Why Men Struggle When It's Time to Retire

Moving from a focused career into something that looks like a down-shift.

Posted Sep 11, 2019

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The work life of successful men is typically all about channeling our energy and attention into producing measurable results—and generating plenty of income.

We begin our career with an ascent that’s typically linear. We learn as we climb, and before we reach the summit we’ve achieved mastery.

But for many men, things start shifting when we reach a certain age. Sometime after 50 or 60, maybe even 70, someone begins to let us know that it’s time to step aside and make room for the next generation. Or maybe we’re abruptly shown the door. However it happens, we are left to begin the search for mastery and meaning in new ways.

It’s what I call Chapter X.  

To move from a laser focus on our career into something that looks like a down-shift or even “retirement” requires creative thinking and a new kind of bravery. That’s especially hard on men because we’re supposed to be driven, aggressive, tough, risk-taking.

Here’s the really rude awakening: Men, when they hit the age when it’s time to down-shift, “impose an added burden on themselves: an outdated sense of masculinity,” says Louis Bezich, senior vice president of strategic alliances at Cooper University Health Care and author of Crack The Code: 10 Proven Secrets that Motivate Healthy Behavior and Inspire Fulfillment in Men Over 50.

Women tend to actually feel good about retirement, viewing it as a time to pursue new goals and meaningful work, according to a survey that TD Ameritrade conducted last year.

Why can’t men be more like women in the way they view retirement? It’s all about how deeply a man’s work and career standing define who he is. Often we spend the first part of our adult lives so focused on our work that we can’t imagine making a 180-degree turn to a life defined by passions outside of our career or close relationships.

For the most part, we haven’t been socialized to deal with a profound change in our identity. And paradoxically, although men are supposed to be risk takers out there in the world, we fear that if we try new skills, habits, and behaviors, we might make mistakes and look completely foolish.

To make it worse, this new world we are entering doesn’t follow the old rules. It’s non-linear. In fact there are no rules aside from those of nature (e.g. it’s probably too late to pitch for the Yankees).

Yet Chapter X can be filled with meaning, mastery, and new beginnings if we man up and face some truths head-on:

  • What made us successful up to now may well be the opposite of what we need to pursue success in this next stage.
  • We have to let go of independence and dominance as our primary goals and seek to become more interdependent with the people and constituencies we value. That includes having a team to support us.
  • There isn’t a blueprint to follow—it’s more of an empty sack to be filled. We can—and must, if we are to live fully—build a personal roadmap as we decide what this new life should include.
  • It’s normal to fear the unknown and to be hesitant about moving forward. The key is to be willing to experiment instead of hiding out in our comfort zones (which is yet another reason that we need a support team).
  • We won’t get it 100 percent right the first time out and that’s okay. Part of this new state of being is embracing a beginner’s mind.
  • Our definition of success may shift in surprising ways as we explore what comes next.
  • That discomfort we feel with the in-between? It’s just our bodies telling us we’re in unfamiliar territory. It’s not fatal; it’s just discomfort that we’ll get through.

As a financial life planner (and being well over 50 myself), not only have I become deeply immersed in this challenge, but I’m also convinced we can make the adventure easier, more fruitful and, frankly, more fun.

Join me on my site, Financial Life Focus, LLC, or on Twitter @FinLifeFocus or LinkedIn.