Philosophy

In May 2014, I flew the nest. Courtney and I found a one-bedroom apartment in the college town of Tempe, Arizona. Rent was $758 per month. Before signing the lease, I called my mom and asked her if she thought I could afford the $379 per month, my half of the rent.

“Well, honey, you have to calculate your monthly expenses. Can you afford it?”

I thought about it. “I don’t know? I think so?”

The day after we moved in, I figured I should get a job. Courtney would appreciate that. The store where I’d been slinging wine and liquor was now an hour’s drive away, so I needed a closer gig.

Around that time, Courtney’s friend from grad school visited. I took it upon myself to show him around his first day here, as Courtney had to work. “Don’t forget, you have to get a job today,” she said as I got in my car. “Oh yeah, thanks for the reminder!”

I wasn’t being sarcastic.

As her friend and I drove around, I looked for jobs. I had experience waitressing, so I stopped in the first sports bar I saw and asked if they were hiring. They were. I could start tomorrow. Sweet. Done with my to-do list for the day!

We drove around some more, and Courtney called. “You won’t believe it,” I told her. “We’re driving by this playground and there’s a rope structure thing that’s, like, three stories high. And kids are climbing to the top. You’d think their parents would be around…” 

“I thought you were getting a job today.”

“Oh! I already got one!”

I was proud of myself. Getting a job could have taken an entire week. And I did it in one day. Before noon!

Fast-forward a few months.

I had become more serious. Responsibility will do that to you. I had a 9 to 5 now. Office job. Sales. The work was stressful and the hours long. But the money was good. If I kept my foot on the gas and kept working harder and faster, I could make more money and buy lots of nice things.

Throughout the next few years, making more money was my only goal. But no matter how much I made or how much I “accomplished,” I was still empty. Was life really just a continuous sprint to acquire bigger commission checks and bigger houses? To go on fancier vacations? That is what I’m spending the majority of my waking hours pursuing? It didn’t make sense to me, but what else was there to aim for? Life started to feel like a sick joke.

One day in 2016, on my way home from work, drained from another day of trying to decipher the meaning of life between an onslaught of phone calls, I was listening to an interview Tim Ferris had with Ryan Holiday, and he said something that shook me. 

Ryan was talking about Marcus Aurelius and how, as emperor of Rome 2,000 years ago, he had been the most powerful man in the world. He could have anything and do anything he wanted. And yet, unlike almost every example I’ve seen of someone with wealth and power, he wasn’t concerned with what he could buy or how many women he could sleep with or how popular he was or any of the other multitude of pleasure traps those with too much time and money ruin themselves in. You know what he was concerned with? How to be a better person. How to control his anxiety and desires. How to do more for people. How to do the right thing.

Whoa. 

It’s one thing to strive to be a better person. It’s another to strive to be a better person while also in a position of absolute power.

Marcus Aurelius, Ryan said, sought something higher than greatness. He sought goodness. And to miss this next point would be to miss the point entirely: it was his goodness that made him great.

Of course, I couldn’t fully grasp the implications at the time. Still, the contours for a different model of success were forming in my mind. Maybe there was nothing inherently good in what I was pursuing. Perhaps that was the problem, the source of my frustration. A meaningful life has a purpose beyond itself. It has a north star, a destination we’ll never quite reach but should always be reaching for. We must pursue something higher, or we’ll walk in circles. Or worse, spiral down.

I immediately devoured everything on Stoicism, though I’m not sure it would have impacted my life as significantly had it not been for Ryan Holiday. He contextualized it. He made it accessible. He championed its validity—something no one was doing with an ancient philosophy—and showed how it’s just as relevant today. 

His advice was pragmatic. He didn’t say, ‘Stay positive and you can do anything you put your mind to!’ He said, “Yeah, things might impede your path, but nothing can impede your will. You can turn any obstacle into an advantage.”

He was explicit. He didn’t say, ‘Humility is good.’ He said, unequivocally, Ego is the Enemy. It was pointed. You couldn’t ignore it. You had to either accept or reject it. (It took me a while to fully accept it, so entrenched was my belief that ego was a good thing.)

When I finally accepted that ego was leading me astray, everything changed. My idea of what was worth pursuing changed. Material things, awards, praise…without ego, what good were they?

When I removed ego from the equation, what I wanted from life became clear: as much time as possible with my wife and family, and a stable job that paid well but left me with enough energy to think and write. I went from trying to decide on a specific career I’d like to have, to thinking about the day-to-day life I wanted to live. I went from thinking about who I wanted to be as a professional to who I wanted to be as a person.

