Life is Hard
The greatest compliment I've ever received

At a budget hotel in Lexington, Massachusetts, my team of Air Force reserve officers and government civilians working on AI policy gathered around the bar. We had just finished our annual Department of the Air Force Data and AI Conference and everyone wanted to blow off a little steam. I had prearranged dinner plans with some good friends in Newton and told the team I’d catch up with them later. By the time I got back, they were quite a few drinks ahead of me.
Then two things happened.
I sat down and ordered a beer. I could sense a bit of a lull in the conversation. Clearly, they had all been talking and my presence stunted that conversation. Amidst the lull, an Air Force lieutenant colonel named Chuck said to me, “So, Joe, what’s the best book on motorcycles and philosophy.” It was an easy question to answer. I’ve never even read the book, but surely it’s Zen and The Art of Motorcycle Maintenance, right?
The moment the words left my lips, the crowd erupted with the “OOhhhhhhs!” and “Aaaaahhhhs!” and guffaws that had clearly been simmering just beneath the surface.
I had no way of knowing at the time, but before I had walked in, the gang somehow found themselves talking about Pirsig’s 1974 novel that has now sold more than 5 million copies. In addition to the officers and government civilians in the room, our lead contractor was also present. At the first mention of Pirsig’s book, the contractor—who had never heard of Zen and The Art of Motorcycle Maintenance—was unphased. Any one of us might be unfamiliar with some random, obscure title, after all.
But then the dominoes began to fall. Chuck started to survey the room. Another had heard of the book, but the contractor had not. Then another, and another. At some point, before I returned from my dinner out, someone said “I bet Chapa knows it, too.”
And that is why the crowd erupted in the way they did when I gave my answer. The contractor was not just dejected, but offended. He said—out loud for all to hear—“This has never happened. I have never been in a group of people where everyone knows about a book that I’ve never heard of.”
Then the second thing happened. As I drank my beer at the bar, naively thinking that the intellectual heavy lifting was done for the day, I was approached by a tipsy patron of the hotel bar. At the conference that day, I had given a talk on what I thought the future of AI infrastructure would look like. The talk was mostly well received, but apparently there was one audience member who still had concerns.
He approached my bar stool and slurred his speech. He was a researcher at a federally funded research and development center (FFRDC). These are organizations like RAND, or the Institute for Defense Analysis, or Mitre, or the Applied Research Lab who do research projects on behalf of the federal government.
It was hard to pin down exactly what his criticism was. I think he was trying to say that my prediction about the future of infrastructure was based on the assumption that trends would continue—which is right, of course. And I think he was less confident than I am that trends will continue. It was a reasonable point and I conceded it to him. But then his demeanor shifted and he became (overly) apologetic. He said he was sorry for being combative. (He hadn’t been). He said he was sorry for being rude. (He hadn’t been). And then he left, presumably for his own room in the hotel.
Again, there was a backstory I had missed.
While I was at dinner, the man had told his story to the team. He had made a major career decisions—years ago, in fact—that wasn’t great for his family. He moved from the East coast to the West coast in pursuit of his dream job. But, ultimately, pursuing that job cost him his marriage. And, of course, that bitter loss tarnished the job. So, now he feels like he sacrificed his marriage for nothing.
Most of us were content to shrug off the whole interaction, but the contractor couldn’t let it go. He kept trying to convince us that all that man’s problems were his own fault. If he had just made better decisions. If he had just decided on a course of action and then stuck with it. If he had just seen what his career decisions were doing to his family. If he had just…
I don’t know what it was, exactly. There was something about the whole situation that made the contractor’s criticisms feel barbed and heartless.
The team grew silent and I felt like someone should say something. So, amidst the contractor’s protestations, I looked straight ahead, sipped my beer and said, “life is hard and we’re all doing the best we can.”
But that must have felt like a challenge to the contractor. So, he doubled down, trying now to convince me that the researcher’s lot in life was his own fault. But I held the line and looked straight ahead. “Life is hard, and we’re all doing the best we can.”
And he kept on. And on. And on. And I just kept repeating my new mantra.
“Hey, life is hard, and we’re all doing the best we can.”
“Life is hard, and we’re all doing the best we can.”
“Life is hard. We’re all doing the best we can.”
The contractor ran out of steam before I did and left for his room.
We were alone now, we few remaining government team members and the bartender, washing glasses before closing down the bar.
“Hey,” the bartender asked me, “are you in a position of authority?”
“No, I’m not,” I said; at the very same moment that Chuck said “yes, he is.”
“Well, you should be,” he said.
And that is the story of how the bartender at the budget hotel in Lexington, Massachusetts gave me one of the greatest compliments I’ve ever received.
And so, after all these years, and all these jobs, and all these AI conferences, and all these life experiences, I leave you with a bartender’s wisdom:
Life is hard. And we’re all doing the best we can.
Credit where it’s due
Views Expressed are those of the author and do not necessarily reflect those of the US Air Force, the Department of Defense, or any part of the US Government.



Life is hard and there are some assholes out there!
The bartender's compliment in response to your generous assumption (or rather willingness to withhold judgment) about the divorced researcher aligns neatly with a principal of leadership that has been solidifying in my perspective for my whole career. The principal is that the most important thing that leaders do is facilitate the possibility of both thriving and contribution, and the most important first aspect in this is to not damage or harm people with the potentially very harmful social and institutional power they wield (thus the importance of withholding judgment). The most important second aspect is that they intervene when the powerful social and institutional system is actively damaging or harming people (I wrote about that here: https://soundingslightlyoff.substack.com/p/real-leaders-intervene)
It might sound obvious, but I feel like it's contrary to how many people view leadership, as a practice of only making judgment calls and taking action. I have had too many leaders who would have benefitted the organization and team and individuals more by withholding judgment and taking no action (wu wei).