A sentence I bet you’ve never heard

“I need to be a little wealthier first, then I’ll be an honest, loving, disciplined, and other-focused person.”

I’ve never heard anyone say this. I bet you haven’t either.

It feels ludicrous to even write. Nobody actually thinks this way. You are either trying to be a good person or you aren’t.

Character is not something, in real life, that you put off until life gets more comfortable. We are either one of those people right now or we aren’t.

And how do we know we are? If we look in the mirror and ask honestly: “Was I a good person today?”

Asking the question is a small but powerful act of showing up, and in my experience is at least 60% of what it takes to have character.

All the accountability we need is to look in the mirror and be honest.

Am I that person or am I not? For real?

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If you’re someone who already looks in the mirror with honesty, you’ll want to read the book I wrote. It’s good enough to charge for, but I self-published it and chose to offer a free version — because the introspection it triggers is an investment the reader makes.

The Seasickness of the Soul

There’s a feeling I’ve come to know well, one I feel on Sundays—but it’s not the scaries.

It’s not just the dread of going back to work, but something deeper. It’s that feeling I get when I don’t know whether I’m able to live and be myself or whether I have to perform. It’s that feeling we get—when we can’t quite tell what is real and what is theater—and it’s not anger or frustration exactly.

It’s less like anger and more like nausea. Not of the body, but of the mind and spirit. It’s a nausea that comes from the blurring of what is real and what is not—and the disorientation that causes.

This epistemic nausea is not the same as moral disgust. I don’t mean the feeling of being sick to your stomach when someone does something so ethically wrong that we are repulsed.

I mean something amoral and dizzying, more akin to being on a boat in choppy waters. The longer we’re on the boat, the more exhausted we get trying to keep steady, and the more we feel like we’re going to throw up. It’s not a repulsion to injustice, but a seasickness of the soul.

To be clear, here’s what I mean by theater and reality.

Theater is the realm of our lives where the point is applause and selling tickets—at least for the people on stage. For the audience, the point is to be entertained, and perhaps to feel something, anything, novel as they deal with the overwhelming drudgery of reality.

At its best, theater is also about ideas—putting a magnifying glass to one small aspect of reality, critiquing it, and showing us a better way.

Reality is less glamorous, but it’s the source of meaning and joy. Reality is the realm where the point is to survive, to love and be loved, to act in a way that makes us and our ancestors proud, to find peace, and to serve others. What makes this hard is that living is struggle.

And to be even more clear, I don’t think the mere existence of theater or the inevitable suffering of reality is the source of this nausea. The nausea comes from when we don’t know whether we’re in reality or theater. Trying to decipher the truth when the two blur makes our heads spin. That dizzying state of being is what causes epistemic nausea.

I was thinking of writing a whole post on the different ways reality and theater blur. There are many obvious examples: reality TV, social media, and the posturing that happens in politics, business, and religon.

And there are more subtle examples too—like the “relationships” people form with AI chatbots, the “friendships” we have with people we may spend time with but who don’t actually know us. Or even the intense pressure and expectations we put on ourselves or our children to perform and achieve.

But does an abstract discussion picking apart the nuances of theater and reality really matter?

Those of us out here in the real world—trying to figure out when to buy groceries during the week, how to pay for day care, fit in 30 minutes of exercise so we don’t gain weight as our metabolism slows, and save money by fixing our damn washing machines before our kids run out of clean underwear—we don’t have time to sit around theorizing. We need to know what this nausea is and how to manage it.

To deal with epistemic nausea, I see one of two options.

The first is: we can escape into theater. We can surround ourselves with the fantasyland of performance, telling ourselves whatever stories we want to believe to feel how we want to feel. To be clear, this does numb the nausea.

The problem with fully replacing reality with theater—perhaps not obviously—is that we never really live. We never really love. We never really serve. We may never suffer, but we never build the character that comes only from overcoming it. I don’t want all that to be pretend. I want to live my life, not perform it as a character in a world I’ve made up.

The other option is, honestly, to just deal with it. If we can’t escape, we must navigate. If this epistemic nausea is a dizziness akin to sea sickness, we have to be sailors. And what do sailors do?

