Kelsey Hightower Fireside Chat: An Unconventional Path to IT and Some Life Advice

Join HashiCorp’s Anubhav Mishra and Nic Jackson as they sit down for a chat with Kelsey Hightower. Kelsey is (in no particular order) a father, an author, a minimalist, a Developer Advocate at Google, and a longtime friend of HashiCorp.

Transcript

Anubhav Mishra: Hello, everyone. Welcome back to the show. This is a new series that Nic Jackson and I are kicking off, called “In Conversation With." We have a very special guest, a friend to the show, almost like family, I guess, at this point. He has spoken at HashiConf multiple times, about all our products, from Vault to Nomad to Consul.

A Quick Story About Kelsey Hightower

I want to tell a personal story to introduce our guest. At HashiConf 2015 in Napa, I was sitting in the front row in the keynote hall. I'm really into schedulers and things like that, and I see this person miked up, and he sits beside me and starts talking to me. I recognize him from YouTube; it's the famous Kelsey Hightower. We started having a conversation. He's super kind, and we take a photo together.

Kelsey goes onstage, does his keynote, kills it, walks down from the stage. I think people were so into Tetris after his talk. People really wanted to talk about how that analogy works with guest schedulers and things like that.

We had a conversation afterwards. He gave me some good advice on Kubernetes. I flew back to Vancouver, where I was based, and resumed my day-to-day operation engineer job. We were using Mesos as a scheduler at that time, and moving to Kubernetes.

Maybe a month after, I see Kelsey in my office. I was like, "What is Kelsey doing here?" He was teaching all our senior engineers, and then I was invited to that meeting too, about Kubernetes. He gave us an intro course on what it's all about. That was really kind of him to fly in. I think he flew back the same day, which is a quite crazy day trip for Kelsey.

From then on I was like, "OK, Kelsey is not your regular technologist, I guess." He’s a person who really cares about people and how they feel and how they perceive technology. And none of his opinions were like, "You should do this." It was mostly like, "You could do this." And that idea is very unique, I feel, in our industry.

Then I Twitter DM'd him and pestered him to review my proposals, and he did. And he became kind of a mentor.

Over the years, I was taking my software into open source.

My first big open-source release was in Portland. It was DevOps PDX. I think ConfigMgmtCamp US was happening at the same time. Kelsey was, again, keynoting at the thing.

He met me, said hello. I said, "Kelsey, I'm speaking. This is my big, new, open-source release." He's like, "When's your talk?" I told him, "It's the last talk of the conference." His keynote was the first talk of the conference. He was like, "I'll stay the whole day."

And he stayed the whole day to watch my talk. And then during that day, he facilitated 3 different panels with a diverse group of people. He encouraged a project that you now know as OPA, which is the Open Policy Agent.

At that conference, one of the creators and I were talking about open source, and he was presenting this idea, and Kelsey was like, "No. You should totally do this. This is a great idea." And now you know this product to be this really big policy engine that people are using today.

There are all these smaller things that define who Kelsey Hightower is. And more importantly, he's a really good friend of mine, and I'm really happy to have him on the show. I would like to introduce staff developer advocate at Google, Kelsey Hightower. Welcome, Kelsey.

Kelsey Hightower: Awesome. Happy to be here.

First Exposure to Computing

Nic Jackson: We're really excited to have you. And we've got, I think, some really interesting questions. I'm interested to dig into your career and your past a little bit, because I think there's so much that folks can learn to help further their own careers.

But I think it's interesting to start right back at the beginning. What are your first memories of using a computer? Do you remember what age and what kind of computer?

Hightower: I probably touched a computer in elementary school, right? You go to school, and they've got Oregon Trail. At that point in time, I thought a computer was a thing that you use for fun. I never thought about being a person writing software or dealing with computers full time. I was into sports and just hanging out with friends.

It wasn't until, I will say, 11th grade that I really got into computers, because I was in this thing called TSA, Technology Student Association, when I was in Atlanta.

As part of that class, we had to do this exploratory world of technology. Photography. We were building bridges and stress-testing them, using AutoCAD to design them. At that point I understood the power of computers.

