The First Rule of Wing Walking

August 20, 2025

Billy Bomar and Uva Kimmey of the Howard Flying Circus wing-walk on a biplane over New York State. 1930.

By Dave Bushy, PCC

In the early 20th century, a common aerial stunt involved people venturing out onto the wing of a biplane in flight.  It was exciting for those who watched from the ground, but at speeds of nearly 100 miles an hour, the job was extremely hazardous for the person who dared to venture out from the cockpit into the rushing air. 

At least a few times in the past, the poor soul involved in the stunt didn’t survive, getting blown off the back of the airplane with tragic results.  They key to survival was to remember what I now call “The First Rule of Wing Walking.”  The rule was deceptively simple and infinitely life-saving: Don’t let go of the first strut (or support wire) until you have a firm hold of the next one.

As I work with clients, many speak about the transitions that they are considering in their lives.  They talk about their plans for changing jobs, moving to a new location, or finally getting the advanced degree they promised themselves.  I spend a lot of time in inquiry, helping them unravel their motivations for the change they are considering.  And inevitably I bring up the first rule of wing walking.

Because metaphorically you can get blown off the wing of life if you don’t have some type of “hold” onto the future.  It need not be tangible.  It might just be careful planning for what you are going to do, or a psychological mindset that says you are ready to make the change you are considering.  Or it could be very real, like prepping for and taking the graduate record exam (GRE). 

It is also so important to explore what you are experiencing in the present before considering the future.   Fully examining it with a confidante or your coach is critical to any decision.  Saying “I’m going to leave this job,” without analyzing what it is that is motivating you might lead to your deciding to pursue something that might not be the right fit, or worse, lands you into the same type of situation that you have decided to leave.

There are those who choose to leave a job without making any plans.  “I’m going to quit and take a few months off,” can work for some, but I have seen a number of people – especially those who decide to retire (at a normal retirement age or perhaps earlier) see the months tick by into years.  That “strut” or hold onto something for which to aim or anchor oneself may be missing for them.  And too often that can lead to a freefall off the back of the airplane called life.

I know the first rule of wing walking worked for me.  I announced my retirement from 34 years in corporate life only after careful consideration, mindfulness and prayer about what I wanted to do next. 

I had decided that coaching was my calling.  Minutes after I gave my four-month notice, I drove to the Gestalt International Study Center (GISC) and enrolled in their intensive coaching certification program. 

I haven’t let go of that strut ever since!

Dave Bushy of Boston Executive Coaches – bostonexecutivecoaches.com – is an ICF-certified coach who was trained at the Gestalt International Study Center (GISC).  Dave is a former U.S. Army officer and senior airline executive who works with leaders throughout the world.

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