uninhabitable for at least a month due to a leak that flooded the place, requiring a full reconstruction of the walls, ceilings, and floors.

So in this plot twist, I have become a transient in my own city. My physical address changes each week. I’m appreciative of the many gracious offers from friends and family for a place to stay, and have enjoyed living in different parts of the city, but life in a suitcase is not filling my Cancer soul.

As a Cancer, I wrap my identity in my home. As I listen to every self-help voice in my head telling me to enjoy the adventure, that this is happening for me, that this uncertainty is growth - my nervous system is not convinced.

Without the stability of a home, and with the looming uncertainty of an answer to the question “what’s next” for me (after this supposed sabbatical I’m on), I am untethered in a way I have never been. I am dealing with it in real time, which is a generous way of saying “badly, some days.”

Without a fixed address, the small architecture of a normal life falls apart. I cannot set steady working hours. I cannot commit to seeing a friend two weeks out. I do not know where I will physically be next Thursday. My calendar has become theoretical. And it turns out that when my location is a moving target, so is my mood. I am sad, anxious, fragile, and overwhelmed. Instability is exhausting even when you know, intellectually, that it’s temporary.

I want community, connection, creativity, purpose, and a home — the lack of which is dragging the other four down.

My actual work is to separate the emotional grounding that home provides from its physical space. My community is - and has always been - all over the world. Connection comes with care for the relationships I build. Creativity travels in my sketchbook. Purpose is not zip-code dependent.

Home is the one desire that I can’t fake my way around.

I don’t know exactly when I move into the next real home. I do know what I’m rebuilding it for, and that clarity is the closest thing to a foundation I’ve got right now.

In the meantime, I pulled up something that I wrote in August 2024 about my last home. It was a few nights before I left my Seattle home — a place that I loved dearly and reminisce about nearly daily.

I’d love to share this with you.

My Hideaway: An Ode to My Seattle Home

Written August 31, 2024

I’ve lived in this house for nine years and this is the first time I’ve sat in this very spot on my front porch. It is the perfect hiding place, tucked behind at least twelve species of Pacific Northwest foliage. The bending tree branches in front of me extend to each other, like hands joined in an arch, at the perfect height so that the couples and families taking after-dinner walks with their dogs can’t see me watching them.

I listen to the hushed rustling of the summer leaves in the wind. They are still thriving in this late summer, not crisp and dying for the Fall yet. The air is warm. Unseasonably warm for this time of year in the PNW - but, then again, who even knows what that means anymore? The PNW has been my home for 25 years - nearly half my life. Enough time to have seen the weather patterns change. Indian summers have become “normal” in the last few years.

I sit quietly, though, anxious. Anxious because my phone is inside and I’m worried that, without it, I am missing this moment. Will I remember this if I don’t take a picture? Will I appreciate this if I don’t do a meditation, right here, right now? Then I become aware of my thoughts, and realize that I must chill, that the only thing that truly matters right now is being present in this enjoyment of one of the last moments in this house.

A soundtrack of Joni Mitchell starts in my head ...

Oh Carey, get out your cane (Carey, get out your cane). 
And I’ll put on some silver (I’ll put on some silver)

... as I notice the sounds of my neighborhood. There are birds overhead. I have no idea how many bird species live up there. I’ve never even thought about it before this second, though I have spent many moments listening to them all carrying on and communicating with each other. Cars go by at a regular cadence. Like an ocean, in slow motion.

Oh, you’re a mean old Daddy
But I like you I like you I like you

I’m wishing I could paint this moment. I’ve had a similar thought countless time while living in this house. More often than not, this sentiment is directed at the front room window. Every morning, it is a new view - a beautiful surprise. Will it be a coral sunrise, or will it be a midnight blue with a fast fade to pale yellow? Will the clouds be cotton white or candy pink? If only I could have captured this view every single day that I lived here. How many pictures would that be?

I moved in here on November 17, 2015. It was a ridiculously cold Thanksgiving that year. The power went out. For four full days. We were freezing. We couldn’t find our stuff, buried in moving boxes in the dark. We couldn't remember where we packed the headlamps. We didn't know how the gas fireplace worked.

3,209. It would be 3,209 pictures of the front room window.

I catch myself again, spiraling in the memories, feelings, and many highs and lows of the last 3,209 days.

I’m not present. I inhale. And then I exhale.

Friends and visitors to this house over the years have told me that it feels like a treehouse. The coolest compliment. I think about this newfound peep spot that I’m sitting in and the word “hideaway” comes to mind.

Come on down to the Mermaid Café, and I will
Buy you a bottle of wine 
And we’ll laugh and toast to nothing 
And smash our empty glasses down

I remind myself to just enjoy this moment. I focus back on here. I am here. This is now. I’m breathing, smelling, seeing, being.

Deep inhale... long slow exhale.

My mind is tugged to the past:“I wonder if Barry would want me to take a picture of this right now and send it to him.”

And to the future: “NYC is going to be so different than this.”

And I think how hard it is to just stay in the present. To stay here. To live now. Why must we need an anchor that is anywhere but where we are?

Oh, you know it sure is hard to leave here 
But it’s really not my home

Joni. My angel, embedded in my brain and my heart. Her words are cosmic, coming from nowhere and sparking my brain into a blaze in a micro-instant. How does she do that?

I decide that it’s time to go inside, but I’m not quite sure what I want to do when I get there. Maybe I’m going to get my phone and come right back out here to take pictures. Or just have the knowledge of this place as my new security blanket.

I remind myself to breathe.

Inhale…

Exhale…

Inhale…

Exhale…

And just like that, “now” is no longer. It’s fleeting but that doesn’t make it insignificant.

Live with Love. Be Unexpected. 😘

I had invested a lot, emotionally, into my visit to Southern Portugal, the region called the Algarve. I had a vision of celebrating my 50th birthday there a few years ago, and more recently, began fantasizing about it as a potential new home. I’m forever searching for my place — nestled between the mountains and the sea, where the weather is perfect year-round, with a thriving outdoors and arts community, and does not require a tech salary to live a decent life. There are few places in the world that match this criteria. The Algarve checks the boxes.

After enjoying a solo week in Lisbon, I was joined by my friend Jamie. She was fully briefed on my future dreams of Portugal living and was up for the reconnaissance. We would roadtrip together to Lagos, a small city in the Algarve about a 3-hour drive from Lisbon. Spending a holiday with Jamie, the Portuguese may say, would be matar saudades, which translates as “killing the saudades.” In plain English, I was crawling out of my skin to see her.

When Unbound became Uncomfortable

In October 2025, when I quit my tech job, I adopted “unbound” as my word-of-the-moment. “Living unbound” meant being liberated from anyone else’s control. I would finally live with autonomy, an overused word in the corporate world to attract people to a dream job. We often hear, in leadership roles, that we will have autonomy. But it never works that way. We are always bound by corporate goals and culture. And if it is not a job that is tethering you, it is a partner, a family, a pet, an investment, or a myriad of other things.

I decided to embrace this gift of living unbound, with an intention to claim agency of my attitudes and actions -- to follow my curiosity and intuition instead of someone else’s mission, or my addiction to external validation.

250 days into my 365-day sabbatical, while in Portugal, I felt a stirring of my joyful unbound shifting to an imposing uncertain, and filling me with an undesirable uncomfortable. Unfortunately, this all came to an emotional peak while trying to have an adventure and a mini-brouhaha for my 50th birthday.

That pull I felt toward Portugal a couple years back had vanished, and I was now feeling a compulsion to leave. I arrived in Portugal with no return ticket home, and an expectation to travel for at least a month. But the discomfort was suffocating. I woke each morning with a headache and a weight of sadness, and each night I suffered eerie and agitating dreams. I wanted the comfort of home, which was a complex feeling because I happened to be in a transition between homes and, therefore, unbound from one of those as well.

Captivated by Lagos Cliffsides

Despite the heaviness I was experiencing, I tried to carpe diem. Having my best friend there helped in every way. We weaved through hordes of tourists, in and out of shops and restaurants, on the stone-tiled streets of Lagos Old Town. We enjoyed the natural butteriness of fresh seafood, paired with the local verde vino (green wine). We took a drive to the nearby surf town of Aljezur to check out newer housing developments (a future home?) and west coast ocean views.

We gazed in wonder at the iconic limestone cliffsides from as many perspectives as we could position ourselves — from the Ponta da Piedade boardwalk, where the bird’s-eye view highlighted the mesmerizing color combination of golden copper cliffs against the cerulean sea; from a sailboat at sunset, serenaded by Fado (traditional Portuguese music whose melancholic feel matched my mood), golden reflections of limestone in the blue-green sea, and new detail in the layers of the cliff rocks; from the beach, where we contemplated all the ways a crashing wave could carve its stories into a single rock; from a kayak as we paddled through the caves created by these very waves, and those layers of rocks were revealed up close as markers of geological eras.

Celebrating 50 Years

I’ve known Jamie for nearly 30 years. She knows me better than most people do. She’s usually the person who I ask to decide for me when I’m in those moments of “I don’t know what to do, just tell me what to do.” Turning the corner to my 50th birthday was another moment in my life that I was grateful to share with her.

My birthday was filled with many things that I love, starting with an early hike on Fóia Summit, in the small mountain town of Monchique, about an hour’s drive from Lagos. Fóia Summit is the highest point in the Algarve, at 900m/3000 ft (still not even the starting point for the hiking trails in the PNW, but whatevs, I’ll work with the mountains available to me wherever I go).

Fóia gave expansive views of the southern Portugal coast, as well as a hazy semblance of what we believed to be Morocco in the distance. After returning to Lagos, we had coffee at our favorite coffee place along with a pastel de nata and carrot cake (because, why not have coffee and cake for lunch on your birthday??🎂), stopping at shops along the way to the beach, where we swam in the sea, and I spent quality time with my sketchbook. On the way home from the beach, we stopped for Aperol Spritzes where the bar next to us was playing Led Zeppelin’s D’yer Mak’er (LZ always brightens my spirit 🤘). After taking refuge in the air-conditioned apartment, we made a tinned fish charcuterie, with a local wine, and had an afternoon siesta.

