The lives people live

I met an old friend for lunch in Malibu. He had a decent exit from his marketplace startup and had become a leadership coach. When we compared notes, we discovered that we both felt an undercurrent of inadequacy. I’ve written about this before.

We each had friends become far richer and more famous and influential than us. We didn’t want to care, but we did. A vicious cycle ensued: feeling bothered about being bothered made us feel even more bothered. 

On the surface we were aware that once you reach a certain threshold of income, the returns in utility decrease rapidly. We thought about what we would do if we were “rich.”

I had a few answers:

  • Fly first class exclusively
  • Stay in really nice hotels when I travel
  • Make bigger donations to UC Berkeley and Diablo Valley College

I couldn’t think of anything else. Is that really the difference between me right now and me as a hundred-millionaire? 

If I had a magic credit card right now with an unlimited balance, what would I be super excited to buy? I couldn’t think of anything, and I’m embarrassed by that. Do I really have every material thing that I want? I could always buy more stuff, but I don’t like clutter. I could upgrade things like my road bike or car, but I don’t like throwing things away.

When presented with this thought experiment, I realized I don’t need to be “rich.” Or, perhaps more honestly, I already am.

What about the first class flights and nice hotels? $10,000 for that flight into Heathrow? Another $10,000 for that penthouse at the Ritz? I could do that now, I suppose. I wouldn’t, but I could, at least for a little while. 

Maybe my point is that being “rich” means $20,000 feels like $20 and maybe what I think I’m missing out on is that I’d like to know how that feels. 

Why? I dunno. Just because. 

My friend had similar answers. We felt better about ourselves after this chat. We paid for our $30 breakfasts and went our separate ways. I told him I’d write a blog post about that conversation. Here it is. 


I think people have six ambitions in life. These are the layers on top of the basic stuff: be healthy, be social, give and receive love, and protect your family. 

When those bases are covered you get to ask yourself an important question: now what? The answer is going to be one of these six ambitions. 

  1. Live a simple life
  2. Have more impact
  3. Be more interesting
  4. Gain more influence
  5. Make more money
  6. Have more fun

You don’t need to pick only one. Most people start with #1 and are content to stay there, but would probably level up to #2 (Have more impact) given the opportunity. 

Our working years are fraught with demands from children, bosses, and financial advisors. We raise families while struggling to compile sufficient assets to retire for twenty years or more. The goals here are obvious: happy kids and lots of savings. 

Upon retirement, volunteering comes into the picture. This is level #2. Lions and Rotary Clubs, substitute teaching, things like that become possible. You work to have some freedom, and when you have freedom, you try to give it away. 

If you’re good at making an impact, then you might discover that people find you interesting. You get good at telling the story about how much impact you’re having. Now you have a following.

With a following comes influence, #4 on my list. You discover that the impact you had, which made you interesting, now makes you influential. Social media becomes useful to you as people begin to follow you because you’re interesting. Your list of friends grows as you get invited into more social circles. This social acceleration begets more influence.

Money naturally follows influence. There are books to be written, speaking and teaching fees to be had. You get interviewed on podcasts and then start making TV appearances. You write a book, do consulting, advise some startups in exchange for equity, maybe invest in some of them directly. This is how fame breeds fortune. Now you’re playing #5, the make more money game.

When you have money you can optimize for fun. You fly first class, join country clubs, attend expensive charity dinners, and go on fancy cruises. You meet more interesting people, which compounds your influence, money, and fun. It’s a virtuous cycle. 

I see these people on Twitter. I read their blogs. I know some of them from grad school and beyond. I’m sure I look at this from the outside through rose-tinted glasses but I think I have it right. They’re having fun, meeting interesting and influential people, and making a positive social impact.

It still starts with the simple life, which, again, is “simple” because all of the basic needs are already met. From here they get absorbed into the other games, working their way up, often intentionally, and sometimes by accident. 

