For most of my life, I did not have a plan. That is not the same thing as saying I had a bad life. I had fun, sometimes a lot of it. I joined the Marine Corps. I worked strange jobs. I met people from very different walks of life. I made good decisions, bad decisions, and plenty of decisions that made perfect sense to the version of me making them at the time. I accumulated experiences I would never trade away now, even if I would not necessarily choose to repeat all of them.
What I rarely did was think very far ahead.
I thought about the next few days, sometimes the next few months, but almost never the next twenty years.
When I was a teenager, I loved technology. The aptitude tests I took pointed me toward computer programming, which in retrospect seems almost comically obvious. Technology fascinated me then, and it still fascinates me now. But I grew up poor in a rural town, and college was not simply the automatic next step after high school. There was no college fund waiting for me and no family safety net capable of absorbing a bad financial decision. If I went to college, I was going to borrow the money.
The adults around me were not especially optimistic about the future of technology either. This was the early 2000s, and I distinctly remember being told that the Internet was basically a fad. One teacher warned me that there were supposedly already more students enrolled in college to become computer programmers than there were programming jobs in existence. The future being described to me looked something like this: take out perhaps $80,000 in student loans, graduate, and then compete with a thousand other graduates for a job paying $30,000 a year.
Whether those numbers were ever remotely accurate is almost irrelevant to the story now. I believed them, and they scared the shit out of me.
When you grow up without much money, $80,000 of debt does not automatically sound like an investment in yourself. At eighteen, it sounded like a trap I might spend the rest of my life trying to escape. I did not talk myself out of technology because I had stopped loving it or because I thought I was incapable of doing it. I was scared away from it. I was a teenager making one of the first enormous decisions of my life with the information available to me, trusting adults who were supposed to understand the world better than I did.
Then another option appeared. A friend of mine was joining the military, so I started asking questions about the different branches. Eventually I asked what, at that age, seemed like the important question: which one was the hardest?
Everyone gave me the same answer.
The Marine Corps.
That was basically all I needed to hear. If I was going to do it, I figured I might as well do the hard one. And if I am being fair to the person I was then, I also knew I could use some discipline.
So I joined the Marine Corps, and it turned out to be a great decision.
I want to make that clear because one of the easiest mistakes when telling the story of your own life is to rewrite every previous chapter according to where you eventually ended up. Technology ultimately became my career, but that does not make everything before technology a detour. I do not believe that at all. The Marine Corps helped build the person who would eventually return to technology, just as many of the experiences that followed it did.
The problem was not that I had chosen the wrong road. The problem was that, for a long time afterward, I stopped thinking very much about where the road was taking me. I was moving, but movement and direction are not the same thing.
When I left the Marine Corps five years later, I still did not really know what I wanted to be. Over the years I worked at McDonald’s, in customer service, in concrete labor, as a shovel bum for an archaeologist, as a bouncer, stocking groceries overnight, and eventually in grocery management. Written down in sequence, that can look like a résumé assembled by throwing darts at a career board. At the time, I sometimes felt that way too.
I do not look backward and dismiss those years as worthless. Quite the opposite. The Marine Corps shaped how I think about responsibility, pressure, leadership, and accountability. Customer service taught me plenty about human behavior when people are frustrated. Physical labor taught me something about discomfort and persistence. Bouncing taught me to read people. Grocery retail taught me logistics, conflict, management, responsibility, and the enormous difference between possessing authority and actually being able to lead someone.
Those experiences became ingredients in the person I am now. I simply did not yet know what I was cooking.
The problem, as I experienced it at the time, was much more practical: I felt trapped. People love telling you to follow your passion. There are endless variations of the same idea: find something you love and monetize it; do something you love and you will never work a day in your life. Those sentiments sound wonderful on motivational posters and coffee mugs. They become substantially less useful when you are miserable at three o’clock in the morning, working a job you no longer want, wondering how exactly you are supposed to convert “I have always loved computers” into somebody paying you to work with them.
I could not exactly walk into Google and announce that I was passionate about computers in 2006 and therefore they owed me a job. Passion was not the missing piece. The bridge was. From where I stood, my work experience did not create an obvious path into technology. I did not have the degree. I did not have the credentials. I did not have professional technical experience.
I could imagine a different life far more easily than I could imagine the road connecting that life to mine. When you cannot see a road out, staying where you are can begin to feel less like a choice and more like reality.
For roughly three years while working nights, I listened constantly to Gary Vaynerchuk. Podcast after podcast, talk after talk, hour after hour. He was one of many people repeating a message I had probably heard a million times in other forms: stop complaining, take responsibility, think about what you actually want, and change your situation.
