The Goalpost
13 Oct 2026
“The hardest financial skill is getting the goalpost to stop moving.”
— Morgan Housel, The Psychology of Money
One idea from Morgan Housel’s The Psychology of Money, one of the best books I have ever read, has stayed with me: knowing when you have enough.
I know that being able to ask “what is enough?” comes from a place of privilege. But even with those advantages, why is the instinct to keep accumulating so hard to question?
Part of the answer, I think, is that we may already have enough without knowing it. We’re playing by rules we never chose, absorbed from the world around us, the ones that say more is always better, without stopping to ask what we actually want (stuff they don’t teach you in school!).
The other part is fear. If we step off the treadmill, what will we do with ourselves? Who are we if we’re not chasing the next thing? When we meet someone new, the first question is usually “what do you do?”, not “who are you?” No wonder stepping off feels so frightening: for many of us, what we do has become who we are. It’s an uncomfortable question to sit with, and it’s easier to keep running.
When I first read Housel’s words, something struck a chord. I realised I’d been guided by some version of this idea all along, just without the language for it.
I spent years in tech, where growth was the default answer to every question, and it sidetracked me. I ran my SaaS business from 2007 to 2024 (sunsetted it and will write about why in another piece). I never wanted it to become a VC-backed unicorn; I wanted it to stay bootstrapped, profitable and small. And it did! And yet something kept bothering me, week after week, for all those years. Deep down I knew what enough growth looked like, and that I should enjoy it. But my mind wanted infinite growth, and nothing I did was ever enough. The goalpost kept moving, even though I was the one who’d set it. Looking back, I wish I’d had the awareness to stay true to what I wanted, rather than what I was expected to want.
As I’ve become clearer about what’s enough, I feel less pressure to perform for society’s sake (still a work in progress). As I grow older, my physical and mental health matter more to me than chasing growth for its own sake.
I’m approaching 50 in the next few years, and I’ve started to picture a simpler future. For me, that means rethinking what true ownership looks like. For example, leaving possessions for your heirs might feel like a gift, but will it give them more freedom or just more to deal with?
Enough doesn’t mean nothing. I still want to own things, still want to build software and still want my investments to grow. But I want ownership that offers freedom rather than friction. The goal isn’t to stop building. It’s to know what I’m building for and to discover what contentment means to me.
One question I now ask regularly is what I can remove that no longer makes sense: from material things to commitments.
I haven’t got it all figured out. But I’m clearer about what I want, and about what I no longer want to carry.
If you’ve ever quietly wondered whether you already have enough, that’s not complacency or a lack of ambition. It might be the most honest question you can ask yourself. ✨
Distill, simplify, repeat.