A Debate: Should You Retire?

Toward clarity about that big decision

Posted Sep 17, 2019

Pixabay, Public Domain
Source: Pixabay, Public Domain

When people are their '60s or perhaps later, that big decision arises: “Should I retire?”

In an attempt to facilitate that decision, here is a debate between a fictitious person and his/her alter ego.

Person: I’m thinking of retiring. Part of it is altruistic: I feel it may be time to pass the torch on to the next generation, and I can afford to retire — Most people could use the income more than I do.

Besides, while I’m still competent and have tried to keep up with the latest and greatest, I’m guessing that a well-qualified younger person would, net, bring more to the table.

Alter Ego:  But you’re still better than a lot of people, and your experience does add a lot that young people don’t have.

Person: Another reason to retire is that I've made incremental changes in what I do but have been in the same career for decades. I’m ready for a change but who’d hire someone my age as a newbie in some different career? I have a better shot at getting to do something new as a volunteer and because I’d have the time if I retired, I’d have a wider range of volunteer opportunities. Plus, I wouldn’t need to have the energy of a young person — I could do it part-time. And not working, I might even have the bandwidth to also take a course now and then.

Alter Ego: But shouldn’t you ease into retirement by cutting back to part-time?

Person: That sounds good in theory but I suspect they wouldn’t let me do that, if only because they wouldn’t mind if I retired. Their turning me down for part-time would pressure me to retire without their accruing any legal problems.

Alter Ego: Well then, how about creating a glide path for yourself, doing a little less work on the job.

Person: I don’t think they’d tolerate that. That would give them an excuse to “lay me off.” I’d rather go out on my terms than get fired, even if they call it “laid off.”

Alter Ego: Well, could you delegate some of your job's stressful work and substitute some mentoring, passing on what you’ve learned over a lifetime to the next generation?

Person: That’s also nice in theory but maybe because I’m not a star or seen as the most likable, I haven’t exactly been buried in requests to be mentored. It might be more realistic to retire and volunteer for a mentorship organization like the Service Corps of Retired Executives (SCORE), mentoring a young entrepreneur or corporate employee, Big Brothers/Big Sisters, or mentor some bright, nice kid at a nearby school who could use a caring one-on-one relationship.

Alter Ego: Remember, once you retire, it’s a one-way street. It’s like that old Roach Motel commercial: You can check in but you can’t check out.

Person: My accountant says that I'm one of the rare ones who can afford to retire even if I live another 20 years.

Alter Ego: But we all know people who get beset by some very expensive illness. Even if you have good insurance, there are deductibles, co-pays, lifetime limits, uncovered services, and so on. You could run out of money. If for nothing else, shouldn't you keep working for the money?

Person: Those are anomalies—We can’t control for every risk. There’s another reason to retire: freedom. Instead of having to get up at 6 in the morning to fight the ever worse commute, I like the idea of sleeping late, lingering over coffee and the newspaper, going to a museum or midday movie, and getting together with fellow retirees.

Alter Ego: You’re romanticizing. After a few months even a few weeks of that, many people regret retiring, especially people like you, for whom work is central to what you value. Plus, you like having structure in your life. So many people flunk retirement.

Person: And many people love it.

Alter Ego: Remember also that if you retire, you’ll be spending a lot more time with your wife. It’s one thing to get along when you’re at work all day but being together 24/7? That can strain even a great marriage and yours is good but has had its ups and downs.  

Person: You’re being too pessimistic. If my wife and I had more time together, we might travel more, maybe get closer. Our marriage has become pretty humdrum: We come home from work, have dinner talking about our workday, and then usually parallel-play: She’ll watch TV; I’ll play on the computer. She’ll talk with friends; I’ll play a video game or fix something around the house. Maybe retiring would help our marriage. But you know, to tell you the truth, I’m still not sure whether I should retire or not.

The takeaway

This debate embeds many arguments pro- and con- retiring. Any of them compelling for you?

The decision to retire is one of later life’s most difficult decisions. I hope this debate helps you make a wise one.

I read this aloud on YouTube.

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