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Retirement. The Reward for Your Work or the Last Station on the Train Track?


For many, life is viewed simply as a timeline where one phase follows logically, step after step.


Graduate from high school and go to college (or start a trade or maybe join the military). Graduate from college and then start your career. Get married and then have children (maybe). Progress through your career and then retire. And that is where this discussion begins.


Is retirement the reward for your work over a 25+ year career? The phase of your life that you work towards, yearn for, and plan for as you advance through the years of your career.


Or is retirement the second to last stop on the train track that is your life? All aboard for the final two stops on your trip! Next stop irrelevance. Final stop death?


I chose to retire at the relatively early age of 57, a little over 36 years into a professional career. I planned and plotted for my retirement for about two years before I walked out the office door for the last time. The financial and logistical planning was the easiest part. The "what will I do with my time" mental debate was more difficult.


The public decision to leave the career and professional reputation I had nurtured over several decades was almost paralyzing. Despite the fear that, on some days, would take my breath away, the final decision was like a bright flash of light.


I was stretching out on a bench (not very comfortable) in the Charlotte airport near midnight, having missed my flight home on a Friday night for (maybe?) the 10th time. My wife was at the lake, and I was not there to enjoy it with her. And then it hit me over the head like a sledgehammer.


What am I doing here? Why am I waiting to retire? As Michael Jordan and Nike advised, "Just Do It," so I did. Three months later, I officially retired.


I am at the point now, almost six years into retirement, where I can confidently answer the friendly question, "What do you do?" My days are full, filled with volunteer work as a business mentor for startup entrepreneurs, a side hustle as a career coach, playing pickleball, and long walks with Rigby (my 4-legged companion) and Sue (my wife of 37+ years).


When will you retire, and what do you think about when you hear the word "retirement"?


It is a question(s) that I ask almost everyone I meet who is over 55, usually over a drink. This word elicits a wide range of emotions and definitions depending on whom you engage in the conversation.


A business colleague once told me I should never tell anyone I am retired. He believed that referring to yourself as retired immediately reduces your perceived value in any conversation. From his perspective, retirement is a terrible word. It signifies the end of your ability to be a valuable contributor to any business entity. I feel sorry for him. His life and sense of self-purpose are inexorably tied to his work.


Does a change in status from employed to retired mean you leave all your years of accumulated knowledge and experience on the desk as you walk out the door and into retirement? From that perspective, retirement sounds like a fast walk to irrelevance, boredom, bad health, and ultimately death. I don't think I like that picture.


But all is not doom and gloom.


Upon hearing the news of my retirement, I have another good friend and former work associate who said: "You won the game." Despite his questionable judgment for supporting only New England sports teams (Patriots, Red Sox, etc.), I like his definition of retirement the best!


Retirement is a destination that we progress towards for many years. It is not an end nor the beginning of some steady decline into obscurity and the grave.


For me, retirement was a new beginning. It is time to reinvest in my marriage and my family. Time to explore many things I missed over the years of long work weeks and life on an airplane. And time to explore interests that had crossed my mind in years past but that I never pursued.


I did not leave my skills, experience, and value in my office desk drawer when I retired. I now have the time and the freedom to grow those skills and soak up new experiences.


Several years ago, I had a discussion with the director of a career center for a large local university. It was a good discussion from which I took away a critical insight. She had a perfect reply when I told her I did not yet have a good post-retirement answer to the "What do you do" question.


She told me that I now had a portfolio career. A single job title, company, or career path no longer defined me. I am free to pursue multiple opportunities and interests all at the same time. She pointed me to an article in the Harvard Business Review that clarified the term "portfolio career" or what the author refers to as "going plural." I love that term and am now fully invested in the plurality of my retirement.


Take the lyrics from Don Henley's song The Boys of Summer when he sings, "Don't look back, you can never look back." He explained that the song was "about aging and questioning the past." You got it right, Don.


Retirement is a dish best experienced when you "eat on the run" and keep moving forward. It's not about looking back and regretting what you gave up or had in your past. Retirement is an open book where you can turn one page at a time, and every page holds a new adventure.


Retirement? Not a bad word, at least for me. What about you?


Dan Troup is The Sunny Side of 57. He loves to reflect and write about life, family, career, and retirement. Check out more of his reflections on his blog site. Also, consider subscribing to The Sunny Side of 57. When not playing pickleball or hiking with Sue and Rigby, he writes a new post about twice a month.

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