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This site went live on February 9, 2022. Today marks our fourth anniversary.
I’m sharing a lesson learned from each year of writing online. If you’re new here and want the full progression, just keep scrolling.
Fourth Anniversary, February 9, 2026:
You can’t predict.
This year, one post accounted for roughly 65% of my website traffic. Not my best writing. Not my most personal piece. Not anything I’d have predicted.
It was “The Soft American”—a post about JFK’s Op Ed in Sports Illustrated, a call to action for America to get fit, just a few months before he took the oath of office.
I published it on December 26, 2024, as part of my ongoing “On This Day” series; Kennedy’s original was published on December 26, 1960.
It was nothing more than a historical curiosity. Something I found interesting. Something I agreed with. And something I’d seen as an issue with the children I’d coached. In addition to highlighting the fitness test and its origins, I also pushed for its return and highlighted the mistakes our elected leaders made in the dissolution of the previous program.
Then President Trump announced he was reinstating the Presidential Fitness Test, and suddenly everyone wanted to know about Kennedy’s fitness crusade. Maybe they wanted to understand my point of view as well. Citizens Free Press linked it. The Washington Post linked it. My little corner of the Flynnternet got a tsunami of visitors looking for context on a 64-year-old essay.
I didn’t see it coming. How could I?
Nassim Taleb calls these Black Swans—high-impact events that are impossible to predict beforehand but seem obvious in hindsight. We can’t forecast them, yet they shape most of what matters. The same applies to creative work. The posts that land, the ideas that spread, the pieces that resonate—they refuse to be predicted.
Scott Adams discovered his own lack of predictive powers while creating Dilbert. Some strips came to him instantly—great idea, quick execution, time to polish. Others he’d struggle with until minutes before deadline. His readers couldn’t tell which was which. The effort invested, the value he put on the idea, and his own personal evaluation of the work, had zero correlation with what resonated.
This is the nature of power laws. A small number of inputs produce the vast majority of outputs. In content, in business, in life—the distribution is never even. One post does the work of fifty. One client pays the bills. One conversation changes your trajectory.
But which one will it be?
Jeff Bezos talks about this in the context of business. In baseball, he says, “no matter how well you connect with the ball, you can only get four runs. The success is capped at four runs. But in business, every once in a while, you step up to the plate and you hit the ball so hard, you get a thousand runs.” It works in technology, investing, and in creative work too. You can hit a thousand-run homer. The outliers aren’t slightly better than average. They’re categorically different.
So what do you do with this information?
Well, understand that you can’t predict the thousand-run homers, all you can do is put a good swing on the ball.
The Soft American wasn’t my best swing. It wasn’t an idea people were clamoring about. It was just an area of interest, and I wanted to put the idea “in play.”
It happened to meet the moment.
You can chase trends and optimize for virality, but that sounds like a real drag. I think I’ll just keep showing up—week after week, year after year—and give luck a chance to find me again.
Third Anniversary, February 9, 2025:
Potential is a comforting illusion.
It’s Super Bowl Sunday, and I’d be remiss if I didn’t mention that the true anniversary of WinWithFlynn.com is Super Bowl Sunday, 2014. If you’re doing the math, that’s actually 11 years ago.
Confused? Yeah, life can be that way.
I was sick with the flu, watching my Seattle Seahawks beat down the Denver Broncos, when an ad from Squarespace caught my eye.
Register a domain with them, and it would cost just 99 cents. So I went to their site, plugged in my tried-and-true campaign slogan “Win With Flynn,” and was shocked to see that nobody else in my family had taken it.
Sold.
And then shelved.
The Flynnternet would need to wait.
The next year they sent an email about renewal, and while they’d charge me more than a buck, I didn’t want to lose my domain. I didn’t want to lose my unbuilt, contentless, home on the internet. So I quickly took action. I renewed it.
Why?
I’ll tell you why.
Schrödinger’s Cat. The famous thought experiment created by physicist Erwin Schrödinger in 1935 to illustrate a paradox in quantum mechanics has been adopted and adapted as a sort of pop psychology thought experiment.
Schrödinger suggested placing a cat in a box with a vial of poison. The vial is rigged to break and kill the cat if a certain quantum event takes place, in his scenario, the decay of a radioactive atom.
Okay, hang with me: Schrödinger says that the cat is theoretically both alive and dead at the same time because its fate is tied to a quantum event (the radioactive atom decay) that exists in a superposition of states until observed.
You still there?
Let’s simplify. The cat is both alive and dead, until you observe the inside of that box, until you open it.
You’ve probably seen this play out in your own life, when someone says, “I just can’t look!” The offer letter, the lotto ticket, the note from their crush, the email from a client.
