Racing to the Ends of the Earth

My journey into endurance sports began unexpectedly, driven by curiosity and a gradual progression. Now at the age of 58, having experienced its benefits, I am consciously and deliberately pushing my limits beyond what I once thought possible.

Sports and exercise have always been important in my life. Although I took health for granted in my younger years, I’ve learned that I simply feel better when I am in shape and exercising regularly. Failure to get sufficient exercise causes me fatigue and triggers aches and pains, so I do not see my daily work-out or training session as penance or punishment, but rather as an opportunity. I love to move, so from my perspective, working out is something I get to do, not have to do.

Whether it’s running, biking, swimming, skiing, or other sports, an hour or two of exercise every day prepares me physically and mentally for anything the world might throw my way. The exercise itself, no matter how intense, is deeply meditative, and longer runs and exercise sessions bring an uninterrupted opportunity to be alone with my thoughts, fostering creativity and innovation. There’s a rhythm to running, swimming, and even walking that generates a kind of rhythm of thinking, and the passage through trails or other landscapes stimulates a channel of thoughts. For me, exercise is meditation in movement. It is a priority for which I will always make time.

Mental as Much as a Physical Game

My transition from daily exercise to endurance sports, however, was not inspired by a need to conquer physical boundaries. Instead, it was driven by my curiosity about the mental aspects of pushing one’s limits. In 2005, I began long distance running to deal with the emotional distress of my father’s Alzheimer’s diagnosis and other trying life events. The greater the stress, the more I valued the run. That said, it evolved from a form of self-therapy to something greater, mental exploration.

‘One side of your mind is cheering you on, while the other half is screaming at you to abandon the effort.’

With endurance sports, you are alone in your head for long periods of time, with increasing levels of discomfort, at times consumed by doubt. One side of your mind is cheering you on, while the other half is screaming at you to abandon the effort. This is a nonstop battle for any endurance athlete and consciously putting yourself in these situations is a form of mental training and exploration. You learn to reframe problems, accept difficulty, silence negative thoughts, and figure things out, emerging from every challenge more evolved than you were when you began. As a brilliant Nike ad campaign Reincarnate suggests, our new self emerges as we push ourselves beyond our old limitations. There are lessons in every endeavor and endurance athletes are reborn as a consequence of each effort. These same lessons transcend sport and have been critically important to my broader successes in life and business.

At this point, the line between endurance sports and the rest of my life is somewhat blurred. Years ago, I started a group called Memory Joggers, which participates in extreme endurance challenges to raise funds to fight Alzheimer’s and other diseases. Through this group, I have run countless marathons and ultramarathons, including the World Marathon Challenge in 2023, where I completed 7 marathons in 7 days on 7 continents. Soon I will attempt a swim from Asia to Europe and back (west to east through the Bosphorus Crossing, returning east to west through the Dardanelles Straight).

I will keep stretching to see how far I can reach, but while the fight against Alzheimer’s will always be a motivating factor, it’s only part of my “why.”

I genuinely enjoy reaching beyond my comfort zone to see if I can meet a seemingly impossible challenge. It’s in the rawness of the experience, the good and bad, when we truly become alive. There are so many moments during an endurance race where you feel half-dead and never more alive at the same moment. These contradictions lead to a deeper understanding and appreciation of oneself and of others. Humans are not meant to shield themselves from challenges and pain, but are instead meant to embrace it fully, let it shape us, teach us, and make us more human.

Many people scoff at the idea of extreme endurance sports, viewing them as overly time-consuming, painful, and beyond their reach. I once did as well. But by reframing the narrative, it became about self-growth for me. At a younger age, many people are outwardly focused, intimidated by what others are doing. They often feel that because they are not “competitive,” there’s no point in participating. But comparing yourself to others is a finite perspective; while participating solely for the purpose of exploration and growth opens infinite boundaries.

‘Participating solely for the purpose of exploration and growth opens infinite boundaries.’

Exercise does not need to be about pain, most endurance athletes will tell you that 80% of the time, your workout should be at an easy to moderate effort level. Improvement comes through consistency, not agony.

Through endurance sports, I’ve overcome my fear of failure. After childhood, many adults develop a paralyzing fear of failure, shrinking away from anything that is uncomfortable or new. When you take risks and reach well outside your comfort zone, then failure is to be expected and even embraced. Only those who live so cautiously that they have not lived at all can avoid failure completely.

In the words of the author Eloise Ristad, “when we give ourselves permission to fail, we, at the same time, give ourselves permission to excel.” I’ve taken this lesson beyond sports, and as a CEO, encourage our employees and clients to try every day “to suck at something new,” maintaining a sense of humor and humility in the process. The trick is to “fail forward,” taking lessons from every stumble.

I recently read that more than 61% of adults feel “stuck in a rut,” characterized by a persistent sense of monotony with regard to relationships, career, or life in general. They feel as though everything is tedious or dreary, day in, day out, and that there's nothing to look forward to anymore.

Being stuck in a rut is a pervasive feeling of “meh,” which seems to get worse as people age. Exercise is a proven antidote and exploring new physical and mental challenges will unquestionably open new opportunities for exploration, connection, and growth. Yes, there may be some moments of discomfort, but that’s just part of the process. Embrace the adventure and keep moving!


Jill Jamieson is president and CEO of Illuminati Infrastructure Advisors, a Distinguished Senior Fellow at Northeastern University’s Global Resilience Institute and founder of Memory Joggers, a philanthropic group committed to raising money and awareness to fight Alzheimer’s disease. In her free time, she is an enthusiastic amateur endurance athlete. Jamieson has explored the limits of her capabilities by running countless marathons and ultra-marathons (including multiple races in Antarctica), racing triathlons, and enduring extreme open water swims across the globe. In 2023 she successfully completed the World Marathon Challenge (7 marathons on 7 continents in 7 days) and is preparing for her first two cross-continental swims. Most recently, she ran a 100-mile ultra marathon in the Arizona desert, swam the Potomac Crossing near Washington, DC, and successfully finished the Escape from Alcatraz Triathlon (for the second time). For readers who would like to follow Jamieson on Instagram, she’s @jayjayjamieson.

Photo caption: Jamieson racing to the ends of the earth as locals stare quizzically on Jumeirah Beach, Dubai, UAE, in February 2023. This was her fourth marathon in four days during the World Marathon Challenge.

Photo credit: World Marathon Challenge.