“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”
– Nassim Taleb
It’s been 7,626 days with a steady W2 paycheck, about 21 years, but today, May 13th, 2024, is my first day of retirement.
No, not retirement like this.

Although I’m not against shuffleboard.
What I’m really talking about is retirement like this.

This is Naval Ravikant. Entrepreneur, founder of AngelList, and all-around smart dude.
I’ve talked about him before.
Naval is like the Dali Lama of X, a wise sage who writes and shares ideas. Like this.

See? X isn’t a total cesspool.
But this post on retirement is the one that really caught my eye.

Say it with me. “Retirement starts when you stop sacrificing today for some imaginary tomorrow.”
Which brings us to Bud Fox. You remember Bud, right?

Wall Street & Vagabonding:
In the (terrific) book, Vagabonding, Rolf Potts talks about Bud.
“Of all the outrageous throwaway lines one hears in movies, there is one that stands out for me. It doesn’t come from a madcap comedy, an esoteric science-fiction flick, or a special-effects-laden action thriller. It comes from Oliver Stone’s Wall Street, when the Charlie Sheen character – a promising big shot in the stock market – is telling his girlfriend about his dreams.
“I think if I can make a bundle of cash before I’m thirty and get out of this racket,” he says, “I’ll be able to ride my motorcycle across China.”
When I first saw this scene on video a few years ago, I nearly fell out of my seat in astonishment. After all, Charlie Sheen or anyone else could work for eight months as a toilet cleaner and have enough money to ride a motorcycle across China. Even if they didn’t yet have their own motorcycle, another couple months of scrubbing toilets would earn them enough to buy one when they got to China.”
Vagabonding is focused on travel, but it hits some deeper notes. Specifically, Potts helps bring clarity to living a meaningful life. And how accessible that can be.
You imagine this future state, you think about what you’d like to do and see and be when it’s all said and done. But at that point, the calculus gets a little fuzzy.
We think the only way to leave the rat race is by making it to some fictional ending, where we’ll be rewarded with a hearty, satiating, block of cheese. But what happens when the boss moves that cheese?
Even more diabolical is when you move it yourself.
And when you finally get a nibble and realize it’s brie (yuck!), you’ll start questioning everything. That’s what happened to me.
Potts provides a different perspective, pointing out that the best experiences in life have more to do with “getting out of this racket,” than they do with having that “bundle of cash.”
And that is what I started exploring.
What were my best experiences? How much cash did they require?
The Mind Virus:
Maybe I was letting Ravikant and Potts have their way with me. Infecting me with some internet mind virus.
Maybe it was a classic mid-life crisis.
Let me clear this up for you; it was both.
But still, I was inspired. And it feels good to be inspired.
Henry David Thoreau was pre internet mind virus, and he said, “The cost of a thing is the amount of life which is exchanged for it, immediately or in the long run.”
The longer I worked, the more life I was exchanging. I was trading out these years in my 30s and 40s for imagined years in my 80s and 90s.
I started having real money fears.
Not that I’d be old and gray and not have enough. My fear was being old and gray with too much, knowing what I traded to get it, all because my math was wrong.
Like Bud Fox, I was working towards a bundle of cash when all that was needed for my ride across China was eight months of toilet cleaners’ salary.
Figuratively of course.
Risk & Magical Thinking:
I told my shrink the news last week. He’s heard me gripe about all sorts of things, but my old job leads the pack. I started telling him what I had planned. It all sounds like magical thinking. I’m fully aware of that.
I said, “I know I sound like Peter Pan right now.”
He laughed. But he didn’t disagree.
Still, this is exactly what we are talking about. Bringing your imagined future into today is going to feel a little bit like Peter Pan if you’re doing it right.
As the day approached, I tried to talk myself out of it. Years of programming tried to override my humanOS.
I can’t just quit my job, I have kids, I have a wife! And a 401K!
The old joke goes like this.
A man asks his wife, “Would you still love me if I lost all of my money?” And she says, “Yes, I would always love you, but I would miss you terribly.”
So, you know, going broke and losing my family is not exactly the lifestyle I’m going for.
But even with that wrestling match between risk and magical thinking, I was trying to find a way out.
I wanted each day to be complete, in and of itself.
What a beautiful idea.
But I couldn’t just pull the ripcord. I needed to take some baby steps.
The first step in the process is to select an arbitrary date in the future and call it a goal.
The second step is to be unhappy until you reach it.
See? Love this magical thinking.
Remember SMART goals? SMART goals are Specific, Measurable, and then there’s the A and the R, but the T is what we are after here.
Time Bound.
No problem. A few flips of the ol’ calendar and my retirement date was set. I even went to the website www.days.to and made it official. They gave me a countdown ticker that I could check…and I did check. More often than I care to admit.
August 1st, 2022. I couldn’t wait.

