The other day, I was in the middle of building a new feature for my padel app (it’s coming out soon 👀) when I told Claude Code to pause.
Nothing was broken. No crash, no big bug. I just looked at what I was building and thought: wait... why am I building this?
Heads up: I’m going to talk about my app for a bit. Hang on with me, even if you don’t care about apps or code. There’s a point here that’s relevant to everyone 😬.
How it started
Quick context. I built this app for myself, to log my padel games and see the stats. My friends were just names in a list on my phone. I logged things for them “offline”, then invited a few of them to try it and give me feedback.
It worked, so I wanted more. People should be able to connect with each other, invite players, make it social. So I kept building, one feature after the other, always on top of what was already there. Each step made sense. Each one answered something I was seeing or something I needed next.
Then I started testing and realized there were way too many use cases. I was creating complex features to cover every possible scenario, and building things just to fix problems that should not have been there in the first place.
It was becoming a bloody mess.
1 degree off
When I stopped and looked back, I saw that the feature in front of me was just the consequence of 10 prior decisions. And every one of them had been made from the same starting point: me, alone, logging games for my friends on my phone.
But the app was not that anymore. It was supposed to be something other people use.
It’s like a plane that is off course by only 1 degree. You don’t notice it at any step of the way. But over a long flight, you end up way off course.
No single decision was wrong. That’s what makes it so hard to see.
Going backwards feels bad
So I did the thing I didn’t want to do. I went back to a whiteboard and wrote down what I actually wanted for the app: what I wanted people to experience, what the core features were. Then I looked at where I was, and where I was heading. They didn’t match anymore.
That meant getting rid of a lot. About a week of work: thinking, design, coding, testing. Gone. And rebuilding from the main goals, not from where I was at the previous iteration.
It did not feel good. I was resistant. I wanted to keep moving forward, and this felt like going backwards. A week of productive work, thrown away.
Talking it through with Claude helped me a lot. It helped me see that it was the right thing to do, even if it didn’t feel like it. That’s the value of bouncing ideas with someone when we’re too close to see clearly.
I knew it was necessary in the long run.
Life works the same way
I think we do this our entire life. We take small steps, each one based on the previous one.
Take school and a first job. Most of the time, getting a job in the industry we studied is totally fine. But sometimes it just isn’t. Maybe we picked that path because of gentle nudges from family. Nobody forced us, but the message was constant. After a few years of studying, we feel it’s not for us, but we keep going. We don’t want to give up. We don’t want to disappoint people. We don’t want all those years to have been a waste.
So we get the job, in that field, because what was the point of all that studying otherwise? And from there, every next step is the logical one.
Years later, we have the money, the house, the car... and a life very far from what we imagined at the start.
It’s the same with relationships. Some people wake up one day, after decades, with a family and everything, wondering how the hell they got there.
We all have dreams when we’re young. Then come the big decisions: school, work, where to live, who to spend our time with. And they compound on each other. The longer we wait, the more trapped we get. (I wrote about this in Don’t build yourself a prison.)
This isn’t only my theory. Bronnie Ware, a palliative nurse, wrote about the regrets she heard most from people at the end of their lives. The one at the top of the list: wishing they had lived a life true to themselves, not the one others expected of them. That’s the 1 degree off course, seen from the end.
My wake-up call
I’ve lived this myself. For me, it took a punch in the face. Losing a child, and the move to Miami that followed (I’ve shared that story before, here).
That was when I looked at my life and saw that most of my decisions (not all) came from the conditioning I received as a child. I was following the path laid out for me.
When my wife Rosie and I graduated, she actually tried to get me off that path. She suggested we go traveling while we were still young, before getting a job.
But I was too sensitive to it (or call it conditioned). I said no, I need a job right after graduation, otherwise I won’t be relevant on the job market.
I had a chance to escape the traditional path early on, and I didn’t take it. I didn’t understand how important it was.
It took years to see where all those small steps had led me. Each one made sense. Together, they took me far from where I wanted to be.
Once I saw how far off I was, I had a choice. Carry on, because breaking everything would cost too much, disappoint people, waste years of studying and work. Or say “fuck all of it” and start fresh.
I’m glad I chose the second one.
It happened in two steps. First, moving to Miami while keeping some professional stability. Then, later, throwing the rest away and going traveling with my wife while working on personal projects. Starting fresh didn’t mean burning everything at once.
Fix or restart?
So how do we know when something needs a fix, and when it needs a restart?
It’s not black and white, but usually, we feel it. Our gut knows when it’s time to scrap things. I don’t think the problem is knowing. The problem is taking action and actually doing it. And that’s because of fear: fear of failing, fear of what people will say, fear of wasting everything we’ve already put in.
When I work with people on this, my approach is to look at the past and the future:
For the past, I go back to why things are the way they are. Are they the result of conscious, thoughtful decisions? Or did they just sort of happen, “because”?
For the future, there’s one question that usually shakes people up: if nothing changes, and you die in X years... would you be ok with the way you lived? Or would you regret not changing things?
So I’ll leave you with that. Where in your life are you still building on top of the last decision, instead of on top of why you started?
J