Author: Robert Schlaff

On the value of trading things you can’t buy.

I was flying out to California last week for the Collaborative Gain conference and ended up next to a guy who was actually reading. He wasn’t scrolling or multitasking. He was on a Kindle, deep in his book, and stayed that way for a long time. He looked about thirty. That kind of focus is rare enough to make me take notice, like a the way a startup CEO might be wearing a hoodie and a Rolex.

So I did what I usually do when something interesting is sitting three inches to my right. I waited for a natural break and asked him about the book. It was a novel, and he seemed a little embarrassed to be reading fiction. I figured out why when I asked him what he did. He’s a Navy SEAL.

Turning thirty, eight years in, Team 5, based in Coronado just south of San Diego, which turns out to be one of the two main bases for SEALs in the country. The way he talked about it was very matter-of-fact, the way a plumber might tell you he does mostly commercial work these days. He loved his job and he loved his teammates, though he couldn’t tell me anything about what he actually did.

He went to the Merchant Marine Academy and met his wife there. She’s still a Merchant Marine. He did ROTC and was on track to be a commissioned officer, then realized that if he actually wanted to be a SEAL, he had to give up the officer track and enlist. He also liked the idea of picking up specific skills, or quals as the SEALs call them. One of his favorite quals was as a SEAL medic, battlefield doctor.

Now he’s applying to Navy med school. The Navy has a program where they run you through a two-year pre-med, then send you through med school, then you do your residency as a Navy doctor. Add that to the eight years he’s already done and the time on the other side, and he hits a twenty-year pension right around the time he finishes residency. He’ll walk out as a doctor with a pension.

I asked him what kind of medicine. He said, “Anesthesiology would be the smart move, but I kind of want to be a trauma surgeon.” I said something about trauma surgery being brutal, long hours, not the money of the quieter specialties. He shrugged, and said, “Yeah, but I’ve got an ego. I’m a SEAL.” He knew it was just his ego talking, and was probably going to go with anesthesiology.

Trauma surgery and anesthesiology seemed like such different things, but to him they were pretty similar. Trauma surgery was easier than you’d think because it’s like battlefield surgery with no one shooting at you. He was impressed with battlefield anesthesiology, because those guys have to intubate someone who’s just been blown up. I asked about the residency part, the famous thirty-six-hour shifts. When was the last time he’d been up for twenty-four hours straight? He said, “Friday. I was up until four to finish a qual and then took a flight at seven.” That thing med students find crushing and horrible, he does it for fun on a weekend.

At some point I realized that he might have a challenge coin. My son Blake and I collect challenge coins. We pick them up during Fleet Week at the Intrepid, and it’s become a small family thing we do together. I even have one from a space launch. So I told him about our family project. He rifled through his bag for a minute with a half smile on his face, and pulled out a SEAL Team 5 coin. The actual handoff was awkward on my end. He tried to pass the coin to me, and I blanked on how this is supposed to work, which is palm-to-palm during a handshake, the coin pressed discreetly into the other person’s hand. He handled it gracefully and gave it to me again, this time with the handshake, the way it’s meant to go. There’s something I love about that tradition, the idea that a coin carries a unit’s history and you hand it to someone as a kind of keepsake for the experience behind it.

I had a few copies of my book in my carry-on to sell. I gave him one. He tried to wave it off and told me I should keep it if I needed it, that he was happy to give me the coin anyway. I told him no, this was the fun part. We’d both just handed over something we were proud of, something we’d earned. His coin took eight years of service. My book took five years of evenings and weekends. Neither one was the kind of thing you could buy.

I’d spent the whole flight being amazed by this guy. The focus, the career, the quals, the staying up until four on a Friday because that’s just how the week went. Everything about his life was something I couldn’t comprehend doing. And then I was standing there holding his coin, and he was standing there holding my book, and it hit me that the admiration ran both ways.

He reads fiction because he just can’t get into non-fiction. He told me his living room has a giant bookcase, and he only puts books on it that he actually loves. If he reads something on his Kindle and it matters to him, he buys the physical copy to put on the shelf. He took a non-fiction book from a stranger on a plane and was genuinely glad to have it. I can’t be a SEAL. He can’t write a book. We’d each spent years making something the other person couldn’t make, and for a couple of hours over the middle of the country, we happened to be sitting close enough to trade.

We took a picture after we got off the flight. Me holding the coin, him holding the book. I’ll keep that one to myself, because posting a photo of an active SEAL online seems like exactly the kind of thing a SEAL would prefer I not do. I’ll admit I also took a surreptitious shot earlier in the flight, which in retrospect was an extremely stupid move. The man is a trained operator whose professional skill set includes noticing things, and if he’d caught me and cared… well let’s be thankful he’s such a nice guy.

