Navigating Career Transitions

"And what they really needed, and I was naive and didn't think about asking these questions or about evaluating this properly, what they really needed was to create a strategy to add on new growth loops and a system for how to execute against that strategy. If we had talked about that as part of evaluating each other, as part of them evaluating me, it would've given me a lot of confidence that it was the right hire to make."

"And for me, the thing that has led me to the places where I do my best work is a feeling of being at home, which is all about trust and trust with the people around me. Can I walk through and feel like these people are going to have my back, they're going to let me take risks, I'm going to enjoy spending time with them?"

"The framework is really that there's impact that you're really trying to drive and that is the thing that is the most important. And the impact is only achievable by looking at two sets of variables, a set of variables related to the environment, a set of variables related to your skills, and really breaking down each and understanding what's happening in the environment bit by bit and what's happening with your skills and where are you hindered structurally within the environment?"

"The thing I took away from Apple, and I think this is true for anybody changing from one major culture to another is most likely the new place hires you because of the values of the organization you left, but not the behaviors. And so I think it's important to recalibrate and say, well, I want to hold onto these values."

"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."

"I told myself, if four years later Uber exits and I make a bunch of money, I owe it to myself to take a risk, because then I'll have four years of savings in my bank, which... Back then I had maybe six months of savings or something. So this was the promise to myself."

"Ultimately you don't realize this, but the value of working at a leader in any space, the quality of talent you work with, the brand, the network effect, so many things accrue to you. I would much rather be the number two or number three person. If you think of it that way, and the leader in a space, than the top person."

"If I'm optimizing for tomorrow and I just want to have a great day tomorrow, I'm going to stay exactly where I am. So many people I see have this happen, where they hit a plateau and they never move past it, because they're not willing to have that hard day, month, week, year."

"And it's a big thing to take a risk because you're taking 10 steps backwards in hopes of making major leaps forward. And I think that's just always kind of been a narrative mostly in my career, which is I don't believe there's such a thing as taking a big leap without first taking a major risk, and that was."

"It became a job by building in public. You don't need a company to hire you. You can hire yourself as a professional vibe coder first."

"I only like doing jobs that I'm highly unqualified for. I like being on learning curves so steep that I'm scared I'm going to fall off. And so I left and I wanted to learn what it took to build something from nothing."

"When I took a step back and was like, all right, what do I want to do next? I really loved the marketplace component at Etsy. And I don't know if this is just says something about my personality, or actually probably your personality too, is marketplace product is really hard, right? You have this constant balancing of both buyer and seller sides or both sides of the marketplace. And I really liked that. And it was something that I was good at."

"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 know nothing else to do, but you'll be sadder or you'll find ways to create war when peace is needed."

"Take three hours during a workday. Has to be during a workday. Block off your schedule, sneak out. People can pull this off. Go for a walk without a destination or do something from your childhood that you used to do all the time."

"The big shift for me actually, when I left my job, I wanted to run away. I wanted to escape work. I wanted to not work. And I more or less accomplished that. I basically lowered my cost of living in Asia to about 1,000 per month."

"The pathless path is basically a shift away from the default. It's a shift away from not knowing what you're doing as a problem to be solved toward an embrace of uncomfort, discomfort, and uncertainty."

"The goal is not to find a job, make money, build a business, or achieve any other metric. It's to actively and consciously search for the work that you want to keep doing."

"Companies are desperate to keep people and are much more open to things like this these days. And the way I frame it is if you're assuming you're going to work continuously in adulthood, that's about 500 months. Try to find three months of that where you can create space."

"You'll trigger insecurities in other people by just existing outside the frame of the default path. And it's the default path in their head of their conception of how the world should work and does work, right?"

"It's no one else's job to help you live in your gifts. What I notice in big companies is people are often annoyed or frustrated with their management for not making their job more interesting. No, your manager's job is to help you perform in the job you are hired to do. It's your job to navigate your career."

"The advantage a smaller company has really is in latency. You can have an idea one day, you can test it the next day, and as a result you can have this really short cycle time between an assumption or a hypothesis and being able to validate that hypothesis. And that's just not true at larger companies where there's a lot more momentum."

"I really took that opportunity to make the transition out of a little bit more enterprise focused internal role at Microsoft to going where I could work on everything from, I don't know, AI technology like Copilot to a cloud hosted development environments like Codespaces, repos, which literally every single developer on the planet is participating in some way GitHub repos in a typical year."

"But the reality is you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it."

"My biggest advice to people is, oftentimes the analysis paralysis of dotting every eye, crossing every tee sometimes chokes you out of opportunities. When you find something that gives you energy, just jump in with both feet. And try to go through that process, and pivot and learn, and pivot and learn and pivot. That's how you would create a great career as opposed to sort of a five year career plan and working backwards from that."

"The form factor of what it means to be a programmer obviously is going to change, but at the end of the day, of course the discipline is all about just being able to tell your computer what's do. And so in that lens, I really think that programming is only going to become more and more important as AI gets more powerful."

"And so I became the de facto product manager and that is when I learned marketing is the product. You don't make a product and then hand it to some marketing yahoo and say, go put a logo on this. That the product we made, and five in a row went gold, saved the company."

"For about a year, I was doing the product job without having the title and I was also the engineer. So I was in this great state where I'd figure out what needed to be built and I would just build it myself."

"Make sure you go somewhere where you have a good engineering partner. Because if you have great ideas of what to build but you can't get them built, then you go nowhere. So that has to be part of your evaluation criteria that you meet and value your engineering partner before you join."

"When I look back on my career and think about the things that I've done, my professional satisfaction is not well correlated with those external metrics and very, very coordinated with do I love the thing we were building and do I love the people I was working with?"

"Every single time I've taken a job where it turned out that I was working with people who had a different set of values or working styles than I had, I knew. You tell yourself that, at least in my case, I tell myself a story about why the thing I suspect might be the case isn't the case."

"There's this belief that everybody needs to be a founder. I think, in some ways, our industry would be much better off if there were fewer founders. There's an entire category of smart, creative, hardworking, talented, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never going to go anywhere."

"And I think I had to unlearn that moving into product because you get a lot of ideas coming from a lot more places in the organization, and ideas are fragile in their agency and it's a hard no can really kill a whole direction that you could potentially go. They could be very high reach and high impact."

"My first job out of college is actually at Microsoft, and I was the Product Manager on Hotmail. If anyone, any listener remembers Hotmail, and I didn't really know what product management was at the time, and I mute it as a interdisciplinary function that will give me exposure to all my other functions so that I can actually decide which function's interesting to me."