Is this hard because it's new or because it's wrong?

There are two kinds of hard in startups, and most founders can’t tell the difference until it’s too late.

The first kind is the hard that comes from building something new. You’re figuring out the product. You’re learning your customers. You’re refining your positioning. It’s hard because you’re doing something that hasn’t been done before, and the path isn’t clear yet. But beneath the difficulty, you can feel something pulling you forward. Customers are leaning in. Early users are coming back. The market is giving you signals that you’re onto something.

The second kind of hard is different. You’re working just as intensely, maybe more so. You’re shipping features, iterating on feedback, optimizing your funnel. You’re executing well by every reasonable metric. But it feels like pushing a boulder uphill. Every win is a grind. Every customer is a fight. You tell yourself this is just what building a company feels like, and you double down on execution.

The trap is this: if you’re good enough, you can make real progress even in the second scenario. And that progress can keep you blind to the fundamental problem.

The difference you can feel

I remember the last time I launched a game that had real product-market fit. From the moment it went live, something was different. Users weren’t just signing up—they were pulling us forward. The retention curves looked right. The referrals happened organically. It wasn’t easy, but it felt easy. Like we were running downhill instead of climbing.

I’ve also been on the other side. Working incredibly hard, making incremental progress, telling myself that this is what it takes. And it is what it takes—if you don’t have strong market pull, the only way to grow is to outwork everyone else. You can do this for years. You can build a real business this way, even.

But you’ll never know if you could have built something 10x bigger if you’d been willing to step back and ask whether you were grinding in the right direction.

The relentless founder’s blind spot

The strongest founders I know are relentless. They don’t give up. They don’t get discouraged. They see obstacles as problems to solve, not reasons to quit.

This is exactly what makes them successful. It’s also what makes them vulnerable to a specific kind of failure.

When you’re relentless, you can convince yourself that any problem is solvable through better execution. Conversion rate too low? Optimize the funnel. Customers churning? Improve the product. No inbound interest? Build better content, run better campaigns, automate your outreach.

All of these things might be the right answer. Or they might be sophisticated ways to avoid confronting a harder truth: you’re executing brilliantly in a market that doesn’t want what you’re offering badly enough.

Signal vs. noise

Here’s what makes this particularly insidious: good execution in a tough market produces results. You’ll get some customers. You’ll generate some revenue. You’ll hit some milestones. These feel like validation.

But there’s a difference between “we closed five customers this quarter through sheer force of will” and “we closed five customers and had to turn away ten others because we’re not ready yet.”

The first is a warning sign. The second is product-market fit.

When I see founders in brutally competitive spaces—industries with infinite noise, where everyone’s inbox is already flooded, where the tenth-best solution might work fine—I worry. Not because they can’t win, but because winning requires perfect execution just to achieve mediocrity. Meanwhile, a slightly different approach in an adjacent space might deliver 10x the results with the same effort.

How to know if you’re in the trap

Ask yourself these questions honestly:

Are you getting wins because you’re working hard, or because the market is pulling your product forward? If every customer feels like a conquest rather than a conversion, pay attention.

Would a less capable founder fail immediately in your market, or slowly? If the answer is “slowly,” that might mean the market has some baseline demand. If it’s “immediately,” you might be the only thing keeping this alive.

Are you seeing surprising success, or exactly the level of success you’d expect from your effort? Product-market fit often shows up as results that feel disproportionate to input. If everything tracks linearly to your hustle, something might be off.

When you talk to potential customers, do they lean in or nod politely? The difference between “this is interesting” and “holy shit, when can I have this?” is the difference between a feature and a must-have.

What to do about it

This isn’t about giving up at the first sign of difficulty. Building anything worthwhile is hard. But there’s a difference between the hard work of creation and the hard work of pushing water uphill.

If you’re in the trap, you have options:

Validate before you pivot. Talk to people who know your space cold. Get real backchannel feedback from operators who’ve been there. Sometimes what feels like a grind is actually just the early stage of something real, and you need perspective to tell the difference.

Look for adjacent spaces with less noise. If you’re building outbound automation in a world where everyone else is also building outbound automation, maybe there’s a fundamentally different approach to the same problem. Maybe the insight isn’t “better outbound” but “what comes after outbound?”

Give yourself permission to explore. You don’t have to abandon ship to test other waters. Strong founders can run multiple experiments. See what gets traction. See what feels different.

Trust the feeling. When you have real product-market fit, you know. Customers pull you forward. Growth feels inevitable rather than manufactured. If you’ve never felt that, you might not recognize it. If you have felt it before and don’t feel it now, pay attention to that signal.

The hardest part about being relentless is knowing when to stop being relentless about the current path and become relentless about finding a better one.

The courage to question

I don’t want to discourage anyone from pushing through hard things. Some of the best companies were built by founders who refused to quit when everyone else would have.

But I’ve also seen brilliant founders spend years executing perfectly in the wrong direction. Not because they weren’t smart enough or didn’t work hard enough, but because their greatest strength—their unwillingness to give up—prevented them from asking whether they should be fighting a different battle.

The question isn’t whether you can succeed through pure force of will. If you’re good enough, you probably can.

The question is whether you should have to.