Learning to Live While Living: Interview with Entrepreneur and Proud Alaskan, Ben Kellie
I originally reached out to Ben after coming across his substack, The Next 30 Trips, and being struck by the impetus for the blog’s origin. Ben writes,“By the time I was thirty, I’d lived a lot of my early dreams: I’d launched rockets, built platforms to land them at sea, traveled, lived in hotels, ate fancy meals — and found myself totally burnt out with no future in sight. I checked all the boxes, did the cool shit, and found it didn’t feed my soul.” It’s true - Ben has an impressive resume. After completing grad school, he worked for SpaceX for several years before leaving to start his own company in the space industry, The Launch Company. Nearly 8 years into that journey, he exited the business and embarked on a two year sabbatical before starting his latest company, Applied Atomics, earlier this year.
I felt compelled to reach out to Ben because he’s seen the other side of success and his writing touches upon something that I believe feels familiar to the ambitious and high achieving among us - the recognition that acquiring the things we’ve been chasing doesn’t necessarily deliver happiness and lasting fulfillment. It’s a recognition that invites us into a more confronting space filled with harder and more mysterious questions: What does bring fulfillment and meaning? How does one actually begin to live a more present and authentic life? How do we embrace the discomfort of uncertainty and slow down enough to be able to find the answers? I wanted to learn from Ben’s experience and get his take on what it’s been like to bring that hard fought wisdom into his latest entrepreneurial endeavor.
Over the course of a wide-ranging conversation, we spoke about:
How the loss of his father defined his first 30 trips
The mental shifts that enabled him to slow down and resist the urge to immediately jump to the next thing during his sabbatical
How he learned to break the hardened shell that had formed around him and get back in touch with the more human aspects of leadership and building a company
What the poet David Whyte’s writing taught him about loosening his grip on control
Finding joy in the process and how that’s enabled him to embrace uncertainty
How he’s operating differently this time around as an entrepreneur
What it means to live while living
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
How would you describe what you do for work?
This was possibly the hardest question you sent over. I think it’s because I’ve had all these visions of what my life was going to be, and then they just shattered. I don't like to admit it, but at the end of the day, I am an entrepreneur. I hate saying it because it feels like everyone in LA in the 90s saying they were an actor. Now everybody in the US is an entrepreneur. Still, I think it is the single best way to describe what I do for work. Other than my own company, I haven't had a W-2 that I depended on since 2015. I'm really interested in flexibility of time, flexibility of location, and diversified income so I guess that makes me an entrepreneur at heart.
I reached out to you because of your blog, The Next 30 Trips, which is about navigating the “next 30 trips around the sun, with an intention to live a more present and authentic life.” Your “first 30 trips” involved working for SpaceX for several years after grad school, starting and running your own company in the space industry called The Launch Company for nearly 8 years, taking a two year sabbatical, and now starting your latest company, Applied Atomics, earlier this year. Looking back now, how would you characterize the journey that you were on during the first 30?
I would describe it entirely as a reaction to my dad dying while I was in college. I had a friend from one of my meditation groups ask me: “What would the theme of the next 30 trips be?” I said, “Memento mori for sure.*” Not in a sad, scary, emo goth sort of way, but more in the sense that I don't think you can appreciate something until you know it's going to end. If you ate 5 star meals every single day of your life, you probably wouldn't appreciate them as much as getting to sit down and know, "This is the only time you're eating at this Michelin Star restaurant."
My dad passed away in 2011 while I was in grad school. I'm a firstborn type-A virgo psychopath, and I spent my childhood trying to please my dad, while also trying to figure out who I was, and really struggling to individuate because I looked up to him so much, and we spent so much time together. When that individuation was forced due to his death, it felt like shifting without a clutch. My response was "Oh, I know what I'm going to do. I'm going to have a big career that defines me, and I'm gonna change the world." Looking back now I can say, "Yeah, you were trying to prove that you weren’t mortal. You were trying to bang the drum, make a little noise in the universe, and prove that you're here.” I think everything I’ve done has been a reaction to that.
*Note: Memento mori is a Latin phrase which means “remember you must die.”
I want to talk about your sabbatical. You wrote a piece entitled “More Than a Rest Stop” about your experience taking a two year sabbatical after leaving the company you founded, The Launch Company. Your writing about fighting the urge to go do the next thing really struck me.
