Pete the Planner: Finding fulfillment in retirement is ultimate challenge

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Peter DunnHere’s what I’ve got so far: Wake up around 7 a.m., make a pot of coffee, delete my LinkedIn profile, journal while listening to Thelonious Monk, work out, go to brunch with my wife, read, check in with my kids, make dinner while listening to an Anthony Hamilton album, clean up, watch a game, then go to bed around 10 p.m.

That’s my first day of retirement.

My vision has evolved over time. At first, it simply consisted of waking up and listening to Anthony Hamilton, then brunch and a workout got added. Journaling is the latest addition. And deleting my LinkedIn profile was a stroke of genius.

The point isn’t to curate a day that is infinitely repeatable; instead, I’m aiming to place a capstone on a life of work. I’ve tried to avoid “win the lottery” type actions and ideas, and I’ve paid special attention to the need for healing and transition.

If you haven’t already, you should start to craft your first day of retirement, too.

Maybe you’ll select a “teenager on the first day of winter break” approach, and sleep until noon. Or maybe you’ll spend your first day of retirement volunteering within your community.

You’ve likely read/heard me rail on a person’s unwillingness to match up a future retirement date with a projected amount of passive income. Ignoring the inevitable and practical need to generate non-work income only makes the task harder. What I’m suggesting today is that visualizing your life as a retired person, or at least your first day as a retired person, might convince you to finally acknowledge the math.

Visualizing a decades-long retirement is not easy. There are too many variables. And as fun as “I’ll just do whatever I want” seems, it’s not practical, inspiring or remotely helpful for most people. It’s quite common to associate work with purpose. When a person isn’t able to muster a compelling retirement vision, it’s not unusual for that person to assume their retirement will feel empty and unfulfilling.

The truth is, the exchange of purpose at work for purpose in retirement isn’t one for one. It doesn’t take a genius to realize going to brunch might not be as fulfilling as whatever mastery you were able to achieve as a working person. This is where opportunity for growth exists. Comparing omelets with work isn’t the way. Retirement is the ultimate challenge.

Retiring successfully, from a resources perspective, will be one of the biggest accomplishments of your life. And retiring successfully, from a personal fulfillment and satisfaction standpoint, might prove to be even more difficult for some people. I’ll be the first to admit, the hamster wheel can be addictive. There’s action, risk, success, failure, comeback stories and deep meaning. What I’ve come to learn is, retirement might hold the same promise, albeit with lower stakes.

You might be wondering what my day two looks like. Me, too.

Part of my discovery process involves evaluating what I like and dislike about my work days. I haven’t gotten that far yet, but I do know I like spreadsheets and helping people. And I don’t like reading contracts and what my brain is like after 3 p.m. Do you remember the old question, “What would you do with your life if money weren’t an issue?” Somehow, some way that question was easier to answer when you hadn’t established a career or lifestyle, and there was no way money wasn’t an issue. Yet as we approach retirement and we earn the right to ensure money isn’t an issue, we find ourselves perplexed by this hypothetical.

Establishing my plan for day one hasn’t yet helped me find purpose in my retirement vision, but it has helped me better understand the dynamics and importance of replicating my likes and avoiding my dislikes.

One last, probably too personal, note. I’ve been well aware of my luck and privilege for some time. Since my days at Pike Township schools, whatever community I’ve been a part of has selflessly supported me and poured into me. This phenomenon has continued into my career, and one of the biggest challenges of my retirement will involve figuring out how to appropriately pay forward all the love I have received. I do my best now, but it honestly feels like it will require my full, undivided attention.

You know what? Day two is starting to come into focus.•

__________

Dunn is CEO of Your Money Line powered by Pete the Planner, an employee-benefit organization focused on solving employees’ financial challenges. Email your financial questions to askpete@petetheplanner.com.

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