Starting Over Isn’t a Response to Failure. It is a Response to Letting Go.

On sunk costs, sabbaticals, and the thing scarier than starting over.

created on MidJourney by @pixiemedley

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. 😘