And maybe you’ve seen Schrödinger’s Plates, a popular internet meme that makes the paradox easy to digest. The dishes are both broken, and unbroken, until you open the cabinet.
During that first year, I’d been dreaming. I’d been dreaming of a business or a blog or both. And when the renewal came due, I didn’t want to stop dreaming. So, I kept right on going. I kept dreaming and renewing, year after year. Well past the golden years for my Seattle Seahawks. Well past any reasonable timeline for a website launch.
I’m sure even the fine, supportive people at Squarespace (and later WordPress) were wondering why the hell I wanted this domain if I wasn’t going to do anything with it.
And then, in 2022, I pulled the trigger.
Hold your applause.
Even that is stretching the truth. Because my first blog posts were under an alias. Under a different domain called ideaguy.com, and then I used Flynns.blog, before finally moving to the site I’d registered years before, as Marshawn Lynch raised The Lombardi Trophy.
It was all a long time coming. So what’s the lesson?
Is it, good things come to those who wait? Is it something about grinding? Oh, I know, it’s about chasing your dreams, right?
No, not quite.
I was a “claim sitter.” During the gold rush, people would stake a claim but never actually mine it, holding onto it as a sort of lottery ticket with endless possibility.
I held the site in my mind that same way, as something with endless possibility. A lot of people do some version of claim sitting. Business plans, novels, whatever the dream might be. They sit on it, and they talk about it, but they certainly don’t dig, because they like the self-delusion of endless unobservable possibilities. They don’t want to see Schrödinger’s dead cat. And I totally get that.
Schrödinger and his contemporaries were studying topics I’d categorize as “Stoner or Scientist.” Ideas that are so wild you’d think they were high as a kite. Stony baloney. And maybe they were.
But in that space, between stoner and scientist, lies our box, and a lesson. In quantum mechanics, the observation determines reality. Our lives work the same way. When I finally “opened the box” and started writing, I wasn’t just discovering success or failure—I was actively creating that future through active participation.
By never looking, never observing, we stay in limbo. Infinite possibility, but nothing observable, nothing real. And for a long time that felt better than observing something unpleasant. The truth.
Your observation, your action, isn’t just revealing the outcome, it’s creating it. It makes it real. That’s what gives it life.
So open the box.
Second Anniversary, February 9, 2024:
Most secrets are overblown.
They aren’t worth the energy required for storage. They are built up in our heads as monumental, earth-shattering, and mind-blowing, but the truth is that nobody cares as much as we do.
How do I know? You probably don’t even remember, but Mexico (yes, the country) came out this past year and straight up told us they have aliens. The remains of mummified aliens. Nobody cared. I mean, people cared for a day or two. Clearly, I still care, but it was just a few revolutions of the news cycle, and everyone had moved on.
Mexico has ET, the real ET, and it looks like ET. Spielberg got that one right. Are they real? I have no clue. But the secret was real.
I kept this website a secret for way too long. From my wife, my family, my friends, and my coworkers. I built it up in my head to be so much more than it was.
I didn’t want to tell people until I had something good; I didn’t want to share because I thought I might quit. And then, when I finally figured out that I wasn’t going to quit and I had something worth sharing, I felt bad for keeping the secret, so I kept it even longer. How is that for building things up in your head? Keep a secret because you feel bad you kept a secret?
When I finally told people, the response was mostly positive or indifferent. So, I told a few more people, and eventually I posted publicly for anyone that was interested. Again, their response was mostly positive or indifferent.
My response, though? Complete and total relief. I didn’t need to hold that secret anymore. Most secrets are like that – somewhere between aliens and a blog post. And nobody cares as much as you think they will.
First Anniversary, February 9, 2023
You are what you repeatedly do.
That makes me a writer.
Not a professional writer (yet), but a writer all the same. And it feels good to say that. I’m a writer, a parent, a husband, an investor, a weightlifter, a reader, a cook, and the list goes on. The fun thing about this frame of mind is I can add to the list whenever I’d like, just by inserting the activity into my daily routine. I can also remove items from the list when they no longer serve me. I’m no longer a snowboarder, and I’m fine with that.
Entrepreneur, religious scholar, open water swimmer, arborist—it’s all on the table. It just takes consistent action.
There’s a scene at the end of The Silver Linings Playbook where Pat (Bradley Cooper) and Tiffany (Jennifer Lawrence) walk into a hotel before their big performance. The lobby is full of dancers warming up. In awe, Pat says, “Look at the dancers. You see them?”
He doesn’t see himself as one of them, but a few minutes later, that all changes. Because he’s a dancer too.
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