They don’t have to start with the simple life, though. It’s possible to enter the game at any level. Some may try to cheat the game by having the most fun while living the simple life. This is where #1 and #6 converge. Some people can bend the game to the point where the two ends meet. 

This achievement requires a uniquely wired psyche. These are the monks, the Franciscans who level up to a plane above and beyond the rest of us. I don’t know how to get there and I believe those who figure it out have a different physical properties than the rest of us. It can’t actually be taught but meditation and mindfulness probably get us close. I think the melding of #6 and #1 is what nirvana is all about. 

Conversely, money is necessary but not sufficient to have fun. Plenty of people with lots of money are unhappy and therefore don’t have fun. They have influence, they make impact, and they’re interesting, but they are deeply unhappy because they’re not having any fun. They could have fun but the momentum of their own mimetic demons keeps them from doing what would actually make them happy. They’re so busy looking around at everyone else’s money that they aren’t able to enjoy their own.

Enough of the hand-wavy stuff. Let’s name some names to bring this down to brass tacks. 

Who is having more fun (#6)

Dave Grohl is the former drummer of Nirvana (prescient, perhaps?) and current leader of the Foo Fighters. He is beyond wealthy and seems to have remained in his prime for the last twenty years at least. By all accounts, he’s a nice guy and a wonderful dad (watch this YouTube video of him singing on stage with his daughter — it’s so, so genuine). He tries to meld the simple life with rock and roll stardom and although it must be an impossible task, he makes it look easy. 

Keanu Reeves is nice. He’s generous. He comes off like a regular guy. I’ve read accounts on Twitter and Quora about him accepting invitations to his fans’ weddings and actually showing up. He makes sure the under-appreciated staff on his movie sets get paid. I include him because being nice is the perfect proxy for having fun. You can’t have fun if you’re not happy. You can’t be happy if you’re not nice. I believe this. 

Barack Obama seems like he’s always been comfortable in his skin. And now, as a former president, wealthy from his books and celebrity, he can have fun. From what I read, he is doing that well. I know one person who knows Obama well and the picture he paints is one of a man who has found his place in the universe. Life can’t be simple for a former president, but I don’t hold that against him. 

Oprah just has to be on this list. I mean… right?

Others I think are here: Bruce Springsteen, Stephen King. They all reached self-actualization: the virtuous cycle of being able to do what you’re “meant to do” all the time and have a lot of fun in the process.

Who makes money and doesn’t have fun (#5)

The list of people who reach #5 but are unhappy and therefore stuck below #6 is long and tragic. I put Donald Trump, Tiger Woods, Bernie Madoff, Tom Brady, and many the lesser-known wealthy people in the “unhappy rich” category here. We all know a couple of them. 

They seem to be self-actualized, but they’re not. Is it because money allows them to pursue their fun and surround themselves with a glossy rich-colored wrapper? 

If you truly love your job, can you reach a steady-state of self-actualization, so long as you still have your job? When Michael Jordan stopped playing basketball, was he still self-actualized? Where does Tom Brady fit in? Many of these guys can’t let go of sport. Let’s start with Tom Brady.

Tom Brady is, by account of most critics who care about American football, the G.O.A.T. He has more Super Bowl rings and MVP trophies than anyone in NFL history. As a quarterback he has the most passing yards and passing touchdowns. To cement his virtuosity, he proved that he could do it without his long-time Patriots and head coach Bill Belichick by taking the Tampa Bay Buccaneers to the Super Bowl and winning it in 2020, when Brady also was named the MVP at age 39, the oldest honoree in NFL history.

So why is it so hard for Brady to retire? Why put his body — and his family — through this ringer again? Just a few months ago, in the middle of the season, his supermodel wife, Gisele Bündchen, filed for divorce. Brady returned for another season after receiving a hero’s reception at his retirement party. Apparently, for Bündchen, it was the final straw.

