Should I Stay or Should I Go? A Founder's Guide to the Hardest Question

Most founders ask themselves this question at some point: Should I leave my cofounder?

If you're reading this, you've probably asked it more than once. Maybe it surfaces during a tense board meeting. Maybe it keeps you up at night after another unresolved argument. Maybe it whispers in the background while you're trying to focus on product roadmap, reminding you that something fundamental feels broken.

This question is normal. It's also dangerous—not because asking it means you should leave, but because most founders never take it seriously enough to actually answer it.

Instead, they stay stuck. They oscillate between "I'm done" and "I need the money." They vent to their spouse, ruminate during family dinners, and replay arguments in their head when they should be sleeping. They exist in a state my colleague and expert cofounder coach Cat Totty calls “the angry spiral”—too frustrated to stay present, too afraid to leave.

Most meaningful change in life is driven by only two forces: pain, and the fear of future pain.

But when founders ask, “Should I stay or should I go?” they’re usually not engaging either one.

They’re venting. Releasing steam. Displacing emotion.

They give voice to the pain without actually sitting in it. They intellectualize the debate without allowing themselves to feel what this is costing them. And they almost never ask the harder question:

What will this cost me tomorrow?

How much more painful will this be six months from now? A year from now? What version of me will exist if nothing changes?

Instead of metabolizing pain or confronting future pain, they stay in analysis mode. And that keeps them stuck, which paradoxically generates more of the very pain they’re trying to escape.

This article is about how to get unstuck. Not by giving you a universal formula (there isn't one), but by helping you understand what this question is really asking and how to engage with it honestly.

Why This Question Arises—and Why It Matters

Let's start with the obvious: this question emerges during hardship.

When the company is struggling, when conflict escalates, when you feel fundamentally misaligned with your cofounder—your brain defaults to survival mode. It looks for an exit. It imagines a life where you're not carrying this weight, where you can start fresh, where the friction disappears.

That impulse is understandable. It's also incomplete.

The thought itself—should I stay or should I go?—is not the problem. In fact, if you take it seriously, this question can be one of the most clarifying experiences of your founder journey. It forces you to examine your values, confront what you're tolerating, and decide who you want to become.

But most founders don't take it seriously. They let it linger in the background, unresolved, until something catastrophic forces a decision. That is choosing unconsciousness. That is avoiding the self-work required to either fix the relationship or exit with integrity.

I'm advocating for the opposite.

The Symbolic Layer: What This Question Is Really About

In couples therapy, there's a principle I use when someone admits they've fantasized about infidelity. The question isn't just whether they should cheat—that's the concrete reality. The deeper question is: What does this fantasy symbolize?

Often, it's not about the other person at all. It's about what's missing in the primary relationship. Intimacy. Appreciation. Physical connection. The fantasy is a signal—a way your psyche is bringing attention to disavowed aspects of your partnership that require re-integration.

The same logic applies to cofounders.

When you think I want to leave, you're not just reacting to your cofounder's behavior. You're reacting to something missing, something misaligned, something that's eroding who you are.

The question is: What is this thought symbolizing?

Maybe it's a mismatch in work ethic. You're grinding 70-hour weeks while they're coasting, and the asymmetry feels like betrayal.

Maybe it's a values misalignment. They're prioritizing personal life over the company, and you feel like you're shouldering the sacrifice alone.

Maybe it's relational distance. You used to understand each other intuitively, but now they feel like a stranger. The old agreements—the implicit assumptions about how you'd work together—no longer function.

Or maybe it's more subtle. Maybe you don't like who you're becoming. You're shorter with your kids. You're venting to your spouse. You can't relax on weekends because you're replaying the argument from five hours ago. You're losing your playfulness, your groundedness, your ability to be present.

If you only engage with this question at the concrete level—do I stay or do I go?—you miss the deeper work. You miss the chance to understand what's actually breaking down and whether it can be repaired.

The Cost of Staying (and the Cost of Leaving)

Here's what I see most often: founders stay in broken cofounder relationships because leaving feels too risky.

They rationalize. We have a $10 million business. The market is good. The opportunity is real. I'll just pull back a little, protect myself, and ride this out.

But here's the problem: that's not actually staying. That's self-betraying.

When you stay resentfully, you're not fully in. You're withholding effort. You're operating in incongruence—saying you're committed while internally checking out. And that incongruence creates friction.

Friction wastes energy. It reduces focus. It degrades execution. It shows up in how you interact with your cofounder, your team, your investors. People sense it, even if they can't name it. It shifts the culture.

And here's the kicker: if you're the kind of founder who wants to scale from $10M to $20M ARR, this half-in approach betrays your own values. You're choosing interpersonal avoidance over the work required to either repair the relationship or exit cleanly.

There's a concept from relationship coach Jayson Gaddis that I think about often: If you don't engage in interpersonal conflict, you internalize it.

That internalization compounds. In a startup environment—where so much of your identity, livelihood, and daily energy is tied to this volatile, high-stakes thing—emotional debt accumulates fast.

So ask yourself:

• What are the consequences of staying in this partnership as it currently exists?

• How does that impact the business? What’s the lost upside? What’s the risk?

• What am I sacrificing? My values? My mental health? My presence with my family?

• What aspects of myself am I losing?

• Am I becoming someone I don't recognize?

These aren't rhetorical questions. They require honest answers.

Because if you stay in a broken partnership without doing the work to fix it, you're making a choice. And that choice has costs you may not be accounting for.