They have anchors to hold steady. To me, unconditional love is an anchor. When I’m nauseous, I turn to my family. Yesterday, when I was particularly seasick, we celebrated our brother’s birthday as a family. When we had a consequential appointment for our newborn, I wanted to call my mom with the good news. Being part of unconditional love—both ways—is an anchor.

Sailors also have rudders. To me, rudders are character: a set of convictions, values, and habits we hold to. It’s saying—no matter what happens, no matter what may or may not be real—I’m going to act like this. No matter who is in front of me, I’m going to treat them like this. However rough the seas, this is who I’m going to be.

Finally, just like boats, we can leave a wake. This is a metaphor about leadership and culture that I really value.

A boat can head into rough waters and leave the trail of water behind it calmer. We can do that too. We don’t have to participate in the misdirection and blurring of reality and theater. When we are in the realm of real, we can be real—instead of posturing, signaling, and bullshitting. And when we are in the realm of theater, we can be honest about what we’re doing and let our performance move the culture forward by challenging the worst parts of reality. That makes the difference between theater and reality clearer—not more blurry.

This epistemic nausea of the mind and soul debilitates me. But can any of us really control it?

Complaining about social media, what famous people do and say, or the distortions of reality made possible by AI doesn’t move us forward. What we can do is anchor with unconditional love, build a rudder of character to keep us straight, and of course, leave a wake—so we leave the seas behind us calmer than the ones we headed into.

We can’t stop the storm, but we can sail through it.

We can’t stop the blurring of reality and theater—but we can at least do this.

Comfort Reveals Character: Like Adversity, Ease Defines Us

How we react to adversity is a true reflection of our character, revealing our true selves when challenges arise—this is a familiar adage that holds much truth.

However, the times of ease and abundance in our lives—moments when we are most comfortable—also define us, yet these periods receive far less scrutiny. This week, I've come to realize that our actions during these comfortable times are equally telling. When the pressure is off, and we are left to our own devices with resources at hand, who do we choose to be? This question, I believe, is as crucial as how we face adversity, for it sheds light on the values we hold dear even when no one is compelling us to uphold them.

The Challenge of Super Comfort

I might become super comfortable for various reasons. Perhaps I’ve fallen into some money, achieved sustainable wealth, gained mastery in my job, or it’s simply sunny and I’m on vacation. Maybe I’ve just gotten a promotion or been recognized for some sort of award. Maybe one of my posts has gone viral, and I’m currently "the it guy" because of it. How do I act then?

Do I lose my hunger to be a better man? Do I let my standards slide? Do I forget about the injustices others face because this mojito I’m palming is just that hypnotizing? Do I take the day off from my duties because I feel like I’m above doing the work in the trenches now that I’ve "made it"? Do I stop diving for the metaphorical loose ball? Will my tastes get more expensive simply because they can, or will I remain the same guy from the schoolyard who went out and worked for it every day and put the team ahead of himself?

When things are rolling my way and I’m super comfortable, who am I going to be? When I feel like I’ve made it, will the game be about "me" or will I walk the walk on it being about "we"?

How We Can Manage Super Comfort

Dealing with super comfort is a real issue, not confined to stratospheric levels of wealth or social status. Owning a house, maintaining a retirement account, having a respected job, and enjoying paid vacation days—these are signs of 'super comfort' accessible to many, not just the super-rich. And here's the crux: I don’t want comfort to corrupt my character.

I've always cared about more than my own comfort, tracing back to when I joined the Brooklands Elementary student council at nine years old. I still aspire to be that hopeful, gregarious lad who believed that serving others was time well spent. Honestly, I don’t want to fade into a life of super comfort and become a self-indulgent navel-gazer. When I enjoy a lazy, restorative moment, I want it to be just that—a moment. Once it passes, I aim to return to something bigger than comfort.

So, if we care about our character and the impact we have on others and our corner of the world, this question is vital: How do we not let super comfort corrupt who we are?

It starts with a strong sense of who we are and what we care about unconditionally. We must literally post our deep convictions on our wall so we can't ignore them once we've 'made it.' Moreover, we must be wary of gated communities. The term 'gated community' often brings to mind exclusive residential areas that are physically gated off from the surrounding world, but it also applies to social circles and activities that are metaphorically gated through economic, cultural, or educational barriers.

