After Everything, What Comes Next

Introduction

After everything, what comes next?

I’ve been asking myself that question a lot lately. Not in the hopeful, “what adventure awaits?” kind of way, but in the “who am I without all of this?” way.

I’m documenting this year to have a record. For myself. For the people who’ve supported me. For anyone curious about what happens when you choose the contrary path. This is my sabbatical year: travel, creative pursuits, and potentially moving from corporate-ladder-climber to independent consultant. But first, I need to figure out who I am when I’m not performing.

For the past three years, I poured myself into Spring Health. I told myself it was different this time - that I’d finally found the place where I could grow, lead, and make an impact. And in many ways, I did. I launched a flagship product with 87% customer satisfaction and 70% adoption. I built systems, led teams, drove revenue. On paper, it looked like success.

But behind the scenes, I was struggling. I worked harder than I ever had, constantly trying to prove I was enough - smart enough, strategic enough, leadership material. I bought into hustle porn. I thought if I just worked a little harder, delivered a little more, eventually I’d be seen. Eventually, I’d get the VP title I’d been chasing my entire career.

It never came.

Instead, I got the same feedback I’ve gotten everywhere: “You’re doing great work, but...” The “but” changes - sometimes it’s about executive presence, sometimes it’s about being too tactical, sometimes it’s vague enough that I can’t even name it. But the result is always the same. I stay stuck.

Spring Health was supposed to be different. I had a mentor, I had visibility, I had wins. But when I asked what it would take to get promoted, the goalposts moved. When I raised concerns about burnout and unsustainable workloads, I was told I needed to manage my time better. When I pointed out systemic issues - shifting KPIs, excessive process, lack of investment in learning - I was met with silence or dismissal.

So I left. No backup plan. No next role lined up. Just the clarity that I couldn’t keep doing this.

Here’s what I know: this pattern isn’t about any of the ten companies I’ve worked for. It’s about me.

I’m an Enneagram 8, which means I’m wired to challenge authority and push back against constraints. That’s served me well in some ways - I’m direct, I get things done, I don’t shy away from hard conversations. But it’s also made me a poor fit for corporate environments that value conformity over candor. I’ve spent my entire career trying to retrofit myself into spaces that were never designed for people like me.

And underneath all of it? A desperate need for approval. I’ve been chasing external validation my whole life - titles, recognition, praise from authority figures I’ve elevated to parental status. Therapy helped me see it, but seeing it and breaking the pattern are two different things.

I will be 50 this year. I don’t have a partner. I don’t have kids. I’m not following the script. And I want to claim my space, my contary-ness. What if I stopped vying for external validation? What if I built something that actually fits who I am instead of contorting myself to fit someone else’s vision of success?

My mom gave me the nickname “Contrary Cortney” when I was little, probably after the hundredth time I insisted on doing things my own way. A few years ago, I started making cocktails as a creative outlet, and the name felt right. It was playful, personal, mine. I didn’t need anyone’s permission to create it. I get the same feeling of flow when I move - especially in nature, when I draw or doodle, when I paint, when I write, and when I have meaningful one-on-one conversations.

I have some threads to follow - consulting work, creative projects - but I’m not forcing a plan. I’m taking this year to travel, to create, to figure out what I actually want instead of what I think I’m supposed to want.

I’m between chapters. The old story - work harder, prove yourself, wait for someone to recognize you - isn’t working for me anymore. The new story? I don’t know yet. But I’m done waiting for permission or “the right time” to write it.

I don’t know what’s next, but I know what I don’t want anymore.

Who Cares

I will be open and honest and vulnerable here because I believe it can still be safe to do that in this scary online web of endless entanglements. I trust that technology can be a conduit for connecting humanity, not just destroying it. If my stories resonate with you - either because you are living them directly, or because the experiences and feelings I share remind you of something you feel similarly about in your life - then you belong here. Welcome 🙏

This is me, doing my best Sara Blakely impression ;-)