DiscoverScreaming in the CloudReflecting on a Legendary Tech Career with Kelsey Hightower
Reflecting on a Legendary Tech Career with Kelsey Hightower

Reflecting on a Legendary Tech Career with Kelsey Hightower

Update: 2023-08-291


Kelsey Hightower joins Corey on Screaming in the Cloud to discuss his reflections on how the tech industry is progressing. Kelsey describes what he’s been getting out of retirement so far, and reflects on what he learned throughout his high-profile career - including why feature sprawl is such a driving force behind the complexity of the cloud environment and the tactics he used to create demos that are engaging for the audience. Corey and Kelsey also discuss the importance of remaining authentic throughout your career, and what it means to truly have an authentic voice in tech.

About Kelsey

Kelsey Hightower is a former Distinguished Engineer at Google Cloud, the co-chair of KubeCon, the world’s premier Kubernetes conference, and an open source enthusiast. He’s also the co-author of Kubernetes Up & Running: Dive into the Future of Infrastructure. Recently, Kelsey announced his retirement after a 25-year career in tech.

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Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

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Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. You know, there’s a great story from the Bible or Torah—Old Testament, regardless—that I was always a big fan of where you wind up with the Israelites walking the desert for 40 years in order to figure out what comes next. And Moses led them but could never enter into what came next. Honestly, I feel like my entire life is sort of going to be that direction. Not the biblical aspects, but rather always wondering what’s on the other side of a door that I can never cross, and that door is retirement. Today I’m having returning guest Kelsey Hightower, who is no longer at Google. In fact, is no longer working and has joined the ranks of the gloriously retired. Welcome back, and what’s it like?

Kelsey: I’m happy to be here. I think retirement is just like work in some ways: you have to learn how to do it. A lot of people have no practice in their adult life what to do with all of their time. We have small dabs in it, like, you get the weekend off, depending on what your work, but you never have enough time to kind of unwind and get into something else. So, I’m being honest with myself. It’s going to be a learning curve, what to do with that much time.

You’re probably still going to do work, but it’s going to be a different type of work than you’re used to. And so, that’s where I am. 30 days into this, I’m in that learning mode, I’m on-the-job training.

Corey: What’s harder than you expected?

Kelsey: It’s not the hard part because I think mentally I’ve been preparing for, like, the last ten years, being a minimalist, learning how to kind of live within my means, learn to appreciate things that are just not work-related or status symbols. And so, to me, it felt like a smooth transition because I started to value my time more than anything else, right? Just waking up the next day became valuable to me. Spending time in the moment, right, you go to these conferences, there’s, like, 10,000 people, but you learn to value those one-on-one encounters, those one-off, kind of, let’s just go grab lunch situations. So, to me, retirement just makes more room for that, right? I no longer have this calendar that is super full, so I think for me, it was a nice transition in terms of getting more of that valuable time back.

Corey: It seems to me that you’re in a similar position to the one that I find myself in where the job that you were doing and I still am is tied, more or less, to a sense of identity as opposed to a particular task or particular role that you fill. You were Kelsey Hightower. That was a complete sentence. People didn’t necessarily need to hear the rest of what you were working on or what you were going to be talking about at a given conference or whatnot. So, it seemed, at least from the outside, that an awful lot of what you did was quite simply who you were. Do you feel that your sense of identity has changed?

Kelsey: So, I think when you have that much influence, when you have that much reputation, the words you say travel further, they tend to come with a little bit more respect, and so when you’re working with a team on new product, and you say, “Hey, I think we should change some things.” And when they hear those words coming from someone that they trust or has a name that is attached to reputation, you tend to be able to make a lot of impact with very few words. But what you also find is that no matter what you get involved in—configuration management, distributed systems, serverless, working with customers—it all is helped and aided by the reputation that you bring into that line of work. And so yes, who you are matters, but one thing that I think helped me, kind of greatly, people are paying attention maybe to the last eight years of my career: containers, Kubernetes, but my career stretches back to the converting COBOL into Python days; the dawn of DevOps, Puppet, Chef, and Ansible; the Golang appearance and every tool being rewritten from Ruby to Golang; the Docker era.

And so, my identity has stayed with me throughout those transitions. And so, it was very easy for me to walk away from that thing because I’ve done it three or four times before in the past, so I know who I am. I’ve never had, like, a Twitter bio that said, “Company X. X person from company X.” I’ve learned long ago to just decouple who I am from my current employer because that is always subject to change.

Corey: I was fortunate enough to not find myself in the public eye until I owned my own company. But I definitely remember times in my previous incarnations where I was, “Oh, today I’m working at this company,” and I believed—usually inaccurately—that this was it. This was where I really found my niche. And then surprise I’m not there anymore six months later for, either their decision, my decision, or mutual agreement. And I was always hesitant about hanging a shingle out that was tied too tightly to any one employer.

Even now, I was little worried about doing it when I went independent, just because well, what if it doesn’t work? Well, what if, on some level? I think that there’s an authenticity that you can bring with you—and you certainly have—where, for a long time now, whenever you say something, I take it seriously, and a lot of people do. It’s not that you’re unassailably correct, but I’ve never known you to say something you did not authentically believe in. And that is an opinion that is very broadly shared in this industry. So, if nothing else, you definitely were a terrific object lesson in speaking the truth, as you saw it.

Kelsey: I think what you describe is one way that, whether you’re an engineer doing QA, working in the sales department, when you can be honest with the team you’re working with, when you can be honest with the customers you’re selling into when you can be honest with the community you’re part of, that’s where the authenticity gets built, right? Companies, sometimes on the surface, you believe that they just want you to walk the party line, you know, they give you the lines and you just read them verbatim and you’re doing your part. To be honest, you can do that with the website. You can do that with a well-placed ad in the search queries.

What people are actually looking for are real people with real experiences, sharing not just fact, but I think when you mix kind of fact and opinion, you get this level of authenticity that you can’t get just by pure strategic marketing. And so, having that leverage, I remember back in the day, people used to say, “I’m going to do the right thing and if it gets me fired, then that’s just the way it’s going to be. I don’t want to go around doing the wrong thing because I’m scared I’m going to lose my job.” You want to find yourself in that situation where doing the right thing, is also the best thing for the company, and that’s very rare, so when I’ve either had that opportunity or I’ve tried to create that opportunity and move from there.

Corey: It resonates and it shows. I have never had a lot of respect for people who effectively are saying one thing today and another thing the next week based upon which way they think that the winds are blowing. But there’s also something to be said for being able and willing to publicly recant things you have said previously as technology evolves, as your perspective evolves

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Reflecting on a Legendary Tech Career with Kelsey Hightower

Reflecting on a Legendary Tech Career with Kelsey Hightower

Corey Quinn