Lenny Rachitsky: uncertainty

Transcript context

…But the short version is that if you have a choice and you choose the easy thing and it works great. If you choose the hard thing and it works great, you did more work, but if it doesn't work and you chose the easy thing, you've actually not learned anything because you chose the... You haven't done a lot of work, you haven't probably worked with the smartest people because they're not usually around on the easy path, and what happens is you've gone through this exercise and now you're like, I've kind of lost. I lost the choice, or I was trying to do something, it didn't work out for me. But if you do the hard path and it doesn't work, actually you still win because you've now done something hard. You've probably worked with smart people, you've learned something along the way that is valuable, and I can give you a quick example. So I meet lots of job seekers and they're like, I go, "What are you doing to try to find a job?" I'm like, "I'm sending out 10 resumes a day." I'm like, "Okay." That sounds kind of easy, and are you really learning anything from sending out 10 resumes a day? Versus I would say to them, "Hey, you know all these companies you're interested in, Shopify might be one of them. Why don't you look at the API Docs and build something, build a Shopify app, build an admin extension, build something on top of Shopify." Even if you don't get a job at Shopify, which is maybe your goal, you've learned something, you've built something, you have things in your GitHub repo now and you can show people. You're learning about the product that might translate to a job you might get somewhere else. So I think that even though it's harder, right? Of course, you can't every day build an app on a different platform. Maybe you can once a day. You will learn something in the hard path. And the same thing happened to me in taking hard courses. I would get worse marks, but I ended up meeting smarter people in those courses because they were there for the same reason I was because the content was hard. And so that's something that I've just realized in my life that if I do the hard thing and I just naturally tend towards doing that, I ended up doing... I went to Waterloo and I did a minor in electrical engineering on top of computer science, and when I did my MBA, I did a minor in financial engineering because the smarter people were in that path and they're still my friends today. So building on the last point you just made, people could hear this and think, okay, if it's harder, that's going to be the right path. Sometimes harder is still a bad idea. For example, joining a terrible company that's extremely frustrating to work at or building, I don't know, a house in a really dumb way, but it's just really hard. What else do you find is important to think about when you're thinking it's not just harder, but also XYZ should probably be true? Yeah, one real one is of course the people, because I find that my path has always focused on trying to pick the best learning journey. Where can I learn the most? And for me, everyone's different. Some people might learn better from books or the domain they're in, but for me, I learn a lot from people, and so I try to put myself in those harder rooms on purpose. There was a time when I was doing my MBA in financial engineering, by the way, and I'm a tech guy and still a tech guy, and all these people were going into finance jobs. There was a point where somebody said to me, "Why are you in this class?" Because they knew that I was doing it for fun, and so it was because it was the learning journey. And so I would say a big part of it for me is yes, there's the how do you win even if you lose, because if it goes poorly, you can still come out of it with skills, but if you actually take the hard path, you'll have these intense working relationships with smart people that again will continue on in your life. And that also just forces you to be in this constant state of uncomfort by going into these rooms and saying, "I don't know anything," and it's harder. And I agree with you. You don't want to do dumb things like, oh, let's just do this thing in a dumb way. That's not what I mean. I mean, let's try to do the hard thing that we can learn from. And by the way, it happens to be on the path. It's just is it might take more manual work or it might not be the way most people do it, but we think we can learn more from that path.…

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