Whoops!
I’m a little late.
But really, what’s 649 days amongst internet friends?
We had that little COVID thing, and the market crashing thing, and then the market ripping higher thing, and I got confused and scared and busy and scared.
But it was still nagging at me. Eating away at me.
I was trading time for money, when every old timer you talk to will advise you to do the opposite.
And then I started losing people. Losing some of the old timers in my life.
I lost my father-in-law and two aunts. Cancer hit all three.
I thought I’d lost my mom too. Twice actually.
My friends were losing people as well. All before their time.
In other words, the signs were all around me that life is short, fragile, and unpredictable. And I didn’t want to trade the days I have left, for money I didn’t need.
As I sat in my Zoom calls, flipping through PowerPoint decks and responding to messages. As I pitched deals and put in my time. I was imagining the future.
But what specifically was I imagining?
More Green Squares:
What did retirement look like? How would I spend my days? Should I get my motorcycle license?
I knew I wanted to contribute and create.
So, I started the blog to share my ideas and on September 19, 2022, I wrote an important post. Important to me at least. More Green Squares, an answer to my question: What does a good day look like?
Of course, a few good days will make a good week, which leads to a good month, a good year, and… wait for it… a good life.
It was freeing to know what I wanted with more clarity, but I was still scared to live that #MoreGreenSquaresLife.
Insurance, and stock options, and college funds, and, and, and…
The programming is persistent.
Employers make the idea of going it alone sound crazy.
You’re not crazy, are you??!!??
Well, you’d be crazy to leave us! We are number 17 on the Southeast Pierce County Best Places to work list!
You’d be a fool to leave. We have bagels and bad coffee every third Friday.
These warnings gave me pause but once I figured out the bagel situation I returned to More Green Squares and what makes a good day. I called it my “Standard Saturday” and it looked like this.
- No alarm but up early
- Walk 30 minutes
- A great cup of coffee
- Write for one album (about an hour)
- Read for an hour or two
- Hit the weights, get the heart pumping
- Laugh, cry, feel emotion (the Valvano method)
- Cook a great dinner
- Be outside, feel the sun, feel the cold
- See friends or family
A good day in my book is a pretty simple thing. No bundle of cash needed. And even if it was, that bundle would be a lot smaller than most people think.
I’d told myself the story over and over again. I was inspired, I worked out the numbers, but I still couldn’t pull the trigger.
Fear.
And then I got some great advice.
Singing to yourself:
As I was working through the numbers and working up the courage to step away, I was also reading the (terrific) book, Petty, by Warren Zanes.
Specifically, I was reading the chapter about recording Wildflowers, one of my all-time favorite albums. Tom was going through a very difficult time with his band and his family. Wildflowers was his “divorce album.” Divorce from his wife and in some ways, his band, the Heartbreakers. Both parties wanted more rock n roll in their lives, but Tom’s writing had changed. He had changed.
““I’ve read that Echo is my ‘divorce album,’” says Petty, “but Wildflowers is the divorce album. That’s me getting ready to leave. I don’t even know how conscious I was of it when I was writing it. I don’t go into this stuff with elaborate plans. But I’m positive that’s what Wildflowers is. It just took me getting up the guts to leave this huge empire that we had built, to walk out. But staying there was finishing me off. I’d become a different person.” After Petty’s therapist heard the song “Wildflowers,” he asked who the singer was addressing. “I told him I wasn’t sure,” Petty says. “And then he said, ‘I know. That song is about you. That’s you singing to yourself what you needed to hear.’ It kind of knocked me back. But I realized he was right. It was me singing to me.”
– Petty, Warren Zanes
When I wrote More Green Squares, I was singing to myself. Same with Antifragile Acceptance and several others.
“There was some bargaining at the end, prolonging the inevitable. He’d stay through Christmas, that kind of thing. Soon enough the bargaining was over.”
– Petty, Warren Zanes
Prolonging the inevitable rang true as well. Through the holidays. Until the next bonus hits, or the next slug of stock options. Maybe I’ll go after we wrap up this project?
Most recently, I thought, ‘I’ll hold out until October, make it an even 20 years at the firm. 20 years has a nice ring to it.’
But why? Was there a Rolex involved?
It was just more bargaining. And I needed to listen to the tune I was singing to myself.
What now?
This is the question I keep getting.
What now?
You see, I’d call our situation somewhat uncomfortably retired.
The pile of cash ain’t that big.
Like, it’s probably going to work, but you know, a bit more income would be neat.
If things go sideways, we might run dry at 82. On the flip side, if we have a nice run, we could make it to 101 years old and have forty-three million in the bank.
These financial models are wild. And they are mostly bull shit.
A few percentages on an investment, compounded. A couple of rate cuts, or inflation spikes. It’s all just fancy guess work.
But my thinking is, why work a job I don’t love, that pulls me away from the people I do love, just to protect against the off chance that the US economy implodes for fifty-seven consecutive years.
Could it happen? Sure, I suppose, but let’s not plan on it. And if it really goes down like that, we might be trading beaver pelts from a shelter in the North Cascades instead of Berkshire Hathaway shares from the golf course.
I don’t really want to be the old dude serving Pink Drinks at Starbucks. I’d screw up that “extra hot, extra dry, half caff cappuccino” every time.
Not because I can’t execute the order.
But because I hate you for placing it.
Besides, I’m more of a Home Depot Garden Center guy anyhow.
I’m getting off topic though. Remember the post from Naval? We haven’t talked about the second part of it yet.