True inclusive spaces are those accessible to everyone. To prevent our comfort from corrupting us, we must actively engage with these places. It's not just about avoiding country clubs or luxury suites at stadiums; it's about ensuring our daily environments—coffee shops, churches, date nights—are not so elite and self-selecting that we go weeks without having our comfort zones challenged. It's about choosing to leave the bubbles of our grad school networks and being open to interactions with diverse groups of people at the grocery store or our kids’ soccer games. The only real inclusive spaces are those that everyone can access, and to prevent corruption through comfort, we must show up in those places.

Super comfort becomes normal when we detach from public life and limit our social interactions to these private, exclusive spaces. It’s easy to indulge in comfort and rationalize elitist behaviors when we only inhabit specific slices of our world.

This is a bit of a rant, and that’s because this idea of corruption through comfort is new to me. How we act when we face adversity defines us, obviously. But how we act when we are faced with super comfort matters just as much. Maybe even more so, because in the throes of being comfortable is when we are most likely to make an exception to the standards of character we have set for ourselves.

Maybe it’s not novel for you, but it is novel for me: I have to fight the effects of super comfort, and that starts by even acknowledging this idea that how we act when we are super comfortable requires introspection and scrutiny.

Just as our character is defined by how we act in moments of adversity, it’s also defined by how we act in the moments where adversity is furthest away.

Learning to Win Ugly

What it takes to “win” is different than what it takes to “win ugly.” In sports what it means to win ugly can be something like:

• Winning a close, physical game

• Winning in bad weather or difficult conditions

• Winning without superstars

• Winning after overcoming a deficit or when your team is particularly outmatched

• Winning by just doing what needs to be done, even if it’s not fancy or flashy

But winning ugly is also a useful metaphor outside sports:

• In a marriage: keeping a relationship alive during adversity (e.g., during a global pandemic) or after a major loss

• In parenting: staying patient during bedtime when a child is overtired and throwing a tantrum

• In public service: improving across-the-board quality of life for citizens after the city government, which has been under-invested in for decades, goes through bankruptcy (I’m biased because I worked in it, but the Duggan Administration Detroit is my thinly veiled example here)

• At work: finding a way to reinvent an old-school company that’s not large, prestigious, or cash-infused enough to simply buy “elite” talent

The point of all these examples is to suggest that it’s easier to succeed when circumstances are good, such as when: there’s no adversity, the problem and solution are well understood, you’re on a team of superstars, or you’re flush with cash. It’s something quite different to succeed when the terrain is treacherous.

I’ve been thinking about the idea of winning ugly lately because as a parent, the fee wins we’ve had lately have been ugly ones.

Generally speaking, I’ve come to believe that winning ugly is important because it seems like when the stakes are highest and failure is not an option - like during a global pandemic, or when a city has unprecedented levels of violent crime, or when the economy is in free fall, or a family is on the verge of collapse after a tragedy - there’s usually no way to win except winning ugly.

I’d even say winning ugly is essential - because every team, family, company, and community falls upon hard times. In the medium to long run, it’s guaranteed. But honestly, I don’t think most people look at this capability when assessing talent for someone they’re interviewing for a job, or even when filling out their NCAA bracket. 

Moreover, as I’ve reflected on it, I’ve realized that my whole life, I’ve been coached, actively, to avoid ugly situations. I was sent to lots of enrichment classes where I had a lot of teachers and extra help to learn things (not ugly). I had easy access to great facilities, like tennis courts, classrooms, computer labs, and weight rooms (not ugly). I was encouraged to take prep classes for standardized tests (not ugly). I was raised to think that the way to achieve dreams was to attend an Ivy League school (not ugly).

If I did all these things I could get a job at a prestigious firm that was established, and make a lot of money, and live a successful life.

What I’ve realized, is that this suburban middle class dream depends on putting yourself in ideal situations. The whole strategy hinges on positioning - you work hard and invest a lot so you can position yourself for the next opportunity. If you’re in a good position, you’re more likely to succeed, and therefore set yourself up for the next thing, and so on.

If you don’t think winning ugly matters, this is no problem. But if you do believe it’s important to know how to pull through when it’s tough, the problem is that the way you learn to win ugly is to put yourself into tough situations, not easy ones. The problem with how I (and many of us) were raised is that we didn’t have a lot of chances to learn to win ugly.

