In the spirit of over-sharing that is this website, I thought I’d post the text from a recent short “speech” I gave in front of about 100 forgiving witnesses.

It’s part of a cool new project launched by my friend Robin Weinberg, who has an Oral History Master of Arts degree from Columbia and is clearly much smarter than me. It’s called WestportVoices, and it is a collection of local community members willing to share their personal stories and spark conversations. The first theme is centered around stories of Transformation, and most of them are incredibly moving, emotional and inspiring.

My story isn’t.

But Robin thought my current personal and professional changes would make for an interesting segment, so I agreed to participate. She interviewed me (along with nine other much more compelling subjects) and posted the audio highlights online and at the Westport Library. You can visit the site here.

Robin also asked several of us to speak at a launch event at the Library last month, and I thought I’d take that opportunity to update my transformation journey. The gist: my midlife crisis has now officially expanded (mostly around my waistline). Read on, please.

My name is Michael Wolfe, and I’m on the tail end of that semi-universal transformation known as (cue dramatic music) the midlife crisis.

My transformation story began in earnest a little less than two years ago.  I like to think of a certain three-week period back then as my own personal Bermuda Triangle of midlife gut punches.  Why a triangle?  

  • On one side, I turned 50. For this of you with marketing backgrounds, this means my membership in the coveted 18-49 marketing demo was officially revoked, and my opinions and purchasing decisions no longer mattered.  
  • On the second side, I left my job, and a career that I had spent over a quarter century cultivating.   
  • And on the third side, my kids left for college.  

Age, career, empty nest.  All the things that defined the top-line of my Twitter bio pretty much evaporated all at once.  

So the big questions, ones I thought I had asked and answered in my 20s, now re-emerged.  Who am I? What defines me? And do I really have to read a book called What Color Is My Parachute at my age?  

So I set out to try and answer all these questions.  And there’s good news to report. My transformation is ongoing, still plenty to work on, but my progress has been solid.  

  • I’ve branched out in my work on many different levels, creative energy is flowing in new and unexpected ways (yes, I have a podcast, because we ALL have to have one by the end of 2020).  
  • I turned 51 without any major personal fireworks.  
  • And the empty nest…if I had to use a word to describe what it’s like to have your kids leave the home…I’d choose AWESOME.  Really, really awesome. Not having a single teenager around to roll their eyes at you and accidentally drive your car into the side wall of your garage is surprisingly enjoyable.

But wait…there’s more.

The other day, I was in my closet getting dressed after a shower, when my son (who was home from college for a visit) came into my room to ask me a question.  He took a semi-long look at my shirtless torso, and was so dazed by the majesty of what he saw that he could only mutter a single word in response.

That word was: “ew”.

Little did I know that my own personal transformation journey came accompanied by significant weight gain and muscle atrophy.  I’d like to take this moment to thank Shake Shack, Jersey Mike’s, Planet Pizza, both local Five Guys franchises and the entire Frito-Lay family of brands for their support on this journey.

I realized that if my personal transformation was going to be truly complete, I would have to address the physical as well as the spiritual and professional.  

So what does a suburban dad in the midst of a midlife crisis do to address that need?

He buys a Peloton, of course.

For those of you who are unaware, a Peloton is a fancy stationary bike with a touchscreen the size of a Jumbotron mounted on the front.  It gives you the ability to take spin classes at home. Just hearing the words “spin classes” gives me bad vibes, not unlike “colonoscopy prep” or “kale salad, hold the dressing”.

Now, for someone who abhors overt displays of physical exertion as much as me, this was a radical step.  My wife’s immediate, well-informed reaction was that I had just spent more than two grand on a towel rack with wheels, but no matter.  I installed the bike in our basement and spent the good part of an afternoon trying to select a user name, finally settling on HowlingWolfe, because the name HugeMistake was already taken.  And I got on that bike and started to ride.

Several weeks in, I’m wasn’t sure of what I was achieving.  Turns out this spinning in place thing is HARD. The other day, my visiting mother-in-law nearly called the police when she heard random moaning coming from inside our walls, which was only me downstairs trying to get through an “Advanced Beginner” class.  I’ve dripped enough forehead sweat on my basement floor to trigger our sump pump.

Despite this new effort, I wasn’t sure if I really felt any impact.  And, like in several of my other transformational pursuits, I began to question my commitment.

But I got on my bike one recent morning and decided to forego my usual pre-recorded classes and take a “live” class, one that is streamed in real time from the Peloton studio and where the instructor can see the names and performance metrics of the thousands of people nationwide who are riding at that given moment.

It was a typical class for me, my standard wheezing and catatonic convulsions keeping time with the beat.  I powered through, chugging water like from a trough and praying for sweet relief or some sign that this was all worth the effort. Just as the class neared its conclusion, it happened.

The instructor looked at her panel, raised her eyes to the camera and said:  “HowlingWolfe, you’re looking good.”

Let me repeat that, loud enough so my son can hear it:  “HowlingWolfe, looking good”.

(Raise arms in exaggerated triumph.)

Looking good.  No matter that the instructor was 50 miles away and couldn’t actually see me, let alone notice the enormous sweat stain covering my exercise shirt (“moisture-wicking” my ass).  In the new digital streaming age, I was “looking good”.

Ladies and gentlemen, my transformation is now complete.

(Pause for laughter, which thankfully came on cue)

But seriously, I realize now that my Peloton experience has mirrored my overall transformation journey.  Sometimes, it feels as if I’m spinning my wheels and literally headed nowhere. But in the end, I need to remind myself that the destination I seek isn’t always so tangible.  As they say, it’s the journey, not the destination, that brings us where we need to be. The ride may not always be so smooth, but, if we allow ourselves, the challenges and changes we experience will only make us stronger, smarter, and more true to ourselves.

From that vantage point, I think everyone on this stage is more than looking good. Congratulations on your own personal transformations, and may your journeys continue, sweat-rings and all.

Thanks for listening.