“You retire by saving up enough money (Bud’s bundle), becoming a monk (FIRE movement), or by finding work that feels like play (Dave’s excellent plan).”
We had a good start on option number one after 20 years of working.
Being a monk sounds less than ideal, but we could leverage that a bit by not being D-U-M dum.
But option three is where we landed.
“Work that feels like play.”
Writing More Green Squares taught me that retirement was attainable and wouldn’t require the big bundle of cash I’d been working towards for two decades.
It also showed me that I was going to be productive.
Reading and writing a few hours a day. What can be created by doing that?
So, I asked myself.
Self – Can you make a few bucks creating and sharing the stuff you write? The stuff you’d be writing anyhow?
Typically, I’m hard on myself, and some version of me would say, “give it up, nobody wants to read your sh*t.”
But on this day, I said to myself, “No fucking problem you sexy bastard!”
I was drunk, but still…
And you know what, even if I end up slanging a few Pink Drinks at Starbucks or helping your kids kids check out geraniums from Home Depot on Mother’s Day 2072, I’d imagine that version of me has a wonderful time doing it. Shoot, it would get me out of the house. Maybe the boss lets me knock off early to see the great grandkids ball game.
I’d rather take that chance. Because trading today for an imagined future is just too risky.
What’s next?
I’ll be here, on the internet, sharing. You’ll see a few more books, some courses, some challenges, some consulting on the side, and maybe even some goodies on YouTube or Spotify.
A few sponsors will show up (Laird? LMNT? Call me!), but nothing that bogs down the site.
I’ll be doing it all at my pace. What’s the rush?
My calendar is empty, my heart is full, and I’m excited to see what I can create.
So, yeah, I’m retired now.
And I think that means I’m starting my best work.
CODA:
As I was finishing this post, my brother sent me a text.

For most of you, this is a sad story and not much more.
Well, here is a little more.
I grew up playing baseball and I never loved the game more than I did in 1992 and 1993. I was playing majors ball at Steel Lake Little League. We had a great team, the Fat Bat Twins. Fat Bat was a local batting cage, and you couldn’t get a better sponsor. Free cage time and space ball.

Once the little league season wraps up each league pulls their best players onto an All-Star team. That team plays other leagues in the district, the state, the region, and if you keep stringing together wins, you’ll end up playing ball in Williamsport, Pennsylvania. The Little League World Series.
That is where I first heard the name, Sean Burroughs.
He is a legend.
In the Seattle area it was Ken Griffey, Jr. who was bigger than life, but for a week in the summers of ’92 and ’93 this kid from LA took over ESPN. A kid that was our age. A kid that could have played in our league.

And he dominated. Twice.
How good was he?
From the Little League website, “Sean became the first American-born player to throw back-to-back no-hitters in the Little League Baseball World Series and went on to lead his Long Beach (Calif.) Little League team to back-to-back championships in 1992 and 1993, setting history as the first U.S. league to do so. During both of those historic runs, Sean had the opportunity to experience those memories with his father, Jeff, as his coach. During his 1993 run, Sean recorded a then-record 16 strikeouts as part of his back-to-back no-hitters and went on to hit .600 through the World Series performance.”
Advancing to Williamsport, through the gauntlet of games and travel and injuries, is incredibly difficult. You need to be extremely good, and extremely lucky.
Sean was both. Twice.
Until he wasn’t.

He played a few solid seasons in the majors. He won a gold medal with the US team.
And he died at 43 while coaching his son’s Little League team. Something I’ll be doing as soon as I close this laptop.
I don’t have much in common with Sean Burroughs, I could never play like he did, but in 1993 we shared the same dream. It came true for him.
At 43, maybe we shared a few more. Fathers often do. Unfortunately, he won’t get the chance.
I’ve still got mine.
Sometimes, when all the signs are pointing in one direction, regardless of where they come from, you just need to trust them, follow them, and see where they take you.
If you enjoyed this post, please share it with a friend.










