Kelsey Hightower challenges the idea that you should “do what you love”

Google Cloud’s distinguished engineer talks knowledge sharing, mentorship, career paths, and priorities

May 30, 2023

Google Cloud’s distinguished engineer, Kelsey Hightower, is a legend in the world of Kubernetes. A technical leader and a gifted communicator (it’s no surprise that he is a regular on the conference circuit), Kelsey’s facility with tackling complex topics in clear-eyed language and common-sense frameworks has gained him a broad and devoted audience. Wherever he is and whatever topic he’s discussing, he is frank and generous with his time and experience. Roadmap is lucky to have him as its inaugural interviewee! 

This interview has been edited for length and clarity.

What does work mean to you? How has that meaning changed since you first started your career?

I’m at a point, at least financially, where I can afford to have a different perspective. When I first started in tech, I needed to work for survival. I’d do any work for survival. I’ve always challenged this notion of “Do what you love.” Do you really love it if you have to do it? And if you have to do it, how do you find love in it? For me, I got really good at figuring out how to work. I haven’t spent an equal amount of time on how to live. We all can learn how to type faster, or to pick up a new programming language. What is it like to not try to increase the score on the scoreboard?

That first 10 years, I wanted to get good at the things that would allow me to be the most creative. This is why programming became an essential tool in my tool belt—because I figured I could take programming and apply it to any set of problems across the largest set of customers. That became my tool of choice to help define the job that I wanted. But even with those skills, I still have to pay the taxes (not the literal IRS taxes) of getting other people on board with the work that needs to be done. That convincing, that communication, that consensus building: that’s what feels the most like work. Ah, I gotta push this boulder up the hill. Let me stretch first. But it can also be very satisfying, because you get a feedback loop.

I’ve always challenged this notion of “Do what you love.” Do you really love it if you have to do it?

Working with customers allows me to keep the human-connection part. Nothing is more satisfying than watching someone else get something out of what you did. Maybe you have your favorite meal you like to cook, and you know it tastes good. You don’t even need to taste it to know. You just sit back and wait for that first bite, when they say, “What’s in this? Can I get the recipe?” When it comes to tech, producing things that make me want to watch someone take the first bite, that’s what keeps me motivated at this point.

How do you think about your career today? What are you looking forward to?

Everyone has a boss. Even if you own a business, you still have a boss. Your customer is your boss. Founders take on a lot of risk, too. The trade-off is there when they have so much equity. But there’s another group of people who make more money than the founders—that’s the people who give the money. They always win in aggregate. So I decided to be on that side of the equation, and I advise a list of companies. I’ve made more than a lot of the founders I know over time. I’m not interested in a situation where a VC cuts me a $10 million check and gets my whole life in return. My time has a different price tag to it. 

You know, being at a large company, it’s like, why do people go to, like, the NBA? Why not just play college basketball and then join the community basketball team? Well, those teams can’t afford to pay for the level of skill an NBA player brings to the court. But you also want to play—work—on the biggest stage, where the biggest problems are, where the goal is as big as it can be. For the past 20 years, big tech has attempted to solve the world’s biggest problems. For me, not just from a compensation standpoint but from an opportunity standpoint, working at a company like Google is the answer to the question “How do you grow?” 

You’ve told the story of your decision to join Google in 2015. At the time, you were also fielding an offer from NASA. Someone there told you to take Google’s offer and return to NASA in the future. Now, almost a decade later, have you ever thought about going back to NASA?

See, the funny thing about that—last year, I was invited to be a part of this program called TOPS [Transform to Open Science], which is basically NASA’s attempt to open up its datasets to citizen scientists. Basically, they want to move in a direction based on open-source philosophies. So I’m working with NASA again! I’m one of a collection of people from the private sector they brought onboard. Next week, I’ll be back on site at [NASA’s] Jet Propulsion Lab. And I’ll get to contribute to this thing that allows more people to tap into this vast amount of knowledge. For me, it feels like, while I’m at a different company, I’m on the same team. If you think about it, the whole world is one big company, and Google is just one department, and NASA is just one department. So it’s not about going back. It’s like I never left.

I’ve also heard you speak about parenting your daughter, Kelis. How have you balanced work with parenthood? Did becoming a parent change your relationship with your career?

When you are working for survival, it’s different. When I had a computer store, I could afford one of two things: I could afford the storefront, or I could get an apartment. If you are by yourself, you can trade off.  I’ll get the storefront and I can sleep in my car. When you are married or have a child, that’s not the right trade-off. Stuff like location, time, and hours need to line up. Parenting is just the higher priority. For me now, my time is now more expensive. It changes how you negotiate. 

This might sound morbid, but you’re not going to always be here. With your kids, you’re literally training your replacement. And you also understand that that’s not a bad thing. There is such a thing as the circle of life. You try to put everything you can into the next generation (though, financially, I don’t think it makes sense to leave too much). For me, that means everything that I’ve learned and all the new things that I want to learn.