Going Home

I made the decision, with Jamie’s help, to follow the calling for “home” - despite not having a specific domicile - and booked a return ticket to NYC to spend time with family. Just having the ticket booked lifted the weight that I was feeling, and the nightmares eased up.

I still grieve about the original plan I had for Europe that did not manifest, but in this new way of listening to myself that I am doing, I have faith that the trip - the long bike trip, traversing many countries, suffering through mountain climbs - will happen when the time is right.

My birthday - and my time in Portugal, as it turned out - ended on a high note with another one of my favorite things, a dram of Lagavulin. Cheers! 🥃 or Saúde!, as they say in Portugal.

Live with Love. Be Unexpected. 😘

My recent Portugal visit wasn’t the exact manifestation of this vision, but it was no less majestic.

Living in Lisbon

I landed in Lisbon on a Thursday morning, after a redeye from NYC. The drive into the city from the airport made me nostalgic for Seattle, following an industrial coastline and watching a summer rain flood the car windshield.

In the coming days, Lisbon’s narrow windy streets, hills, and colorful building facades validated the initial US west-coast vibe that I felt during that morning ride from the airport, and morphed from a Seattle to a San Francisco feel.

Lisbon infused me with creative inspiration everywhere I looked - from traditional painted tile covering building facades, endless shelves of ceramics, urban street art, and contemporary art galleries. I gave myself some playtime with a graffiti art class, where the palm tree I adopted as my go-to doodle as a kid was given a new personality with a couple cans of spray paint and a cement wall.

As I walked around the city, the words “I could live here” kept coming to mind. It’s picturesque, has great food, and the people are friendly.

The magic of Miradouro and the subtlety of Saudade

If the artistic detail on the streets of Lisbon appealed to my inner artist, the miradouros stirred my inner philosopher. Miradouro - the first significant Portuguese word that I learned on this trip - means “to admire a place” and is also used as a noun to define various lookout points from the top of Lisbon’s hills where tourists and locals peer out onto the speckled terracotta rooftops and pastel yellows, corals, and aquas of the buildings below.

On my first visit to a miradouro, I sat on a bench, enjoying a solo acoustic guitar serenade of some of my favorite classic rock songs. Did someone put this guy there for me, specifically? He played a lot of my favorite tunes, and the waterworks started. This show of emotion had me wondering if there was something more deeply biological about viewpoints (and jet lag, to be fair) that was stirring this emotional outpour.

I dug a little into this and learned that what I experience at great heights is indeed a universal human response. Viewpoints diminish our egos, enabling us to contemplate our interconnectedness. With this “forest for the trees” perspective, we inherently understand our individual role as a piece of the whole - a single tree. This understanding that we feel aids a natural meditative state where our brains are still, and thrive in creative problem-solving rather than execution of details.

This may explain my experience of “feeling” the mountains in Sri Lanka before I saw them, which I wrote about in this post. If I ever thought that my fascination with mountains was apropos of nothing, my time in Portugal squashed this thought. The natural, biological contemplation that I’ve been experiencing in midlife - my 50th birthday, to be specific - is amplified by viewpoints that bring on emotional overwhelm.

And, as if Portugal hadn’t gifted me enough with miradouro, I learned another uniquely Portuguese word that communicates the emotional overwhelm I was feeling: saudade. Saudade is the longing for a memorable past that is gone, like ‘nostalgia,’ but also encompasses the anticipation of a future moment when an aching is satisfied.

I cannot think of a more perfect word to encapsulate my complicated feelings at the start of my 50th trip around the sun, especially as it coincides with my sabbatical and career transition.

A medieval fairytale in Sintra

A highlight of my trip was found in Sintra, a 40-minute train ride from Lisbon city center, and a portal to medieval castles, palaces, gardens, and caves. Together, they oozed with inspiration for future sketches, paintings, and stories.

The main attraction of Sintra is Pena Palace, a colorful fairytale palace, resembling a Disney park attraction. I was moved by its tragic existence -- a summer home built by a King for his Queen, who died before enjoying its lavishness -- and disappointed by the ridiculousness of its only real and lasting use as a tourist trap.

Sintra hosts several structures which I found more interesting, if not as colorful, as the Pena Palace.

The Moorish Castle was built in the 8th century and used through the 12th century by the Moors to defend the region from attack. I decided that if I was alive during that time, I would want the job that put me at this castle, guarding a view instead of fighting a war. I would spend my time tracing landscapes of rolling hills to a patchwork of green fields, admiring sunrises and sunsets, following an infinite horizon out to sea, and imagining the commerce and commune happening in the towns below. Maybe I’d have a sketchbook with me, although I suppose that would be the medieval equivalent of burying my face in social media while on the job - probably frowned upon.

The gardens and hiking trails in the Parques de Sintra gave me a much-needed nature fix, as well as a muse for some sketches. I came upon a gazebo, wrapped in the arms of wisteria branches and gently covered with white, pink, blue, and purple hydrangea. I perched myself in front of it, pulled out my sketchbook and started to see what might want to flow. Luckily for me, the gazebo acted as a stage for many groups of tourists, so while I got my solitary sketch time, I also enjoyed some good people watching.

The main attraction for me was the Quinta da Regaleira, another palace. It was much smaller, less ornate, more cracked and creepy, and the one that I would choose a thousand times over the fairytale Pena -- if someone were to ever build a palace for me, that is.

On the grounds of the Quinta da Regaleira was also the Initiation Well. I felt its mythology as soon as I entered it. Dark, echoey, damp, cool, moldy, spooky - all of which reverberated with me as deeply sensual. The well spirals down nine flights to a network of caves that open into lush and peaceful corners of a pond with waterfalls and tropical plants.

Adeus Lisboa, for now

Lisbon left a loud impression on me of creativity, colorful facades, and life contemplation. I had the perfect ending to my Lisbon time - which was also the beginning of the next part of my trip - when I met up with a lifelong bestie from Seattle. Together, we would roadtrip to the dramatic seaside cliffs in the Algarve, the southern region of Portugal.

I will cover the Algarve, where I officially celebrated turning 50 😬, in part two.

Stay tuned...

Live with Love. Be Unexpected. 😘

I fall in love so readily, so easily.

I find one special and unique quality to throw my ever-loving being into it, head first. I imagine a future - how my life will change because of this cosmic connection. I envision my world as a saturated photograph, from this day forward, because of this meeting.

This adoration of newness consumes me, be it a person, place, or thing. My curiosity consumes me and I commit to it, becoming mesmerized and enchanted -- like a spell, or a drug.

I used to think my curiosity was a superpower. Now, I realize it can also be my kryptonite.

The reality check of habits vs. decisions

I am leaving for Portugal in a week. The outlook on my trip is very different today as compared to a week ago. A week ago, I had been planning a two month European adventure through several countries to celebrate my 50th birthday and ride a bike over miles and mountains that I adore so much. Today, I’m mourning this plan, as I’ve made the decision to abandon it. I’m devastated, even though I know I’ve made the right choice for me.

I won’t dwell on the many factors that contributed to my decision to drop this plan - most of them are beside the point. But there is one factor, which is exactly to the point:

The excitement of this trip morphed into feelings of dread and white-knuckling that were excruciatingly familiar, reminding me of the ickiness that consumed me in the months leading up to quitting my job. I woke up with a headache every morning. I felt chronically detached, irritable, and foggy. My emotions were constantly rumbling, like a torrential downpour completely consuming me or distant thunder, warning of its impending doom.

Rationally, these feelings did not make any sense. The plan included many of my favorite things - travel, biking, mountains - and I was under the impression that the plans developed out of decision-making with my own best interest in mind. But all of this - even my favorite things - started feeling wrong. When I stopped forcing myself to execute the plan and instead paused to figure out why my body was revolting, I saw clearly that the “decisions” I had been making were not decisions at all - they were habitual actions. I had been performing them in service of my pre-sabbatical self, not for my current self or my current life. I was reverting to old habits in order to create a familiar - and therefore, comforting - environment in this crazy, uncertain new post-sabbatical life that is unfolding.

Taking responsibility means deciding

There are a few things that hit hard last week -

The burnout from my job is deep inside my psyche and my body. Four months of travel did not heal my burnout, nor did I manage to free it in the ocean in the Philippines, shake it off in the mountains in Vietnam, or drop it in the rice paddies in Bali. My recent situation unintentionally tested the waters of ‘falling in love with work’ again and showed me that the wounds are still raw.

I need to change my psyche + body foundation in order to get different results. I don’t mean to state this as a simple “step 2” of a recovery plan. I understand this is a lifetime of continuous work. But for now, my goal is to choose my work and my loves - not just carefully, but differently.

Not only do I need to change the foundation, I can change it. This is where I am now.

I had a poignant lesson of “taking responsibility” in Da Nang earlier this year. After a challenging bike trip in Northern Vietnam, I decided to visit Da Nang to take a few down days. I envisioned basking in beach time, but it rained the entire time I was there. I failed to do research on Da Nang, or the hotel I stayed at and neither were doing it for me in those conditions. I was cold and uncomfortable and generally bummed out by my predicament.

After explaining the lack of enthusiasm for my current situation to a friend, I concluded with, “Oh well, it’s all my fault - I didn’t really research any of this before I came here.”

To which he said, “Well, yeah. Who else’s fault would it be?”

Touché.

How exactly does one change their psyche and body foundation? That sounds hard.

Changing the Psychosomatics

I learned recently that psyche + body is the origin of the term “psychosomatic.” Pretty cool. I always associated this term with someone who thinks they are perpetually sick. But now the word has a whole new meaning for me - of agency, rather than lack of agency.

In learning how to lean into my intuition - as I talked about in this post), I’m doing psychosomatic work. I’m learning to listen to my body’s language - how it communicates a “yes” or a “no” to me.

