I Ran The Boston Marathon. Here is What I Learned

By Ted Harrington

I recently ran The Boston Marathon – the oldest, most prestigious, arguably most important marathon in the world.  It was by far one of the most fulfilling experiences of my entire life.

Throughout the course of preparing for, attempting, and executing this feat, I noticed some striking parallels between running and entrepreneurship. Like many of my peers in the information security business, I’ve personally found that to defend against adversaries requires the near-constant state of adaptation that is inherent in the entrepreneurial mindset.

As one of those borderline-insane people who runs without music, I had many hours running to think, and much of that time was focused on the things we are doing at our security consultancy Independent Security Evaluators to try and change the world, and how we operate our business in pursuit of that ambition. Here are some of my takeaways from this immensely fulfilling, perspective-granting experience:

1) Pursuit of that which might be impossible.  The data is pretty overwhelmingly stacked against completing a marathon. At least 79% of runners get injured each year. Less than half of one percent (0.5%) of the American population has completed a marathon. Even the origin legend for the race length is based on an elite soldier dying from exertion at this distance! But the kind of person who sets a goal to run this type of race is not deterred by these statistics; in fact, many see the long odds as instead a motivator to pursue it. A quote that deeply inspired me during my marathon training as well as during my own entrepreneurial path is from President John F Kennedy: “we choose to go to the moon and do the other things, not because they are easy, but because they are hard.”

So too it goes with entrepreneurship. According to the US Small Business Administration, 33% of business don’t survive 2 years, 50% don’t survive 5 years, and over 66% don’t survive 10 years! As with marathon runners, those who are drawn to entrepreneurship do not see these stark metrics as reasons not to pursue this, but rather as a reason to do so. Entrepreneurs see words like “impossible” and characterize the “im-” as merely a hurdle to overcome. This is especially true for security entrepreneurs, who are seeking to solve problems that never come to a discrete conclusion.

2) Steady state of problem solving.  Training spanned more than 5 months, and throughout that entire duration, there was not a single day that I was not dealing with some sort of physical issue. One day it might be a foot blister, then next it might be leg cramps, and the next it might be stomach distress, and so on and so on. With each new issue, I found myself going through a progression of identifying symptoms, diagnosing root causes, researching possible solutions, implementing solutions, and trying again if the fix didn’t work.

So too it goes with entrepreneurship. One day we might deal with a personnel issue, the next we tackle changes in the market, and the next we tend to the needs of a customer. Security entrepreneurs in particular are constantly battling with how to deal with the extreme shortage of qualified talent that is vital to pursuing effective security missions. As with marathon training, to be successful as an entrepreneur requires one to constantly be identifying and resolving problems. This process is never complete; rather it is the steady state of an entrepreneur.  

3) The most painful bits immediately precede the sweetest bits.  As Harvey Dent declared in the blockbuster film The Dark Night: “the night is darkest before the dawn.” The Boston Marathon course is world famous for the hill series notoriously known as Heartbreak Hill. Although this name describes the highest peak of the series, it actually refers to the entire series, which spans 5 different summits over a roughly 4 mile stretch. What makes this even more difficult is that it comes deep into the race, from miles 17-21, when most runners’ legs are beginning to wobble. But Heartbreak Hill isn’t even the bad part; you’re on a high once you conquer them, and now have some seemingly easier rolling downhills to the finish line. But for me, these last 5 miles stretched on into infinity. Energy reserves were completely depleted. Feet were throbbing from the pounding on the pavement. The body was beyond dehydration. The soul was on the verge of being crushed. But I found a way to endure through it, and an excruciatingly long period later, I found myself make the famous turn onto Boylston street and for the first time all day, I laid eyes on the finish line. As a smile spread across my face at the realization I would finish this race, at that very moment I hear through the insanely loud crowds my brother, his wife, and my dad screaming my name. I hobbled over to them and had three of the most rewarding hugs of my life. With spirit renewed, I set out to finish what I started. The roar of the crowds along this last mile is deafening. You witness the best parts of humanity, as runners put aside interest in their own finish times to literally carry each other across the finish lines. And then, 25 yards from the finish, I spot my wife – who has selflessly supporting my pursuit of this mission every step of the way – and my mother – for whose charity I worked so hard to raise funds for in the process. Stopping to kiss each of them gave me that lightning bolt of euphoria, of purpose, of mission completed. I then had only one thing left to do: sprint across the finish line, arms held aloft, spirit soaring.

So too is it with entrepreneurship, where the bad often precedes the good. Long-time customers leave, forcing entrepreneurs to adapt and fill the revenue voids somehow, and in so doing often find new ways of optimizing the organization to a place superior even to before the customer left; such gains are sometimes only ever possible by going through the lesser desirable setbacks first. This rings true especially for organizations who find themselves with award winning security programs only in the aftermath of first suffering devastating security breaches.

