How I ‘escaped’ Alcatraz

Swimming a mile and a half in choppy waters off San Francisco seemed like an insurmountable challenge — until I did it.

Illustration by Emma Roulette

By Michael Workman

James “Whitey” Bulger couldn’t do it. Neither could Al Capone.

But I thought I had what it took to escape from Alcatraz, the island prison off San Francisco that held two of the most infamous criminals in U.S. history.

Well, it wasn’t an “escape” in the traditional sense. It was a mile-and-a-half swim, from just off the island to shore — an annual event organized by a company called , which organizes races on land and water across the country.

Originally built as a military prison, Alcatraz became a federal penitentiary in 1934 and closed in 1963. The federal government says no inmates ever escaped, although five are listed as

In other words, this would be no easy race. I’d spent many mornings doing laps in the pool, and I’d completed mile-long swims in relatively calm open waters. The waves and strong currents off San Francisco, combined with the distance, made this swim a much bigger challenge.

But I had a personal reason for taking it on. My marriage was ending. I needed a distraction — something far outside my comfort zone. And so, on a whim, I signed up. A few months later, as the race was approaching, I realized I needed to train.

I don’t have many moments of pure epiphany in my life, but this was one. I said to myself: “I’m ready.”

And so on mornings when the tide was high, I’d wade into the beach in Boston, where I live, and swim around a long breakwater into a small bay. The water was cold and briny. Most days the surf was calm, but some days the wind whipped the waves higher. Often, as I returned to my starting point, exhaustion made the trip back around the breakwater feel twice as long.

As time went on, though, I felt myself getting more and more confident in the water. Even when a stray wave sloshed water in my mouth, or it seemed like I was swimming in place against the current, I was able to maintain my stroke.

One crystal clear morning, I swam for 25 minutes or so and paused in the middle of the bay. I took off my goggles and scanned the horizon, feeling the “runner’s high” that sometimes comes with strenuous exercise. I don’t have many moments of pure epiphany in my life, but this was one. I said to myself: “I’m ready.”

On the August morning of the race, the roughly 1,000 participants gathered on what would be the finish line: a sandy beach just west of Fisherman’s Wharf. At first it was difficult to see Alcatraz through San Francisco’s famous fog. But the haze soon burned away, and it was time to board a ferry to the start of the race.

Once the ferry pulled away, an announcer gave instructions: Don’t swim directly toward the finish line, as the strong currents of the bay would push us past the inlet. Instead, swim to the left of where we wanted to end up, then turn right nearer to land.

And if the boat began to sink? Normally, the announcer said, he’d give detailed safety instructions. But to the endurance swimmers on board, he had only one direction: “Just jump in and swim to shore.”

A few minutes later, the ferry pulled aside Alcatraz. As I approached the door to jump off, my mind was racing. How rough would the water be? Could I really swim a mile and a half? My turn came and I leapt away from the boat.

As soon as I plunged into the cold water, my anxieties melted away. I felt the same sort of confidence I had experienced on that sunny morning in Boston. An epiphany. “I’ve got this,” I said to myself. I bobbed to the surface and swam to the starting line.

We had been instructed to swim toward a decommissioned naval ship that had seemed impossibly far away at the time. As its shimmering gray hull crept closer into view, I realized that it was time for me to turn — and that many of my fellow swimmers had already done so. This race was going to be longer for me than most.

Nevertheless, I was going to complete it. As I stroked into the inlet for the finish, I increased my pace, kicking as hard as I could. I reached the shore, clambered out of the water, and ran across the line, feeling exhilaration and relief, mixed with a healthy dose of pride. I had found a way to escape — from my history, my fears, and myself.

Michael Workman is design director of Experience.

for weekly updates from , a digital magazine that examines the power of experience to spark ideas, solve problems, transform industries, and drive personal growth.

Originally published at on July 10, 2019.

Experience Magazine

Stories from the intersection of humanity and technology

Experience Magazine

Written by

The world is changing. Experience guides you through. Published by Northeastern University at expmag.com

Experience Magazine

A magazine about the power of experience at the intersection of humanity and technology. Published by Northeastern University

Experience Magazine

Written by

The world is changing. Experience guides you through. Published by Northeastern University at expmag.com

Experience Magazine

A magazine about the power of experience at the intersection of humanity and technology. Published by Northeastern University

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface.

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox.

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store