The Founder’s Dilemma: When to Keep Going vs When to Let Go
Let’s talk about something most founders think about but rarely say out loud: “Should I keep going… or should I walk away?”
We glamorise grit in startup culture. Push through. Hustle harder. Don’t quit. But what happens when it’s not working? When your gut is screaming no, but your fear says keep pushing?
This is what I call the founder’s dilemma. And I’ve felt it more than once.
This is what I call the founder’s dilemma. And I’ve felt it more than once.
Here’s the truth:
Sometimes quitting is the right thing. And knowing when to stop takes more strength than blindly sticking it out.
I’ve spoken to so many founders about this. One of the people who influenced how I think about quitting is Steven Bartlett. We first crossed paths when I pitched in the Den. What I remember most wasn’t just his backing, but Steven’s approach to clarity.
He’s one of the few voices in business who talks openly about the value of quitting, and I’ve always respected him for that.
“I made a flowchart to help me know when to quit a business.”
— Steven Bartlett
I’ve spoken to so many founders about this. One of the people who influenced how I think about quitting is Steven Bartlett. We first crossed paths when I pitched in the Den. What I remember most wasn’t just his backing, but Steven’s approach to clarity.
He’s one of the few voices in business who talks openly about the value of quitting, and I’ve always respected him for that.
“I made a flowchart to help me know when to quit a business.”
— Steven Bartlett
📌 How to know when to quit something 👇🏽
“I’ve always found it easy to quit… I’ve quit two of my companies out of the blue with a high-level of peace, conviction and certainty, so I tried to make a flow chart to show the mental process my mind goes through when I quit something – and why I’ve always felt sure that the decision was the right one. You can apply this to your work, relationships or anything else in your life.”
“I’ve always found it easy to quit… I’ve quit two of my companies out of the blue with a high-level of peace, conviction and certainty, so I tried to make a flow chart to show the mental process my mind goes through when I quit something – and why I’ve always felt sure that the decision was the right one. You can apply this to your work, relationships or anything else in your life.”
Steven’s framework breaks it down simply:
- If it’s just hard, ask: is the challenge worth the potential reward?
- If it sucks, ask: could you make it not suck?
- And if yes, is the effort it would take to make it not suck actually worth it?
But here’s what makes it tricky:
Sometimes what you’re experiencing is just a rough patch. A stuck phase. A confidence dip. And I know the feeling—because I’ve been there too.
Ask yourself this:
- Do I still believe in the core idea?
- Is the pain from a temporary problem—or a fundamental flaw?
- Would I be excited to start this again from scratch?
- If someone offered to take it off my hands for free, would I feel relief or regret?
What I’ve learned:
It’s not weak to quit. It’s smart to evaluate. The strongest founders aren’t the ones who grind the hardest—they’re the ones who know where to place their energy.
Quitting the wrong thing gives you back your time, your brain, your energy—for the right thing.
Quitting the wrong thing gives you back your time, your brain, your energy—for the right thing.
Final thought:
If you’re stuck in this decision, borrow Steven’s lens. Get brutally honest. Write it out. Let your gut speak.
Keep going—if there’s still fire. Let go—if there’s only ashes.
Either way, you’re still a founder.
Keep going—if there’s still fire. Let go—if there’s only ashes.
Either way, you’re still a founder.