To help me with this, a friend recently rapid-fired yes/no questions at me, so that I could feel and learn my instinctive responses -- Where do it feel it? Was it in my gut, my arms, my chest? I felt it in my solar plexus - that weirdly named area deep in my core between my heart and my stomach. What did it feel like? Was it a dull lull, or striking pricklies, or an energetic hum? I felt something like an electric shock shoot up to my neck - subtle, but present.

For some of the questions she asked me, there was a clear answer, but for most of her questions, I felt nothing. Paralyzed. I attribute this numbness to the years of habitual reacting I’ve been treading through, and the burnout that is still inside me.

What fills/drains my cup?

In order to dig new neural pathways, I need to create a clear intention to hear and understand my body’s yes/no signals. So, I found a way to use a spreadsheet as a tool, rather than a bible, for decision-making. I started tracking three things at the end of each day:

1. Was my day more draining than filling, or more filling than draining?

2. What specific people, things, activities, and places filled my cup?

3. What specific people, things, activities, and places drained my cup?

By the end of the week, I had created two very satisfying lists:

1. What filled my cup? → Do more of this!

2. What drained my cup? → Do less of this!

I even made a Lovable app for this. Check it out here.1 The purpose is to help me recognize personal habits and patterns so that I can do more of them - if they fill me - and less of them - if they don’t.

My current freedom from attachment to a job, career, partner, home, etc. is not the same thing as having freedom from responsibility for my life. And if taking responsibility for my life can bring me into a dark place, it can also take me to a place of great relief.

Live with Love. Be Unexpected. 😘

Sometime between when I arrived back home from my travels at the end of April and now - early June - I’ve become as lost as the day that I stepped away from my career. I still proclaim to be “on sabbatical” but somehow took on a volume and intensity of work and passion projects that made me busier and just as stressed as I was when I had a job that was grinding me to my core.

It doesn’t feel like this happened gradually. It feels like I’ve been pummeled by those ocean waves I was so afraid of in Sri Lanka, which followed me to Brooklyn and crashed on me in the supposed safety of my urban apartment. The irony is comedic. The waves crashed, I survived the ‘washing machine,’ and when my head bobbed above the water and I looked around, I found myself in a place that I desperately didn’t like and didn’t want to inhabit.

And now I’m thinking - “How did this happen? No one did this to you, Cortney. You did this to yourself. You made a series of choices that brought you exactly here. And for what purpose?”

I have never in my life been in a period of more freedom than I have now. It has had its moments of magic - as was the case with my travels earlier this year - but also a responsibility to my mental and emotional health that I’ve neglected recently.

Disconnecting From Old Habits

I’m reading and re-reading the last article I wrote because I wrote it for myself. I was deep in a place of knowing how my current state of distress was caused by my life-long habit of over-intellectualization. A habit I want to break, first by acknowledging it and naming it. I recognize that it shrouds my ability to feel the expansion and contraction of my body. It is a habit that behaves exactly like an addiction.

I ended up in this current state of overwhelm, sadness, and exhaustion because I’ve moved in the direction of intellectual yesses rather than visceral yesses. I’m struggling with understanding the range of feelings in my body - it can’t be as binary as either a Yes or a No. Certainly, something that feels intriguing may not feel like an immediate Yes or a No. It may feel magnetic. And when it does, can there be a wrong reason for this magnetism?

This sabbatical is still teaching me every day, including the hardest lessons about my own decision-making. And what I keep finding at the root of it is a need for external validation, fed entirely by my habit of over-intellectualization. I can’t say ‘yes’ to wading in the shallow water - I must swim out to where the waves are the biggest and scariest. I can’t say ‘yes’ to one glass of wine - I must consume the whole bottle. I can’t say ‘yes’ to a 3 mi run in the park - I must traverse an epic trail across several hundred miles. I can’t say ‘yes’ to sketching for pure enjoyment for an hour - it must be the source of the next greatest art company.

This need for external validation comes from my fear of being mediocre. If I’m being, doing, or making something extraordinary, my core being - all of the intellect, passion, and instinct - cannot be ignored or denied. And this, to me, justifies the perils of drained energy, or even resulting disease.

So I’m stuck right now.

While I still want to be extraordinary, and I still crave the external validation, I no longer want the energy drain, and I care more about my longevity than I do about the short-term discomfort of over-extending myself.

The way to get myself unstuck from this place is to let go of my fear of mediocrity.

A Helpful and Soulful Reframing

I went to a spiritual advisor recently, to get another perspective on this - I’ve already talked the ears off of my friends and family who will listen. It wasn’t my first visit, but it was the first time I was told that I’m a new soul. This surprised me greatly. I’ve always thought of myself as an old soul. I don’t have a good basis for thinking this, I just do. But hearing that I’m a new soul filled me with an immediate wash of warmth - like the comfort of a warm blanket or a healing hug.

In an instant, I thought of all of the things in my life I’ve tried to accomplish - with tenacity, ferocity, passion, discipline, strength - and I’ve objectively failed at. I’ve often felt like life is harder for me than most people. Others seem to dance with ease to ultimate success through situations in which I give 110% and barely move the needle. This has always puzzled, frustrated, and saddened me, as much as I try to let it go and just be ok with “doing my best.”

And in an instant, upon hearing that I am a new soul, it occurred to me that maybe my job in this life is not to accomplish any of those things, from a societal/objective perspective. Maybe my job is simply to nurture this new soul - fill it with love, allow it to explore its wonder, keep it safe from corruption - so that after I’m gone, it can grow and flourish with a solid base of understanding. It’s not up to me what happens in its next life, but I can take care of it while it inhabits me.

Without Conclusion

I haven’t felt much like writing lately, as I don’t want to disrupt the narrative of a woman in charge, who claimed her freedom - herself - by leaving a career that did not serve her and is on a mission to make a life for herself that is more authentic. But if I’m being honest (that’s the entire point), then that narrative will be disrupted with uninteresting moments of relapse into old patterns, and the messes to clean up as a result from those relapses. I offer my apologies to the reader (this includes yours truly) who wants a resolution to my current fears - I don’t have one right now.

Maybe one day, my creative fire will be sparked by this whole idea, and a brilliant creation will come out it. Then again, maybe that won’t ever happen, and this moment of my sabbatical will just live here, as one of a billion mediocre posts on the internet.

Live with Love For Yourself. Be Unexpected. 😘

I’ve been alive for 49 years. And I’ve spent a lot of this time over-intellectualizing everything. From the time I was little, I was not satisfied with the status quo and therefore had to gather and process information to make connections, decisions, and opinions. As I got older and discovered the marvel that is spreadsheets, and the SUMPRODUCT formula, I could calculate my thoughts with weighted criteria and validate my decisions with data. 🤯 Mystery of life solved.

But the mystery of life was not solved. No matter how honest I was with myself about the options in front of me, and their importance to me, and no matter how many times I followed what the calculations told me to do, I still somehow ended up in burnout - in a job that I loved, but a career that was not serving me. How is it possible that my precious spreadsheet could stray me so very afar?

Perhaps this obsession with decision making through spreadsheets is what took me over ten years to finally make the change in my life that I needed to and I quit my job. There was no spreadsheet that was ever going to tell me that I will be better off, financially, in the long run if I stepped away from my career without a plan for income. And the more I tried to make the spreadsheet tell me this story, the more my heart and my gut revolted. Until it was pointed out to me, repeatedly, by therapists, friends, and coaches:

I need to trust my intuition more than my spreadsheet for making big life decisions.

That all sounded very woo woo to me. How does one go about listening to their intuition? Is there a spreadsheet for that?

After finally taking the leap to put a career that was not serving me in the rearview mirror, and take my foot off the gas, a lot of clouds are clearing. And behind those clouds - I think I see it - is my intuition.

I’m not an expert on this. I’m just someone in the process of learning how to listen to my intuition. And here’s what I am learning.

Intuition is a feeling more than it is thought. It usually is a simple feeling - like “I like this” or “this feels bad.”

Separating Intuition from The Gut and The Heart

My Leadership professor in my MBA program told us that great leaders know how to balance logic, passion, and experience — in other words, the head, the heart, and the gut.

Intuition is different than the feeling in my gut, which feels all rumbly when I need to make an urgent decision with great gravity. I also find that it fires to warn me against something, rather than to push me in a particular direction.

Intuition is different from “listening to my heart” which is more of an ache, a desperate longing for something. If intuition gives me a generalized feeling about something, the signals from my heart look a lot like the second and third tiers on a feelings wheel. They help identify, in detail, where I’m at in a particular situation.

Balancing Bali in a Spreadsheet

Recently, when I traveled to Bali, I arrived on rocky ground, emotionally. I felt overwhelmed with the SO MUCH of it. Both overjoyed and totally uncomfortable. I found myself hunched over my laptop on my first night, deep in a spreadsheet I titled “Ubud Personal Retreat.” I was building a 10-day retreat for myself, from the long list of suggestions I received for yoga classes, restaurants, meditation classes, art classes, cultural immersion, and excursions. There wasn’t time to do everything and I had to find a way to do it all in 10 days. Structure would make me feel better, I told myself. I spent a couple blissful hours in my room hiding from my overwhelmed self, fully immersed in a color-coded schedule with time-blocked activities and back-ups for every single day.

I stared at it and felt my chest tighten. Not in excitement, but just stress. In Bali.

That tension - that low-grade, spreadsheet-induced dread - was my intuition talking. Not dramatically. Not in the voice of a guru. Just me. Just my voice. A quiet, slightly annoyed whisper: this is not why you came here.

I closed my eyes and this voice spoke a mantra I come back to every now and then: Be here now.

And then I closed the laptop and I went to sleep.

Bali was rocky for the first couple days. Intuition spoke, but I wasn’t quick to fall in line. I ached for more structure, but my intuition wanted me to just be, whatever that means. But somewhere in the middle of that rocky Ubud river, someone mentioned an open mic night. Then someone else did. I couldn’t find a group to go with, so I went alone. That was the moment when Bali opened her arms to me and allowed me to fall into her motherly embrace.

