What Does a Crazy Running Streak Have To Do With Retiring Early?

I just hit 66 months running at least one 20-mile long run each month. I also retired at 42. Those two things might sound unrelated, but they both came from the same mindset: I do hard things.
So what do these things have to do with each other? More than you’d think. The way I run for long distances is exactly how I approached building wealth and retiring early, one mile, one dollar, one decision at a time.
The 5.5 year streak has been hard. I live in St Louis. We have high humidity, high temperatures, lots of rain, really low temperatures, and plenty of snow. We’re in the middle of the country. We get it all. I can’t dodge the weather.
I also can’t dodge injuries, sickness, etc.
Retiring young is also hard. Less than 1% of people retire in their 40s like I did.
Let’s get into the article.
Table of Contents
I Don’t Avoid Hard Things, I Look for Them

Most people flinch when something feels hard. I lean in. I’ve built a habit of running toward discomfort because that’s where real progress lives. There’s power in being the type of person who says, “I do hard things,” and means it.
Early retirement wasn’t easy. Neither is running 20 miles every single month. But doing hard things on purpose makes the next hard thing a little less scary. That mindset changes everything.
Retired at 42: How I Think Differently Than People Still Working
No Shortcuts. Just Sweat.

You can’t fake your way through 20 miles. There’s no hack, no app, no shortcut. You lace up, you suffer a little, and you finish. That’s it.
Investing works the same way. Especially in real estate, where most of the work happens before the payoff ever shows up. I didn’t get to early retirement because I found some magic system. I just did the work.
You want to win? Show up and grind.
Time, Money, and the Stuff You Give Up

I’ve had plenty of chances to do something else with my time. Three hours running means making changes, eating different the day before, skipping out on stuff. I’ve had to say no to comfort and convenience over and over again.
Same thing when I chose long-term wealth over short-term dopamine hits. I wanted to blow money just like everyone else. But I didn’t. That’s the only reason I’m here now, retired and having fun.
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Comfort Never Built Anything Worth Bragging About

Running 20 miles doesn’t feel good. It never has. Neither did watching my friends (or people I didn’t like!) spend freely while I stacked rental properties and lived below my means.
Sacrifice doesn’t feel good in the moment, it burns. But I never once regretted it. Because comfort might be fun short term, but discomfort builds something better: options, freedom, and peace.
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You Can’t Do It Alone

There were so many moments I wanted to quit either during runs or just during the streak. Life, weather, mental fatigue, vacations, and injuries all make it hard to just keep going. But someone always pulled me through, running friends, my wife, people who wouldn’t let me slide.
Same thing happened during my path to financial independence. I was in my late 20s, under $1M of debt, making less than $50K, and 2008 came swinging. My portfolio dropped 50% in one year.
My real estate portfolio got punched in the face. I could have walked away. But I didn’t. I had (nonfinancial) support, and I have grit. Both matter.
Or there was the time I was sued: How To Deal With Getting Sued As A Landlord
Not Every Day Will Feel the Same

Some days I float through a long run. Other days, it’s a war just getting out the door. That’s life. That’s investing. That’s marriage, business, parenting, all of it.
You don’t get to pick your energy level or how well things go. You just show up and do your best anyway. The early retirement plan didn’t work every year the way I imagined. But I adjusted. And I kept showing up.
Related Video: 9 Mental Shifts Required for a Successful FIRE Journey
The Market Doesn’t Care About Your Plans

I’ve run in wind chills near zero and in heat indexes pushing triple digits. I don’t get to pick the weather. I just go. The market works the same way. It doesn’t care if you’re “ready” to invest or need a perfect time to buy property. It’s going to swing.
You can either ride it or sit on the sidelines forever. The people who win are the ones who keep moving forward, no matter the conditions.
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I’m Stubborn Enough to Win

I’ve never been the fastest. I’ve just been the one who kept going. That applies to money too. I didn’t time things perfectly, or do any get rich quick plan. I just refused to quit. That’s the kind of strength that matters.
Consistency beats brilliance every single time. Being strong-willed isn’t about ego, it’s about momentum.
I Became A Millionaire In my 30s: Here Are 25 Things I Know, That Most Never Figure Out
No Excuses, Just Execution

If I say I’m going to do a 20-miler this month, I get it done. It doesn’t matter if I’m busy, tired, traveling, or sore, I figure it out. Same with my money. I didn’t make excuses about my income, my background, or the market. I made it work.
Excuses don’t get you to retirement. Action does. So I just kept showing up and doing what needed to be done.
The Real Key: Just Show Up

This is the one that matters most. You can’t run 20 miles if you don’t show up for the first one. You can’t retire early if you never take the first step.
Showing up when it’s hard, slow, or inconvenient is the whole game. I don’t finish those runs because I’m special. I finish because I start. Every time. That’s the difference.
The Mindset Shifts That Make People Wealthy (Or Keep People Broke)
Run the Race, Retire on Your Terms

Running 20 miles and retiring early both look crazy until you’re the one who’s done it. Neither happens overnight. Both take discipline, sacrifice, and a little bit of stubbornness.
You don’t need to be the smartest, the fastest, or the luckiest, you just have to keep going. Every long run reminded me I can do hard things, and that mindset is exactly what made early retirement possible.
Most people give up too soon. Don’t be “most people”. Show up. Do the work. Win your freedom.
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