But it was just something that I was doing as extracurricular. That's probably when I really started to say, "Hey, this is a thing."

I remember writing my first program in TI-BASIC. Everyone had the graphing calculators in school. And that's when I started copying programs. I can't say I was really writing programs, but I remember you would copy the programs, type them in perfectly. And then you could play Snake on your calculator.

Jackson: Were you thinking about computers as a potential career? Or was it something else that had you interested? I was going to be an archeologist, believe it or not.

Hightower: Honestly, I don't know if I knew what I wanted to be in high school. I just wanted to be successful at something; I didn't want to be a failure. You've got to remember, I grew up in Long Beach, California, back when we had the D.A.R.E. programs, just say no to drugs.

And there were a lot of statistics back then, too, about gang life, gang activity. These statistics said, "Hey, as a black male, you may not make it to the age of 25. You may go to jail or die before then."

So a lot of things that were seeded for me growing up were just to get past those statistics; I didn't want to be a statistic. Going into computers was probably the least of my concerns. It was more like: graduate, don't be a failure, and then figure things out. My timeline for what I wanted to be didn't go much further than that at age 25.

First Job and the College Decision

Jackson: Did you go on to college? Or did you just, after high school, go out and get a job?

Hightower: I worked in fast foods from 10th grade on. I got my first job at McDonald's, and I was 15. As soon as I turned 15, I got the work permit signed and I would walk to work right after school, and I would work.

I don't know if it was even legal at the time, but I used to work open to close on the weekends. I would pull in 40 hours, plus overtime if I could get it.

I was living with a single mom, and you try to chip in where you can. Buy your own school clothes, maybe help with the light bill or something like that. At that point, I matured quite a bit. I'm 15, I'm getting straight A's in school, and at the same time I was going to work after track practice, when I was still playing sports.

And going to work, I saw people that were in their 30s and their 40s working at McDonald's.

I kind of understood that this was a good thing for now, but it wasn't the thing that I wanted to do forever. I stayed in fast food, whether it was Subway or places like Pizza Hut, and those were really good ways of earning my own income.

After I graduated from high school, I went to the local community college, Clayton State University in Georgia. Fine university, I think it was growing, or it was a college and became a university. But looking at the classes, I was like, "This isn't me. This is not what I want to do. I don't want to go through this for 4 more years, and then figure out what I want to do."

Also, I didn't want to be in serious debt. I remember I went to the bookstore and got an A+ book. Like, "Hey, I want to get into computers. That sounds like a job that doesn't require a 4-year degree." And I just started studying for the A+ certification from CompTIA. That led to a lot of things before I got my first official job.

But that was the thing that said I could do this, and I had a certification path to prove it to myself.

Early Life Influences

Jackson: I'm interested in early influences. You mentioned that there were people you were seeing working in fast food that made you think, "I don't want to do this for the rest of my life." But back then, or maybe at the beginning of that college experience, was there anybody that stood out? Anybody that you really looked up to, or that you drew influence from? Anybody influential? Manager? Co-worker?

Hightower: Yeah. My mom got married, and my stepfather played a big role, because he had a master's degree. I would always look up on the shelf and see that he had a master's degree, and you would see his Ph.D. also. And he had a thesis that he'd written, and he had it printed out in book form.

So I knew what the bar could be. Even though college wasn't the path for me, I just knew what the bar was.

He was also an entrepreneur. He had vending machines. Back then, you would go get the Coca-Cola machines and stock them yourself, and you could make money that way. And he had various side businesses and real estate.

I think that was probably my first influence: that you can be an entrepreneur. You can go out and define what you want the world to be.

And then just watching my mom. I've told this story in the past about her teaching herself to touch-type after coming home and deciding that, "Look, I want a job, and that job requires me to be able to type at a certain speed."

She just had that flipbook, sitting in there, teaching herself to get there, to that speed.

In the work world, that first job at McDonald's, it took me about 6 months to become the shift manager. So you have this person that's 15 years old telling people when to clock in and clock out.

We didn't have spreadsheets back then. You have this large sheet of paper, filling in the cash drawers as people come in and out, and we would fax those to corporate. And then you would drop the money in the safe, and then of course they would come pick it up.