The Fixed vs. Growth Mindset Trap

Let's say you've tried. You've had the hard conversations. Maybe you even raised your voice. Maybe it felt like you got through for a moment, but then everything snapped back into place.

Now you're convinced, “This person can't change.”

Maybe you're right. Maybe your cofounder has developmental limitations, blind spots, or a personality structure that makes certain kinds of self-awareness or relational flexibility genuinely difficult for them.

But here's what I see more often: founders project a fixed mindset onto their cofounder as a way of avoiding their own interpersonal risk.

You tell yourself, "They're incapable of this," because that's easier than admitting, "I don't know how to facilitate this change, and I'm afraid of failing again—it’s too draining."

You assume their brain works like yours, that they should be able to see what you see, monitor themselves the way you do. When they don't, you conclude they're broken.

But most of the time, you haven't actually exhausted your options. You've just exhausted the options you feel comfortable trying on your own.

And here's the hard truth: you can't fix this alone.

If you could, you would have already. You don’t just need new tools and frameworks. You need a new process—one that introduces accountability, reflection, and facilitation that you can't generate by yourself.

Why Cofounder Coaching Is the Most Underutilized Resource in Startups

I know what you're thinking. We've already tried talking. We've read books. We've vented to mentors. Nothing worked.

But let me ask, have you actually worked with a cofounder coach?

Not a generic executive coach. Not a therapist (though therapy has value). Not an advisor who listens and nods. A trained professional whose entire practice is built around cofounder dynamics.

Most founders who consume content like this—who read articles, listen to podcasts, talk to ChatGPT—never actually engage in structured cofounder coaching. And I believe it's the most underutilized resource in the entire startup ecosystem.

Here's why it works:

1. It forces honesty you can't generate on your own.
When you're in the dynamic, you can't see your own contribution. You're biased. A skilled facilitator surfaces the patterns you're blind to.

2. It creates mutual accountability.
Reading a book is passive. Talking to a coach means someone is tracking whether you actually do the work—whether you apply what you learn, whether you follow through.

3. It provides a neutral third party.
Your cofounder can't dismiss the feedback as your opinion. A coach reframes the issues in ways that bypass defensiveness.

4. It gives you information to make a decision.
Even if the relationship doesn't improve, you'll walk away knowing you tried everything. You'll have clarity on whether the dysfunction is fixable or structural.

Sack up. Commit to three months of weekly or biweekly cofounder coaching. Yes, it's expensive. Yes, it takes time. But if you don't do it, you're choosing to stay stuck.

And if after three months of good-faith engagement, nothing changes? Then you have your answer. You've exhausted the options. You can make a decision—stay or go—with integrity, knowing you didn't leave anything on the table.

But until you've done that, you're wasting time. You're spinning your wheels, oscillating between anger and avoidance, while the emotional debt compounds.

The Question Beneath the Question

The real work here is identifying what's actually driving this question.

Is it the cofounder relationship itself? Or is it something deeper?

• Are you afraid of who you'll be without this company?

• Is this the "devil you know"—predictable, even if toxic?

• Are you avoiding the unknown because starting over feels too risky?

• Are you questioning your own ability to build something new?

These are identity questions, not just business questions. And they require self-inquiry that most founders avoid because it's uncomfortable.

But if you don't do this work, you'll make the wrong decision. You'll leave a salvageable partnership because you're burned out. Or you'll stay in a destructive one and make your life miserable because you're afraid of failure.

What to Do If You're in the Angry Spiral

You know you're in the angry spiral when:

• You swing between "I'm leaving" and "I need the money" on an ongoing basis.

• You vent constantly but never take action.

• You feel resentful but can't articulate what you actually want.

• You're waiting for your cofounder to change without doing your own work.

If that's you, here's my challenge:

Stop avoiding the interpersonal conflict.

Have the conversation you've been avoiding. Not the surface-level "we need to communicate better" conversation. The real one. The one where you name what's actually broken, what you're afraid of, what you need.

And if you can't do that on your own, bring in someone who can facilitate it.

Because the truth is, the worst-case scenario isn't the conversation going badly.

The worst-case scenario is that you stay stuck in this liminal space, losing yourself piece by piece, until the decision gets made for you.

The Most Typical Cofounder Coaching Outcomes

Let's be honest about what happens if you invest in this work.

Worst case: After three months of coaching, things don't improve. But now you have clarity and information. You know it's not salvageable. You can exit with integrity, or you can stay with full awareness of the trade-offs. Either way, you're no longer stuck.

Best case: The relationship transforms. You develop new communication patterns. You realign around shared values. You build a partnership that's not just functional, but energizing.

Middle case (and most likely): You don't fully repair the relationship, but you make it workable. You clarify roles, boundaries, expectations. You create enough space to execute without the constant friction. And if you do eventually part ways, it's amicable—preserving equity, reputation, and sanity.

All three outcomes are better than where you are now.

Final Thought: Sleep at Night

I want you to be able to sleep at night knowing you gave this everything.

Not just your solo effort. Not just late-night journaling or advice from well-meaning friends. But structured, facilitated, accountable work with someone trained to help cofounders navigate this exact question.

If you do that and it still doesn't work, you can walk away clean. No regrets. No "what ifs." No replaying a messy exit that cost you your company, your upside, or your relationship.

But if you don't do it? If you stay stuck in the angry spiral, avoiding the hard conversations, internalizing the conflict? You'll look back and wonder why you wasted so much time.

The question isn't really "Should I stay or should I go?"

The question is: Am I willing to do the work to find out?