Lenny Rachitsky: uncertainty

Transcript context

…" But they don't think about what happens next, and when it happens, when they succeed, their North Star, their entire way of wiring their career, themselves, it has been around getting to that place. And I think that if you're going to get there 30 years in and you have a 60-year career, a lot of the discussion I've been having with myself and with others has been, you probably need to start working on that North Star now. What's the second thing? What's your career next look like? How do you ensure that you are always going to have something important and motivating to do with your career? Otherwise, you'll keep working because you had no nothing else to do, but you'll be sadder, or you'll find ways to create war when peace is needed, or you'll spend money in an attempt to earn more, or you'll find habits that are bad. And I really want us to have long 60-year, 70-year careers, not just 30-year or 10-year, which is why I enter this into the vocabulary out there. That is really resonating with me. I had a similar experience. I had a startup, and my whole goal was just like, "I just want to start a company." That's my goal. That's all I got in life. I want to start a company and then maybe sell it, maybe go somewhere with it. So I did and then we sold it to Airbnb and then I got to Airbnb and I was just like, "What the hell do I do now? I don't have any other goals." And it was pretty sad. Exactly how you're describing. It was just like, "I guess I'll just work here and I don't know, maybe I'll start another company, but I already did the thing I wanted to do. " Your story is I think very inspiring because what you did is you said, "I think the thing that I want to do is give, but I want to do it in my own way and I want to create something, but I want to do something that I think I can do for 30 years and I want to do it." It has lots and lots of spokes to it. So you reinvented yourself professionally, but you created a new North Star. My sense is, for every one of you, Lenny, there's a hundred that could do that, that could do giving, that could do things that could scale, but that end up falling into what got them to be successful in act two and they get stuck. So this is the reason why when you hit your skip, keep looking for the next skip, is the point I'm trying to make. And I think you're an inspiration for a lot of folks who have seen you transition and realizes life after just being a tech professional entrepreneur, there's got to be ways to do more of this for all of your listeners. And I think it's never too early to start thinking through. It's actually quite powering to think that you have such a long career. You can make mistakes and you can do some amazing things down the road.…

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