From 29 to 56, I have completed 75 marathons. Here are seven and a half lessons from 27 years on the road.
Standing on Boylston Street watching the Boston Marathon, you will hear the same thing over and over: "I'm gonna run it next year." I understand the emotions. Watching runners tear up as they see that finish line, hearing the crowds roar for that final quarter mile push is electric.
What those spectators do not see, or underestimate, are the thousands of miles logged in darkness, the months of preparation; the early morning runs when everyone else is sleeping. When I crossed that finish line as a bandit runner at my first Boston Marathon at 29, I was so overwhelmed that I immediately set a goal: 50 marathons by age 50. I hit that goal and kept going. Now at 75 marathons, here is what all those miles have taught me:
1. Big Goals Require Big Planning You cannot wing a marathon. Those 26.2 miles demand months of structured training, careful nutrition, and mental preparation. Business milestones work the same way. Success is not accidental; it is architected through deliberate practice and preparation.
2. You Can't Sprint a Marathon At mile six, if your goal is breaking four hours, suddenly running faster will not get you there because you still have 20 miles ahead. Success in business follows the same principle: it is not about heroic bursts of effort but a consistent, sustainable pace. One percent improvements compounded over time create extraordinary results.
3. Individual Sport, Collective Spirit Running is solitary, yet the camaraderie of fellow runners makes races fly by. Business success works similarly. While you may be the one making decisions, the people running alongside you make the journey meaningful. Your success is amplified by those who share the path.
4. Persistence Beats Talent Every marathon tests your will to continue. When entrepreneurs tell you their secret to success, it usually boils down to: "I didn't quit." The ability to keep moving forward when everything hurts separates finishers from spectators.
5. Love the Training, Not Just the Trophy We're a results-obsessed culture, fixated on finish lines and final outcomes. But here is the truth: if you only enjoy race day, you are missing 99% of the experience. My best days are not just the races; they are the quiet morning runs that make race day possible. In business, if you do not love the daily work, the victories feel hollow.
6. New Finish Lines Keep You Moving After hitting 50 marathons at 50, I could have stopped. Instead, I set a new target: 100, no deadline. Once you achieve a milestone, the next goal keeps you sharp, hungry, and growing. Complacency is the enemy of excellence.
7. Balance Passion with Practicality Love what you do but ensure it is sustainable. Running teaches you that passion without proper pacing leads to burnout. In business and marathons alike, sustainability beats intensity over the long run.
7.5. Minimize the Chafing (Literally and Figuratively) Here's the bonus lesson: just like preventing those painful rashes during long runs, reducing unnecessary friction in work and life saves you from a world of hurt. Sometimes the smallest preparations like Body Glide for runners or clear communication for teams prevent the biggest problems. A little prevention beats a lot of pain, whether you are at mile 20 or in the boardroom.
The view from 75 marathons looks different than it did at the starting line of my first. Each race taught me something about persistence, pace, and purpose. Whether you are training for your first marathon or building your next venture, remember: the journey shapes you more than the destination ever could. Best of luck to anything you hope to accomplish.