There was a vibrant bohemian crowd at the open mic. Tons of local musicians, as well as tourists stopping by trying to get on the set list for the night. I sat at a table with strangers, who slowly became friends. I listened to a traditional Javanese drum circle, followed by a 12-year-old guitarist playing “Sweet Child O’Mine,” accompanied by a local band.

It would be easy to check the box on the open mic night on my spreadsheet - if I was following it, that is - but I could not in a million years have scheduled that feeling of joy and freedom from that night into a calendar. No weighted criteria would have surfaced it.

I found the right thing, at the right time, because I was finally open enough to hear it.

Bali ended up being one of the richest sensory memories of my entire trip. (My full Bali experience is a story I’ve already told - you can read more about it here.)

The spreadsheet didn’t get me there. Getting quiet did.

Actively Quieting My Intellect

I’m starting to track the moments that give me a special feeling, and note how I got there. Was it intellect or intuition that brought me there? I’m also actively practicing putting my intellect in a time-out so that my intuition and I can get better acquainted. It’s like making a new friend. Conversation isn’t always natural, but the more familiar I get with her, the more I am growing to trust her.

Live with Love. Be Unexpected. 😘

The first time I used AI was in 1991.

I was 15 years old. I was a piano player and songwriter. I hand-wrote every single song on sheet music. I figured out the key signature, the time signature, every rest, every 16th note and 16th rest (I was fond of syncopation). And I wrote each of these down, with a pen (not a pencil) on staff paper. It was tedious. It was also necessary, because handwritten sheet music was necessary to copyright my songs.

Until one day I learned that I could buy a MIDI sound card, connect my keyboard to it, and the sheet music would write itself.

I tried it. My mind was blown.

Magic was happening before my eyes. And more importantly, I got my time back. Time I could now spend composing and producing instead of transcribing. The MIDI card didn’t write my music. It handled the part that was getting in the way of my creative process.

I’ve been thinking about that moment a lot lately, because I’ve been deep into MidJourney animation. And I cannot get it to do what I want it to do.

You want to know why?

Because I am not a digital animator. I don’t understand the technology, the terminology, or the unwritten rules. To a professional animator, MidJourney is handling the tedious parts of their craft, the “sheet music” parts. The parts that eat time without feeding the work. But I don’t know enough about animation to even identify what those parts are. So I’m fumbling through MidJourney getting amateur results, wondering why the magic isn’t happening.

The MIDI sound card didn’t make me a better composer because it was powerful. It made me a better composer because I already was one. I knew music theory. I understood structure, melody, and harmony. I knew what I was trying to say before the tool ever entered the room.

Technicians — animators, software developers, marketers, product managers, doctors, lawyers, writers — are not going to lose their jobs to AI. Not the ones who understand the core of what they actually do. If you know your craft at a molecular level, AI becomes exactly what that MIDI card was for me: the thing that handles the sheet music so you can get back to the song.

I want to acknowledge the fear behind AI, as I’m just like all of us in this day and age - I’m trying to figure it all out. I see the benefit of it, but I know it is not all puppies and rainbows. AI is also making us lazy in ways that sadden me. We are losing our curiosity. We are outsourcing our critical thinking. But, to be brutally honest, AI is not responsible for starting that slide. Smartphones put us on that slide 25 years ago. The dependency on computers to do our thinking was already well underway before ChatGPT, Claude, or Gemini was even a concept.

The Call to Action for Artists and Technicians Alike

Don’t resist AI because you think it’s going to take your job or kill your craft. Resist letting any technology do your thinking for you. Learn what your superpowers are without the tools. Hone them. Really lean into them. Because when you know what you’re actually made of, you’ll know exactly how to use AI to put your own unique, irreplaceable songs on sheet music.

Live with Conviction. Be Unexpected 😘

A few years ago, substantially late to the party, I saw The Godfather — a GOAT according to basically every film critic on the planet. Despite my lack of interest in guns, violence, and blatant machismo, I owed it to my love of cinema to check this one off the required watch-list.

To my surprise, I loved it. The story, the performances — neither were overrated, and I was wrong about the machismo. But what stayed with me wasn’t the acting, the writing, or the directing. It was the women. Specifically, their minimal roles and absent perspective. Every female character reads like an afterthought — token wives and girlfriends whose stories are conveyed through their clothing rather than their voices. Critics have called the women in The Godfather “silenced,” “stupid,” and “victimized.”

I don’t know much about being a gangster’s wife, but I know something about being a woman whose story gets overlooked or taken for granted.

I am surrounded daily by women-in-charge, at every life stage: women who run entire households so their husbands can be heroes at work; women who give up careers and personal happiness to have children; women who “have it all” at the expense of their mental health; women who are afraid to speak, or shamed when they do. Their stories are not told in mass media, let alone explored with any depth. We assume every housewife has the same experience, every working woman has the same experience, every woman in love has the same experience. In flattening these stories, we erase them.

Of the AFI’s Top 100 Movies of All Time, only 14 feature a female protagonist. Of those 14, only 3 center a struggle that isn’t romance. Women are more than wives, girlfriends, and maidens in love. Where is the story of the woman in her 20s trying to understand sexy versus slutty? The woman in her 30s who hasn’t found her career or her partner, and is being told by her doctor that the “window is closing”? The woman in her 40s who has never felt comfortable in her female body and is contemplating top surgery? The woman in her 50s whose estrogen is in freefall, sending her into soul-searching questions about her marriage, her sexuality, her career, her home, her friends?

These stories are told every day by brave women who are bashing stereotypes simply by being honest. Every time a woman tells her authentic story, she becomes a soldier against the patriarchy. And that is viewed as a threat rather than an act of heroism.

Enter, The Muses

While on a creative writing retreat in Costa Rica, I heard one of these stories of powerful, adventurous, intelligent women.

📣 Check out the video below to learn more. Come join me at an upcoming event to learn more about bringing the story of The Muses to life. Fill out the RSVP at the end of this article.

It’s called The Muses and it is about 9 High Priestess Celtic Druids, bonded in an unbreakable sisterhood. The story completely captivated me. It was written by one of the retreat facilitators, Cat Lindroth. Cat is a Yale-educated history major and social impact entrepreneur and has spent two years writing The Muses.

As Cat read one of the stories from The Muses, the hair on my arms stood on end. My brain was lit up. I could feel the story in my gut. I could see it all unfolding in my head - on a big screen. I envisioned nothing less than an epic historical fantasy. I needed to make this story!

I said to Cat, “I want to help you produce this. I want to make this story real. Where do we start?”

She said: “It starts on a bike. In Croatia. This summer. Riding to Switzerland.”

If you know me, you know she had me at “bike.” 🚴

The 1,000-Kilometer Journey

In mid-July, Cat and I will ride our bikes nearly 1,000 km from Croatia to the Swiss Alps, through the lands that were sacred to the Celts in Central Europe, publishing the first 14 stories along the route using poetry, song, AI animation, and video footage.

Cat and I are especially feeling the synchronicity with The Muses call-to-action this summer, as she turns 40 and I turn 50. We’re really doing a thing 😜

RSVP: We would love to see you

Before we leave, we want to share more about The Muses with you, so we will be hosting three events. At these gatherings, Cat will read the first three bardic poems in the story, we will share more of the historical inspiration, and will share our vision for how we will bring the story to life — soliciting your input on where we take this.

Ideally, you will connect with The Muses as much as we have and you will become part of the group of ambassadors and patrons that we are seeking to bring this story into the world.

At these events, we will also open the mic to you. If you have a poem, a song, or a story you are aching to share, we want to hear it.

The three events are:

• May 31 in Wilmington, Delaware Event Full

• June 7 in New York City Event Full

• June 13 - Virtual

Reserve Your Seat

You will receive more event details when you complete the RSVP

Live with Love. Be Unexpected. 😘

I started carrying a sketchbook with me when I moved to NYC. I was inspired by my aunts, Betsy and Andee, who have done this as far back as I can remember. I told myself I don’t draw, I doodle. The sketchbook gave the shapes and colors in my head a playground where they could come to life.

In my recent travels, I carried it with more intention. Little by little, one line, one shape, one shadow at a time, I learned to draw actual things. I sketched nearly every day — not to master a craft, but for the pleasure of seeing the world differently and capturing it somewhere other than on my phone.

I did this with childlike play and curiosity. I expected I may get a little better at it over time, but what I didn’t expect was what happened every time I sketched in public. People stopped. They glanced. They started talking to each other and to me.

In Cambodia, I watched the sun rise over Angkor Wat with my sketchbook open, roughly sketching the shape of the temples, the river, and the big red orb rising before me. A couple sitting next to me glanced over. I heard the woman say quietly to her husband, “I wish I could draw.” I couldn’t help myself. “You can,” I said. “You just might not know it yet.” They laughed, complimented my “talent” — a word I always push back on when it comes to my drawings. I commented on their American accents, and we launched into a conversation that was immediately interesting and meaningful.

The three of us watched the sun come up together, and then we went our separate ways into the temple ruins. That night, at a random restaurant on Pub Street — a busy, touristy street in Siem Reap — I sat down with a view of the street and was just about to open my sketchbook again when I noticed them. The same couple, being seated at the table right next to mine. What are the chances?! I joined them for dinner. Art brought us together.

It happened in Vietnam. In the Philippines. In Costa Rica. In Thailand. Consistently, reliably, almost without exception: the sketchbook was a magnet.

One of the greatest compliments I received was a request from a fellow traveler for me to sketch something in his travel journal. Imagine — my drawing is etched in his chronicle of his latest vacation. How freakin’ cool. What an honor. 😍

There is No Wrong Way to Make Art

Somewhere between childhood finger-painting and adulthood, most of us absorbed the idea that art belongs to artists — a separate class of humans who were born with something we weren’t. And so we stopped. We became observers instead of makers. Consumers instead of participants.