Then one night, sometime around three in the morning, I was at what felt like the absolute lowest point of my relationship with that job. I was miserable, exhausted, angry, and completely unsure how to get out of the situation I kept complaining about. In my headphones, Gary said some version of what I had probably heard from him before: shut the fuck up and change your situation. Stop complaining. Think about what you love to do, and do that.
For whatever reason, that night it landed.
Nothing mystical happened. There was no beam of light coming through the ceiling of the grocery store. Gary Vaynerchuk had not discovered some secret principle of existence nobody before him had ever articulated. In fact, that may be the most interesting part of the story. I had heard the idea before, probably repeatedly. The difference was that the circumstances and the words finally met each other at exactly the right moment.
I have started thinking that wisdom may have a readiness requirement. Sometimes the idea is not new. You are. An idea can pass through your life a hundred times without leaving much behind, and then experience builds enough scaffolding underneath it that the same words suddenly have somewhere to land.
That night, they finally had somewhere to land for me.
The realization was not immediately, “I should become a cybersecurity professional.” I was nowhere near that specific yet. It was something simpler and much larger: I am allowed to change this.
Written down now, that sounds almost embarrassingly obvious. At three o’clock in the morning, it felt revolutionary.
I started asking a question that, in hindsight, seems absurdly overdue: what do I actually enjoy doing?
Technology.
It had always been technology.
So I enrolled in college for computer science. That path eventually bent toward cybersecurity and then into the work I do now. For the first time in my adult life, I had deliberately changed my trajectory.
I had started steering.
Near the end of my time in grocery retail, a manager unintentionally made leaving much easier for me. He was probably in his fifties. From what I knew, he was not married and did not have children, and work seemed to occupy an enormous portion of his life. At one point he tried to convince me not to leave. He told me that he had once faced a choice himself: go to college or commit to the company. He had chosen the company, and then he pointed to his own life as proof that he had chosen correctly. The message was essentially: I committed to this company. Look at me now. Look at how well I’m doing.
I remember hearing him and experiencing almost exactly the opposite reaction he intended.
He saw himself as the destination I should aspire toward. I saw a possible future that terrified me.
I do not mean that as a judgment of his life. Maybe he was genuinely happy. Maybe the company gave him exactly the career and sense of purpose he wanted. If so, good for him. The important thing was that I knew immediately that it was not the life I wanted. If I had still been sitting on a fence, his words were a wrecking ball smashing into me from the other side.
Sometimes we discover what we value because someone shows us something beautiful and we think, I want to become that. Other times someone unintentionally shows us a possible future and every part of us responds, absolutely not. Both can provide direction.
He was, in a sense, handing me his map and telling me that the road had worked for him. By then, I had enough experience to understand that his destination did not have to become mine.
That may have been one of the first times I truly understood something that now feels fundamental: direction matters, and direction can be changed.
You are not disqualified because you started late. But once you realize you are drifting, start steering.
I did not make what I consider my first serious career decision until I was around thirty. That is later than the timetable many of us imagine we are supposed to follow. We are handed a remarkably tidy version of adulthood: figure out what you want at eighteen, go to college, start your career at twenty-two, progress steadily upward, find the right person, build the right life, and by thirty somehow transform into one of those mysteriously competent adults who seem to know what they are doing.
My life did not happen that way, and I no longer think that matters very much.
There is time to figure your shit out. There is time to change careers. There is time to discover that a goal you have been pursuing was never really yours. There is time to learn emotional skills you probably should have learned ten years earlier. There is time to admit that the person you have been does not have to be the person you remain. There is time to start becoming more deliberate.
That does not mean there is unlimited time, and it does not mean drifting forever carries no cost. It means arriving late to the realization does not disqualify you from acting on it. The realization can come at thirty, forty, fifty, or later. Once it comes, the important part is what you do with it.
Career was simply the first place I learned that lesson.
Around that same broad period of my life, something else fell beautifully into place. I met the woman who became my wife. I sometimes tell her that I wish we had met when we were younger, and part of me means it completely. When you love someone, wishing you had more time with them seems almost unavoidable.
There is a problem with that alternate history, though. If we had met ten years earlier, she would not have met the man I am today with ten fewer years on his face. She would have met me ten years earlier. And I am reasonably confident the emotionally illiterate version of me from those years would have given her some excellent reasons to break up with him.
Alternate histories are seductive because we tend to rearrange events while allowing our present selves to remain unchanged. That is not how life works. Earlier me had different priorities, different blind spots, different emotional skills, different insecurities, and different ideas about relationships. I can simultaneously wish I had more years with my wife and recognize that some of the years before her were spent becoming someone capable of creating the relationship I value now.
