The Barkley Blueprint

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The Barkley’s Marathon–widely considered to be the worlds most difficult endurance race–is run annually in the hills of eastern Tennessee.  

The application process is unusual—a paltry $1.60 entry fee, a license plate from your home country and a required essay—”Why I should be able to run the Barkley.”

Since 1986, only 17 people have finished the Barkley Marathons—just 23 finishes total out of roughly 1,400 entrants. That’s a 1-2% finish rate. The first woman finished in 2024.

Barkley’s Course Facts:

• Distance: Five 20+ mile loops

• Elevation Gain: 60,000 feet

• Navigation: Maps and compass only (no GPS)

• Aid Stations: None except for water drops

• Books: Runners must tear pages corresponding to their bib number from hidden books to prove they completed each loop

What makes Barkley’s so challenging?

It’s not just the 100+ miles of rugged terrain—most entrants are seasoned ultra runners, yet 98% don’t finish. 

The real challenge is psychological: navigating uncertainty and isolation while pushing your body through exhaustion and harsh conditions.

Sound familiar?

Entrepreneurship is NOT a marathon.

The saying, “Entrepreneurship is a marathon, not a sprint” is not quite true.

Yes, marathons are long—but they’re predictable.

Anyone who follows a structured training program and runs a measured race will finish. Over 90% of entrants do.

Why are traditional marathons “easy”? 

The course and finish line are well marked and include thousands of other runners and cheering fans. 

As rough as I’ve felt at mile 20, knowing there were just six miles left—and that I wasn’t suffering alone—made it mentally easier to keep going.

Entrepreneurship is more similar to the Barkley’s Marathon

Barkley’s conditions are brutal.  Sixty hours of sleep deprivation, weather and extreme physical exertion impair the mental faculties required to navigate Barkley’s obscure course—often when it is dark.

It’s lonely.  Runners might not see another human for hours at a time.  Whether they’re lost, injured or exhausted they are enduring it all alone.

The Barkley’s Blueprint

What makes a successful Barkley’s finisher also makes a successful entrepreneur—mental fortitude, navigation skills and decision making under uncertainty.

Mental Fortitude

Emotional resilience: Can you keep going when the outcome is uncertain?

I can only imagine the difficulty of drearily running through a dense forest on a dark and rainy night searching for obscure landmarks. A major navigation error could end ones chances of finishing—and often does.

Barkley’s runners use a pre-commitment framework to decide thresholds for quitting before the race starts. Typically this sounds like, “Unless I’m injured or lost beyond recovery, I keep moving.”

For those making the leap, pre-committing to the journey and it’s inevitable challenges is essential. It may sound something like, “Unless I’m completely out of resources or learning nothing, I keep going.

Pain tolerance: Are you okay with failure and looking stupid?

Barkley’s competitors deal with blisters, cuts, frostbite and muscle strain on top of their physical fatigue.

For entrepreneurs, the scrapes and bruises are to our egos not our bodies.

Failure is not a bug of entrepreneurship but a feature. Success is a numbers game, and your first version (or first fifty) probably won’t be the winner.

Tie your identity to the process not the result. Runners aren’t defined by races but by showing up daily and running.

What is the equivalent in your work?

Self-reliance: Are you okay being misunderstood and unsupported—even by those closest to you?

From the outside, your journey will appear futile—riddled with uncertainty, struggle and failure. Why?

Society trains us to think linearly. From kindergarten on most people’s lives are a series of incremental steps within a prescribed path with regular checkpoints—sounds like your basic marathon.

You pass a grade, graduate from school and get a job, receive regular promotions or a raise-then the finish line—retirement.

With entrepreneurship, there are not always visible or objective measures of progress such as job titles or retirement account balances.

As failures accumulate—your knowledge and understanding of what does and does not work increases. Similar to a financial portfolio-your talent stack and experience will increase the likelihood your future efforts pay dividends.

Remember—while you may care what others think—you can’t control it. Most people focus on themselves and their own insecurities. Don’t let them project those onto you.

Navigation Skills

Learning from mistakes: Can you build and apply a framework to learn from failure?

Humans are bad at self evaluation. We tend to focus on causes that minimize harm to our ego but this keeps us from truly learning from failure.

John Kelly changed his mindset for each race. His goal changed from finishing to learning something new.

Treat each of your efforts as experiments with objective criteria set prior to their execution.

Planning: Can you construct dynamic plans focused on key leverage points?

Plans are worthless, but planning is essential.

In Barkley, runners know wet feet or dead headlamps can end their race—so they pack extra socks and batteries.

The act of planning reveals key leverage points and risks. The skill isn’t having a perfect plan—it’s knowing how to build, adapt, and learn from one, especially when making the leap.

Self-directed: Do you define success on your terms?

At mile 21 of my first marathon, a guy passed me who looked totally unprepared—wrong clothes, not a runner’s build—but he flew by.

I was frustrated, then remembered a mantra: “Run your own race.” 

No one else has your mix of strengths, challenges, or goals. Learn from others, but don’t let their definition of success shape yours.

Decision Making Under Uncertainty

Lack of complete information: Can you act without knowing everything you think you need to know?

Analysis paralysis hits everyone. But the best learning comes from doing—not from another podcast or book.

Real work is building your product, talking to customers, or creating something someone can use.

At Barkley, runners start each loop with only a rough map and a general idea of where to go—there are no markers, no certainty. Waiting for perfect clarity means you never move. The same applies here.

Ask yourself daily: “Did I get closer to someone paying me, thanking me, or using what I make?”

Ambiguous Outcomes: Can you stay focused when the range of potential outcomes is infinite?

Barkley’s competitors treat every loop as the last one they’ll get to stay focused.

Possibly the greatest obstacle to your progress will be the Shiny Object Syndrome—the tendency to be easily distracted by new opportunities.

The best defense against SOS is to define and document your core goals and values then ruthlessly use them as a guide to direct your focus.

Judgement and Heuristics: Do you have a set of value driven decision frameworks to guide your journey?

You will never have all of the information required to make a decision.

Decision frameworks improve your decision making—collect and test them to discover the ones best align with your values.

Barkley’s runners use a similar framework to one of my favorites—the classic Pareto Principle - “Which 20% of actions will produce 80% of the results?”

In runner’s parlance—if it saves considerable energy and time, its worth the risk.

The Next Step

When things get hard—and they will—your mental fortitude, navigation skills, and ability to make decisions under uncertainty will be tested.

Just like Barkley competitors need mileage to qualify, your talent stack is the baseline. It’s what lets you build and deliver value to the marketplace.

To endure the course of setbacks, isolation, and ambiguity, you need more than skill—you need the mindset to keep going when there’s no map, no crowd, and no clear finish line.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.

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