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After Addiction and Ironman Failure, This Founder Adopted a Rule That Changed Everything

May 8, 2026
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After Addiction and Ironman Failure, This Founder Adopted a Rule That Changed Everything
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Opinions expressed by Entrepreneur contributors are their very own.

Key Takeaways

Rideout believes most individuals fail as a result of they “negotiate” with themselves as a substitute of performing.

He says taking the simple street early value him alternatives, together with the possibility to pursue an MBA.

After quitting an Ironman race, he vowed by no means to stop once more, irrespective of the situations.

Most authors would take a victory lap when their ebook turns into a nationwide bestseller. Not Ken Rideout.

“I might have been happier if it made the New York Occasions record,” he says of his new memoir, Every part You Need Is On the Different Aspect of Arduous.

For Rideout, successful isn’t sufficient. The actual take a look at is how shut you get to the usual you set for your self, and the way shortly you increase it once more.

Rideout is an elite endurance athlete, entrepreneur and former Wall Avenue dealer. He’s additionally one of many quickest marathoners on this planet over 50 and a recovering opioid addict who spent years battling dependency earlier than getting sober in 2010. He appeared not too long ago on the One Day with Jon Bier podcast to speak about self-discipline, coping with ache and why most individuals fall in need of their targets.

Associated: Easy methods to Go away Your Legacy, Assist Others and Elevate Your Authority

Cease negotiating with your self

Rideout doesn’t spend a lot time deciding whether or not he appears like doing one thing. For him, that’s the place most individuals lose the every day battle.

“As quickly as you cease negotiating with your self, it’s superb what you’ll be able to accomplish,” he says. “I’m simply doing it.”

He sees that inside debate as the actual impediment. The second you begin weighing whether or not to behave, whether or not it’s getting up early, making a name or pushing by a tricky stretch, you’ve already created an exit ramp.

Rideout’s strategy is to take away that possibility completely. If one thing must get completed, he does it. “You rise up and also you deal with your rattling enterprise,” he says.

Associated: A 4-Step Information to Overcoming Obstacles

Pay now or pay later

Rideout got here to this mindset by watching what occurs if you don’t put within the work early.

“I want I had studied,” he says. “I want I had the choice to go get my MBA at Harvard or Yale.”

As a substitute, he took what he describes as the simple street by the primary half of his life not placing the laborious work in academically. That selection didn’t really feel pricey on the time. 

“However by not learning and all the time taking the simple street, I eradicated the potential to have the ability to do these issues,” he says.

That sample caught. It confirmed up in different components of his life, from profession selections to habits that adopted him for years.

“The simple street by no means pays nicely,” he says.

Now he treats effort like a invoice that all the time comes due.

He taught himself the right way to be powerful

Rideout wasn’t all the time wired this manner. He describes himself as “very timid as a child.” However that modified when he walked into the Somerville Boxing Membership. At first, he hated each second of it. He had no pure inclination in the direction of boxing. No hidden left hook. Only a recognition that avoiding concern wasn’t working.

“I mentioned I’d relatively get within the ring in a managed setting and learn to do that than get right into a scrap on the street and be fully a fish out of water,” he says.

That have grew to become a template as a result of it confirmed him one thing he hadn’t believed earlier than.

“You’ll be able to educate your self the right way to be powerful,” he says.

The sensation by no means went away. He nonetheless didn’t need to step into the ring. The distinction was that he stopped treating that feeling as a motive to again off.

Associated: 5 Suggestions for Difficult Your self to Carry out Exterior of Your Consolation Zone

Quitting as soon as was sufficient

There’s one second he hasn’t let go of. On the Ironman World Championship in Hawaii, Rideout dropped out mid-race. 

It was a mistake he nonetheless regrets. “The sting of quitting by no means leaves you,” he says.

That call hardened into one thing he carried ahead. Two years later, he got here again underneath worse situations. He had pneumonia main into the race and knew early on he was in hassle. This time he says, “I used to be going to drop useless earlier than I stop.”

He walked, ran and pushed his means by the course, ultimately ending after greater than eleven hours. It wasn’t his greatest efficiency. However this time, he completed.

His subsequent race

At 55, Rideout has no plans to decelerate. He’s inspired by the early success of his ebook and is fielding curiosity from movie producers. His most important focus now’s his expertise company, Rideout Sports activities and Leisure, the place he works with medical doctors, scientists and well being and wellness leaders (disclaimer: I’m a accomplice within the firm). With no races at the moment scheduled, he admits he can really feel a bit unmoored with out one thing like a 155-mile ultramarathon to concentrate on.

However his strategy hasn’t modified. “It’s by no means a negotiation with your self,” he says. “You rise up and also you deal with your rattling enterprise.”

Key Takeaways

Rideout believes most individuals fail as a result of they “negotiate” with themselves as a substitute of performing.

He says taking the simple street early value him alternatives, together with the possibility to pursue an MBA.

After quitting an Ironman race, he vowed by no means to stop once more, irrespective of the situations.

Most authors would take a victory lap when their ebook turns into a nationwide bestseller. Not Ken Rideout.

“I might have been happier if it made the New York Occasions record,” he says of his new memoir, Every part You Need Is On the Different Aspect of Arduous.

For Rideout, successful isn’t sufficient. The actual take a look at is how shut you get to the usual you set for your self, and the way shortly you increase it once more.



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Tags: addictionadoptedChangedDrug addictionfailurefounderhealth and wellnessIronmanKen RideoutmindsetruleTriathletes
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