I do not mean that everything happens for a reason. I am suspicious of that phrase. It is too easy to look backward at suffering, mistakes, or bad circumstances and retroactively declare them necessary simply because something valuable eventually emerged afterward. I do not know whether they were necessary.
I know something simpler: the person I am today was built out of the person I was yesterday. The experiences I cherish, the ones I regret, the decisions I would repeat, the ones I would never make again, the years when I moved deliberately, and the years when I drifted all belong to the same life.
Growth does not require contempt for the person I used to be. In fact, I hope the person I am ten years from now can look backward at me today and see things I still have not figured out. If he cannot, something has probably gone wrong.
Now I am nearing forty, and another question has begun demanding my attention.
For much of my life, the big question was what do I want to do? I finally found a pretty satisfying answer. Technology. Cybersecurity. Digital forensics. Building things. Learning. Work that makes my brain light up rather than watching the clock and wondering how many hours remain before I can leave.
Answering that question created enough space for another one to become audible, and this one is much harder:
What kind of man do I want to be?
My daughter is eleven. My son is three. Twenty years no longer feels like an abstract span of time. I can see time moving in front of me. My daughter is already forming ideas about adulthood, relationships, fathers, men, work, responsibility, anger, kindness, failure, success, and how people treat each other when things go badly. My son is at the beginning of that same process. Whether I consciously decide to teach them or not, I am teaching them.
They are watching.
Suddenly whether I have a fulfilling career feels like only one small part of the equation. What kind of father do I want them to grow up having had? What kind of husband do I want my wife to experience? What kind of leader do I want people to encounter? What do I do when I am wrong, and can the people around me safely tell me that I am wrong? How do I respond when someone disappoints me? How do I behave when I disappoint myself? What does ambition look like when it is healthy? At what point does discipline become rigidity, confidence become arrogance, patience become passivity, or protecting my children become preventing them from learning how to stand on their own?
Most importantly, what traits do I want to possess, and if I can identify them, can I work backward and deliberately develop them?
I spent much of my life asking what I wanted to do. Near forty, I finally began asking what kind of man I wanted to be.
That question is the reason these essays exist.
The problem is that humanity has apparently been arguing about the answer for several thousand years.
One of my favorite television shows ever made is The Good Place. It is hilarious, but it is also a four-season ambush in which a network sitcom slowly convinces you that you have opinions about moral philosophy. Underneath all the jokes, bizarre afterlife bureaucracy, and frozen yogurt, the show continually returns to a deceptively simple question: what does it mean to be a good person? Then it spends four seasons demonstrating why the question is anything but simple.
Intentions matter. Consequences matter. Rules matter. Character matters. Circumstances matter. Relationships matter. Inconveniently, those things do not always point in the same direction.
Michael Schur eventually took the philosophical obsession underlying the show and turned it into How to Be Perfect, his own exploration of several traditions humans have developed to answer questions about how we ought to live. I find that search fascinating. I also find it slightly terrifying.
There is something almost cruel about sincerely deciding you want to learn the right way to live and then discovering that extremely intelligent people have spent thousands of years producing incompatible answers. Aristotle wants to talk about virtue and flourishing. Consequentialists want to evaluate outcomes. Kant wants to discuss duties and principles. The Stoics want to examine virtue, judgment, and the distinction between what lies within our control and what does not. Buddhist traditions begin raising uncomfortable questions about attachment and even the stability of this “self” I have apparently decided to improve. Existentialism eventually returns a significant portion of the problem directly to me.
Excellent. Very helpful.
I went looking for directions and discovered an argument between cartographers.
That is where I began wondering whether the problem might be the question itself. Maybe I am not supposed to discover the philosophy. Maybe there is no single system waiting somewhere in a book for me to recognize it as the correct answer. Perhaps these traditions are attempts by people who explored different parts of the territory and came back with different observations. One might warn me about a cliff. Another might tell me where someone found water. Another might contain a route that worked beautifully for the person who drew it but leads me somewhere I do not want to go. Some maps handed to us by people we trust simply turn out to be wrong.
I have experienced that already.
I do not need someone else to hand me a finished map of my life. I want to study the maps people have left behind, understand what they discovered, and decide what belongs in my own field notes.
Maybe Aristotle gets some things spectacularly right and other things wrong. Maybe the Stoics understood something powerful about resilience while leaving ideas that can become unhealthy when stripped of their nuance or pushed beyond their proper limits. Maybe Buddhism can teach me something without requiring me to become Buddhist. Maybe General Mattis belongs in the same notebook as Marcus Aurelius. Maybe a fictional football coach can teach me something about leadership that sticks harder than anything I find in a management textbook. Maybe The Matrix belongs in the conversation. Maybe a ridiculous Canadian comedy sketch I heard more than twenty years ago belongs there too.