If you want to learn more about challenge coins and the traditions behind them, 99% Invisible did a great episode on the subject.

There’s this thing that happens on crowded sidewalks in New York. Two people are walking toward each other in a rush, both trying to navigate around the other. One steps left, the other steps left. One corrects right, the other corrects right. And suddenly you’re doing this little dance with a stranger, each of you making it worse by trying to fix it.

I heard something recently that reframed the whole thing for me. The problem isn’t that people are clumsy or oblivious. The problem is that two people are both trying to control the same thing at the same time. Both are trying to help. And it creates a gridlock where they both end up blocking each other. One of them has to let go.

So instead of trying to solve the problem and evading the other person, I tried something different. I started doing nothing. I slow down slightly and let the other person choose. They make a move, I follow, and we’re past each other in a second. The hard part is that slowing down feels wrong. Every instinct says to move, to fix it, to be the one who figures it out. Standing there, barely moving, while someone walks toward you feels almost rude. But that discomfort is the whole point. The moment I stop trying to solve it, it solves itself.

And the failure mode, the case where both people let the other choose, seems like it would be horrible—no one would move. But actually it’s fine. We drift past each other slowly, a little awkwardly, and nothing bad happens. No collision, no real delay. The worst outcome of doing less turns out to be pretty manageable.

But it’s not just about sidewalks. I was talking to a friend recently who said, half-joking, that he needed to do less. He meant it as a complaint about being overloaded. I took it as a goal.

Oliver Burkeman makes a version of this argument in Meditations for Mortals. He pushes back on the idea that importance and difficulty are the same thing, that if something matters it should feel hard, and that easy means you’re not really trying. He offers a different question: what if this were easy? Not as a feel-good slogan, but as a way of living. What if you built your life so that the default was things that felt natural and really wanted, and the hard stuff was something you looked at deliberately and decided was worth doing.

I’ve been trying to live this way. I’m doing less and holding things more loosely. I’m noticing when I’m doing that sidewalk dance inside my own head, overcorrecting, making things harder than they need to be. The goal isn’t to stop caring. It’s to stop treating caring and straining as if they’re the same thing. When I’m doing something because I want to, I’m better at it. Not because I’m more focused or disciplined, but because I’m not fighting myself the whole time.

Getting out of the way is a skill. Whether it’s on the sidewalk or in my own head, I’m still learning it.

This really is unfair.

I spent last year working on myself—figuring out how to relax, how to unhook from things that were bothering me. I read The Happiness Trap and Feeling Great, and I was well on my way to cleaning up the issues in my life.

But now that things are cleaned up, I have a big problem—one that everyone has to deal with at some level—the existential question of, “What should I be doing with my life?”

Jean-Paul Sartre wrote that we are “condemned to freedom.” It’s a quote that seems a bit glib—the kind of thing an aloof Frenchman in post-WWII Paris would use to pick up women in a cafe. But it’s an incredibly powerful idea.

We normally think of freedom as a blessing. We live in the USA. Freedom is our birthright—as American as mom and apple pie. But we tend to view freedom as pushing back the things that we don’t want to do. However, freedom also means we have to decide and be responsible for the life that we lead.

And that’s terrifying.

As I tried to answer this question, I’ve discovered that there are three levels of the answer, each one more abstract and fundamental.

Level One: Big E Existential—The Goals That Give Life Direction

This is what we normally think of when we think of existential questions. Am I accomplishing the things I want to accomplish? Am I doing things that really matter in the long term?

I like to use the model from Acceptance and Commitment Therapy (ACT). In ACT, the answer is simple: figure out what you want to do and then spend your time doing it.

I use a Bullet Journal for this.

It gives me a simple way to plan for the future and make sure I stay on track, making sure that I’m spending my time on things that matter.

It also helps me understand that I’ve used my time well and done things that are aligned with my values. You see, I have an awful memory. Without my Bullet Journal, when I look back and think about last week, I often can’t remember what I did. I’ll feel this existential void like I hadn’t done anything at all. And when I feel like I haven’t done anything that matters, I panic and overcorrect. I hyperfocus on some new project or goal. I feel like I need to fill this huge emptiness with something bigger, something important. But this whipsawing between projects means that I accomplish even less—leading to a vicious circle where I actually am getting less done. With my Bullet Journal I have an accurate accounting of what I’ve done and see if I’m living my goals. If not, I can just slowly adjust and point back at my goals.

But here’s what I discovered: even when my Bullet Journal showed me I was accomplishing my goals, something still felt missing. That’s when I started to understand the second level.

