Financier to Trucker


“The last thing I expected at age 50, after 30 years of full-time employment, was to find myself preparing to attend tractor trailer school. I was a partner at a large private equity firm. I really enjoyed my work and my colleagues. I finally came to terms with the fact that I wanted to start a new phase of life, so I made the difficult decision to retire.”

In addition to chronicling his adventures/misadventures learning how to drive a sixteen wheeler for the first time, along with several other 50+ers, Peter used his LinkedIn post to reflect on some of the more common obstacles to making a smooth transition—whether by choice in his case or necessity.

“When I was struggling with “how to retire”, the most impactful insight came from Tom Gilovich, a leading psychologist and former chair of the Cornell Psychology Department. He told me that I was more likely to find fulfillment and balance in retirement if I focused on my “internal resume” and stopped worrying about my external resume.”

After prioritizing what he really enjoys doing most and refocusing on “non-toxic” individuals rather than institutions, he set-out on the steepest learning curve possible. In addition to truck-driving school, he helped kickstart several non-profits like DonorsChoose and trained to become more proficient at his hobbies: magic and playing pool.

“At the risk of sounding overly prescriptive, file your external resume away with all those lucite tombstones that no one cares about. Only you can definitively decide if you want to create a new portfolio of activities or primarily focus on a personal passion. Either path can be more balanced and satisfying than you expect…and might unnecessarily fear.”

Be sure to read the comments to his LinkedIn post which are equally revealing. Like he says:

“We’re in this together”