People ask me for career advice a lot. I never know quite what to say — there are too many paths to a good career to pretend mine is the right one. So I won’t call this advice. But here are three lessons from my own career that have made a real difference. Take what’s useful, ignore what isn’t.

Be a Generalist

My career has been built on being a generalist. I know that sounds like faint praise — most people hear “generalist” and think “jack of all trades, master of none.” Someone who knows a little about a lot. That’s not what I mean.

The kind of generalist I’m talking about knows a lot about a lot. You won’t have the depth of a true subject matter expert in any one area — but to people outside that area, you should look and sound like one. And in every field you’re engaging with, the actual experts should think of you as a quasi-insider. That’s the bar.

Getting there requires one thing most people find uncomfortable: admitting what you don’t know — constantly. Every time you hear a term or concept you don’t fully understand, ask about it. Write it down. Look it up later. The game of being a generalist is a game of relentless learning, and it starts with being honest about the gaps.

And by the way — it has never been easier to do this than right now. With tools like Claude and ChatGPT, you can go from “I don’t understand this concept” to “I understand it well enough to talk about it” in minutes. The barrier to filling your knowledge gaps has basically collapsed. If you want to be this kind of generalist, AI is an enormous unlock.

But learning across domains isn’t just about personal development — the real payoff is what it lets you see. Every organization is made up of parts that interact in ways that are hard to predict if you only understand one of them.

Here’s an example from my time at Upstart. When we updated our ML models, it could change the mix of borrowers who got approved — shifting the credit spectrum of our loan portfolio. That shift might or might not fit the capital market structures we had in place, which affected how much funding was available, which in turn changed which marketing campaigns and channels were bringing in the right borrowers. Model changes rippled from data science to capital markets to marketing in ways that weren’t obvious from inside any one of those teams.

It wasn’t that people in marketing or capital markets weren’t paying attention — it’s that it wasn’t really anybody’s job to look across all of it. It’s easy to get siloed into your part of the business without seeing how changes elsewhere are affecting yours. And it’s not just seeing those connections after the fact — it’s being able to anticipate them. To look at a proposed model change and think: how does this impact our capital partners? Our funding availability? Our marketing costs? Sometimes that’s a knowledge problem, sometimes it’s an information flow problem. Either way, the habit of stepping back to ask “how does this ripple through the rest of the organization?” is rare and incredibly valuable.

If you’re the kind of person who’s curious about everything and has never been able to pick a lane — that might be a superpower, not a weakness. Lean into it.

Get Shit Done

Being a generalist isn’t the right path for everyone. This next one is: learn to Get. Shit. Done.

I know — that’s vague. I wish I had a magic playbook. But it starts with a mindset, and it’s one of the most consistently valuable traits I’ve seen in the people I’ve worked with. I think of it as the ownership mindset.

Here’s what I mean. There are people who do their part. They complete their tasks, hand things off, and move on. And then there are people who own the outcome. They don’t just do their piece — they own the end-to-end result. When something gets stuck at a handoff point, or a dependency falls through, or something just isn’t working — they don’t shrug and say “well, I did my part.” They figure out what needs to happen and they make it happen.

It’s the advice I give my kids all the time: finish the job. Not just your piece of it. The whole thing. Get it over the line.

Barack Obama gave similar advice — his number one career tip is “just learn how to get stuff done.” Be the person who projects “let me take care of that, whatever is needed, I can handle it.” He’s right. In any organization, there are people who seem perpetually busy but somehow never finish anything. And there are people who just make things happen. Learning to be the second kind of person is one of the most valuable career moves you can make.

The unsexy truth is that most of the value in execution lives in the last 10% — the follow-through, the loose ends, the stuff nobody wants to do. The person who chases down that last piece and actually ships a finished product is worth their weight in gold. That’s the GSD mindset: own the outcome, do the unglamorous work, and deliver.

Punch Above Your Weight Class

The last lesson is about what you choose to take on. I borrowed this framing from Mark Suster, who wrote about hiring people who punch above their weight class — people willing to step into roles one level above their previous experience. The phrase stuck with me because it captures something I’ve found really important, not just in hiring but as personal career advice.

The idea is simple: don’t shy away from roles, projects, or challenges that feel too big for you. Actively seek them out. I think of it like skiing — if you’re not falling down every now and then, you’re not pushing yourself hard enough to actually improve. The same is true in your career. If every assignment feels comfortable, you’re probably not growing.

When I was hired at Google, I remember thinking, “I don’t actually think I’m qualified to do the thing they want me to do — but I think I’m qualified to learn how to do it.” That’s been the internal monologue for almost every job I’ve taken. The Google Apps for Education role, joining the founding team at Upstart, taking on business development for a company whose product I didn’t fully understand yet — none of those felt like things I was obviously prepared for at the time. I bet on my ability to figure it out rather than waiting until I felt ready.

This pairs with getting shit done. You can GSD without ever putting your hand up for the bigger challenge. You can volunteer for stretch roles without having the execution chops to deliver. Either one alone is valuable. But doing both — consistently delivering and choosing things that scare you a little — is more than the sum of its parts. That combination is what builds a career that accelerates.

People who punch above their weight tend to volunteer for tasks where they know how to do some of it but not all of it — and then they find a way to deliver the whole thing anyway. Their work is bigger than their title or experience would suggest. Over time, that’s how careers compound — not by waiting for someone to promote you into the next challenge, but by already doing the work before anyone asks.

Looking back at the moments that mattered most in my career, they were almost all moments where I said yes to something that felt too big — and then figured it out along the way.

Wrapping up

So that’s it — three lessons, none of them the usual career advice. Learn a lot about a lot of things so you can see connections other people miss. Own outcomes end-to-end, especially the unglamorous last 10%. And say yes to things that feel too big. None of this is universal — but it’s the mindset that’s driven most of my success. Maybe some of it will work for you too.