Art, in its original and most essential form, has never been about mastery. It’s been about meaning-making. Looking at something — a sunset, a building, a face, a feeling — and expressing something. The impulse is human. It predates language.

There is no right way to make art. There is no wrong way to look at it, talk about it, or be moved by it. The only thing you can do wrong is convince yourself it’s not for you.

Human Connection Happens in the Flesh

My sketchbook drew me to strangers, who became new friends, reliably. I have not connected with nearly as many people through dating apps, Instagram, or any other digital community as I did with art.

We can connect through a screen. I’ve done it. I do it. This Substack is, in a certain sense, a form of connection — you’re reading words I wrote, something in them resonates, and that resonance is real. But it is a different animal from what happens when two humans are face-to-face, flesh-to-flesh, in front of a shared thing, talking about it together.

When you’re sitting next to someone, you can observe their gaze as they speak. You can see the nuances of their face and body language. You feel their energy when your eyes lock, however briefly. You can see that they are not performing to pacify an algorithm. They are practicing humanity.

Art is social infrastructure that gives us joint purpose.

Rebuilding Our Humanity

Our lives have become swallowed up by computers and devices instead of being fed by in-person human connection. We are more connected than ever, by every measurable metric, and somehow also lonelier. The research is grim and consistent: loneliness is at epidemic levels across age groups, countries, and demographics. Digital connection is real and it helps. But it is not how humans are meant to connect. We are walking around, many of us, chronically underfed in a specific and essential way.

Even though — maybe because — I’ve made a career in technology, I’m motivated to reverse this trend and rebuild our humanity.

What I build next will be centered on a mission of human connection. It won’t scale like an app or deliver a 10x multiple. It doesn’t need to. I’m not building for extreme wealth. I’m building for our humanity.

Art — visual, musical, culinary, literary, physical — has always been the mechanism by which humans recognized each other as fully human. A work of art says: I noticed something. I felt something about it. I made this so you could feel something too. And when it works, even imperfectly, it creates a bond that transcends the specific object. It says: we are in this together. We are made of the same stuff. We see the same world, even when we see it differently.

That’s not a luxury. That’s not a business. That’s not even a product. That’s a fundamental human need.

The path back runs through the art all around us — and the art we are in the process of creating.

So, dear humans, go forth! Be human! Make something. Share it. Let someone react to it. Look at what they make. Tell them what you see.

Live with Love. Be Unexpected 😘

I really had hoped that we moved past the phrase “mid-life crisis.” But I still hear this phrase and it gives me full-body aches, and not in a good way.

Like Winston Churchill, who said “in crisis is great opportunity,” I love a good crisis for the character test that it creates. But I object to mid-life being a crisis.

I understand the expectations that the world has for me, and fortunately (sometimes unfortunately), have always navigated contrary to them. I understand that a woman on the brink of 50 years old, with no job, no children, no pets, no partner, and living in a temporary situation looks like a person in crisis. I understand that this snapshot description of my life sounds empty, lonely, scary, … maybe it even resembles a crisis.

But things are not always what they seem, and we could all do with questioning our viewpoints o have an honest tally of what has been decided for us by the patriarchy versus what we’ve really immersed our minds in to develop a unique point of view.

It is a Reawakening, Not a Crisis

I feel so the opposite of a crisis. I feel like I’ve shed dead skin, emerged from a cocoon, bloomed in the Spring … all of these nature analogies apply.

All of my circumstances (except my age) were my doing, after heartbreaking, tearful contemplation with myself and the people closest to me. I made mindful decisions, not because I was being mercurial or irresponsible, but because I was doing what we all want — molding my one life into one that enables the best version of myself to unfold.

If I’m ashamed of anything, it is not that I am unmarried, unemployed, childless, or don’t own the home that I live in — it is that it took me nearly 50 years to get to the place where I could honor myself more deliberately. The re-awakening is the knowledge that I am in charge of my life. All of it. All of the roses, the buds, and the thorns. I get to decide what environment I need around me to be the highest priestess version of myself.

And by the way, we all have this power. You don’t need to be in mid-life, or on a sabbatical, or recently divorced to claim this power.

It’s Ideal but it is Not Easy

I should mention — reawakening to a new, better life is not like floating effortlessly in a rubber tube down a peaceful river with shades on and a beer in hand, marveling at a mountain view.

It’s hard. It’s time-consuming. It requires faith. It takes a specific kind of courage — brutal honesty with yourself in a world that is trying to tell you what to think and how to feel, from every conceivable direction.

If I Knew Then What I Know Now

There are many things I did in my life up to this point to make this transition easier. And there are things that I wish I did differently. A lot of people reach out to me, passionately expressing their desire to do what I’m doing — quit their job, travel, rebuild — but they can’t because of this, that, and the other. I hear you. And here’s what I say to them about achieving that ideal picture of life: If you are questioning your life, then you are already fucking doing it!

Maybe you are not in a financial position to quit your job. Or maybe you don’t really know what you would do if you quit your job. Or maybe you have kids or parents who need you. Maybe you have a health condition that dictates your life.

You will get over, through, or around each of these barriers.

I’ve always been obsessed with setting goals and creating to-do lists that get me to that goal (I can’t help it, it is an occupational hazard of being a product manager), but I am being drawn to a new type of guidance. Less action, more affirmation. Something that resembles a love letter from my intuition — a manifestation of my wild mind to bring me back to my power when I’m feeling foggy, defeated, or frazzled.

If my intuition were to write that love letter to me, here are some things it may say:

• Know what you want and what you need.

• Allow your wants and needs to evolve over time. Don’t get too attached to any of them.

• Get comfortable with articulating your wants and needs out loud, face-to-face, with other humans.

• It helps to defend your wants and needs - not to be argumentative, but to be certain for yourself.

• Listen to other people. Like, really, listen. Don’t just stop talking when they are talking. Stop thinking of your own shit when they are talking.

• Question authority, with curiosity. Including - every now and then - your own compass.

• Cry! From faintly teary eyes to deep, heaving sobs. The physical release is an absolute necessity for your body and mind.

• Hug people. Tell them how you feel about them. Give them your respect and honesty.

• Get used to living in a little discomfort. Not a ton of it - the comfort:discomfort ratio is going to be personal to you. Find that ratio.

• Your mobility is a sacred gift. Move your body every damn day.

• When you are sad, depressed, or feeling “off,” this is the time that you need to get brutally honest with yourself. Know that your courage will be tested the hardest in these moments.

Your power emerges when you get out of the rut

I had a friend point out to me this week, when I expressed frustration about all of my creative ideas stomping on top of each other that none of them are being expressed, that my brain has been working in one way for so long that it is behaving a bit wildly right now as it finds its new course of freedom.

While I cringe at the phrase “mid-life crisis,” I could get behind “mid-life rut” because it more accurately describes what is happening. Churchill said the opportunity lives inside the crisis. I'd take a different angle: the opportunity lives inside the rut. The crisis is just what it looks like from the outside.

Live with Love. Be Unexpected. 😘

In Costa Rica, I expanded my notion of spirituality. I had a guided psilocybin ceremony, during which I experienced — what I can only describe as — an exorcism. My guide named it a “soul retrieval” which is a gentler description, but my adoration of spooky things is going to insist we name it an exorcism 😈

Doesn’t matter what we call it, the intention and the resulting outcome was to cut the cord on thoughts or beliefs that have been weighing me down for a very long time.

I knew exactly the cord to cut.

It formed over thirty years ago. On the other end of the cord is a soul-sucking worm that has dosed me daily with an elixir of shame and hateful contradictions to my self-worth. Fighting against its control of my waking thoughts and nightly dreams has often felt like a one-woman battle for survival.

And I’ve tried to rid myself of it. Oh man alive, have I ever tried. With therapy, with meditation, with endless hours on a bike. Through confessionals with my closest friends, and over-sharing with near-strangers.

And yet. This snarling, persistent worm — with its controlling black eyes, indigo slime-oozing bloated body, and venomous drool — did not let go.

So when I learned that a cord-cutting would be a part of my psilocybin ceremony, I was as hopeful for relief as I was skeptical about its effectiveness.

The ceremony was transformative. After the exorcism/soul-retrieval, I felt physical relief. Additionally, throughout my following 3 months of travel, the daily obsessive thoughts — both waking and in my dreams — ceased. And in the days that followed the ceremony, self-forgiveness started to unfold. For the first time, I understood that ‘teenage me’ did not have the skills, knowledge, or experience that ‘current me’ has, and I should not be judging her for not doing better.

But two questions remained:

• What was my flaw 30+ years ago (during my high school years)? Was I complicit in the trauma that happened?

• And how has that event and its emotional impact contributed to the battles I’ve fought in my career and my romantic relationships?

Clearly, the cord between the worm and my subconscious had been severed, but there were practicalities I still hadn’t settled.

The answers to these questions have come in bits and pieces over the years, through therapy, meditation, books, conversations. But without a utility drawer to put them in, they just ended up like rubber bands, paper clips, matchbooks, and safety pins: tucked in wrong drawers, cluttering space meant for something else, lost when I needed them most.

That utility drawer — in the form of articulate, rational, and complete sentences — came to me in Sri Lanka, thanks to the quiet, the time, and the immersion in nature.

The Right Words, Finally

One morning in Ella, unceremoniously, the words came to me as I was showering, brushing my teeth, and getting dressed for a hike on Little Adam’s Peak. The words did not arrive with fanfare. They did not come during meditation, or with a beam of sunlight shining down on me at the summit of a mountain. They did not jolt me awake in the middle of the night. They emerged slowly — the way a long morning takes all the way through coffee, breakfast, a shower, and a commute before you unfold to a fully-awake state.

But even though they came without ceremony, they came clearly.

Over thirty years ago, during high school, I experienced what I can now call a predatory, manipulative, and sexually abusive relationship.

I’ve never wanted to see these words as the truth because doing so requires that I see myself as a victim. Victim. That word is the problem. By not calling it what it was, I denied my reality, holding that teenage girl to standards I had the privilege to learn over many years, expecting her to have the knowledge that I was still acquiring in real-time.