Once I clarified how I wanted to live, I realized my best bet would be to get my degree. It would take years—a fact that had always deterred me. But now I gladly embraced it. Because it was my way forward. It was in my control. Maybe nothing would change once I had my degree, but that wasn’t my concern. I knew I was doing the right thing for the right reasons. Everything else was background noise. My goal was to pass one class, then the next. Learn to write one line of code, then the next. There would be setbacks and obstacles, but I could adjust. I could be patient. And I could be happy all the while.

The Stoics called this euthymia—the tranquility that comes from knowing you’re on the right path. (I’ll never forget where I was when I read one of my favorite lines in The Daily Stoic: “Who cares if someone is bubbly when times are good? What kind of accomplishment is that?”) The Stoics had a sober, constant joy—joy they controlled by doing the right things each day. As Ryan put it, “Here’s how to guarantee you have a good day: do good things.”

Ryan showed me what was worth pursuing and how to build the life I envisioned in 2016: a life of love, service, wisdom, balance, and time. It’s the reason I’m able to write these newsletters.

And it’s the reason I had to go to Texas.

As I shared in May’s email, Courtney and I flew to Austin, Texas last month and then drove down to Bastrop to visit Ryan and Sam Holiday’s bookstore, The Painted Porch. (What’s especially cool about their bookstore is that they only sell books they’ve read and recommend. You can get great recommendations just by browsing their website.) It was surreal being there in person. We browsed for about an hour, bought ~15 books, then went across the street for lunch.

After we ate, we decided to drive back to Austin, having accomplished our mission of going to The Painted Porch. But as we made our way to the parking lot behind the strip of stores, I felt disappointed. I knew full well before we went to Bastrop that there was less than a 1% chance I’d be able to meet Ryan. But being there, being so close, made me forget about the near-zero odds thing. Knowing I might never be this close again, and knowing, according to his daily schedule posted all over his socials and therefore not creepy for me to know, he’s likely there right now, writing in his second-story office above the bookstore, the guy who almost single-handedly turned my life around…I at least wanted to meet and thank him!

On a whim, I decided to walk to the back of the bookstore. I climbed the ramp to the wooden deck with picnic tables and took a picture of the famous orange wall painted with ancient philosophers.

“I don’t think you’re allowed to be up there,” Courtney said.

“Yeah, you’re probably right,” I sighed, looking around.

Then, in an upper window, I saw a white guy with dark hair taking a swig from a water bottle.

“Holy shit. I think I just saw him.”

I asked Courtney what I should do. Run around to the front of the store and ask if it was okay to say hi to him? Or would I just embarrass myself when they told me no?

Courtney asked, “What will you regret more: trying and failing, or not trying at all?”

“That one.”

Ten seconds later, Ryan zoomed out of the back door, deep in conversation with possibly his assistant, walked past us, and rounded the corner. I looked at Courtney. This was it.

I walked quickly to catch up, and just as he was about to enter an obscure side door, I called out, “Ryan.”

He turned around, and I began to apologize.

“I’m so, so sorry. I know how busy you are.”

“No, no, no, you’re good,” he smiled, walking toward us.

I shook his hand and told him how long I’d been following him and his work, and he seemed genuinely surprised and flattered. He asked us where we were from and what we’d been up to and what books we picked up. Courtney said something that made him laugh, and then she took a picture of us.

I don’t say this lightly when I say he could not have been sweeter to us. Just the nicest guy. I don’t remember much of what I said, but Courtney assured me it was nothing weird. One thing I do remember was tearing up, looking him directly in the eyes, and thanking him for everything he’s taught me. It was an experience I will never, ever forget.

One last thing.

While writing this email, I realized that we met Ryan exactly ten years to the month after moving in together. I really am not trying to be sappy, but I feel something essential would be missing from this newsletter if I didn’t state the obvious: I would never have cared enough to learn philosophy if it wasn’t for Courtney. Not only that, she’s been teaching me Stoicism, unknowingly, this whole time. She’s the one who, after I failed the first test I took in my first week back in school and said I was going to drop the class and try it again next semester, put her foot down and said she wasn’t going to watch me quit every time it got hard. She’s the one who showed me what self-reliance looked like. The one who, after I told her my crazy idea to travel 1,000 miles for a bookstore, took her phone out and booked our flight without a question.

While Ryan’s teachings and Stoic philosophy got me on the right course and guided my sail, it’s been my wife, all along, lighting the way home.