You are so committed to sharing your knowledge, particularly with people who are coming up or just getting started. How do we build institutional knowledge, industry knowledge, intergenerational knowledge?

You share it. That’s the trick. Someone has to share it.

Some people can’t afford to share. You’ve got a small restaurant, you’ve got that special secret sauce, and the only reason why people come to your restaurant is that no one has been able to figure out how to re-create your sauce. You can’t afford to put that recipe online right now. You have to keep that close. 

But if your restaurant is so successful, you can be like, You know what, I’m just going to open-source the recipe for the sauce. It doesn’t matter if we get no other customers. The whole world will have access to the secret sauce. There are some things in the world that are so important they need to be shared.

There’s a buddy of mine who was into conspiracy theories. And there’s a common theme in conspiracy theories that a single person has a piece of critical knowledge. Like they have a way to cure cancer or make AIDS go away. They have some magical medical cure, and the only people who have experienced it are people who have drunk the magical potion this person made, I don’t know, in their living room. But no one else knows the formula. The conspiracy is that the government is out to get this person, the one person in the world who knows how to cure cancer, because how can we allow cancer to be cured when there’s so much money to be made? And that’s why he’s selling it as a potion from his living room.

Man, think about that for a second. I’ve watched enough James Bond movies. What would I do in that scenario? It doesn’t require any 007 skills. All you’ve got to do—if you really do have a cure to cancer, let’s say you really do have it—you can share it. You beat the whole system. 

Tech is infamous for how your job can be your identity. This was really epitomized by the heyday of corporate campuses designed to meet nearly every need workers might otherwise go home for. But a lot of the advice you give runs counter to the idea that you are where you work. Instead, you often advise that decoupling your job from your identity allows you to be more strategic in your career.

Sometimes you’re never going to get the raise at the current company. You may never get the promotion you deserve at the current company. And that’s why you need the leverage of your skills—because then you can take the show on the road and negotiate a better deal for yourself. Ideally, you get to decide what price you're willing to take. But when it comes to the business of being an employee, it’s not fair. Not everyone gets access to all those opportunities. But when they’re present, boy is it a good idea to go out and renegotiate.

What’s the best advice you’ve received from a mentor? What does mentorship mean to you? 

My goal for mentorship is to be the person I wish I had. You can’t be anything you want to be, because society ain’t set up that way. But you can be the person you work at. I know it can be mean. I know it can be brutal. But you can work around the machine, you can confuse the machine, you can make incremental improvements. Life is full of people saying, “This is bad, that is bad, everything is bad.” I’d like to spend some time as a mentor to say, “It’s not all bad.” We can affect some people.

Mentorship can show up in every aspect of your life. When I think long term, I think about my mom. Short term, I also like to talk to people in Lyft rides. The drivers all have interesting things going on in their lives. One time, I was in a very good mood, and I was getting out at the airport, and this guy says, “Your attitude will determine your altitude.” That stuff sticks with me.

Another piece of advice I like, I got while I was at Puppet Labs. I went to present to the engineering team, and I did something that maybe they thought we shouldn’t be doing, or they thought was too hard to maintain. I was feeling a little bummed out that, as a remote employee who flew from Atlanta to Portland, this was the reception I would get for a project I made work. And a coworker told me, “F— all of that feedback. Don’t be afraid of your own power.” The product is still up, and, 12 years later, people still use it. It was a good idea and I’m glad I did it. Don’t be afraid of your own power.

What surprises you in your current work?

Here’s something that caught me off guard. I was doing a fireside chat, telling my stories, answering the technical questions. I’m pretty good at that stuff now. And, you know, you make eye contact in the room and you can see people are tuned in all the way. Afterward, this person comes up to me. He’s maybe 24 or 25. He says, “So I’mma be honest. When I was coming to this thing, I ain’t know who you were. But listening to you speak, I now know who I am.”

To me, that was like—I realized when you can share your life experience, when you can share the things that you’ve gone through in such concrete terms, another person sitting there in real time gets to do a bit of self-reflection and self-evaluation. Maybe you gave them permission, maybe you helped them match the pattern just right and right then. 

Every time this happens (and it still happens) it’s feedback that says, “Kelsey, all this other stuff—all the score keeping, the checking account, all the other accolades—all of that doesn’t matter compared to this. At the end of the day, these are the people who will remember you in a very different way. They’re not going to say, ‘Oh, well, he didn’t have more money than this other person. He only had this job title. He didn’t write that much code.’” They’re going to tell a different story about me. 

At a certain level, you think you’ve said all you can say, you think you’ve done all you can do. There’s still so much work to do, and I know I’m not going to be able to do it all by myself. I’m not going to be able to do it forever. But when this keeps happening, when I hear from people who respond to me telling my story and sharing what I know, that’s why I still do the work. It doesn’t have to scale. I’d rather be slow and consistent than scaled out and temporary.

This is the end mark. You have reached the end!

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