4) The destination matters.  But so too does the journey. It is said that you don’t run the marathon on race day; you run it in the many months of training in preparation for race day. In the structure of training I found value on many levels: my daily regimen provided time for much needed critical thinking; it forced consistency in an otherwise highly irregular travel schedule; it gave me long stretches of euphoria (yes, the “runner’s high” is very real, very good feeling); it changed my perspective on almost everything; I got to explore new parts of the city I live in, as well as explore cities I traveled to in new and exciting ways. I came to view the training runs themselves as the enjoyable pursuit, rather than a means to an end. As accomplished runner Catherine McKiernan puts it, “running is meant to be enjoyed, not endured.”

As a security entrepreneur, this also rings true to me in that with entrepreneurship; you set big, lofty goals, and relentlessly pursue them until they are achieved. But it’s important to also be present along the way, to acknowledge the interim victories, to praise the people who help us get where we are going, to keep in perspective how far we’ve come since we started. We should always be keeping our eyes laser focused on the horizon, but also be cognizant of the many great things happening in our immediate environment during the pursuit.

5) It takes a village.  Distance running is in many ways an individual pursuit; if I were to skip a workout, or quit on a long run, or cheat on my nutrition, no would notice or probably even care. On race day I am the only one accountable for my own performance. But that doesn’t tell the entire story of marathon training; this particular pursuit engages a community. I leaned on friends who had run the distance before, to guide me on everything from gear to nutrition. I leaned on friends and family for moral support, as they cheered me on during the unseen hours of effort in training. Over 115+ people donated to the cause I raised funds for. On race day I relied on the other members of my charity team; one of them ran me across the starting line, and the other ran me up the Heartbreak Hill series. All of these people played their own roles, and each contributed to my ability to accomplish this daunting task. And because of them, the celebration was that much sweeter.

So too goes it with entrepreneurship. One must engage a community, learn from those who have been there before, draw on the support of peers and mentors alike. Entrepreneurship requires a steadfast gaze on the strategic horizon, but no one can get there alone. The best leaders don’t just develop themselves, or just develop teams; they develop other leaders. And in so doing, build a community.

6) Purpose matters.  To be able to run this distance requires an almost absurd level of sacrifice, dedication, and execution in preparation. Throughout that process there are countless moments where you’re too sore, don’t want to get out of bed, or are plagued by self-doubt. But in each of these moments, you call on your purpose, on the reasons why you are doing this. In my case, my why was defined by a handful of reasons: (a) growing up on the route, this race has always inspired me, even before I knew why – I’ve always had the innate need to run it; (b) this is ridiculously hard, and I wanted to do something not just despite being hard, but because it is hard; (c) it provided me an opportunity to raise awareness about and funds for a cause which I deeply care about; and, (d) it provided me an opportunity to do something special and life-altering with my mother, for whose charity I ran to raise money. In each of those moments when I found myself struggling with the burden of the regimen, I was able to call on my why, and it got me moving.

So too is it with entrepreneurship. As the Cheshire Cat so eloquently summarized in Alice in Wonderland: “If you don’t know where you are going, any road will take you there.” This has long been one of my favorite business philosophies, and one that I quote often in the various talks on security that I deliver. This wisdom, imparted on my by a mentor many years ago, speaks to the importance of having a purpose, so you can find the path to get you there; if you don’t have a goal, you won’t know how to navigate the paths that present themselves. Entrepreneurs are faced on a daily basis with competing decisions that often all seem like equally good options. By having a firm grasp on the purpose for why the business exists, the decisions both become very clear how to proceed, as well as guide an entrepreneur down the path that always remains consistent with what you set out to accomplish.

7) The pounding produces power.  Make no doubt about it: training for a marathon entails holistic abuse. Over the many months of preparation, you constantly are damaging bones, muscle, heart, and spirit. I’ve hurt in places and ways I never imagined possible. I’ve become comfortable with self-doubt. But each of these abuses, day by day, make you stronger.  Months later, you have very resilient bones, muscles, heart, and resolve. You are a changed person; stronger, more confident. Prepared.

So too is it with entrepreneurship. Sometimes it feels like we take 100 steps back for every step forward. Each interim win is quickly overshadowed by a dozen imminent, business-threatening crises. Our best people quit. Market conditions change. Our biggest gambles explode in our faces. But none of these stop us. Each setback, day by day, enhances our ability to deal with the next setback. And then suddenly you realize, years later, all of the pounding made you more capable at this game of entrepreneurship.


On Patriots Day, April 17, 2017, I counted myself amongst the 26,411 finishers of The Boston Marathon. In the process, my teammates and I raised $35,001 for Boston Partners in Education, of which I personally raised $11,279, finishing as the top fundraiser on my team. Our total raise enabled 70+ disadvantaged kids to get off the waitlist and be enrolled in Boston Partner’s revolutionary mentorship and academic opportunity program.

From this experience, I am a changed person, and hopefully a better entrepreneur. As for what goal is next, I still have yet to decide. But you can be assured that whatever it is, it will be hard!

About Ted Harrington

Ted Harrington is Executive Partner of security research & consulting firm Independent Security Evaluators.  He has been named both 40 Under 40 and Executive of the Year.

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