But you were also in charge of closing the store, making sure everything is locked up, everything is clean and ready to go. I'm 15, and the store manager just kept telling me, "You need to learn these things. You need to learn how to be responsible."

I used to run those shifts at night. He taught me a lot about what it meant to be responsible, show up to work on time, and then be accountable to the team that's under your management. So at 15, I started learning a lot about business, what it takes to actually do the job and be responsible.

First Experiences in Tech

Jackson: How long did your first real job in computers last? What were the trigger points when you started to think, "I want a promotion." How did you go about that? How did you keep developing yourself?

Hightower: It's funny, but when we talk about technology, sometimes we don't talk about the whole person, and we don't understand the whole person. It's really hard to understand the decisions that they make.

For me in particular, my first job was starting my own business. I didn't have the confidence necessarily back then. At this point, I'm 19, 20. And I'm looking at these job openings, and everybody wants 10 years of experience in everything, with acronyms you can't pronounce. And I didn't have the confidence to say, "I'm going to just go walk in there and say, 'This is something that I want to do.'" And I didn't go to college, so I didn't have the internships and that progress. I decided to get a contracting job with BellSouth.

This was when DSL came out. BellSouth was using contractors and paid per job. You would drive out, set up the DSL modem, and hook it to people's computers. And I thought, "A lot of people need other things when we're doing this kind of stuff." So I decided to go out on my own.

I had built up all these business relationships during that time, so I opened a computer store. And what's interesting about that is, when I opened that computer store, it became the headquarters for building PCs, fixing viruses. And I was also able to hire 2 of my friends, and we would go out and get these monthly contracts, where we were the IT department for the local dentist office and the local insurance office.

They would call us whenever they needed another CAT5 drop, or if something were to go down. At 19, 20 years old, you don't have a ton of cash. It's not like the startups, where you go and raise $10 million before you have a business model. This is a world where, if I don't sell computers, I can't pay the rent on the leased building in the plaza we were in.

I only had about $1,000 in disposable, usable income, and I had to make a decision. Do I sleep in my car behind the computer shop? Or do I get into an apartment complex? And I chose to say, " I'm only 19. I don't have any kids. I don't have a family. I can just tough it out."

I did that for a little while. I probably did that for about 6 months until I built the business up to the point where I could afford to get both, and do both, and expand the business just a little bit.

There's a tangent I won't go down, but I also managed comedians. Because I had this business sense, I got into the entertainment business as a manager, helping a lot of the comedians develop their talent and making sure that they got paid for their work.

We'll cover that later, but those were the foundational components so that when I went into the job market, I wasn't looking for a job, because I had already been the boss.

That's a very important mindset that I was glad I was able to develop, because a lot of the stress that I think people go through in the enterprise is believing that they're going to work themselves up a ladder and please the boss. And I know what it's like to be the boss. I have empathy for keeping a business running, and the challenges that a business could face.

When I got my first job, I was more interested in skills than a paycheck. So I bounced around quite a bit. Each of those jobs lasted maybe 3 or 4 months. It was like, "All right. I learned enough here; time to go to the next one."

On Learning New Things and Then Moving On

Mishra: Kelsey, how do you make the leap, though? I didn't know that you had a lot of business sense even before joining the technology industry. But how does one go about jumping into something new? What's the framework that you use to take something on that you might not have done before?

Hightower: At that point, my mentality was, "No one's going to work at the same place for 30 years." It wasn't that I needed to have loyalty at that time. But I knew what you could do with skills. When I learned how to deal with Active Directory and how to do all of these things, I knew that I could turn that into revenue. I saw this as an investment in itself.

My very first job as a contractor was in a Google datacenter. I'm a system administrator. I'm learning a lot about Linux details, how to debug hardware at scale, and I'm seeing, luckily for me, what the very best datacenters looked like.

This is the early 2000s. These are the world's best datacenters. And I'm learning these things in detail, and I start to understand, "Wow. Now that I have these skills, I can go and get a 25% raise by just switching companies."