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Books Read This Month:

-I bought Composed by Rosanne Cash while at The Painted Porch last month. It took a while to get into, but once I did, I thoroughly enjoyed it. One story in particular stuck with me as a beautiful example of kindness. Rosanne was sitting at home and talking with her stepmother, June, when the phone rang. June picked it up, and after a while, Rosanne wandered into a different room—it was obvious June was in a deep conversation. When Rosanne returned to the room 10 or 15 minutes later, June was still fully absorbed in conversation. Finally, about 20 minutes later, June hung up and, with the biggest smile, said what a wonderful conversation she just had. June went on and on about the woman she’d spoken with—how many kids she had, a personal loss she recently experienced, where she lived, etc. Rosanne asked, “Well, June, who was it?” June said, “Why, honey, it was a wrong number.”

–In the Heart of the Sea by Nathaniel Philbrick…wow, this is one of the best real-life thriller/adventure stories I’ve read. An enraged sperm whale sank the Essex whaling ship in the early 1800s. Only 8 out of the 22 on board survived the three months of torture that followed. (Endurance is another shipwreck story I read recently, which was good, but I liked this one more.) I won’t spoil it and give away details, but their ordeal was unimaginable. It reads like a thriller. It’s no surprise it won a National Book Award.

-My friend recommended When the Game Was War by Rich Cohen, and it’s one of the best sports books I’ve read. Cohen brings together the journeys of the NBA’s four most prominent names in the 1980s—Isiah Thomas, Larry Bird, Magic Johnson, and Michael Jordan. It’s an entertaining read, but there’s also great stuff on leadership, craft, and opening doors for others. On a side note, I think we’re living in another golden era of basketball with Caitlin Clark and Angel Reese. 

-Though I loved Courage is Calling and Discipline is Destiny, Ryan Holiday’s newest book, Right Thing, Right Now, about justice, might be my favorite of his virtue series. It’s about kindness and doing good for others and ourselves. But it goes way beyond that. He shows how idealism and sentiment aren’t enough. If we want to make lasting changes in the world, we need to understand the force that drives it: power. We may not like it, but that’s the way it is. “Anyone who wants to do good in this world,” he writes, “must be a student of power. Anyone who wants to do something other than sit around and wait for change must read Machiavelli and Robert Greene.” It reads as an urgent wake-up call that the world desperately needs.

P.S. If you’re new to Stoicism, there’s no better place to start than with The Daily Stoic.

In 2006, Jackass star Steve-O was at the height of his career. At the red-carpet movie premiere for the second Jackass movie, he felt on top of the world. Or so one would have thought. But, as he recently shared, he felt like he was at his own funeral. He worried he and his team would never again produce something as good, that it would be downhill from there. On top of that, he was terrified his fame would disappear any moment. These worries spiraled into addictions, arrests, an intervention, and a 72-hour involuntary psychiatric hold after he emailed friends saying that he was, “ready to die.” Destructive behavior would consume him for the next 8 years.

It’s shocking, isn’t it? Here’s a guy who got everything he wanted, only to feel like he was at his own funeral. 

But it’s also not shocking. It’s natural to think that money or fame or status will fix us. But, of course, it never does. External things can’t penetrate the mind; a mind prone to worry will worry regardless of circumstances.

Quoting Socrates, Seneca wrote, “All your bustle is useless . . . You must lay aside the burdens of the mind; until you do this, no place will satisfy you. . . .because you flee along with yourself.” If you want to escape anxiety, he continued, “what you’re needing is not to be in a different place but to be a different person . . . . You need a change of soul rather than a change of climate.”

This isn’t just Western philosophy. The Buddha also recognized our inclination to search for happiness outside of ourselves. As Karen Armstrong writes, the Buddha believed humans were unhappy because they were “ceaselessly yearning to become something else, go somewhere else, and acquire something they do not have. . . .”

The problem is that if we don’t maintain our perspective, the goalposts move. No matter where we go or how much we acquire, it eventually becomes normal. We end up in an endless cycle of needing more.

Soon after Henry Ford created his assembly line in 1913, a huge problem arose: employees kept quitting. They would simply walk out midshift. The work provided no cognitive stimulation or personal satisfaction or agency. In other words, it sucked. The attrition rate was so bad that when Ford needed to hire 100 employees, he had to hire 963. It was costing a fortune. He needed a way to cut costs and increase production. His solution: he would increase wages.