I, for example, learned to win ugly in city government, at the Detroit Police Department…in my late twenties and thirties.

There, we caught no breaks. Every single improvement in crime levels we had to scrap for. Every success seemed to come with at least 2 or 3 obstacles to overcome. We didn’t have slush fund of cash for new projects. We didn’t have a ton of staff - even my commanding officers had to get in the weeds on reviewing press briefings, grant applications, or showing up to crime scenes. Just about any improvement I was part of was winning ugly. 

By my observation here’s what people who know how to win ugly do different:

No work is beneath anyone: if you’re winning ugly, even the highest ranking person does the unglamourous work sometimes. You can’t win ugly unless every single person on the team is willing to roll up their sleeves and do the quintessential acts of diving for loose balls, grabbing the coffee, sweeping the floor, or fixing the copy machine. 

Unleashing superpowers: If you are trying to win ugly, that means you have to squeeze every last bit of talent and effort out of your team. That requires knowing your team and finding ways to match the mission with the hidden skills that they aren’t using that can bring disproportionate results. People who win ugly doesn’t just look for hidden talents, they look for superpowers and bend over backwards to unleash them.

Discomfort with ambiguity: A lot of MBA-types talk about how it’s important to be “comfortable with ambiguity”. That’s okay when you have a lot of resources and time. But that doesn’t work if you’re trying to win ugly. Rather, you move to create clarity as quickly as possible so that the team doesn’t waste the limited time or resources you have.

Pivot hard while staying the course: When you’re winning ugly, you can’t stick with bad plans for very long. People who have won ugly know that you don’t throw good money after bad, and you change course - hard if you need to - once you have a strong inclination that the mission will fail. At the same time, winning ugly means sticking with the game plan that you know will work and driving people to execute it relentlessly. Winning ugly requires navigating this paradox of extreme adjustment and extreme persistence.

Tap into deep purpose: Winning ugly is not fun. In fact, it sucks. It’s really hard and it’s really uncomfortable. Only people who love punishment would opt to win ugly, 99% of the time you win ugly because there’s no other way. Because of this reality, to win ugly you have to have access an unshakeable, core-to-the-soul, type or purpose. You have to have deep convictions for the mission and make them tremendously explicit to everyone on the team. That’s the only way to keep the team focused and motivated to persist through the absolute garbage you have to sometimes walk through to win ugly. Teams don’t push to win when it’s ugly if their motivation is fickle.

Doing the unorthodox: People who can win pretty have the luxury of doing what’s already been done. People who win ugly don’t just embrace doing unconventional things, they know they have no other choice.

Be Unflappable: I’ve listed this list because it’s fairly obvious. When it’s a chaotic environment, people who know how to win ugly stay calm even when they move with tremendous velocity. This doesn’t necessarily mean they don’t get angry. In my experience, winning ugly often involves a lot of cursing and heated discussions. But not excuses.

Sure, I think it’s possible to use this mental model when forming a team or even when interviewing to fill a job: someone may have a lot of success, but can they win ugly?

But more than that, I am my own audience when writing this piece. I don’t want to be the sort of husband, father, citizen, or professional that only succeeds because of positioning. At the end of my life, I don’t want to think of myself as someone who only succeeded because I avoided important problems that were hard.

And, I don’t want to teach our sons to win by positioning. I want them to succeed and reach their dreams, yes, but I don’t want to take away their opportunity to build inner-strength, either. This is perhaps the most difficult paradox of parenting (and coaching at work) that I’ve experienced: wanting our kids (or the people we coach) to have success and have upward mobility, but also letting them struggle and fail so they can learn from it, and win ugly the next time.

The Easiest Way to Become Popular

To me, it’s not so much that being popular great, it’s that being unpopular is usually terrible. To articulate why, I look to the greatest explanatory model for social dynamics there is: high school.

I’ve been on both sides of popularity in my school days. When I was unpopular, I was constantly stressing about girls, being harassed, being lonely, or missing out on having fun. When I was popular, I flourished. I had a lot more fun and it was a lot easier to just be myself and have energy when I was liked and not constantly feeling under siege. 

