Alcatraz

“If you stay in shape, you never need to get in shape.”

– Robert Gonzalez, my high school swim teammate

At age seventy, my favorite physical activity is swimming, which maintains cardiovascular health and muscular strength without undue impact on the joints. I’ve found no better way to turn back the clock. Last year, while working out in the pool at the Y in Winsted, Connecticut, I started talking to the guy in the next lane. “I’m seventy-four years old, swim three or four times a week, love it,” he told me. “It’s funny. All my friends are falling apart, but there’s nothing wrong with me!” Just what I wanted to hear. I high-fived him and encouraged him to keep it up.  

Whenever I drive to the pool, two mantras bubble up: “You never regret a workout” and “There’s nothing 2,000 meters won’t cure.” My typical swim workout takes fifty minutes, including an easy 400-meter warm-up followed by eight 200-meter intervals, totaling 2000 meters, nothing crazy. Every time I climb out of the pool, I feel reborn.  

But in December 2023, ten months before my seventieth birthday, I sensed my swimming was getting stale. I seemed to be going through the motions, which is always a signal for me to consider a competitive event. Needing a big play, I signed up for the Alcatraz Sharkfest Swim.

Alcatraz is one of the world’s iconic swims—over three hundred competitors swimming across San Francisco Bay in fifty-eight-degree water, navigating 1.6 miles of heavy chop and current from Alcatraz Island to Fisherman’s Wharf. I had done it once before, in 2011, and that first experience was as intimidating as anything I’ve ever tried.

Three months prior to the 2011 race, I hired a coach, a seasoned triathlete named Steve Pyle, who outlined a training and nutrition regimen that positioned me for success. In our first conversation, Steve shared the very words I needed to hear: “Alcatraz will be challenging, but you can do it. You gotta be ready to jump into big, cold water. You want to be so prepared, it’s no big deal.”

Those words were perfect. He did not sugarcoat it: It will be a tough swim, but if you do the work and put in the time and training, you’ll be so prepared, it’s no big deal. I still invoke “no big deal” to inspire the prep needed to execute a big play, whether it’s a major presentation, speech, or launch.

Tony Robbins has a great line about using the power of your calendar: “If you talk about it, it’s a dream. If you envision it, it’s possible. But if you schedule it, it becomes real.”  

Drawing on Steve’s training program from 2011, I mapped out a new plan for 2024. From December 15, 2023, to June 15, 2024, I calendared exactly one hundred workouts—each one a stepping stone toward race day on June 16.

When I jumped into San Francisco Bay on race day, I had 101 workouts in the bank and placed 174th out of three hundred swimmers—and second among all swimmers my age or older. Even more satisfying, I completed the race in 41 minutes, within a minute of my time in 2011.