THE PATH UP THE MOUNTAIN IS THE BEST PART This column originally appeared on Wicked Local.







Sometimes it is the journey that is most rewarding. 


In 1983, my high school’s guidance department got their hands on a computer that resembled the robot from Lost in Space. Every kid in my grade was called down to choose a career that would be put into the computer which would then spit out a conclusive report detailing why or why not this career choice was appropriate. At the time, I had realistically veered away from my dreams of playing for the Red Sox and although inspired to shoot for the Navy’s Officer Candidate School in Newport I had yet to achieve required success in any math class that required fractions. I showed up prepared and offered a completely practical response: mailman. I had seriously considered the idea. I had already worked as a paperboy so I felt like I had experience, liked the idea of having a government job (already contemplating retirement at the age of 15 in an Alex P. Keaton kind of way), and always wanted to drive one of those little Jeeps. I even liked the idea of being outside and walking my route, so if my position called for territory in the city I was on board. Instead, I found myself influenced first by the disapproving face that my guidance counselor made in response to my choice and then by the results of the computer report.  The dream was over. Years later, I received accolades for independently paying for and earning degrees from Northeastern University and Boston College, but I still think that if I had followed my original plan I would now be closing in on retirement as the nation’s Postmaster General.


I was doing stand-up comedy at Catch-a-Rising Star in Harvard Square in my early twenties doing shows with the likes of Kevin Flynn, David Cross, and Louis C.K. I even gained the attention of Steve Allen near the waning days of his life who at one point sent me a letter of continued comedy encouragement labeling me as, at least, a funny driver from his office in Beverly Hills. Already feeling old, however, the prospect of traveling the country playing clubs in places like Gun Barrel City, Texas to Weasel Creek, Idaho before hopefully earning a few minutes on Carson seemed too far off in the distance. Instead, I began to pursue a career as a history teacher, which I think of as a similar job except that your act is geared toward a specific subject and the crowd is not allowed to order drinks. 


In 1999 I was invited to attend the Major League Baseball Winter Meetings in Boston by a couple of upstarts from the Portland Sea Dogs who were staying at the Marriott Copley Place where I was working as a doorman. We talked baseball and they liked my vision (I had yet to wear glasses). They offered me the chance of lifetime, an internship that would have me working in an entry level position with the Sea Dogs (who were, at the time, a Florida Marlins affiliate) that would set me up with a career in baseball.  It was a paid internship but it would pay a paltry $300 a month which I thought at the time was too much of a financial step backward for someone approaching the ripe old age of 31. Despite the impressive tour I was given of Hadlock Stadium in Portland that winter, I walked away from the offer. If I had dared to take that leap at the time I am sure that I would currently be working for Theo Epstein’s staff with the Chicago Cubs. Epstein and I think alike including his habit of covertly leaving jobs while wearing a gorilla suit, a move that I have been forced to utilize on more than one occasion. 


Looking back, I think I would have enjoyed life as a Major League Baseball umpire although I’m sure that the so-called computer in 1983 would have disagreed wholeheartedly. I would have saved countless dollars on Northeastern and B.C. (although Boston College made lovely improvements to Alumni Stadium with my hard-earned cash in 1994), been able to watch a lifetime of baseball games with optimal seating, and work a job where (until recently) being right and wrong makes very little difference. With the wisdom that I now possess as I approach the age of 50, I think I would have actually enjoyed being mired in the minor leagues doing games unceremoniously with the hope that I would someday be working in the Major Leagues - even if I never got there. 


Rather than your eventual destination, it is the path on the way up the mountain that is often the best part. 


Just be sure that your gorilla suit is not at the cleaners. 



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