So that's what I would do. I would just go out and say, "How much are you guys paying? All right. Let's move." It's not your family that you're leaving, and friends will persist longer than a job. Once you have a foundation, and you go interview for the other job and you land it, you're a 2-week notice away from moving up in the world.

On Skills and Personal Responsibility

Mishra: That's super interesting. I feel like, when we don't have family and a lot of responsibilities, we have more tendency to try things. For example, I'm definitely a different person than I was 4 years ago in terms of how I perceive a job and what I want to get out of it.

You mentioned you learned a lot about Linux, and a lot about the operating system level, and I'm sure about how to run a datacenter, and things like that. Power and networking, racking servers, and things like that. So, was that through your teammates? Was that through reading books, checking stuff online? What was the combination like?

Hightower: One thing that I'm always surprised about is meeting people who believe that it's the responsibility of the employer to teach you new skills or send you to training. Early on, I always felt that I was responsible for my skillset. I was responsible for learning.

For me, that meant going to the bookstore every chance I get: Let me get a book on Python, a book on Bash, a book on Linux. Let's do Linux from scratch. Let's do all of that stuff, because I just see that as a mental exercise. If you don't go to the gym, you won't get any stronger.

So at work, when there was a chance to do a new project, I was all over it. It's like, "Who wants to go and swap out RAM in 10,000 machines?" "I'll do it."

And then you learn about single-bit memory errors. You learn how to look at the debug output from the kernel and what that means. And how you can check for these things during the burn-in process.

I just started learning everything possible. And then when I thought I had hit the ceiling, I would have to go and make that jump. So you can learn from your colleagues. You can learn from various opportunities that you see. And normally when those opportunities seemed to die down was when I decided to say, "Hey, it's time to make a move."

Milestones: Being Debt-Free and Becoming a Leader

Mishra: Looking at that phase of your career, where would you say that you thought, "OK, I made it. This is a major milestone for me. I have learned a lot throughout this process. I've gotten good financially. I'm able to take care of my family, myself"? And also felt somewhat of a security blanket?

Hightower: I would say 3 years after opening that computer store. I used to drive a Suburban. I'm only 5 foot 9 and I'm driving this large vehicle. I'm talking about the full-sized Suburban with the barn doors that open from the back. It was a pretty expensive car.

I took the car back. I voluntarily repossessed the car. I went to the dealership and said, "I'm done with this debt and car notes." And they were like, "It's going to mess up your credit." I was like, "I don't care about any of that. I'm going to be debt-free from this day forward." And once I did that, I had enough money to pay the gap, how much you owe versus how much the car is worth. I didn't have a ton of cash, but I was like, "I'm out of this."

I paid the whole thing off. It was like 10 grand more, and then 10 grand out, but no car and no credit cards. And I'm like a clean slate. And that was the milestone when I said, "Now I'm free. I'm never going down this road again. I don't care about buying fancy clothes or shoes or watches or cars. I am done with trying to impress everybody else. I'm finished with that."

That was the first milestone that let me focus on everything else. I would say the next milestone was that I had a job for 3 years before going into the open-source world. Before I was working at Puppet Labs, I used to work in this financial institution, and that gave me a bit of experience of what it was like to work in corporate America.

I stuck around for 3 years because I decided that technology wasn't the only thing I was after. I started to learn how to change an organization, how to stick around long enough to earn the trust in others and to show them that we can do things differently and then actually do it. It takes a while to do those kinds of things.

That was the other milestone. When I left that job, I knew I had transcended the definition of a job or a role, and at that point I felt like I became a leader. I can be in any situation, big or small, and power through it and get us where we need to be.

On Living a Minimalist Life

Mishra: When you said that you paid off your credit card bills and stuff, you didn't want to impress anyone after that. You were going to just be you. Now, on your Twitter profile, people see that you're a minimalist. Did that change happen at that moment, or maybe a little further down the line in your career?

Hightower: No. Debt-free was the milestone, because in order to be debt-free and stay debt-free, you have to change the way you live. Debt-free isn't a temporary thing. It's a thing that you have to maintain.