Applying the 6 levels framework here, I rationalize Brady’s decision by assuming that he can only have fun as a quarterback. He’s self-actualized only when he’s the starting QB of an NFL team. He must love it more than anything else. More than his legacy, more than his family, more than his health. He was already on top — where else is there to go but down? Sadly, that appears to be the reality of the current Buccaneer season.

Brady is not fulfilled by money, influence, or impact. He’s clearly not able to live the simple life. Because he defined fun so narrowly, he made a deeply damaging decision to return for another season. I will be curious to see how he navigates life after the NFL, which he will inevitably be forced to do.

Donald Trump is, by all accounts, an unhappy person. He appears to have fun sometimes, but but most of his public time is spent lamenting his victimhood. He has influence, impact, and money. My armchair analysis (I’ve never met the guy, obviously) is that he had the most fun as the leading role in NBC’s The Apprentice, and in fact the success of the show catapulted his political career.

Was Trump happy as president of the United States? Not from what I have read, certainly not the way that Bush, Clinton, and Obama had fun. He was fixated on the press, his detractors, and then distracted by COVID and the subsequent economic fallout. I don’t recall seeing any footage of him having fun, except perhaps a telescopic picture or two of him on the golf course.

Trump, like Brady, is seeking a sequel. Why? The answer for Trump is different. While Brady had fun on the field, I believe Trump conflates the exorbitant amount of influence and impact he gets as president with fun. He is seeking an end that he cannot reach with the means at his disposal. In the quest for #6 he fills up his time seeking copious amounts of #5 and #4. That’s what his recent third run for the oval office is about.

The list here goes on and on. It’s every wealthy, over-worked, divorced professional who drives an expensive car, lives in a fancy home, and is a member of the best country club. And yet they are deeply unhappy. We work with them, we went to school with them, and we hear about them on podcasts. They have everything in the world, but they’re not having fun.

Thought experiment: the remedy

Can you have self-actualization while doing nothing? Lao Tzu would say yes. 

Picture a man in a box: no social media, no FOMO or reference points. He’s given a menu of 1,000 unique tasks he can do to earn money. Over time, he discovers a few that he really likes doing. He eventually settles on one of those tasks and gets good at it. Maybe he tries one of the others again but discovers he really does prefer to do the one task. He keeps doing it and keeps being rewarded with “money” that he believes can be traded for future fun.

In this hypothetical universe, does he ever stop working? If so, when? If work is work, and not meant to be fun, when is enough, enough? With no reference points, the man in the box probably accumulates enough money, based on some exchange rate, to last a long time. Then he stops working and trades money for fun. He should be happy.

We know from studying human psychology that we can’t help comparing ourselves to others. This is the mimetic desire I read about in the book Wanting by Luke Burgis. We are programmed from an early age to mime those around us, and that very much includes material possessions. If we can short-circuit that tendency, we find happiness faster.

Personal takeaways

I’m in the vicinity of #3 right now. That’s not to say I’m not having fun. I am! But I haven’t reached “peak Ryan” yet so I can’t claim the mantle of #6. I’m working my up to it and enjoying the process. It is fun, it’s just not that kind of fun. The pinnacle takes time, for me at least, and I won’t feel it until my professional career is more mature and I’ve done a lot more writing.

I know I’m not content with the simple life, #1. This may be a foible. I want to make an impact. I want my impact to be appreciated, making me interesting. I see myself as someone who can be influential — should be influential — but I also recognize that I need to work for it. I expect that influence to coincide with even more money, and I imagine that having impact, influence, and money will bring me ultimate fulfillment.

As I write this, I present myself with the question: can I not have “ultimate fulfillment” without impact, influence, and money? That seems like a sad state to be in. Is there no fun without #6?

Of course there is. My 6 steps are not a hierarchy, each level up being better than the previous. Rather, it’s a sequence I see from observation. It’s not a hard and fast rule. The melding of #1 and #6, for example, is very real. The same could be said for #2 and #6, and so on.

I’m still working my way through this thinking, finding my bits of impact and influence along the way, and, of course, trying to have some fun.

Leave a Reply