I do not want to join a philosophical team. I want to understand what people have discovered. I want to know what each worldview sees especially clearly, where it fails, and what happens when its virtues are pushed beyond balance and become vices of their own. I want to compare ancient prescriptions with what modern psychology tells us about how human beings actually behave. I want to listen to philosophers, psychologists, leaders, writers, soldiers, scientists, fictional characters, comedians, and ordinary people who learned something worth preserving.
Then I want to steal from them shamelessly.
I do not yet know what philosophy, if any, will emerge from that process. I hope I am disciplined enough not to decide before doing the work. The point of these essays is to document that exploration honestly, including the places where I change my mind. Earlier versions of me should be allowed to disagree with later versions of me. If I reach the end of this project believing exactly what I believed at the beginning, then I will have spent a great deal of time reading without learning very much.
These essays are also not intended to become instructions for how anyone else should live. I am not trying to draw you a map. I am leaving field notes from the territory I explore. If something I find helps you navigate your own terrain, wonderful. But it remains yours to navigate.
There is another danger I want to acknowledge at the beginning, because otherwise this entire project risks becoming exactly the kind of self-improvement machine I do not want to build. Self-improvement can become another form of self-destruction. It is possible to become so obsessed with developing the person you want to be tomorrow that you spend your entire life treating the person living today as an inadequate preliminary version.
I do not want that.
There has to be a balance between becoming and being, ambition and gratitude, the future and the present. I do not want to spend twenty years constructing the father I aspire to become only to discover that my children grew up while I was busy optimizing him. My children do not need a finished father. They need a father who is still willing to grow.
That means this project will not have a deadline. There will be no promise to publish an essay every Tuesday because some algorithm rewards consistency. An essay gets written when I have read enough, thought enough, and lived enough to believe I actually have something worth saying. Maybe that takes a month. Maybe it takes a year.
There is a line from Ti Kwan Leep that has stayed with me: “And to a true student, a year is as a day.”
I increasingly like that as a rule for this project. There is no prize for racing through a philosophy so I can write about it faster. If I need months to understand something before I have earned an opinion on it, then months it is. If my understanding changes later, I want that visible too. I do not want to quietly rewrite the person I used to be so that he conveniently agrees with whatever I believe ten essays from now.
If this project works, I should contradict myself occasionally. I should reread something I wrote and realize that I no longer believe it quite the same way. That is not a flaw in the project. That is evidence that the journey is actually happening.
Eventually, I expect I will become thoroughly exhausted from reading people explain how to live and decide that the healthiest remaining piece of personal-development advice is to close the books and go live for a while. When that happens, I want to write one final essay. It will not claim to contain the answer. It will simply be a snapshot: this is what I believe today.
Even then, I will not be finished. None of us are, not while we are alive.
Which brings me back to something ridiculous that has apparently been sitting quietly in my brain for more than twenty years waiting for me to catch up with it.
The Frantics performed a comedy sketch called Ti Kwan Leep. The sketch is absurd, which is part of its charm, but buried inside the absurdity is a line I heard when I was young and simply never forgot:
“Tae Kwon Leap is not a path to a door, but a road leading forever towards the horizon.”
I heard that before I had a career, before I knew my wife, before my daughter and son existed, before I knew I would eventually return to the technology that fascinated me as a kid. I heard it before I spent years believing I was trapped, before I stood miserable at three o’clock in the morning and finally realized that being stuck and remaining stuck were two different things, and long before I began wondering not merely what I wanted to do with my life but what kind of man I wanted to become.
I could not have explained why that line mattered when I first heard it. Maybe I simply was not ready for it yet.
I think I am now.
There is no finished version of me standing somewhere at the end of this road. There is no door marked PERFECT SELF that I eventually unlock after enough books, accomplishments, failures, leadership lessons, therapy, exercise, meditation, success, disappointment, or wisdom. There is only the best man I can currently imagine becoming from where I am standing today.
I can move toward him. If experience teaches me to imagine someone better, I can change direction. If I discover that one of the maps I trusted was wrong, I can choose another road. If I realize I have been drifting, I can steer. And if I began steering later than I wish I had, that does not disqualify me from the journey.
You are not disqualified because you started late. But once you realize you are drifting, start steering.
I do not know where this road ends.
For perhaps the first time in my life, I am comfortable with that.
The horizon was never somewhere I was supposed to reach. It was there to give me a direction.