Before Ella, my version of the story named me as “the problem.” I blamed myself for what happened and spent thirty years trying to fix something about myself. I have been trying to find logic, retrospectively, from a situation that had none. After Ella, I understood: I didn’t do anything wrong. He did.

That girl — high school me — was a victim of abuse who turned into a woman who has been paying the price for impossibly not having the skills or knowledge to protect herself when she was a kid.

I have given a lot of energy over the years to the guy who did this to me — trying to understand his motivations and behaviors. But he does not deserve my energy — he never did. The person who deserves it is that teenage girl. To her, I want to give my deepest apologies for not being there for her, and for every scarred, imperfect, evolving version of the woman she became.

What the Summit Made Clear

When I got to the top of Little Adam’s Peak, I found a remote lookout where I could be alone and silent. The words that had come to me that morning rose again. This time more slowly and deliberately, making sure I heard them now that I was still.

And then the pieces connected.

My drive to get him to love me — my first experience with love — was so consuming that I abandoned everything I wanted that didn’t gain his approval. I was so focused on earning his love that I hushed everything my heart was asking for. I went along with things that made me feel terrible because the alternative — losing his approval — felt worse.

I had an interesting illustration on this lesson on my plane home while watching the movie Wuthering Heights. Catherine denied herself what her heart was asking for, which was frustrating at best. But her choice to silence her heart deeply affected everyone around her … Oi! The only words that came to me were, “What a fucking mess you’ve made, Cathy!”

In my career, the pattern shows up as me always trying to please my boss or my CEO — deferring, shrinking, performing — for the sake of acceptance. In romantic relationships, I silence myself for fear of rejection.

The unconstrained contemplation this sabbatical afforded me helped me to see it clearly: a blind drive for acceptance and external validation has conditioned me to override my heart’s requests. Whether the stakes are small — what to eat for dinner, when to schedule a meeting — or big — deciding to get married, defending a promotion — I’ve hushed my heart for the sake of ensuring acceptance from whoever I needed it from most: my spouse, my boss, my CEO, my family.

Mourning Endings (Which Are Really Just Beginnings)

The complete understanding of my evil worm brings waves of feelings, but mostly longing and devastation over the unattainable: a past that cannot be revised and a future that cannot be known. And yet there is wistfulness — a relief that the past is in the past — and more confidence to soldier forward, as I always have, but this time without the extra weight of a wicked worm in tow.

Before I left Ella, I bought a bracelet strung with carnelian stones. A reminder. Of the feeling in that moment on the mountain. The complete freedom from self-blame, from self-sabotage, from thirty years of trying to fix the wrong person. A reminder to move forward confidently, boldly, in the direction of my own heart.

All we have is each other

I am moving forward with a new perspective, in deeper service of myself, and know that the healing is ongoing. New experiences — like leaving a job that is not serving us, and traveling the world — can catalyze healing. But if there is a magic way to heal, it is with authentic human connections. These connections reveal our whole selves — past, present, and future dream selves — simply, boldly, and realistically.

I don’t know the details of what lies ahead for me — in career, love, or life — but I know that I want human connection to be at the center of it. I want to have a hand in rebuilding our humanity that has been lost through the universal trauma of pandemic isolation, power-hungry governments, and digital-first experiences. One way that I can start doing this is through authentic, vulnerable, and honest story-telling. Sharing what feels most personal almost always reveals what is most universal.

Personally, I’m ready to be free from the bitter elixir of self-doubt and shame, and would rather partake with you in a celebratory cordial that fills us with love, joy, hope, and courage. 🥂

May your life be filled with kisses, gratitude, and contrary

Thank you for being on this leg of my journey with me ❤️

If you read my last article about Bali, you may be disappointed to learn that this piece is not going to be erotica. Or maybe you’re my mother and you’re relieved to learn this. Either way, I want to set clear expectations for what you are reading 😜 (though the erotica is coming! …hmmm, pun intended?)

This is a story about what happens when you stop fighting what is, and let the detour take you for a ride. Sri Lanka had a different plan for me than I had for it, and it was perfect.

My feet are not yet planted back on NYC pavement. I am writing this from my hotel in Sri Lanka, the conclusion of 8 countries and 95 days of solo sabbatical travel. It will not end in a heart-melter, where all my wounds are healed and I ride off in the sunset with Javier Bardem. You probably never expected that story from me anyway. 😜 Let’s get to it.

An Out-of-Sync Arrival

My first day in Sri Lanka was April 14, Sri Lankan New Year’s Day. As with every New Year’s holiday across the globe, Sri Lanka was quiet and closed, which set the tone for my arrival.

My Sri Lanka plan was to spend 10 days in Mirissa, along the south coast, learning how to surf. This was meant to be a moment to face my fears, settle into beach time, pay my final worship to the sun, and make connections with my last group of travel companions.

When I arrived at surf camp, my host was not able to greet me, due to the holiday, so I changed into my swimsuit and went to the beach. The heat was suffocating. At first, I blamed Sri Lanka, then I realized that I’ve been on the road long enough to be part of the changing seasons into summer — “from hot to fucking hot” as I learned they described summer in Thailand. As much as I love the heat, I was unmistakably uncomfortable and potentially on the brink of heat stroke. My air-conditioned hotel room brought solace. Sadly.

That evening, I met a few other travelers at Surf & Yoga, my home for the next 10 days. We helped our chef, Hassid, prepare dinner, two Sri Lankan curries. I learned that the camp is exceptionally quiet right now, due to the war. Usually, they have ~50 guests but they only had ~10 at this time. I was disappointed to learn that everyone that night was scheduled to leave in the next two days.

Facing My Fears 🏄🏻‍♀️

The next morning, bright and early, I had my first surf lesson. This was kinda a big deal, and not in a bragging sense. More in a holy-shit-today-I-might-die sort of way.

As much as I love the ocean, she scares me. And I have a rule: don’t ever not do something just because it scares you. If fear is the only reason I’ve got, that’s my subconscious screaming at me to go fucking do it.

So that’s why surfing.

The possibilities of failure in surfing (in every trivial or absolute sense of that word) are endless: being pummeled by a wave, drowning, or being knocked unconscious by the “washing machine.” Losing a contact lens right before the next wave punches me in the face. Losing two contact lenses. Getting eaten by a shark. Getting eaten by a crocodile. Getting hit in the head with my surf board. Someone else’s surf board hitting me in the head.

And yet — Goddddddesss, I freaking love the ocean. The sun. The waves. The water. The ocean, while a source of paralyzing fear, is somehow also a happy place for me.

My lesson started on-land with instructions for how to “pop up,” then we progressed to the whitewash, the tail end of a wave with just enough momentum to practice standing, without the physics and skill required to catch an unbroken wave.

As my instructor Madu took me deeper, we were getting dangerously close to the scary waves. You know, the ones that were going to kill me. Surfboard in tow, my anxiety peaked. I stopped moving and shouted: “Where are you taking me? I am NOT comfortable!!” (High-five to me for saying that out loud.) Madu deserves heaps of credit for patiently guiding me through the anxiety.

After at least 1001 pop-ups on the whitewash, I was getting a fantastic workout and genuinely enjoying myself.

When your heart and mind are ready, but your body is not

Later that day, I felt an ear infection coming on. Being an avid swimmer, I’m no stranger to this dreaded feeling. But had to ask myself … ‘Is it? Could it be? Why now?’

The next morning the pain was real and my ear was clogged up. I went to the medical clinic to confirm what I already knew, and got some antibiotic ear drops. The number one cure for an ear infection is to keep the ear dry, so that was it. No more surfing until this thing was kicked.

I missed two lessons before becoming enmeshed in a classic case of the blues. I was at the ocean, unable to carry on as planned. It was hotter than the gates of hell and I couldn’t go in the water. The pain was outrageous, to boot. It was clear that this was not an easy or typical run-of-the-mill ear infection.

The tailspin of ‘what is the universe trying to tell me?’ ensued, rattling my head around the way I feared those deadly waves were going to do to me. And yet here I was, doing it to myself.

In Search of Greener Pastures

A few other travelers at the camp mentioned Ella, a town 2 hours north of Mirissa. It was described as “peaceful, but touristy,” with “beautiful views and a few great hikes.” My ears perked at the mention of hikes and after some research I made arrangements to escape to Ella for a couple nights until the ear infection cleared up.

The area around Ella is a hotbed of plantations for tea and spices. In a short detour before arriving in Ella, my driver took me to a spice field, where I was greeted by a lean Sri Lankan man, wearing sandals, sarong, and a warm smile.

“Ayubovan,” he said, looking warmly into my eyes, hands in Namaste. “This is how we say hello in my country. It means ‘may you live long.’” I tried it back and he nodded approvingly, still smiling.

He walked me through his garden of labeled spice beds, explaining each plant's role in Ayurvedic medicine. There was a mix of oils that made a “shaving cream” that removed hair on my legs in within 15 minutes. A plant for arthritis. One for spider veins. He examined my legs and said, without holding back:

“You have cellulite. This will help.”

😳 I hated — and when I say ‘hated’ I mean ‘loved’ - his honesty.

He looked at my face and pointed to the scar above my right eyebrow. “This is from chickenpox?” He had a remedy for that, too.

As we walked around, he asked, “How old do you think I am?”

Cheeky bastard. This is a trap. He looked 63. I guessed 78. He was 81.

“How old am I?,” I asked. Gotta admit, I expected to hear 35-to-37, which I had become accustomed to hearing. He looked me dead in the eyes and without skipping a beat, “You are 49. Maybe 48.”

I wanted to punch him right in the face! 😡 And at the same time was dazzled. 🤩

“How do you know how old I am?,” I asked.

“It’s in your eyes. I see the expression in your eyes,” he said.

I learned his name is Dr. Susa and he is a third-generation Ayurvedic Doctor. He set out to Himalaya on his own to learn everything about Ayurvedic medicine. When he returned home, his knowledge impressed his father, who then agreed to pay for his degree.

