I’m not sure what makes someone at the ripe, old age of 17 think these kinds of things. I was just that kind of teenager, I guess. I have a really distinct memory of resolving when I was about 17,  to live my life without regret. For me, that meant always taking advantage of the opportunities to go new places, do new things and meet new people — even when those opportunities took me into scary or uncertain circumstances.

Crossing the Finish Line

My “no regret” spirit undoubtedly led me into training this year for an Olympic-distance triathlon (1.5K swim, 40K bike, 10K run) as a 40th birthday present to myself. After dealing with a knee injury which nearly kept me from participating in everything but the swim; this past Sunday I slowly completed my first triathlon. I’m hoping it won’t be my last.

What I didn’t know when I got into the lake for the first leg of my race last Sunday morning was that at the same time, extreme distance swimmer Diana Nyad was jumping into the ocean for a fifth attempt at swimming from Havana, Cuba to Key West, Florida. These two endurance events cannot be compared. Swimming more than 100 miles in shark and jellyfish infested ocean water makes a triathlon seem quaint.

Given this coincidence of timing, I became fascinated with Nyad. Why would someone attempt such a thing in her 60s? Who is this person who has the resolve to attempt it, at any age? I searched her name and came up with a treasure trove of interviews, articles and speeches.

In a 2011 TedTalk, Nyad spoke about the existential crisis that led her to attempt this feat. Her mother died at the age of 82. Shortly after, Nyad turned 60 and she was surrounded by an ocean of regret and failure. (Despite holding a number of distance swimming world records that have still not been broken since the 1970s.) She decided she didn’t want to live that way anymore and resurrected an old dream — to be the first person to swim from Cuba to Florida without a shark cage.

[youtube=http://www.youtube.com/watch?v=c6mhFgAjqwA]

“The remedy for that malaise [regret] was for me to chase an elevated dream … something that would require utter conviction and unwavering passion, something that would make me be my best self in every aspect of my life.”

Now, basking in the glow of her incredible success, it’s easy to forget the intense disappointment she has experienced during three failed attempts at this swim in the last three years. In 2011, she met the goal of living without regret, but failed to finish the swim after two jellyfish stings nearly stopped her heart. “My journey now is to find some sort of grace in the face of this defeat. I can look at the journey, not the destination. I can stand in front of you and say I was courageous.”

I personally find Nyad more inspiring in the failure than in her success. It’s easy to bask in the glow of achieving your biggest dream and move forward. It’s much harder to stand on a stage after failing and share what made the experience meaningful. Nyad is more inspiring because she chose, at the age of 60, to pursue a dream rather than live in regret.

My triathlon victory had nothing to do with the finish line. The victory was in quieting the “I can’t” mantra that had plagued my thoughts as I dealt with the arduous training process made even more difficult by my knee injury. Just before the race, I was doing a training run to prepare myself for the late summer heatwave. I was rounding a corner, feeling the heat zap my strength. I felt my head, and my spirit, bow in defeat. Then, I realized that the heat didn’t defeat me, I chose to be defeated by it. No matter what happened I could choose to move forward with humor and grace and enjoy an incredible experience. And, that’s exactly what I did.

Endurance sports are a metaphor for life itself. We face seemingly insurmountable challenges that are made even more difficult by the uncontrollable — the injuries, the heat, the jellyfish, the sharks. In those moments of struggle, we always have the choice to retreat in fear OR take a breath and move through the suffering and come out the other side into a more authentic experience of joy and peace.

I’m reminded of a quote from social work researcher Brené Brown’s book The Gift of Imperfection: “Owning our own story can be hard but not nearly as difficult as spending our lives running from it. Embracing our vulnerabilities is risky but not nearly as dangerous as giving up on love and belonging and joy — the experiences that make us the most vulnerable. Only when we are brave enough to explore the darkness will we discover the infinite power of our own light.”

Regret only happens when we retreat from challenge in fear and shame. Failure simply demonstrates that we took risks, made ourselves vulnerable to experiencing disappointment, but also to experiencing the joy, love and peace that comes from living fully in the moment.

What moment of struggle defined you? How did you move through the challenge? The disappointment?