“Throughout this time, I woke each morning with a fresh idea coupled with a surge of near-manic energy to build whatever it was. It was bullshit, of course. A hairbrained plot conjured to escape the long recovery. I pursued a few, but the energy never lasted long. Those “ideas” were nothing more than the bored throes of an overactive mind used to driving forward at all costs, unhappy to find itself relegated to the backseat, disconnected from a body that simply couldn’t go.”
Having worked with clients taking sabbaticals in my coaching practice, I’ve been privy to how intense that time off can be mentally. So many fears come up - being left behind, losing your drive, taking “too long” to find the next thing, and many, many more. Looking back now, what do you think were the most important mental shifts and identity changes you made during that time?
I think there were two really big shifts, which were not born from any sort of wisdom, but rather from being out of other options. I decided to trust my intuition and trust myself. I've always been pretty good at paying attention in the sense of: What's the feeling in this room? How do I feel right now? But I didn't necessarily always trust what those feelings told me.
When I was a lead engineer at SpaceX launching rockets, everyone would tell me that life would be different after the rocket goes up. I ended up feeling worse. It felt like, "Well, what did we really accomplish? I'm the same person." After that happened, I thought, "Oh, I know what I'll do. I'll go build the landing barges." So then I went and built the landing barges. It still wasn’t working. My next thought was, "Well, I'll move home, and I'll start a company." I then sold that company and found myself staring at the same realization again: "Huh! I'm still the same person. These external things aren't curing me." At that point I had to be like, "Well, shit, I've known for a long time that it was all internal problems, but now I guess I really have to face it."
I’d taken mini sabbaticals along the way before the big one. I took a leave of absence from grad school while my dad was dying to take care of him. At that point I’d already had the thought, "I don't even really want to be an engineer.” I loved the tool sets that I was learning, but I knew in my heart that it wasn’t a true calling. One thing I often say very openly now is that if I had any courage at all I would have been a writer, but I didn't trust that I wouldn't just starve to death. I didn't believe I could make it work, and I didn't trust myself to find a way.
Then, after grad school, I had this really clear moment of defending my master's thesis, followed by eating a slice of pizza, laying down in the quad, and thinking, "Oh, my God! I'm done! I can't believe I did it." It was so hard because even though I’d taken time off to be with my dad I still finished on time. I really didn’t take the time to mourn him properly. Then, the next day I woke up and was feeling antsy so I said, "I know what I'm going to do. I'm going to write a Matlab script that takes landsat data and scales it so that you can 3D print at any location on Earth."
I think that was my first indication that I was avoiding something. Not too long after that, I started at SpaceX which dominated all my attention. Eventually, I left SpaceX and moved to Seattle, and that was when stuff around my dad really started coming up. Being a hundred percent honest, I wasn't able to deal with it then. My whole identity had been tied to being a space engineer so when I got the call to build the landing barge, I immediately took it and fled from facing those feelings.
My personal motto is, "I'm dumb, but I'm not stupid." I had to accept this time around that I would get antsy and have a million ideas, but I now knew that those ideas weren’t real. It's like falling in love with every person you meet at the bar, right? Maybe you have a nice little moment, but it’s probably not a thing. I had to realize that the discomfort was the process, and I had to be okay with it.
You were an entrepreneur, and now you're an entrepreneur again, but it sounds like your identity is materially different. How so?
My wife is from New Orleans and I love the concept of lagniappe.* I'm just treating everything as lagniappe and saying, "Well, you know that this isn't going to solve the big existential questions that live in your little heart, but building this company could be a ton of fun and a path of discovery.”
The shift that I'm trying to grapple with is that the work happens inside, but we move externally through the world as a way of processing that work. The original issue is that I was expecting external validation like, "Here I am, life. Knight me, tell me I'm special, or prove to me that I'm one of God's best little guys." At a certain point I realized that wasn’t happening. The approach now is, "Yeah, man, you’ve got to do the internal work.” I could sit in a cave for 40 years and meditate and get there, but I'm trying to do it while moving through the world. The idea of trying to see everything as lagniappe is really about being able to say "Well, you've already done the things that you know don't work so now just enjoy the ride."