Level Two: small e existential—The Moments That Make Us Real

There’s another type of existential meaning that’s just as important but harder to pin down. It’s about being seen. It’s about the small moments each and every day where someone recognizes who you really are. It’s about existential validation—that feeling of truly being seen because someone recognizes the authentic you.

I learned this from someone on my team—actually a combination of people on my team over the years. Let’s call them Jamie. Jamie was very competent but since graduating from college a decade ago, they’d never been given a chance to grow, leaving them with a feeling that they weren’t good enough. They even told me they wanted to work on their self-confidence.

At our first team meeting they introduced themselves. “Hi, I’m Jamie,” they said, in a monotone voice. “I’ve been at the company for 5 years. And well, that’s about it.” They finished quickly because they didn’t want to waste other people’s time—because they’d been trained that they weren’t important.

So I worked with them—starting with that introduction they made. It’s a short little speech but it sets the tone of how other people will think of you. I had them practice it at the beginning of each 1:1 meeting we had. I did my own intro as an example.

They quickly started to get it. They started to own their story, be proud of themselves, and the work they did. They stopped looking like a shrinking violet and blossomed into a beautiful flower.

After a few months, they wrote, “Thank you so much for working with me on my self-confidence. Your support, not just one time but over many meetings, made a significant difference for me, both professionally and personally. You really listen to me and tailor your guidance to what I really need. You don’t understand how rare that is in a manager—at least in my experience. I’m so privileged that I can share my problems with you, knowing that you’ll come back with solutions that will really help me out.”

Watching Jamie transform taught me something about myself. All my carefully tracked goals couldn’t compare with that moment of genuine connection. When Jamie looked up from the practiced introduction with such pride—I’d made a ding in the universe.

But even this wasn’t the full picture. Because to truly be present in those moments—to really see Jamie and be seen in return—required something deeper.

Level Three: The Self Underneath It All

All of this comes back to an idea that’s part of many traditions—that there’s a true transcendental existence underneath everything else. Ralph Waldo Emerson talked about this as transcendentalism, this idea of touching something deeper in yourself. Julia Cameron, in The Artist’s Way, calls it “The Creator.” Religions call it a soul.

The point is, there’s something inside people that’s bigger than us. It’s really hard to explain cognitively, but you know it when you feel it. It’s the difference between going through the motions of life and actually living life.

ACT therapy calls it “the self” or “self-as-context.” It’s the underlying you that’s really there. So in ACT, you’re not anxious, you’re noticing the feeling of anxiety. You don’t feel like a failure, you’re noticing the feeling of shame and sadness that you didn’t accomplish something. That true you is always underneath, always there noticing the things that happen in your life and making decisions about it.

Here’s what I’ve learned: this deeper awareness—the ability to step back and notice what’s happening—creates the space where I can make the right decisions. Without it, my Bullet Journal becomes list of To Do’s and mentoring others becomes a task I should do for my annual review. But when I’m grounded in that self that notices, I have room to choose. I can decide to do things that align with my values as opposed to just respond to my anxiety. I can genuinely connect with the true self of other people. That space—that pause between noticing and reacting—is what makes the other two levels of meaning possible.

But when I’m grounded in that deeper self—the one that’s just noticing—everything changes. I can look at my journal without judgment. I can be with Jamie without trying to fix anything. I can just be present with what is.

You can try this for yourself, if you know how to meditate. Try meditating and noticing some things. Then ask yourself “Who is doing the noticing?” It’s quite an experience if you can get it right.

This may seem clinical and exhausting, but it’s actually the opposite. It allows you to be truly present in the moment. This is the only way to not be buffeted by the outside world and do things that you think are important to you.

So here’s what I’ve learned: existential meaning isn’t one thing. My Bullet Journal gives my life direction. Those moments with Jamie remind me I’m not alone. And that deeper awareness—the self that notices—makes both of those work without turning goals into obsessions or connections into performances. The easy thing is to avoid the question entirely, to let other people’s goals fill the void. The harder thing—the thing I’m still learning—is to live on all three levels at once.

Sartre said we are “condemned to freedom.” We are condemned to responsibility and making choices. Albert Camus had a different take on existential suffering—that it’s all futile. In The Myth of Sisyphus, he wrote about the Greek king condemned by the gods to roll a boulder up a hill for eternity—only to watch it roll back down each time he reached the top. But Camus concluded, “One must imagine Sisyphus happy.” Even though Sisyphus was condemned to never achieving his goal, he didn’t have to be unhappy. He could find meaning in the struggle itself. That’s what these three levels give us—ways to create our own meaning through the goals we pursue, the moments we’re seen, and the self that does the noticing. It’s still unfair that I had to figure this out. But at least now I have a map.hat I had to figure this out. But at least now I have a map.