The Inside Edge of Impossible
Every Friday, I send an email to the Castle team which is in theory about our accomplishments, strategy, and culture, but which really just ends up being about whatever’s on my mind. Last week’s has stuck with me more than most, so I’m sharing a lightly edited version here.
Today, I want to expand on the question from our last All Hands meeting about staying motivated and dealing with anxiety when you’re scared about the future.
Sometimes, for some startups, everything goes smoothly — or at least seems to — and your momentum builds and builds on itself. We’ve been through those stretches before, and I have no doubt that we will again.
But other times, like during the phase we’re in now, something crucial appears broken everywhere we look, and our jobs can start to feel like we’re pushing a boulder up a hill, inch by miniscule inch.
When this happens, I take solace in knowing that those smooth feelings can be dangerous. Sometimes they just mean you’re blind to a problem that’s already there, or failing to anticipate a problem that’s just around the corner.
Other times they’re accurate, and everything really is going smoothly — and might even stay that way, effortlessly, for so long that it starts to seem permanent.
But then you hit the inevitable rough stretch and it strikes a dozen times worse since you’ve grown complacent from the easy years, deprived of practice dealing with deep, company-quaking obstacles.
As much as I hate to quote Peter Thiel, who continually manages to out-douche himself, he once explained this idea in a way that I think about all the time. He was asked about the origins of the so-called PayPal mafia: the disproportionate number of people on the early PayPal team who went on to build hugely impactful companies of their own.
Peter’s answer was that most people have one of two startup experiences. One is that their startup fails, and they get discouraged, and they never try again.
The other is that their startup succeeds wildly, but in the lottery model, like Google and Facebook, where the company essentially “strikes gold” early on and just rides the wave from there.
And when you spend your formative working years pulled along by a once-in-a-generation rocketship, you’re left prone to quitting the next time around as soon as things inevitably get hard
PayPal, Peter says, fell into a third, rarer category: it was “just hard enough.” The early PayPal team learned that startups are really hard — so hard that they’re just on the inside edge of impossible — but that with determination, stamina, and a healthy dose of luck, success is still possible.
Of course, I can’t guarantee that the trough we’ve been in lately is of the hard but not impossible variety. As much as I don’t believe it’ll happen, we might fail — every startup might.
But if we do, I know we’ll always regret not giving it our all on the way down. And I know we’ll regret it even more if our time together comes to an end without us all having savored every last moment.
Earlier I used the metaphor of pushing a boulder up a hill. Here’s the thing about a boulder, though: you can’t always tell whether you’re pushing uphill or down.
In the beginning, the uphill feels just like the downhill, but the effort gets just the tiniest bit easier, almost imperceptibly so at first, until suddenly you realize the boulder starting to roll, faster and faster, of its own momentum, and you realize you have to start running just to keep up. I have a hunch we’re going to feel that momentum coming sooner than we think.
I’d like to conclude by telling you a secret. Whenever I give one of those pep talks in our All Hands meetings, or write an update like this one, you guys are really my secondary audience. If I’m honest, the first person I’m talking to — the first person I’m trying to inspire, the first person I’m trying to comfort — is myself.
But it’s often much easier to support someone you care about than it is to support yourself. So that’s my final piece of advice: instead of trying to assuage your own anxiety, assuage someone else’s; instead of trying to motivate yourself, motivate someone else.
You won’t even notice how well it’s working at first, but I promise you that before the day is up, you’ll start to feel something shifting inside you.