*Note: Lagniappe is a Cajun-French word that means “a little something extra.”
In a piece called “Carcinization,” you write about the intensity of working in the space industry for over a decade and your recognition that you didn’t want the shell you found hardening around yourself to continue hardening.
“As more responsibilities landed on my plate — running systems, to running teams, to running entire projects like the landing barge — I had less and less emotional reserves left to deal with the human element of my role. Further, as the pace ramped up, I didn’t have time to properly guide people or care for myself. There was never enough time to properly explain things, to onboard people into new roles, to even stop and have a complete thought. I ate my meals on the go, doled out my orders on the go, and meted out my version of perceived justice on the go. Where once there was space for thoughtful conversations and advice, there remained only room for curses and rushed impatience with everyone and everything around me that wouldn’t match the speed with which I conducted my life.”
I think many entrepreneurs find themselves in a similar space, hardening themselves to withstand the pressure and criticism that comes their way and, in the process, losing touch with the human aspects of leadership and running a company. What were the biggest shifts you made in breaking the “hardened shell?”
I think the impetus was my kids. What really pulled me out was watching my son and daughter and saying, "Well, these guys are having a great time, and they're here right now, and at the same time they're only 9 and 4, and they're only going to be 9 and 4 for 12 months. They're different people every day, and I want to be here with them.” I realized that even when I was with them, I wasn't living the same life they were. I thought I was doing a great job. I would say, "I'm at dinner every night, I pick them up from school, and I spend all this time with them,” but I wasn't happy at work and that extended past work hours, and distracted me from being present with the kids.
That was another moment of being forced to notice something. I think that one of my superpowers is that once I finally learn something, I live it. I said, "I can either keep doing this and be miserable, and it's not gonna work out, or I can try to fix it. Maybe it still doesn't work out, and I end up in the same place anyway, but at least I'm a little bit happier."
That's where the pushback started to come from. Being 100% candid, it was also coming from the fact that people I was interacting with professionally, especially clients, were reminding me of toddler children. I felt like I was parenting other people’s kids all day long, and my actual kids were a lot better behaved. I said, "I think I'm done raising other people's kids."
Ultimately the shit rolls downhill. They're in a toxic stressful environment, and it's rolling down to me as the contractor. I had to take down the crispy crab-like walls, but I still had to put up some protection by saying, "Hey, I'm here to help you" and "I just can't do it anymore this other way."
The crazy thing is we started getting more business because of it. Instead of letting the words and everything bounce off a hard shell, I let the words and the emotions in without absorbing them. The absorption is what really gets you. If it was truly all bouncing off, you'd just be like the guy from Office Space walking through life like everything is awesome.
In your piece, “Slow,” you write: “I struggled to let go of the illusion of control, the thought that my constant attention was what enabled our company’s success, and the idea that the team always needed me engaged. Finally, though, I realized that my team didn’t need me at my most they needed me at my best. My best wasn’t working 12-hour days. My best wasn’t stressing over every small detail. My best came when I was rested, centered, calm, and engaged. That meant slowing down.” You talk about how letting go of the illusion of control took you years (and still takes frequent reminders). What shifts or realizations were most impactful in your journey to easing your grip on control?
I think it was reading David Whyte, honestly. I listen to What to Remember When Waking yearly. He'd been a corporate engineer and left that life behind to become a writer. Like I said earlier, if I had any courage at all, I would just be a writer. He’s someone I look up to because he actually made the shift and had the courage.
There’s this great story in there where he's running around frantically because everybody's at the meeting except for David, and he can't find David. My visceral response was, "Oh, man. I feel that." When I ran out of options, the cure finally felt less painful than the disease. I began to sit down, go to therapy, meditate, exercise, and eat healthy food.
As I said before, I’m dumb but not stupid. I finally had to grapple with the question: When am I going to stop doing all of this? I realized that it was easy to let go of a person I didn't like. I didn't like being the guy that goes too fast, drinks a pot of coffee a day, and then drinks a bunch of beer at night to wear off the caffeine. I had to ask: Is this me, or is this some story I'm living? I realized more and more it was some other character I was living. I let it all go, and now I drink 25 bubble waters a day.
