Most of our cultural virtues, celebrated heroes, and catchy slogans align with the idea of "never give up". That's a good default! Most people are inclined to give up too easily, as soon as the going gets hard. But it's also worth remembering that sometimes you really should fold, admit defeat, and accept that your plan didn't work out.
But how to distinguish between a bad plan and insufficient effort? It's not easy. Plenty of plans look foolish at first glance, especially to people without skin in the game. That's the essence of a disruptive startup: The idea ought to look a bit daft at first glance or it probably doesn't carry the counter-intuitive kernel needed to really pop.
Yet it's also obviously true that not every daft idea holds the potential to be a disruptive startup. That's why even the best venture capital investors in the world are wrong far more than they're right. Not because they aren't smart, but because nobody is smart enough to predict (the disruption of) the future consistently. The best they can do is make long bets, and then hope enough of them pay off to fund the ones that don't.
So far, so logical, so conventional. A million words have been written by a million VCs about how their shrewd eyes let them see those hidden disruptive kernels before anyone else could. Good for them.
What I'm more interested in knowing more about is how and when you pivot from a promising bet to folding your hand. When do you accept that no amount of additional effort is going to get that turkey to soar?
I'm asking because I don't have any great heuristics here, and I'd really like to know! Because the ability to fold your hand, and live to play your remaining chips another day, isn't just about startups. It's also about individual projects. It's about work methods. Hell, it's even about politics and societies at large.
I'll give you just one small example. In 2017, Rails 5.1 shipped with new tooling for doing end-to-end system tests, using a headless browser to validate the functionality, as a user would in their own browser. Since then, we've spent an enormous amount of time and effort trying to make this approach work. Far too much time, if you ask me now.
This year, we finished our decision to fold, and to give up on using these types of system tests on the scale we had previously thought made sense. In fact, just last week, we deleted 5,000 lines of code from the Basecamp code base by dropping literally all the system tests that we had carried so diligently for all these years.
I really like this example, because it draws parallels to investing and entrepreneurship so well. The problem with our approach to system tests wasn't that it didn't work at all. If that had been the case, bailing on the approach would have been a no brainer long ago. The trouble was that it sorta-kinda did work! Some of the time. With great effort. But ultimately wasn't worth the squeeze.
I've seen this trap snap on startups time and again. The idea finds some traction. Enough for the founders to muddle through for years and years. Stuck with an idea that sorta-kinda does work, but not well enough to be worth a decade of their life. That's a tragic trap.
The only antidote I've found to this on the development side is time boxing. Programmers are just as liable as anyone to believe a flawed design can work if given just a bit more time. And then a bit more. And then just double of what we've already spent. The time box provides a hard stop. In Shape Up, it's six weeks. Do or die. Ship or don't. That works.
But what's the right amount of time to give a startup or a methodology or a societal policy? There's obviously no universal answer, but I'd argue that whatever the answer, it's "less than you think, less than you want".
Having the grit to stick with the effort when the going gets hard is a key trait of successful people. But having the humility to give up on good bets turned bad might be just as important.