A long extract from a good episode of the Tim Ferriss show – link below.
The thing that I think is important to communicate is, despite things having been relatively smooth in that macro sense, it [building and running multi-billion-dollar online payments company Stripe] often is just extremely hard. I remember early on after one particular meeting back in 2011 or 2012, just after the meeting the API broke… the core stripe payments engine broke, and so our customers just couldn’t get paid, and couldn’t accept payments from their customers. And we didn’t have many customers back then – maybe there were a hundred or something – but that was still a hundred businesses, it felt like a huge deal. And we fixed it, it was only down for maybe thirty minutes or something, but I remember feeling really bad about that, and then I remember just reflecting on the enormity of the challenges that we would face in the future, and all the work that we still had to do and all the stuff that was still broken, the people we had to hire, and all the customers that we’d have to convince to use us that we had not yet convinced, and it was just this moment of vertigo. I just remember being immensely dispirited and talking to John [Collison] about, well, “Is there really actually any point in doing this?”
And what’s important to me about that moment is not that things were actually all that bad, but kind of the opposite: objectively they were fine. That day wasn’t really much worse than the previous day, but I think that there’s this kind of inevitable thing when you’re creating something where on the one hand you just have to be very optimistic because if you weren’t optimistic you wouldn’t bother doing it, especially in the face of such hardship and uncertainty. You also have to be pessimistic, because there are tons of problems and you have to be very tuned to spotting them so that you can go fix them.
And so you kind of exist in this superposition – this juxtaposition – of kind of pessimism and optimism and you’re kind of an extreme on both axis, and that’s just like a weird psychological state. And to remain in it, as you must, for many years, is just not normal.
And I don’t want to overstate it – there’s all the obvious acknowledgements about, we’re immensely lucky, among the luckiest people in history to have food and shelter and health and all these things. But humans hedonically, the hedonic treadmill is very powerful and we rapidly adapt to take all those for granted. And so the fact that maybe in the scheme of things we should feel very grateful and lucky, and you can tell yourself this narrative to try to keep things in perspective, the reality is that it is just pretty pummeling on an ongoing basis, even for Stripe, which perhaps from the outside might look like this really neat little story. There have been many moments where it just seems hard.
The thing that I think is important to understand… is that it’s kind of intuitive that if a company or a new effort of any sort is not going well that things will feel hard, and you’ll often feel dejected, and life at least insofar as work goes is not great. But the weird part is that even if things are going well and the effort or the company is succeeding, things will still often not feel great. And no-one told me that before I started. I thought that well, if the company is succeeding then clearly it’s going to be, not necessarily fun, but at least it’ll feel good day to day. Whereas the actual reality is that you’re always necessarily operating at the outer edge of what you can handle, because if you had spare capacity you’d just take on more. And so you’re therefore inevitably always on the cusp of feeling like you’re you’re going to fall over.
Even as we record this podcast, at this moment, I feel right on the edge of what I’m able to handle. And on the one hand I don’t wish it were otherwise in that I enjoy testing myself and finding my limits and developing and stretching myself, but on the other hand, when you stretch your muscles, that’s painful.Patrick Collison – The Tim Ferris Show #353