Riding a Dead Horse
“How do you know when it’s time to let go?” Simple question. Not easy to answer. The trap is hope without direction - waiting for something to change while not changing anything yourself.
Someone asked me during a sparring session:
“How do you know when it’s time to let go?”
Simple question. Not easy to answer. I’ve wrestled with it myself. Ending PIRATE Summit after over a decade of pouring my heart into it wasn’t an easy decision. But it was the right one. Because I learned my lesson about letting go 15 years earlier. Looking back and reflecting on it helped me navigate the end of PIRATE Summit better.
🏴☠️
Before we dive in - a quick thought.
I’m pondering doing another PIRATE Night. Last year we expected 300 people. More than 500 showed up. It was pretty humbling. We’re thinking end of June this year. If you want to get involved - bring your community, co-create something - just reach out! If there is enough interest and support we might just make it happen.
🏴☠️
My first real startup was a digital headhunting platform. We launched in 2008. The idea was solid. Then the financial crisis hit and recruiting froze overnight.
But we stayed. We told ourselves: great startups are built in hard times. That’s a true thing. It’s also, in our case, the story we needed to keep going - which is a different thing entirely.
The reality was that we were running a zombie business. Not dead, not alive. Too weak to succeed, too stubborn to quit. And the longer we stayed, the more the story hardened. We’d invested so much time, energy, and money that leaving felt like admitting the investment was a mistake. So we kept investing.
In the years after, I thought quite a bit about why we didn’t quit earlier.
We weren’t in denial exactly. We weren’t blind. We could feel that something was wrong. The Monday morning energy had a flatness to it. The way we talked about the company had quietly shifted from excitement to justification. Going through motions that used to mean something.
But we were still hoping. Not actively building toward a turnaround - just hoping. Waiting for the thing that would make it make sense again. If we held on a little longer, if the market shifted, if one more client came through, maybe the horse would run again.
That’s the trap. Not ignorance. Hope without direction. Waiting for something to change while not changing anything yourself. Riding a dead horse and telling yourself it’s just tired.
It took four years. Four years is a long time to ride a dead horse.
When I finally made the decision, it didn’t feel like defeat. It felt like dropping a backpack full of rocks I had no reason to keep carrying. I expected grief and self-doubt. There was some. But mostly what I got was space - and a strange clarity that had been unavailable to me for years.
So back to the question: how do you know when it’s time to let go?
Here are my thoughts, after that experience, quite a bit of self-reflection and years of sitting with founders at similar crossroads.
You rarely get a clear signal. The horse doesn’t send you a letter. What you get instead is a gradual shift in the quality of your own thinking about it - from building to justifying, from momentum to maintenance, from genuine belief to performed belief.
When you notice you’re working harder to convince yourself than to move the thing forward, that’s worth paying attention to.
The second thing: ask what you’re actually waiting for. Not in theory - specifically. What is the concrete thing that would change, and what would have to happen for it to change? If the honest answer is “I don’t know, something” - that’s the horse. That’s the waiting without direction that keeps you on a path that isn’t going anywhere.
And the third thing, which is the hardest: separate the decision from the identity. We stayed partly because leaving felt like admitting we were wrong, that we’d failed, that the years were wasted. But the years weren’t wasted - they were the cost of learning something real. The decision to leave wasn’t a verdict on the past. It was just the next right move.
Letting go isn’t the opposite of strength. It’s what becomes possible when you stop spending strength on the wrong thing. After all, strength isn’t proving your worth to others - or to yourself. It’s honoring it.
The sparring work I do with founders is the most fulfilling work I do. Questions like this one are why. They look simple on the surface. Underneath, they're about how we stay honest with ourselves under pressure - and how we recognize when the story we've built is serving us or quietly trapping us. It takes real courage to choose your path.
I got off the horse eventually. At least three years late, but eventually.
The horse was dead. I just needed to stop waiting for it to run.
🙏
Be kind,
Manuel