Avoiding the Dreaded ‘Now What?’

Phil Goldstein

Several friends of mine are considering retirement. I thought perhaps a cautionary tale here in North Forty News about my own experiences filling the extra free time after I retired might prompt a reconsideration of those plans.

You often hear it said, “I’ll cross that bridge when I come to it.” But for some reason, you don’t hear it much when someone’s talking about what they’ll do with their increased free time post-retirement. That infers that those approaching retirement know exactly what awaits them and how they’ll handle it. I didn’t.

I retired at age 56. My father retired at 60 and wished he’d done so sooner. I thought I’d learned from his lesson and, having heeded his advice that I save well and invest better, retirement seemed feasible from at least the affordability standpoint. Besides, my wife Amy, as a department head with two master’s degrees, earned an excellent salary teaching middle school special education, loved her job and insisted she should teach for at least another 10 years. Meanwhile, my doctor told me I’d surely live longer once I quit lying awake nights obsessing over work, and the dogs were all for it because they’d have company during the day.

I lasted two weeks in retirement. I didn’t welcome all the free time. 

In retrospect, I missed the identity-fulfilling productivity and relevance, although I surely didn’t think of it that way while working. So, I tried replacing a single 80-hour-a-week headache with multiple productive endeavors. 

Fortunately, a consulting firm in my field learned of my availability and made me the proverbial offer I couldn’t refuse. I also could accept or decline any assignment, thus maintaining some semblance of retirement. 

But I still had too much spare time, so I sought other hopefully gratifying engagements.

I volunteered for the presidency of our HOA but only because nobody else would do it.

I’m now in my 11th year because still, nobody else will do it.

I accepted an appointment to Timnath Planning Commission. Two reappointments later, I still find public service rewarding, primarily because it provides identity and relevance.

Since most everyone else in our community plays golf, I’ve even played a few rounds. However, if I wanted that much frustration, I’d have continued working.

I dabbled then quickly un-dabbled in candle making. (Please don’t ask.)

I tried building an essay-oriented website, but I’m an analog guy in a digital world, and I soon gave up. I don’t do social media either; it’s certainly time consuming, but sharing mundane daily activities with the world’s not exactly productive.

I increased my workout duration, which of course increased injury downtime, so timewise, that’s unfortunately a wash. I learned then began coaching pickleball. Sadly, I’ve suffered the ignominy of getting fired by a few students who didn’t share my belief that winning’s a good experience. 

I relearned nap-taking, which is an acquired skill after the age of four.

Fulfilling a 50-year ambition, I began taking drum lessons and joined friends in their neighborhood basement band. 

I read even more than usual but watched increasingly less television. I eventually yielded to social pressure and subscribed to Netflix, but I quickly exhausted the few series I enjoyed and now must wait a year for their return.

Two nonprofits recruited me for my financial and operational management experience. While flattered, I declined, believing I’d not find the contributory gratification I needed with that business model.

Although it would kill some time, I forego helping with Amy’s pet sitting sideline. It’s quite enough that I do her domestic bidding, but I draw the line at employee status.

And of course, I dusted off my 47-year-old journalism degree when North Forty News offered this column last year, a blessing given how much time’s involved in writing this every few weeks.

Meanwhile, in February 2020 my part-time consulting took the same hiatus as did the jobs of so many others, and I’m again left with too much free time.

So, here’s a typical day for me now: 5am, out of bed; 530am, feed and walk the dogs; 6am, workout; 730am, breakfast, personal finances, HOA issues; 830am, writing and rewriting column; 9am, house and yard chores; 930am, drum practice; 10am… now what? And of course, if Amy feeds and walks the dogs, which she usually does, now what? happens even earlier.

Overall, this retirement thing’s pretty good. I just don’t think you’ll know what it’s like until you get there. If you prefer idleness and banal TV, then no problem. If not, you’d better have a plan for avoiding the dreaded… now what?


Phil Goldstein writes Tales from Timnath periodically for North Forty News. Phil is an 11-year Timnath resident who proudly serves the Town of Timnath as chair of the Timnath Planning Commission. Phil is finally using his journalism degree after getting sidetracked 48 years ago. The views expressed herein are Phil’s only. Contact him with comments on the column or suggestions for future columns at [email protected].




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