I think the funny thing about control is that you can’t really say, "Okay, I'm done with control. Now I'll never feel the need for it again." I think it's one of those things that you're constantly having to practice and relearn. When you find yourself shifting back in that direction of moving too fast and seeking control, what helps you reset?
It's a great question. Again, back to David Whyte. The paraphrase of what he says is, "Any life that is small enough to plan, or that you could plan, is too small to live." I remind myself that life is a lot better at creation than I am.
As I started to relinquish control, I saw the positive aspects almost immediately, and I realized that I was holding myself back by trying to control every experience. A great example is the company I had before Launch Company. I had a little drone company called K2 Dronotics that actually became The Launch Company because nobody would hire me to fly a drone, but everybody was calling to hire me to design launch sites. As I let go of control and let the business evolve from what I thought it should be to what customers actually wanted, things really started to move. Again, it was being willing to notice and act on what I noticed. It isn’t easy, and it’s something I have to constantly remind myself of and practice.
What were some of the biggest changes that you began to notice when you started loosening your grip on control?
Life was a lot more interesting. Not to turn this into a relationship blog, but I kept dating the same type of person over and over again, with the same result. Eventually I had to ask myself, "Hey, man, how's this working out?" The answer was obviously, "Not good." I decided, "I'm done dating. I'm going to focus on raising my daughter, and I'm going to focus on me." Then just a few months later, I met my wife, we became long distance friends, I invited her to road trip to Alaska, and she moved up. The rest is history, and it’s been an amazing adventure. I thought, "Wow, if I had tried to plan that or control that, it wouldn't have happened.” I also lost 50 pounds from not worrying as much, having crazy cortisol levels, and soothing through carbs and alcohol. I just woke up in the morning and felt better.
Related to seeking control is the idea of grasping for certainty. In “Waiting for Certainty,” you contend:
“If you wait for certainty, you’re going to be waiting a long time. Of course, that’s not an excuse to go forth, move fast, and break things being sloppy, either. The means matter, after all. Instead, we just have to make the best decision possible in the moment with the information on-hand, then be ready to iterate. If you can overcome the tempting tendency toward the false-safety of squishy KPI’s, compound metrics, and endless discussion and instead continue the march toward your literal, or metaphorical, launch day, then you’re golden! All that’s left is to focus on hitting the ocean, which is another challenge altogether.”
What realizations or insights have helped you get comfortable making decisions with the information you have at hand rather than getting stuck in endless planning and discussion cycles?
I think that is actually natural for me, because my dad was a bush pilot in Alaska. Every time you get in the plane, it's a new situation. If you treat it as a routine with certainty, Alaska is sure to humble you. Being able to adapt as things change is something I’ve always been good at. We were out on a camping trip one time and ended up getting weathered in for an extra week or so. We were out of food and literally scavenging berries and trying to catch fish and stuff. Even at age 8, I knew we’d figure it out. So, a comfort with uncertainty is fairly baked in. The final thing I’ll say is that I enjoy the finding out part. The ultimate answer has never been that satisfying. The process is what's satisfying. Selling a company wasn’t what I thought it would be, but the journey of building that company with friends was fun. I actually think certainty is kind of boring, and life's a lot more fun when it's just happening.
I have to ask how you operate tactically because I'm super curious. How do you approach long term planning and stuff like KPI tracking in your company?
Strategically, we start at the end, and we work to now. Tactically, we have OKRs and KPIs because our investors want them. What I saw a lot of at The Launch Company’s clients was people building beautiful spreadsheets of OKRs and KPIs, and then wrapping those metrics around themselves like a security blanket. Many of those companies ended up running out of money and died. OKRs and KPIs have their place, but it’s easy to miss the forest for the trees.
I think about it in terms of the Alaska Bush pilot mindset which is basically, “We're putting together a flight plan, but do we know where every single cloud, ice storm, bump, or other airplane is in the sky? No, we do not.” I think you do need a plan because winging it can quickly turn to chaos, but you do have to be able to adapt your plans. We put together plans annually that look a few years out so we’ve got our flight plan, but we're very adaptable in how we get to each of those things now.
You started your current company, Applied Atomics, earlier this year. I was intrigued by the questions you posed in “More Than a Rest Stop” regarding approaching work differently this time around. You asked, “Can a startup be built while remaining in balance? Rather than pursuing work as an end (selling companies, boosting ego) can it be a Way? How might our work inform the larger Work of our lives?” How are you pursuing work differently this time?
