Why No One Tells Founders "It's over, move on."

No one tells Founders "Hey, you know what, it was a good run but you should probably stop killing yourself and just take the mulligan on this one." No one ever actually tells us it's OK to quit.

Instead, we build up this narrative in our head that we've got to burn through all of our savings, exhaust our health, and basically run ourselves into the ground to prove we didn't give up. But here's the problem — everyone else gave up a long, long time ago. They just never told us — and never will.

Investors Have No Incentive to Tell Us What's Up

When we were kids playing sports, and we were obviously winded, our coach would pull us out and tell us to take a breather. If our investors were our coaches, they'd hand us some amphetamines and tell us to push harder. And when we passed out on the field, they would still leave us out there to see if we could be helpful in some way.

This isn't a knock against investors — they aren't our damn coaches. They aren't there to be the guiding hand parent through our careers — that's our job as grown-ass adults. They knew months ago that our startup was dead — but what's the incentive to tell us to stop going after it? None. So we can't rely on them to pull us aside and walk us off the field. It's not gonna happen.

Our Staff Can Simply Quit

Our staff, on the other hand, the loyal soldiers that they are, really aren't chained to this thing like we are (thankfully). They may feel "really bad" about how things turned out, but they have a lot of optionalities that we don't.

What they won't do, especially as they are finding out that they are about to no longer be gainfully employed, is put their hand on our shoulder and say "You know, you've done everything you can. We appreciate it, but you should probably move on." They are simply focused on how to get outta dodge as fast as possible and into a more sustainable life situation (just like we should be.)

Friends and Family Look the Other Way

We would like to think that if no one at work will tell us to wrap things up, at least we can rely on our friends and family to let us off the hook. But that's even less likely. Our friends are rarely going to tell us to abandon our hopes and dreams while our family probably still doesn't know what we do for a living, to begin with. In either case, we're still not left with anyone that can definitively tell us "let's wrap this up."

You know who can? Other Founders. If we want an honest look at what we're doing, we should talk to other Founders about the lay of the land, especially ones that have had to wrap up a startup themselves. I've had to go down that path at least 4x in my career and can absolutely assure you that me — and many Founders like me — can definitely let you know when it's time.

In Case You Missed It

What Happens After I've Made It? We always dream about our startups making it big. But what happens when they really do? What happens when all of the risks actually turn into the payouts we had always hoped for? Are we actually happier?

What to Expect in the First Year (podcast) As Founders, we think we know how our products and businesses will look and function for years to come, but as with time, it's nearly impossible to expect the unexpected.

Growth Isn’t Always Good. In many cases, our focus on growth runs counter to what our goals really should be: becoming a better startup — not just a bigger one.