It changed the way I saved money. It changed the way I thought about money. It changed my relationship with work and time. I started to understand like, why would everyone want to pay me for my time? How much is it actually worth? And once you start to understand that time is probably worth more than money, then you treat both differently. You start to invest in yourself. You spend your time a little more wisely.

Minimalism came later, because what I was doing started to have a new definition. I'd watch other people who had decided to downsize on purpose or focus on only the things that are meaningful. Some cultures outside the US had these philosophies, but my world wasn't about that.

But when I saw minimalism, I knew how to attach the changes I had made to some worth that I can just sum up, really quickly, where I was in my life. That's why I tend to describe minimalism as the foundation for what I'm doing. But I think it came before that.

A Day in the Life of Kelsey Hightower

Mishra: At home, what is the typical day in the life of Kelsey, from when you wake up to when you go to bed?

Hightower: A day is going to be different based on what's happening around you. Over the last couple of weeks, there's been a lot of police brutality, some attention put on things like racism happening in the world and its impact on society. There's COVID-19. So let's talk about a day during those periods of time, because they're fresh.

I like to believe that I'm successful because of the work that I do. I like to believe that I'm successful for the value that I brought to me and others. But then you start to get these reminders that your success can't save you from all the ills of society. And I have to think, "Can I go for a run today?" Because if I go for a run, if I forget my wallet, could I end up in a bad situation? I have to think about those things.

My days are very dynamic. A lot of people see me as a developer advocate who gives talks. That is a small fraction of my job. My job is way more strategic. What products should we be building? What is the market doing? What's the analysis? What's the runway? What's the P&L?

You look at all of these things. If there's a focus on customer adoption, what are you asking them to adopt? You have to understand it.

Part of the job is being technically strong. I still write a lot of code. Last week I started working on a thing to give people bill badges from their cloud bill status. That's a small service that runs on top of GCP, calls the cloud build API, but then generates SVGs so that people can put them in their readme.

Then I will work with the product team to say, "Maybe this thing should be a real feature." So we'll start with an open-source project that we believe is going to be part of the baseline set of features that you need from a bill system. All the popular things have it. And just something about bill status is very important for open-source projects, so you can communicate quickly the status of the particular tree that people are looking at.

Then I'll go into a meeting with some executives from our Fortune 500 and switch gears completely. They don't care about Kubernetes. They want to know what a business relationship with Google looks like. What's beyond the tech? You have to understand their business.

Before those meetings, I have to listen to earnings calls. I look at the stock price. I look at their earnings. I look at their competitors' earnings. Then I try to tease out the most challenging thing to them. Then I look at the HR job openings to see if they're even hiring in the direction for the things that they say they want help on. Because if they're not hiring, then there's a disconnect in the management chain. Now you're ready for that meeting.

From that meeting, I may jump on a podcast, or I'll jump on an interview like this one, where we just talk about either technology or me as a person. And as soon as this meeting wraps, I'll be in a DNI council meeting, talking about inclusion and equity for all Googlers. My day is going to be multifaceted because that's just who I am. I'm a whole person.

On Context Switching and Wearing Many Hats: 'My foundation is I'm a human.'

Mishra: So it's very easy for you to switch contexts. A lot of people have a really difficult time switching context from one thing to the other. They might have a difficult time just switching projects, even if they're just a software engineer working on multiple projects. It's very difficult. What would you say helps with switching contexts?

Hightower: Switching context is hard depending on what your context is. But you've got to remember, my foundation is a human. I'm a human first, so I'm never switching context away from that. It's just a human writing code. I'm writing this code to solve humans' problems.

When I jump into another meeting, it's a human talking to another human about how to solve human challenges. When I'm on these interviews and podcasts, it's my experience as a human who happens to be an engineer, who happens to be a developer advocate.

So it never feels like a context switch, because as a human, you're always context switching, right? Sometimes you're sleeping. Sometimes you're watching Netflix. The phone rings, and you have to decide if you want to answer or not. We're always making these decisions.

For me, my context is not necessarily pinned to being a software engineer.

On Finding Work/Life Balance

Mishra: I guess there is a common route to it. And once you find that route, it helps with everything around it.

How do you balance work and life? How do you go about moving from being a father to a husband to a person who's so visible in the community, who talks to so many people on a day-to-day basis?