I get why people, myself included, will go to great lengths to avoid being unpopular. For me, it wasn’t that being popular was great, it was that being unpopular was much worse. 

And the simplest way to avoid being unpopular is to become popular. So how to be popular? Again, it’s informative to think about high school.

One road to popularity is to be the best at something, to have a niche. It’s easy to be at least somewhat popular when you have a lane - whether it’s academics, athletics, arts, or an extra-curricular activity. If you’re the best in the school at something or have a varsity letter on your jacket you earn the respect of your peers.

Another way is to have rich parents. Which I don’t actually mean flippantly; it’s not about being able to buy “friends”. But rather, if you have access to money, you don’t have to say no to fun stuff. You can go to the movies whenever someone’s going. You can take your friends to concerts and sports games, or host fun gatherings at your house with ping pong tables, nice food, and maybe even a pool. Money doesn’t buy friends, but it creates opportunities to have fun and make friends.

In my experience, character and leadership also matter. In high school, if you’re genuinely nice and can transcend the pettiness of the cafeteria or the hallway, people want to be around you. If you can rally people around a shared purpose - whether it’s a charity drive or social change, people want to be around you. If you can stand up for injustices or do something innovative, people want to be around you.

But those three strategies - being a star, being rich, or being a leader - are actually pretty challenging. The easiest way to be popular is to be aggressive.

We have likely all seen this play out, it’s basic in-group out-group stuff. We can be popular by talking crap about people behind their back or bullying other kids. By excluding others, we can build strong cohesion with our peeps (which makes us popular), albeit cheaply and darkly. Also, if the rest of the school knows you roll deep and are willing to be mean, most would prefer to stay out of your way instead of challenge your dominance.

The easiest way to be popular is to be aggressive. Sadly, it works almost every time.

And yes, maybe in high school the stakes aren’t as high because everyone’s awkwardly going through puberty, and everyone leaves in four years anyway. Everything’s made up and most of the time, the points don’t matter.

But these dynamics don’t stop in high school. I’ve seen them play out in every organization and company I’ve ever been a part of. And after high school, it’s not just that people try to become more popular, they try to become more powerful. The stakes and consequences get bigger and realer.

And yes, in the real world - whether it’s in the workplace, at church, or just socially - some people gain power by being a star. Or they gain power by being wealthy. And luckily, in some cases people gain popularity and power by leading people toward an inspiring, noble, shared purpose.

But damn, lots of people take the easy way. Like at work, people get aggressive at the water cooler by demeaning a project team, their boss, their direct reports, their peers, or the customer. Or in social settings, people gossip about the other people in their club, the congregation, the neighborhood, or even their extended family.

A lot of times, I think people intend to lead with integrity and do start with a noble purpose in mind, like: ending the patriarchy, saving the American dream, stopping racial injustice, or preserving freedom. And they inspire people and lead them to achieve something meaningful. And then they get popular, and then they get powerful. And it’s great, because you’re doing what you think is right and you’re popular, too.

But at some point the streak ends. And not everybody is a Dr. King or a Gandhi. Not everyone realizes they have to do the work of self-purification to stay true to their principles and integrity. And then that well-intentioned person devolves into aggression, and brings in all the chest-thumping, and the outrage, and the vitriol to stay popular. And they become a bully in the end, when all they wanted to do at the start was noble and virtuous.

The easiest way to be powerful is to be aggressive and it’s so easy to fall into unintentionally. This stuff starts in high school but for damn sure doesn’t end there.

A through-line of my writing and thinking is the concept of intentional choices. Some choices we make have huge consequences for ourselves, for others, and for the culture itself. These are the choices we should make intentionally, but it’s so easy not to. How to be popular is one of these unassumingly consequential choices.

I think we all want to avoid being unpopular and powerless (because it sucks). The choice we have is how. What path will we take to avoid unpopularity? What strategy will we use to become more popular?

Will we try to be a star and make a huge contribution to earn respect? Will we use our money to create amazing, memorable, experiences that bind us with others? Will we build a deep sense of purpose and fellowship by leading with integrity? Or will we make ourselves part of the in-crowd by making someone else an outcast?

The choice of how to be popular is one we should make intentionally.