Anytime You Wish

Jul 16, 2021


As leaders, we sometimes feel like we are “doing time”. What can a famous prison break teach us about getting caught and doing “good time”?

While visiting San Francisco, I heard something not everyone at my location heard. I was just over a mile from the mainland. My hair was frenzied by the same wind the seagulls seem to navigate with ease. The swift current and frigid water swirled around the island-- once a camping spot, lighthouse, military fort, and maximum-security prison. As my only means of getting home departed the 22-acre Isla de los Alcatraces (or Isle of the Pelicans), the ferry captain calmly, yet sternly reminded, “You may leave anytime you like on any boat you wish.”1

Today, Alcatraz Island is a national park and the site of 14 different attempted prison breaks. My favorite attempt was made by Frank Morris and the Anglin brothers, John and Clarence. All were known flight risks and intentionally transferred to the inescapable penitentiary. Against advice, Warden Dollison allowed the brothers to stay in adjacent cells, just as they requested.

In June of 1962, after months of planning and preparation, the escapees waited for lights out. They wiggled through expanded air vents, leaving in their cells flesh-colored papier-mâché heads topped with human hair. Climbing up a utility corridor, they carried a vacuum cleaner motor to pump the raft and lift vests fashioned from glued and heat-pressed raincoats. Over the hospital roof, they continued, to the boat dock and into the 55°F waters. Never to be seen again…or were they?2

As leaders, we sometimes feel like we’re doing time, making us want to escape, too!

What can we learn from the prisoners of Alcatraz?

  • You’ll Get Caught: Many a criminal has admitted to breaking the law because they sincerely believed they could outsmart the legal system. Consider the impact even your ethical choices have, should something go awry or be discovered. Think about the impact of a delayed performance review, an error in a report, or a conversation deferred. What would you stop doing if you were outed?
  • Do Good Time: You can do good time or bad time. At Alcatraz, poor behavior was addressed with time in The Hole, or solitary confinement. Men passed time in the dark by bouncing buttons on the cement floor. Schedule activities to foster more teamwork; celebrate recent wins. Seek to be inspired and inspire those around you. How can you make the most of your time while enduring challenges?

A new theory suggests those three escape artists anchored their raft to the 12:10AM prison ferry bound for San Francisco using the missing 120 ft electrical cord. Officer Checchi spotted a white party boat from the shore in the early morning hours before it sped off under the Golden Gate Bridge. A facial recognition expert confirms the two men photographed at a Brazilian farm by a family friend in 1975, are very likely the Anglin brothers.3

I was told, “You may leave anytime you like on any boat you wish.” ...But, that wasn’t entirely true, when I was ready to leave, I waited and waited and waited… “Is this what it is like being a prisoner on The Rock?” I wondered. After an agonizing 25 minutes, I left the island by ferry just as the escapees may have 60 years ago. What freedoms do you enjoy in your work? From what do you need to escape? What do you need to fight through?

Sources: 1 Britannica: Alcatraz Island; 2 Britannica: Alcatraz Escape of 1962; 3 History Channel: Alcatraz Escape: The Lost Evidence; Alcatraz History: The Great Escape from Alcatraz.

by Michelle Sugerman • Leading Synergies, LLC • © All Rights Reserved

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