Tom Brady, Retirement Remorse & The Retirement Planning Questions You Should Be Asking

It’s official, after 20 seasons of cold in New England and heat in Tampa, Tom Brady finally retired. No wait, he’s back!

After only 41 days, football’s GOAT has retirement remorse and is making a U-turn back to the field. Brady tweeted his decision.

“These past two months I’ve realized my place is still on the field and not in the stands. That time will come. But it’s not now. I love my teammates, and I love my supportive family. They make it all possible. I’m coming back for my 23rd season in Tampa. Unfinished business LFG”

First, the obvious caveat. Tom Brady is, well, Tom Brady. Few of us can match his skills and achievements. He does, however, have what many of us (at our own level) work, plan, and hope to enjoy in retirement – health and wealth. And, he has a lot of it. Brady and his family could spend effectively another complete lifetime retired and enjoying what he, and his supermodel wife Gisele Bündchen, have amassed and achieved.

What happened? Why not enjoy another lifetime on fulltime holiday? None of us can truly know what the decision calculus was for Brady to return to the field, but Brady’s unretirement may be a cautious tale for the rest of us.

Retirement planning, in the classic sense, is about ensuring financial security and sketching out what amounts to ambiguous goal-setting for a future life. Brady’s return to work, for whatever reason, should give us pause and cause us to ask – are we really prepared for retirement?

Even if, on an astronomically different scale than Tom Brady, we have financial security and decent health (sorry Tom, unlike your diet, bread, pasta, ice cream are three of my basic food groups) – are we confident that we will be happy in retirement after a few weeks, months, years, even decades in?

Unlike Brady, few of us are retiring in our 40s. Recently, however, many people have decided to call it quits in their 50s. Whether early retirement is because the investment market has been kind to their portfolios, or they are just exhausted after the pandemic, these early retirees are adding years to traditional retirement.

Retirement for most of us will amount to nearly one-third of our adult life – retiring in your 50s will add at least a decade more. If Tom Brady, with millions of dollars stuffed in his hoodie pocket, multiple homes, private jets, a young family, and I am sure many, many offers to be purposeful and engaged, experienced retirement remorse after only 41 days – what’s your plan going to be to fill your decades of retirement?

In an earlier article, I suggested that the pandemic shutdown was your retirement firedrill. How did it work out for you? Were you prepared? What did you learn?

Yes, I know, none of us could travel. Despite travel being the ‘big thing’ we plan to do in retirement, very few of us will spend decades doing non-stop travel. There are all the other things we tell our family, friends, coworkers, and ourselves, that will keep us busy and happy in retirement. So, did they?

Did you find hobbies and games that excited you – day after day after day after…?

Did you find yourself developing a near intimate relationship with the cashier at the local home improvement store?

How many times did you paint the spare bedroom, clean the closets, study how to downsize, consider the color choices of paper lining for the shelving of your kitchen cabinets?

How many languages did you learn over the last two years? Did you develop new and improved culinary skills?

Maintaining friends during the pandemic shutdown was certainly difficult. Did ‘social distancing’ from work colleagues and friends make you think twice about how truly socially connected you are to others outside of the workplace and home? What do those connections portend for your social wellbeing in retirement?

Did the extra time spent with family provide insight into how family life might be in retirement? Was it all you hoped for, or did you find the terms ‘best divorce lawyers in your area’ in your partner’s web browser search history?

Not all of us have an open multimillion dollar contract and a welcome back clause to return to work, but all of us must do better than only planning for the financial dimensions of retirement, we must prepare for living in retirement.

Retirement remorse is not just a risk for Tom Brady. It is a retirement risk for all of us. We must do longevity planning, not just retirement planning as it is done today. Even with health and wealth, truly identifying what we will do in retirement, where we will do it, and with whom, long before leaving the proverbial field, is critical to our wellbeing in life after work.