Hightower: I love to clean up. The thing that's powerful about cleaning up is that, when someone walks into a room that they didn't clean, they know someone else did it. There are only 3 people in my house, so they can guess who cleaned it.

You're representing who you are as a person when you clean. When I take the time to get the corners or to polish something, you know that when someone walks in, it's nice and clean and healthy, so we can all just be present in it. That's something that I do all the time. That's not like, "Oh, I cleaned this week." No, no, no. That's the thing that is just normal for me.

The other one is just making sure that I'm invested in their lives, too. My wife has a career. She's progressed nicely in her career. I like to learn about her challenges. I'll share what I've learned in my world, and she shares what she's learned in her world.

We're collaborating on our careers, right? She gives me input on my career. There was a time I was going to chicken out on a GopherCon talk. I wrote this poem, a remix of "Still I Rise," by Maya Angelou, and it was called "Gophers Rising."

The morning of, I'm coming out of my hotel room, and I was just freaking out. I was like, "I don't feel like I can go read a poem right now." This was also during a time when there was a lot of visible police brutality in the news. I was just not in the right mental space to even be at GopherCon that year.

I remember coming out of the hotel room. I called my wife and said, "Hey, I'm not going to do it. I'm just going to chill out, lay low." And she said, "OK. We support you." That kind of thing.

About 2 minutes later, she called back. She was like, "That's unacceptable. You give all this advice about challenging yourself, taking things to the next level, pushing through when it's hard, having the courage to do these kinds of things. And I just can't let you off the hook." And I was like, "OK." So I got there and I had found the courage on the walk to the convention center to just give the poem.

I was on that stage, and it was dead silent. And once I'm done, it's important to share the success, right? Because I always tell people, "There's no way you succeed by yourself." That's a good example of having my wife give me that confidence boost, right when I needed it, to go onstage.

And as soon as you're done, the first thing is not to tweet that you killed it. The first thing is to call your family and say, "Hey, I killed it." Or, "I felt good that I did it. And thank you for pushing me." And that keeps the balance, because now they're part of my whole life. I just don't turn them on and off when I go to work.

Advice for Young Techies

Mishra: In terms of advice, there are a lot of young engineers and a lot of young girls, boys, and everyone else trying to get into tech. Graduation this year wasn't the best for folks. What advice would you give in a time like this?

Hightower: Specifically to people new in the industry: There's always going to be something to learn. You're going to have this feeling again, at some point in your career, because you're going to be new to some new technology change. It's not like you're just going to learn the current state of things and be good to go forever.

It's weird to say I'm a senior engineer, but the thing is you can be a mature engineer and be humble enough to know that it's going to be a cycle. You're going to be really good at stuff, and you're going to be new to stuff. And you should always try to figure out a world where you can be new to stuff, because that's how you're going to grow.

Be careful not to go out and get 20 years of 1-year experience, right? You only have a limited time to make an impact, so use it wisely.

The other thing I would say is that, in many cases, you are going to be your toughest critic. You're going to always compare yourself to other people. You're always going to believe that you don't have permission to do a thing until you yourself are the expert. But by that time, it's way too late.

I really got comfortable with learning in public. Just taking that away and just saying that's not going to be a barrier for using my voice, attempting to learn something new or even asking for help. And I would say this, that even later in my career, most of my success comes from being able to learn in public. And that really means a lot, if you understand what that means.

Going to work and saying, "Look, I don't know." Ask a question, and that might save you weeks or days. And if you're saving weeks or days, you can take that time and put it into something else, versus pretending or trying to avoid impostor syndrome.

I would just say make sure that you make the best of it, and you have to control and be responsible for how you level up.

Mishra: Kelsey, this was really an amazing conversation. Thank you for everything that you do for the industry.

Thank you for also considering HashiCorp as part of your family, and we love to have a conversation with you. I know this one was not touching on any technology stack, or Hashinetes, or any topics like that. But we really wanted to explore and learn from you. We really appreciate you making the time.

Hightower: Awesome. Thank you.

Jackson: Thank you so much, Kelsey.