How Did I End Up Here Again?

I quit Google because I wanted to work for myself.

Two years into my own startup, I was sitting in a hostel in Spain at 3am, slightly drunk, writing code because a customer deadline was looming. My friend was asleep across the room.

I had earned the freedom to work from anywhere, and I was using it on something that felt suspiciously like the thing I’d left.

How had I ended up here again?

Maybe you know the feeling: the same arguments keep turning up in different relationships, and the same restlessness arrives in a new city. You quit smoking and started doomscrolling. Then you quit doomscrolling and went back to smoking.

An alien watching us from a distance might reasonably wonder if we have any idea we’re doing this.

Sometimes, barely.

But even when things go well, a similar pattern appears. We find work we love, pour ourselves into it, and eventually drift toward something else. We finish a project we’re proud of and wake up the next morning wondering what to do now.

We keep returning to questions we thought we’d answered.

What do I want? What matters to me? What comes next?

The four phases

I call this the Life Loop:

The Search → The Calling → The Work → The Conclusion → The Search…

The Search is the stretch where we don’t know what comes next. We look around and try things, with varying patience for everyone asking what our plan is.

Eventually, something catches our attention: a person, an idea, a way of life we want to explore. That’s the Calling, the moment a possibility starts to feel worth moving toward.

So we move toward it, and we encounter the Work.

The business needs customers. Learning the instrument requires practice. The relationship involves another person who, inconveniently, has their own ideas about how the relationship should go.

Now whatever we imagined has to come up against reality.

At some point, a chapter reaches some kind of Conclusion. We finish something, leave it, lose it, or outgrow it. Sometimes we get exactly what we wanted, but then there’s an outcome to handle and an experience to make sense of. What do we understand now? What do we want to carry forward?

Then another Search begins.

These movements overlap. You can be committed to your career while completely unsure about your relationship. Sometimes a new possibility appears while you’re still figuring out how to leave the last one.

A loop or a spiral?

Navigating this process depends a lot on noticing what’s happening while we’re still inside it.

That’s considerably harder than recognizing it afterward.

Looking back, things can seem obvious: of course you needed to leave, and of course that conversation mattered.

Living through it, you’re mostly trying to figure out what to do on Tuesday.

And when you find yourself searching again, it’s easy to think:

I thought I was past this.

But are you really in exactly the same place?

Maybe you spot something sooner. You’re willing to admit something you couldn’t admit last time. You have a better understanding of what you want, even if you still don’t know how to find it.

That’s where the image of a spiral makes sense to me. We return to familiar questions from a different vantage point.

Going around again doesn’t mean we’ve learned anything.

We can leave a demanding job and recreate it somewhere else because we still need to feel indispensable. We can chase another achievement, hoping that this one will finally let us feel successful enough to relax.

Experience gives us material to learn from, but whether we learn from it requires some attention.

That’s what I mean by moving through the loop consciously.

Going through it consciously

When something draws our interest, can we notice what we expect it to provide? Maybe we want to build a business. Maybe we also need it to prove that quitting our job was the right decision. Walking away then feels like admitting we should never have tried.

Once we’re deep in the Work, it’s useful to ask now and then whether we still care about what we’re working toward.

After that night in Spain, I stayed at my startup for another six months.

In hindsight, the work was clearly no longer aligned with the life I wanted. But there was always another feature to build, another obligation waiting. I kept asking what needed doing next and hardly considered whether I wanted to keep doing it.

Continuing to do what you’re already doing is remarkably easy.

When something ends, we get a chance to look at what happened. What did we enjoy? What did we keep tolerating? What would we do differently?

From reflection to action

I’m building Hazel to help people make sense of these moments while they’re happening and figure out what to do next. She’s an AI you can talk to about your life.

If six months ago you wanted to leave your job, and today you’re considering one with many of the same demands, that history seems worth talking about. Maybe your priorities have changed. Maybe you’re about to recreate something you were relieved to leave.

Hazel can bring what you’ve shared before into that conversation, including what you hoped would change and what actually happened when you tried.

But the conversation has to lead somewhere beyond itself.

Reflection without action is useless.

You can spend weeks discussing whether you’d enjoy making music again. Playing with other people for an evening gives you something new to reflect on.

Hazel can help you locate a local event or meetup to try, then talk through how it went.

The goal is to shorten the feedback loop: try something in the world, talk through what happened, and use what you learn to decide what comes next.

And when you find yourself searching again, it helps to remember more than the fact that you’ve been here before. Maybe last time you took the first opportunity because you were tired of looking. Maybe something you tried mattered more than you expected.

Next time I find myself wondering how I ended up here again, I’d like to ask another question:

What do I know this time that I didn’t know before?