No. #03: Staying or Leaving: How Do You Weigh a Decision That Has No Clear Right Answer?

A few months ago the company I'd always assumed would be part of my future started shifting in ways I couldn't control. I work at a family business (have done for years). And like a lot of people who grow up around one, I never really chose it. It just gradually became the path. The unspoken assumption. The thing that was always going to be there.

Until it wasn't… Not in the way I'd imagined anyway.

Without going into details: the ownership structure changed. The future I'd assumed was mine started looking different. And suddenly I was facing a decision I'd never had to face before.

Do I stay and help build something new from what remains, take my stake in it, push through? Or do I leave and walk away from the familiar path entirely and finally figure out what I actually want?

That's where I am right now. And if I'm honest it's one of the hardest places I've ever had to sit. Not because the answer is complicated exactly. Deep down I know which way my gut leans, I’ve known it for a while now. But knowing where you lean and actually being able to go there are two completely different things.

The thing nobody tells you about a real crossroads

Both paths come with a version of regret attached.

If I stay, I might spend years inside something that doesn't fit. Going through the motions of a life that was chosen for me rather than by me. Always wondering what would have happened if I'd been brave enough to find out.

And if I leave I might walk away from something real and rare, something most people would take without hesitation. And end up somewhere that disappoints me just as much except now I have less security, less ownership, and no one to blame but myself.

There's no clean choice here. Just two different kinds of loss. And at some point I realized that the decision isn't about finding the right answer. It's maybe about choosing which regret you can live with. I've been sitting with that for a while.

The two doubts I keep coming back to

When I try to move toward leaving I hit the same two walls every time:

The first is what I call the dream job question.

Is what I'm looking for even real? Or is it one of those things that sounds beautiful in theory but falls apart the moment you're actually inside it? What if dissatisfaction is just what work feels like after a while. Regardless of the job, regardless of the choice you make, what if some people simply aren't built for dream jobs? Not because they're settling, but because they're honest about what work actually is?

But I've experienced recently (unexpectedly) what it feels like to do something that doesn't feel like work. Where hours pass without noticing, where Sunday mornings don't feel wasted. Where you're tired at the end of it but it's a different kind of tired - the kind that feels earned rather than drained. That's not proof of anything. But it's a data point I didn't have before. And it still needs to stand the test of time.

The second doubt is the regret question.

What if I leave and five or ten years from now I look back and realize I made a mistake? What if I walk away from something real, something with genuine upside, something my family built, and end up in another job I don't like, working for someone else's vision, with nothing to show for it but a salary?

I went down a Reddit rabbit hole recently. Reading posts from people who had left family businesses. The comments were overwhelming to say the least. Most of them were some version of the same thing:

You're an idiot for walking away from that opportunity.

And for a moment I believed them. Maybe I'm too privileged to see what I have. Maybe I'm being naive and ungrateful and I'll only understand when it's too late.

But then I thought about what those commenters are actually imagining when they say opportunity.

What people see from the outside versus what it actually is

They imagine the ownership. The autonomy. The financial upside. The prestige of having something real attached to your name. That's the opportunity they think I'd be walking away from.

They don't see the version I know from the inside.

The fact that you never fully relax. Not on holiday, not on weekends, not at dinner with people you love. Because the company is always there, there’s always something that needs attention, always something that could go wrong, and the weight of it sits on your shoulders specifically because it's yours.

The fact that other people's livelihoods depend on your decisions. When there isn't enough work to keep everyone busy, that's on you. When customers don't pay and you still have to make payroll, that's on you. When the market shifts and the company needs to stay competitive, that's on you too.

The success and the failure both land squarely on you. And they don't stay at the office. They follow you home. They sit next to you at dinner. They wake you up at three in the morning when you should be sleeping.

I'm not saying it isn't worth it… for the right person, in the right business, with genuine passion for what they're building, it absolutely is. I've seen what it can look like when it works.

I'm just saying that pretending to be that person, for the sake of not wasting an opportunity, for the sake of not disappointing anyone, for the sake of what it looks like from the outside… it feels like its own kind of mistake. And a slow, quiet, expensive one at that.

Where I actually am

Still in the middle of it. No resolution to offer you.

What I've come to understand is that both doubts are legitimate. The dream job question deserves to be taken seriously and not dismissed as naive or idealistic. The regret question deserves to be taken seriously and not dismissed as just fear.

They're both worth holding honestly, without rushing to resolve them. Without letting the weight of other people's opinions (and Reddit commenters or otherwise) make the decision for you.

What you can do:

Think about what the two strongest doubts underneath your decision are - not the practical ones, the deeper fears underneath. Then write them down.

Now ask yourself honestly about each one: is this telling me something true that deserves my attention? Or is this just the sound of change being scary?

There's a difference. And knowing which one you're dealing with changes everything about how you hold the decision.

Want to go deeper? Copy this into Claude or ChatGPT:

"I'm weighing a major life decision and I have two strong doubts holding me back. Here they are: [describe your doubts]. Help me explore whether these are rational fears worth listening to or emotional resistance to change. Ask me questions to help me get clearer."