The Compound Effect of Leadership: What a 365-Day Push-Up Challenge Taught Me About Habit Formulation

A year ago, I embarked on a self-discipline challenge. At 54 I was starting to notice my age. I have been a runner since my early forties, love surfing and other outdoor pursuits, but I have never been a gym guy as I much prefer outdoor activities.

Because I travel a lot for work, maintaining a consistent fitness routine has always been difficult. It is too easy to hit stop on a treadmill in a hotel gym, whereas running outside forces the discipline to finish the workout just to get back home. Looking for a way to improve my upper body strength, prepare my paddle fitness for the few times a year I get to surf,  and challenge my self-discipline, I decided to try a challenge I had seen online: adding one push-up a day.

On April 25, 2025 I began. I did one push up and that was way to easy, so that day I did thirty push-ups in a row. The next day I did thirty-one push-ups. And off I went, each day adding another push up.

What followed was a 365-day masterclass in the compound effect—and it completely mirrored the behavioral changes we coach executives through every day.

The Deceptive Ease of the First Step

In the beginning, it only took about one minute per day and with only increasing by one push up per day it wasn’t too taxing.

This is exactly how organizational change feels on day one. Committing to a new leadership habit—like asking one extra coaching question during a 1:1, or spending five minutes a day recognizing team members—feels incredibly easy at first. The enthusiasm is high, and the effort is low.

Hitting the Wall and Adapting the Strategy

 As the days went on, the additional push-ups did become more challenging. On day thirty-two I completed sixty-two push-ups. My arms were burning and I knew I had hit my consecutive limit.

At this point, many leaders abandon their new initiatives. When the friction increases, the instinct is to quit. Instead, I decided to continue with the challenge but to alter the strategy. I would do a set of fifty push-ups, then take a break and later in the day do the additional push-ups.

As a leader, when your system breaks down, you don't abandon the goal; you adapt the process. By pacing the work throughout the day, it was not so difficult to knock them out daily. As a byproduct, I started to notice improvements in my physique. My posture started to improve and my muscle tone was better. The compound effect was taking hold.

Discipline is Tested in the Disruptions

 The biggest challenge came with work travel. One negative of the travel was doing pushups on the nasty carpet or bathroom floor of a hotel room.

Habits aren't tested when you have complete control over your schedule and environment; they are tested in the disruptions. I did push-ups in Palo Alto, in Athens, Greece, in Malibu, in Asker, Norway, in Pittsburg and several other cities around the globe.I recall a specific evening in December 2025 when I was with a client in San Francisco. We had spent the day in a workshop, then at a happy hour and we were sitting down for a holiday dinner in the hotel lobby restaurant when I realized I still had over 150 push-ups left to do. I excused myself from the table and found an open ballroom, dropped down on the floor and knocked out two sets of fifty push-ups. I wrapped up the remaining ones in my hotel room.

Then there was the other time that I went into the handicap bathroom at London Heathrow airport  just to finish some push-ups.

I was committed. Leadership discipline works the exact same way. If a leadership behavior is truly a core value, you execute it whether you are having a perfectly balanced week in the office or fighting jet lag in an airport terminal.

The "Now What?" Dilemma

 April 25, 2026 was the day I completed the challenge. I completed seven sets of fifty push-ups and another 45 all in one day. I had proven to myself that I had the self-discipline to complete this challenge. I felt great.

As I write this it is April 26th and I have already done two hundred push-ups today. I am sure I will do 396 today, but the question is where do I go from here. Keep adding, count back down or maintain a daily number?

I am unclear what to do, but I do like the physical and mental games I played for the past year. For leaders, achieving a massive milestone—whether personal or professional—often comes with this exact sense of "Now what?"

The answer lies in recognizing that the true reward wasn't hitting 395 push-ups in a single day. The true reward was forging the daily discipline required to get there. The goal simply provides direction; the daily compound habit is what actually drives the transformation.