He took me to his student (I assume) for a face massage with sandalwood oil, a head massage with red coconut oil, and a leg massage with the magic anti-cellulite potion. I left with a few Ayurvedic oils — for the skin, the hair, and yes, the legs — his WhatsApp number so we could stay in touch, and genuine affection for this lovely, lovely man ❤️

My Sri Lanka

The view of Ella Rock from my hotel balcony hit me like a bear hug from an old friend. And I knew instantly that this was the great purpose of the ear infection — it brought me here.

I hiked Ella Rock and Little Adam's Peak. In between, I sketched, journaled, drank a couple cocktails, and sat in nature. The infinite emerald in every direction filled me with homesickness. Everything reminded me of the Pacific Northwest, more in feeling than in facade. Mountains are so deeply embedded in my body, I swear I feel them before I see them. This is what I mean when I say that mountains have my heart.

Ella Rock was my travel companion. I fell in love with her complex beauty rather quickly. She watched over me from my hotel room balcony. She was the first thing that I saw when I opened my eyes in the morning. She held me at her summit — peaks of Yala National Park to the south, and layered mountains disappearing into a haze to the north. She sat patiently as my muse for an afternoon sketch, baring her ridges and textures for me to trace with my pen and massage with my colored pencils.

Ella didn’t give me the surfing I planned for, but it gave exactly what I needed — solitude with a view, and space to feel what was coming to the surface.

Part Two is coming. It’s got some heaviness that I’m still processing. Stay tuned.

Thanks for being with me. May your day be filled with kisses, gratitude, and contrary 😘🙏

Ubud is Balance

My flight arrived into Denpasar late. I wouldn’t get settled into my room in Ubud until after 2am. I saw Nano’s message when I landed:

I exited customs in a brain fog of travel fatigue, saw the line of drivers, each holding a sign with the name of a weary traveler, and diverted my eyes to the ground, scanning the lineup of shoes.

Adidas shoes … ‘What kind of adidas shoes?,’ I wondered. 'Sandals? Sneakers? What color?’ This was asking a lot of my brain, but the fog lifted when I saw a sparkling-eyed young Balinese man walking toward me with a blinding white grin, hand outstretched, and adidas shoes. “Welcome to Bali!” said Nano.

Nano was my host for the week. On the journey to Ubud, he introduced me to his home with this simple phrase and - I realize in retrospect - advice: “Ubud is balance.”

Ten days from that moment, I would learn that balance is not a graceful stillness, held like a mountain pose, or tree pose. Balance is the stillness of a spinning top, found inside and amongst chaos, when you stop fighting the current and your ride it. Breathless, soaking, and stupidly alive.

My ride through the rapids

I came to Ubud to center my artistic spirit at the Artists in Residence (aka AIR) Ubud, expecting the energy of a lazy river pool, but instead found myself in a ten-day trip down a whitewater river.

The rapids were embodied in the crowds of tourists, flocking to Insta-worthy yoga shalas, plant-based everything, sound baths, crystal healing, and luxury spa days with dirt-cheap price tags.

The rocks of the river were made of the Balinese culture, holding urgently to the river floor — sandalwood incense, frangipani flowers, Hindu temples, warungs, coconut leaf offerings, rice paddy villages, silver- and batik-making, and statues of Hindu gods.

I was reminded of my trip on the Zambezi in Africa, after which I swore I would never touch whitewater again. But since this is only a metaphor and not actual whitewater, let’s continue to ride it…

I became swept up in the first of many rapids on the Ubud river - a realization of gentrification, challenging my authenticity values directly. My way of riding the raft involved a ruthless Ashtanga yoga class (at Radiantly Alive Yoga), a multitude of fresh fruit juice and smoothie bowls, and a near-orgasmic spa day in which I submerged into an underworld hot/cold plunge encased by stone carvings of Hindu-inspired fantasy creatures at the Hotel Tjampuhan Spa.

After the next series of rapids, my coping expanded. I traded moldy clothes packed in NYC two months prior for Bali boho-chic fashion, a pack of Marlboro Lights, and 2am conversations - deep and dirty - with people spanning more than 40 years on either side of me.

Continuing down the river, hitting calmer waters, I was purified in a temple and learned the art of silver-making (at Okta Silver Class, friends of Nano and his mother).

More rapids, and I surrendered to the freedom of wrapping my legs around the passenger seat of a motorbike enveloped in the Bali night air, and a spontaneous snorkeling trip on Nusa Pineda to swim in terrifying circles with a school of manta rays.

And there I was, living Nano’s phrase, Ubud is balance. Several contrasting things can be simultaneously true. Ubud catalyzed this truth that I’ve been too controlled for too long to live out loud.

Just to feeling something

After a couple days, I accepted the whirls of unexpected chaos that Ubud was delivering, but was not prepared for what the universe delivered next.

A woman with a melange of ethnicity and accents and cinnamon curls with honey highlights that resembled Vogue-era Madonna in look as much as attitude. In the physical sense, she was in her late 20s, but in the metaphysical, I’m certain she was reincarnated a dozen lives or more.

She played with spiders — 3-inches in diameter — letting them crawl on her face “just to feel something.” She had a face-off with a manta of a 6-foot-span, as though she owned the ocean instead of the other way around. Her sensuality was uninhibited, and her idea of intellectual foreplay was impossible questions about consciousness and the universe.

Being in her orbit made me aware of my own inhibitions — in my words, my mind, my body. She gave language and appetite to things in me that were dormant or unreachable. At first it was electric. Then it felt like a demon goddess had locked my gaze and demanded I take advantage of this moment before it slips away forever — electricity morphing into terror. The terror that my most voracious, vivacious self is already behind me. That the door is closing on me.

But Ubud looked that demon goddess dead in the eye and called her on her bullshit. The door is not closing. It is wide open. I have many more playful, electric, wild, sensual, demon-slaying stories to live and tell. That is a promise.

What Ubud Unboxed

Over thirty years ago, I declared a part of myself broken and unworthy, and put her in a box. The part of me that is unguarded, unabashedly sexual, and unwilling to ask permission or offer explanation.

I didn’t throw her away but I separated her from the rest of me, convinced that her proximity to the “good” parts - the tenacity, the empathy, the humor, the strength, the ambition - would contaminate them. That she was the thing most likely to undo me.

So I kept her contained in that box. And when I did let her out, it was never freely. It was strategically - for control, for attention, for survival. Weaponized, not integrated. Useful, but not whole.

Ubud unboxed her. Not with a single dramatic moment I can point to and package neatly for you. With ten days of accumulated electricity: a tending to my body with wellness regimens, a woman who showed me that spiders can crawl on your face without killing you, night air on a motorbike, uncensored communication, and an inspiration for erotic writing - sparked by a woman beside me and a man a thousand miles away - that consumed an embarrassing amount of brain space. ALL of Ubud was showing me the way I’m supposed to be. ALL parts of me coexisting, refusing to stay in separate boxes.

I am not two different people. All of it belongs in the same body, in a messy entanglement. Separating them was not protecting me. It was self-abandonment dressed up as self-control.

Well, that was scary

Excuse me while I take a couple deep breaths…

Articulating this has been terror-filled. Hitting the ‘publish’ button will be another whitewater rapid to run, with the help of these promises to myself:

• I will not conform to a story of who I’m supposed to be at this point in my life.

• I will not apologize for my appetite - sexual, material, fantastical, or otherwise.

• I will not let fear or past trauma censor my thoughts, words, or actions.

The door is open. I will walk through it with all of the tenacity, humor, and strength I’ve always had, but going forward I will be wearing boho-chic and a playful smile, carrying a chronicle of feminist erotica. I can leave the cigarettes, helmet-free motorbike rides, spiders, and 6-foot mantas in Bali.

May your day be filled with kisses, gratitude, and contrary 😘🙏

My travel bucket list is long. A snorkeling and island-hopping expedition in the Philippines was not on it, so how did this destination manifest for my sabbatical?

I’d landed on Southeast Asia as my primary region and had a few anchors locked in. Everything else was open water, filled in through recommendations from friends and free dives across the internet. Palawan, Philippines rose to the surface through a search I was running on must-see destinations for nature lovers, cross-referenced with my indulgent sabbatical goal of turquoise waters, velvet-soft sandy beaches, and sun-drenched skin. (I paid my dues living in the PNW for 25 years. The sun and I have some catching up to do ☀️)

My travel consultant, Claude (yes, that one), helped me connect those dots. What followed precisely matched what I was looking for, so I booked the trip.

The Philippines is an archipelago of over 7,000 islands, so island hopping isn’t a travel style so much as a geographic requirement. A snorkeling expedition here is the country-tour equivalent of a camper van in New Zealand - it’s just how you see the place.

I should be upfront: I am not a snorkeler. The last two times I attempted it - once at the Great Barrier Reef, once in Key West - I experienced a memorable combination of sea creature fright and sea sickness that culminated, at one point, in purging into my snorkeling mask. It’s not an activity I’ve chased since. What drew me here was the picture-perfect sea-and-sand dreams. The snorkeling was secondary, but clearly also an opportunity to finally do it right as the Philippines makes the cut as a top snorkeling destination in the world.

I booked a 6-day/5-night expedition with Tao Philippines, who consistently ranked among the best tour operators for solo travelers in my searches, from El Nido to Coron. We traversed the miles of exactly the turquoise water I’d been seeking. I never had my fill of it. I never will.

Here’s what I found between the open sea and the bamboo beach huts (aka “tukas,” a name coined by Tao Philippines’ eco-architecture).

