I’ve been doing this for two decades now. Building things, mostly alone. A few successes, more failures than I’d like to count, one exit that actually worked, and a lot of years in between that never made it into any story I’ve told publicly.
People ask me sometimes what it’s like, being a solo entrepreneur for this long. I never quite know how to answer honestly in the time a normal conversation allows. So here’s the longer version — the one I don’t usually give.
The romance wears off faster than you think
There’s a version of solo entrepreneurship that gets sold to people — the founder as lone genius, building something extraordinary through sheer will, answerable to no one. I believed some version of that myself, twenty years ago. It’s mostly fiction.
The reality is quieter and considerably less glamorous. It’s a Tuesday afternoon with a bug you can’t find, no one to pair with, no one to even explain the problem to so it becomes clearer in the telling. It’s making the same decision five different ways in your head because there’s no one in the room to disagree with you and force you to defend it properly. The romance of “no boss, no rules” wears off somewhere around month three, once you realise the freedom you wanted also means there’s no safety net, no second opinion, and no one coming to save the thing if you get it wrong.
What you gain that nobody tells you about
But here’s what the critics of solo building rarely say, because it’s harder to package into a warning: the clarity you develop is unlike anything a team environment produces.
When there’s no one else, every decision is genuinely yours. Not “yours after consensus,” not “yours after the meeting where five people diluted it into something safer.” Yours. That forces a kind of decisiveness that teams, for all their strengths, structurally resist. Committees don’t ship bold things. Individuals with conviction sometimes do. I’ve built things solo that would have died in a meeting room if I’d needed anyone else’s buy-in first.
You also develop a strange, hard-won fluency across disciplines you’d never naturally choose to learn. I’ve written code I had no business understanding, negotiated contracts I had no formal training for, learned enough marketing, enough finance, enough operations to hold an entire business together with duct tape and stubbornness. None of it was efficient. All of it made me considerably more capable than I would have become inside a team that let me stay comfortably specialised.
The cost that never fully goes away
I won’t dress up the cost. Building alone for this long has genuinely cost me things I can’t get back — evenings, weekends, the easy presence of mind that comes from not carrying an entire business in your head at all times. There’s a specific kind of exhaustion that comes from being simultaneously the founder, the strategist, the person who fixes the printer, and the person who has to find the energy to be optimistic in front of everyone else even when you don’t feel it yourself.
Depression and anxiety have both visited me more than once across these two decades, and solo building has a way of making both worse, because there’s no one to notice you’re struggling before it becomes serious. In a team, someone eventually says “you don’t seem right.” Alone, you can go a genuinely long time before anyone — including yourself — properly clocks it.
I’ve had weeks that nearly broke me. Not metaphorically. Actually close to the edge of what I could carry. I’ve learned, slowly and imperfectly, to recognise those weeks earlier than I used to. That recognition is itself a hard-earned skill nobody teaches you in advance. You learn it by going through the weeks that hurt.
What building with a team actually gives you that solo never will
I’ve worked with teams too, at different points across these twenty years, and I want to be honest about what that gave me that solo work structurally cannot.
Teams catch things you miss. Not occasionally — constantly, in ways you don’t notice until you’re back to working alone and the mistakes that would have been caught start slipping through instead. A good team member disagrees with you at exactly the right moment, and that disagreement, uncomfortable as it feels in the moment, has saved me from decisions I’d have deeply regretted.
Teams also share the emotional weight in a way solo work simply cannot replicate. A bad week, inside a team, gets absorbed by more than one person. A good week gets genuinely celebrated by people who understand exactly what it took to get there, rather than experienced alone at a desk with no one to tell. I’ve had wins, working solo, that I couldn’t properly celebrate because there was no one in the room who understood what the win actually meant. That’s a specific kind of loneliness that doesn’t get discussed enough.
And teams create momentum that a single person, however driven, cannot generate alone. Multiple people moving in the same direction at once cover more ground than one person working twice as hard. I’ve felt the difference directly, moving between solo periods and team periods across different ventures. Solo is slower. It’s not close.
Selling something you built alone is its own strange grief
I’ve sold a business before — one I built essentially by myself, over years, through the same pattern of solitary decision-making and long, quiet stretches of uncertain progress. People expect the exit to feel purely triumphant. It doesn’t, not entirely.
There’s a genuine grief in handing over something you built with your own hands, alone, to people who will now make decisions about it that you have no say in. Nobody warns you about that part. The money is real and the relief is real, but so is the strange, disorienting sense of loss that comes from watching something that used to be entirely yours become something you no longer fully recognise.
Why I keep choosing this, over and over
After two decades, I could give you a long list of reasons solo entrepreneurship is a genuinely difficult way to build things. I could also tell you why, knowing everything I know now, I’d probably still choose it again.
There’s something about carrying full responsibility for an idea — the successes and the failures both landing entirely on you — that produces a kind of ownership I’ve never quite felt any other way. When it works, it’s the most satisfying thing I know. When it doesn’t, the failure is unambiguously mine to learn from, without the diffusion of blame that teams sometimes allow. That clarity, painful as it can be, has made me better at this with every attempt.
I’m building ShopWithMore the same way I’ve built most things across these twenty years — largely alone, around a full-time job, with all the exhaustion and clarity that combination reliably produces. I don’t know yet how this one ends. But I know, after two decades of doing this, that the version of me who keeps choosing to build things alone has learned something real each time, even in the attempts that didn’t work.
If you’re building something alone right now, and it’s costing you more than you expected it to: I see you. It doesn’t mean you’re doing it wrong. It might just mean you’re doing the actual, unglamorous work that building something real always requires.