Curtain's Going Up. Will Your Second Act Be A Hit?

Bob Goldman on

Hate to frighten you, but something awful is going to happen when you retire from your current job.

You're going to get another job.

Your next job may not be as terrible as the job to which you currently cling, but it's not the job you want, which is no job at all.

Blame it on the stock market. Blame it on inflation. Blame it on the bossa nova. It really doesn't matter. When the curtain comes down on your first act, the curtain on your second act is going to rise.

Or so I learned in "6 Steps to Finding Your Second Act in Retirement," an article by Mary Kane in Kiplinger's Retirement Report.

It isn't easy to find up-to-date statistics on the number of workers still working in the 65- to 69-year-old category (aka the Ancient Ones), so I'm not even going to try. If you need numbers to tell you whether you will have to work beyond your sell-by date, check out the balance of your retirement account, or the total cost of your weekly shopping list.

"But finding a second-act career isn't easy," as Mary Kane reminds us, "even for those with a track record of professional success." Which means that for those of us who have a track record of professional instability and mind-boggling torpor, finding the perfect retirement job will be nigh on to impossible.

We have neither the time, nor the space, nor the energy to examine all six steps, but let's take a closer look at three, the better to keep you from turning a step into a misstep.

No. 1: Begin early

"The best time to start mulling a second career is when you are still working," says financial adviser Brian Sheahen, "ideally at least five years before your retirement."

One aspect of your personal feasibility study is to "coordinate the timing of your transition with your spouse."

Makes sense. The second careers that appeal to many people will involve removing their noses from the grindstone to embrace careers that offer ample amounts of personal satisfaction but minimal or zero salaries. Consider the highly compensated, hard-charging senior executive who decides they want to fashion a second career of writing poetry, or painting pictures, or churning out weekly workplace-humor columns.

As inspirational as such a second act may be, the spouse of the person making this transition may not be totally enthusiastic about having to bear the burden of making all the money and paying all the bills.

This is why I recommend keeping your spouse in the dark until you emerge from your stodgy but well-paid chrysalis to become a glorious butterfly of artistic discovery.


There may be a period of adjustment as your spouse comes to understand your need for embarking on such a journey of self-expression, which could last for years, or for however long it takes for your spouse to convince you to express your self-expression in between shift changes at McDonalds.

I'd say five minutes should do it.

No. 2: Do a "midternship"

Many community colleges and universities offer classes for "older adults looking for new careers and purpose." You can find a listing at One resource you definitely should consider is offered by the University of Wisconsin, which has a one-year program that includes a "midternship -- an internship for older adults -- at a local nonprofit."

This is an excellent idea for the senior second-actor, since it will provide experience in what could be the most difficult part of starting a new career in your 60s. Namely, being bossed around by know-nothing whippersnappers in their 20s and 30s.

Of course, you can access your years of experience and plug away, while taking advantage of the guidance provided by a bunch of teeny-bopper managers who know nothing of life or business. Or, you can quit immediately and start looking for your third act, in which you star as a grumpy know-it-all.

Trust me, it's a part you can play really well.

No. 3: Tackle the internal work

The business skills you bring to your second act may not impact your success. That's why you are advised to "reflect on childhood experiences that mattered to you and made you happy."

The idea of turning your second childhood into your second career may seem strange, but it could work. All you need to do is find a position where you spend your days battling evil aliens and supervillains.

Wait a minute! That sounds just like your current job.


Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at To find out more about Bob Goldman and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at




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