When Mother Nature tells you to slow down, do as you’re told

Watching fish is a surprisingly effective meditation. One of the first creatures that caught my attention was a turtle, who I felt compelled to stalk to see what it was up to, where it was going, who it was meeting. At first, I found fish boring - they seemed to swim along with nothing to do - but I liked looking at them, nonetheless. I fell madly in love with the colorful Parrotfish, who I nicknamed Drag Fish because they reminded me of drag queens, boastfully swimming amongst their peers, knowing full well that they were the most fabulous of them all🫰

I found myself studying different species’ behaviors, patterns, and interactions. Since I didn’t know anything about their actual species names, I made up names and stories for them. There was the Witch Fish (solid black ‘angelfish’ with a subtle and ominous burgundy iridescence that swam in small groups, like witches doing research for a spell they are brewing), the Aztec Slider (white fish with an aztec-like pattern who slithered on the ocean floor, slurping up food along the way), the Zombie Fish (ugly, disfigured grey things that swam so slow they seems as though they were going to just tip over … 🤔 come to think of it, that may have actually been a dying fish).

I found personalities and patterns in each - the anemone fish (aka “clownfish” like “Nemo”) form little families, seeming to always have two adults protectively circling a patch of hairy white coral, from where the babies pop themselves out every so often to say ‘Hi.’ I hovered above a school of thousands of herrings swimming in precise inexplicable synchronicity, morphing into branches and changing formation like a kaleidoscope.

I didn’t have a proper underwater camera, and the one time I tried to take photos with my phone in a dry bag I was flustered and distracted. In fact, this entire trip was a digital detox. We didn’t have wifi or cell signal until the second to last day of the trip.

When we slow down and allow nature to consume our senses, the thoughts, visions, and ideas that follow fill us with a thick, syrupy sweetness. The kind you don't want to rush.

The mission-first business model proves sustainable again

Tao Philippines turns 20 this year. It’s the second organization I’ve encountered on this sabbatical (Elephant Nature Park (ENP) was the first) that is shaping a Contrary Cortney business philosophy: the idea that leading with mission, community, and integrity doesn't compete with profitability, it drives it. The parallels are striking enough to be a curriculum:

Both are 20+ years old with consistent growth. Both were devastated by typhoons (Tao in 2013, ENP in 2024) and rebuilt stronger, thanks to the help of the community, from which they already had strong foundations prior to the disasters. Both center women’s empowerment and local knowledge. Both treat tourism as a vehicle for education for workers, community, and travelers alike. Tao’s stated philosophy: “The future is community.” 🥰

One notable difference: at ENP, Lek and Darrick (the owners) are everywhere. You feel their presence even when they’re not in the room. At Tao, I only learned who the founders were through a commemorative magazine. Mission embedded, not embodied. A different model, not a lesser one.

One thing I’d push Tao on: women are described as being “in charge,” but they’re largely operating behind the scenes. The stories of Tao’s women deserve to be told as loudly as the men’s, not just for equity’s sake, but as an active investment in the next generation of women watching.

The universe is a better matchmaker than we are

One of the things that I am starting to love about solo travel is the journey from “stranger” to “travel companion” with the people who materialize around each experience.

Our group represented 10 countries: expats living across Asia, kids ages 9–14, couples and families, and a handful of us pushing the average age up from the back. I was the only American and one of just three solo travelers. Fair warning for solo travelers considering Tao: the reviews skew heavily solo-friendly, but my group didn't reflect that. It didn't diminish the experience - the connections I made were real - but if your energy recharges around other solo travelers, go in with open eyes.

I almost always skip political conversation, but it was hard this time, given Trump’s current war. The world is genuinely confused and concerned by Trump’s reckless actions against democracy and humanity, and, as an American, I feel a sense of guilt for not being able to provide answers or claim enough ownership on behalf of my country. In the Philippines, this feeling sank deeper. The tuk-tuk and taxi drivers weren’t shy about the 2–3x jump in gas prices since the war began, costs that are meaningfully cutting into whether they can feed their families. The weight of that conversation stays with me.

Another thread that has been surfacing, unprompted, in my travels is a Western envy of simplicity. I felt it deeply in Cambodia, it was a topic in Vietnam, and it surfaced again in the Philippines. The SE Asian pace of life is viscerally appealing, but most of us don’t have the cultural tools to actually inhabit it. So we absorb what we can and carry it home like a puzzle with several pieces lost or left behind.

The ocean is a healer. I’ve heard that the minerals in the water, combined with the sun, are restorative to our immunity, vitality, and mental health. I don’t need to know all of the science, I felt it.

If you want to check out all of my pics from this trip, go to my Google Photo Album here.

Signing off with kisses, gratitude, and a little contrary! 😘🙏

I am approaching the halfway point of my one-year sabbatical. When I left my corporate job, my goal was simple: heal from toxic thought patterns and see what I would naturally gravitate toward without work pressures hanging over my head. I was excited to live without boundaries, which included a plan to travel for an extended period of time. I wanted to visit the places I’d always wanted to go without consulting anyone else’s agenda, and to do it without time restrictions.

I’m now in my tenth week on the road. I’ve been to Seattle, Palm Springs, Costa Rica, Singapore, Cambodia, Vietnam, Thailand, and am writing this from the Philippines. This is the longest I’ve ever traveled, and the first time I’ve traveled solo internationally for non-work reasons.

I love to travel (but I also enjoy cozy nights at home), and I am no stranger to self-discovery (it is my nature to be in a constant mode of self-reflection) - but when I was planning this trip, and even after I started, I genuinely wasn’t sure how much I would like extended solo travel. I thought: Would I be frustrated by all of the time in airports? How long before I would itch for the comforts of home? What could I really learn about myself in travel that I could not learn while living in the great city of New York? Am I going to feel isolated and lonely? And if I do, how will I handle it?

Those turned out to be the right questions. Here’s what I found.

You will be “solo” but you will not be alone.

This is both a practical tip and a philosophy.

From a safety standpoint, someone should always know your itinerary, especially when you’re moving frequently across countries. But the deeper gift of telling everyone is what it unlocks socially. Because I talked openly about my sabbatical - on LinkedIn, on Instagram, on Substack, in every conversation - I ended up with a trusted driver in Siem Reap who became a memorable part of Cambodia. I reconnected with a friend in Singapore I hadn’t spoken to in 26 years. Friends offered their family in Thailand and Sri Lanka as emergency contacts in case I needed one.

None of that happens if you quietly disappear into your itinerary. Solo travel is not actually solitary. I am socially alive because I show up to every interaction without distraction, without a companion to default to. That changes everything.

You will follow your own curiosity - not a partner’s and not a stranger’s.

Trip Advisor, Viator, Get Your Guide - these are useful tools, but the richest experiences of this trip happened when I was guided by my likes and curiosities instead of the highest rated tours on travel websites. When I wandered without agenda. When I talked to local people who weren’t in the tourism service industry.

The thing to do in any given place is almost never the thing you will remember most.

You also need to throw FOMO out completely. On a trip this long, you cannot sustain the pressure to experience everything, everywhere. I embraced days of relaxing and reading in an air-conditioned hotel room when my body asked for rest. That’s not wasted travel. That’s the whole point of taking a holiday.

You will find your people.

Before this trip, I’d absorbed a lot of ambient noise about solo female travel - the implied danger, the “don’t go out after dark alone,” the “just be careful.” I want to report back plainly: I have not felt unsafe or disrespected once across multiple countries. In fact, I’ve joked that I’m more unsafe in Brooklyn (where I live) than in any of the areas that I’ve traveled to!

I found a global community of women moving through the world independently and with extraordinary self-possession. They are everywhere. And they are not a “type.”

The solo female travelers I’ve met on this trip so far range from 19 to 66 years old. Married and unmarried. Seasoned travelers and first-timers. From ten different countries. Almost universally, they are at a crossroads: a career transition, a relationship change, a nagging question they haven’t answered yet, a version of themselves they’re becoming. And although they travel alone, they are not seeking isolation. They joyfully and vulnerably connect. We find each other on group tours, sitting next to each other at coffee shops and bars, or admiring the same local sight - and the conversation ignites immediately.

Sisters, let me tell you - the electricity is real, and it will find you. There is a global sisterhood of women mid-becoming - sometimes quiet, sometimes spectacularly not - and solo travel drops you right into the middle of it.

You will receive a gift from the hard days.

The hardest days of this trip have also been its most instructive. The day I woke up with a sore throat and rode in the support van instead of on my bike so that my body could rest. The day the words wouldn’t come when I tried to write. The day my elephant drawing looked like a scary sea creature. The day I sat with something grief-shaped and leaned into it with full body sobs. The day I was critical of a new city - finding fault with everything, mostly because I was grieving the last place - and curiously wandered anyway until I found myself falling in love with something about it.

I’ve stopped fighting any discomfort. It’s just part of the process.

Without your usual comforts of home to fall back on, you need to find new coping mechanisms to move through the hard days. That’s where resilience is built. And oddly, it’s also where curiosity grows. Discomfort becomes an unexpected driver of adventure.

You will see yourself crystal clearly.

The greatest gift of this trip hasn’t been any single destination. It is having uninterrupted time and space to listen to my own thoughts, without pressure to draw a conclusion or act on anything. I can hear what is poking at me, and am undistracted enough to recognize repeating thoughts. My real values. Where I’m genuinely willing to compromise. What makes me curious versus what I think should make me curious.

Solo travel didn’t create anything in me that wasn’t already there. It just held up a mirror long enough for me to actually look.

I have one month of planned travel left, and I’m intentionally going to be more stationary than everything that came before.

First, I’ll be staying in Ubud, Bali, Indonesia, at an artist’s residency to connect with my creative energy, experience the mecca of spiritual wellness and healing, do daily yoga, meet other artists, and go deep with creative curiosity I’ve been carrying.

Finally, I will end in Mirissa, Sri Lanka, where I’m taking surf lessons for ten days (BTW, I do not know how to surf!), continuing daily yoga, exploring Ayurvedic healing, and seeing elephants in the wild - which will be a rewarding moment after volunteering with them in Thailand.

It feels exactly right to end where I began - with a spiritual slap in the face and a reawakening of my physical strength.

If you’ve been thinking about solo travel - even a short trip, even somewhere familiar - stop thinking and start planning. You will surprise yourself with what you find looking back at you.

Thank you for reading. I hope you find your contrary 🙏