I'm very much figuring it out right now. We incorporated in January and raised a pre-seed. I had never raised venture capital before and was actually against it for a lot of businesses. I think it's a very powerful tool in the same way that chemotherapy is a very powerful tool; it can kill you or it can save you. It’s a tool, but it has to be used in the right way.
A company is a bunch of people with the same goal, and we are organized in a company because that's the system we live in. If I’d been born a 1000 years earlier, I’d be organizing people in a completely different way. At the end of the day, I think a company represents the intersection of people’s energy and ideas, and I see my job as managing that energy. That means no assholes because assholes wreck the energy. It also means keeping people's energy up.
One of my favorite books is Wind, Sand, and Stars by Antoine de Saint-Exupéry. He’s got the famous quote about building the ship*, and that’s really what I think a lot of my job is. People are investing their time to build this company, so I have to be clear on what we’re building and why. We are absolutely going to have to work hard, but it comes in ebbs and flows. There are people I know at some hard tech companies who are bored to tears. They say things like, "We don't do anything. I make good money, but we just go to meetings all day, and we're not building.” On the other hand, you talk to people at SpaceX who are like, "I forgot what my partner's face looks like, and I don’t know my children’s names.” Those are the bounding cases, and I’m trying to land us in the middle.
I think about it like exercising. If you told me I had to wake up fresh out of bed and sprint every day for 8 hours, I'm just not gonna do that, but there are some days when a sprint feels really good. You stretch your legs, feel strong, breathe the fresh air, feel the sun on your face, and it feels awesome. You just don't sprint every freaking day. On the other hand, if I told you to get up and go for a walk every day, some days a walk may be the most restorative thing on earth, but if you had to literally walk all day every day, it could turn into a death march. The key is variety and balance.
*Note: The quote from Antoine de Saint-Exupéry’s book is, “If you want to build a ship, don't drum up people together to collect wood and don't assign them tasks and work, but rather teach them to long for the endless immensity of the sea.”
How are you approaching your role as the leader of a company differently this time around?
I think Launch Company was the experiment to see if I could build differently within aerospace. We gave a lot of young people in Alaska their first real engineering jobs. We hired launch experts around the US with experience to work with those young people and gave them a lot of freedom and flexibility. I think one mistake I made was not being willing to have some hard conversations early enough. I want to have those hard conversations earlier while maintaining my humanity. I think that when you’re leading a company, it can feel like your job is to eat bad news and solve problems all day long. It’s really easy in those instances to drain the emotional well and become burned out and angry.
My biggest focus is becoming worthy of this work. I have to deepen my emotional well so that I can have those hard conversations. If I know a hard conversation is coming, I need to make sure I can go for a walk, breathe, or do something to center myself so that I can have the courage and the emotional reserves to have the hard conversations earlier. Not doing that hurt my last company. We kept people way too long that weren't happy, and we weren't happy, but we were working so hard to make them happy. That doesn’t serve either party well.
Many people I interview for the No Directions blog have created lives that are uniquely theirs in terms of how they live, work, and build their lives. What does the life that is uniquely yours look like today?
As a kid, I remember being so worried about the idea of, "I'm going to be an engineer. I'm going to sit at a desk from 9 to 5, and then I'm gonna wake up and be 60." I expressed that fear to my dad when I was 18, and he laughed like this big belly laugh, and said, "Son, if that's what you're worried about, there's no way it's gonna happen.” I really rebel against the current American way of working and living that we’ve had for the past 100 years, and the belief that this is how it has always been and will always be. That has never sat well with me, and it’s definitely informed the way I’m living and building now. There are many amazing lives to live, and I’ve been fortunate to cycle through quite a few in the first part of my life.
I’m always thinking about, "Well, how can I work on Alaska? How can I be a good example to a place I love? How can I be a good example to the children I'm trying to raise?" I went through a lot of painful lessons to figure out who I think I am, or at least to figure out who I'm not, and so I’m trying to be intentional about honoring that. I guess what I’m saying is that I’m really trying to live while I’m living instead of trading this lifetime to achieve some goal that doesn't ever really come.