The results were incredible. Employee attrition plummeted; the pay was too good to leave. Ford called the wage increase, “one of the finest cost-cutting moves we ever made.” Then he sped up the conveyor belt. Production tripled. Employees were working harder and faster, anxious to keep their well-paying jobs and maintain their new lifestyles—lifestyles that had grown with their income, “keeping them,” as Jackson Lears said, “at routinized jobs in factories and offices, graying but in harness, meeting payments regularly.”

That image—graying in harness—reminds me of a short comic strip I saw years ago: a young guy sprinting after a flurry of money, eventually collecting a sizable amount, only to look up and see he’s now an old man.

It’s not that we lose sight of what’s important on purpose. It’s just that it’s so natural and easy to think we’re lacking something when we’re not. That’s why one of my favorite parts in Epicurus’s The Art of Happinessis when he talks about how little our nature requires. Nature doesn’t care if your house “does not gleam with silver and flash with gold and if there are no paneled and gilded ceilings re-echoing to the lute,” he said. Nature has everything it needs, content to “recline on the soft grass beneath the branches of a tall tree near a stream of water and joyously care for their bodily wants at no great expense.”

This, Epicurus says, proves that power and riches “in no way profit the body of a man.” He adds that they don’t profit the mind, either. It’s our imagination that makes us feel something is lacking when it isn’t. (Our imagination is what marketers—dubbed “consumption engineers” in the early twentieth century—play on.)

The Roman poet, Horace, who wrote much about contentment, said that the good life is found in having what is sufficient, and a steady mind. Reason and good sense banish anxiety, not vacations and luxury.

Besides, he continues:

“If neither Phrygian marble or the wearing of purple that surpasses the brightness of stars, cannot relieve the sick man … Why should I labor to build a hall with doorposts to attract envy? … Why should I exchange my [modest home] for riches that bring bigger burdens?”

His psychological message, Stephen Harrison writes, “is that great riches bring anxiety rather than escape from it.”

This is true for us just as it was true for Steve-O. It wasn’t until he went to work on himself that he turned his life around. It wasn’t until he stopped counting his bedpost notches, and started counting his days of celibacy, that he found happiness.

Rich is the person who adds bricks not to what can be blown down or taken away, but to their inner citadel—that reliable place of resilience, calm, virtue, and wisdom inside us all. The place we can flee to whenever we’d like, and come back better for it. The place that fortifies us as we fortify it.

Bolster that place and rest easy knowing that wherever you go, whatever you do, it will be right there with you.

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Books read this month:

–The Wright Brothers by David McCullough was so good I added it to my list of favorite books. I loved how stoic the brothers were, how they went about their work diligently and without frenzy. How Wilbur whistled while he worked, refusing to rush preparations on his plane even as a large crowd and impatient reporters waited for him to fly. What I found especially beautiful was how loving and supportive their family was. Just a great book and McCullough’s smooth writing made the pages (I really didn’t mean to add a pun here) fly by.

–His Majesty’s Airship by S. C. Gwynne is another book I’d been wanting to read, and I thought it would be a good follow-up to The Wright Brothers. Imagine: a giant airship, about 6 acres in surface area, with a cloth-like exterior, full of people and helium, nearly impossible to steer, reactive to the tiniest shifts in weather, ready to explode at the slightest bump, moving slowly and at low altitude over the city. Why anyone thought these balloons would be the future of travel is beyond most historians, though the answers lie somewhere in ego, ignorance, good intentions, and a tragically flawed sense of competition.

-I loved David McCullough’s The Wright Brothers so much that I read another of his, John Adams, which I also quickly added to my list of favorite books. Wow, I didn’t know what a great guy Adams was, how strongly he opposed slavery and supported women’s rights. And unlike his peers, he actually practiced what he preached. He had an unflinching sense of duty, acted urgently, and was committed to his family. And through all of his professional and personal hardships, he did his best to move forward in good spirits.

-After reading and loving The Daily Thoreau last month, I decided to read Henry David Thoreau’s Where I Lived, and What I Lived For, and I LOVED it. It’s one of the best books I’ve read. Thoreau spent years living in a self-sufficient home in the New England woods and wrote about his experience. His goal was to live simply, and he encouraged his readers to do the same. One of my favorite stories is how he decorated his desk with 3 pieces of limestone, only to be horrified when he realized they required daily dusting. Throwing them out of his window in disgust, he wondered why he would dust his furniture “when the furniture of my mind was all undusted still. . . . I would rather sit in the open air, for no dust gathers on the grass, unless where man has broken ground.”