Confessions of an Aging Dreamer

Jack Crager
5 min readMay 31, 2021


This entry in The Out There Side blog series was written for a forthcoming anthology about midlife.

The other night I had a strange dream: I’d showed up to work at some office building but I couldn’t find my desk. They’d moved me, and everywhere I thought my cube might be, somebody else was working. Finally I saw M, a good friend and reliable editor, so I asked her where I was supposed to be. “I don’t know anything,” she replied, “because I just got fired.” I thought, “Whoa, if M is fired, there goes all my reliable editor’s work. At least I still have my grocery store job …”

I awoke with a jolt — thinking that dream hit a little bit too close to home.

In reality, I’ve spent more than a decade bouncing around between freelance jobs. My editor friend M was laid off a few years ago when her publication abruptly folded (and she joined me on the freelance circuit). And these days my steadiest work comes from a grocery store gig.

This is not exactly how I foresaw things back when I had a cushy corporate magazine staff job — back before the financial crash of the late aughts and the virtual collapse of the magazine industry — and the future stretched out far and (day) dreams were for the asking.

I still have dreams, aspirations, lofty visions; and helpful friends, folks with their own dreams … but as midlife marches on, they increasingly seem to fall by the wayside, ceding to the lonely little footpath known as Reality.

Honestly, it ain’t a bad trail. “When it comes to the important things in life,” a childhood buddy recently confided, “I have to say that I’m extremely lucky.”

I concur. My social support system is rock solid: home family (wife, daughter, dog), extended family (siblings, nieces & nephews, in-laws, cousins) and friends (out the wazoo). We own a “small but charming” apartment in our favorite hood (UWS) in our city of choice (NYC).

As for friends, I have especially come to value bonds from my hometown — which have lasted more than half a century — as well as friendships with new folks you meet here and there. A rich source for the latter is said grocery gig.

Without naming names, let’s just call the store TK’s (journalese slang for “to come”). The place is a hotbed of temp talent, with a crew full of aspiring artists, musicians, students, adjunct profs, washed-up journalists … and (especially during Covid) theater people: actors, singers, dancers and writers from the nearby Great White Way (dark as of late) side-gigging through the pandemic. Turnover is frequent — you never know when someone’s dreams will call them away. Yet many stick around for the flex hours, the health care, the social scene.

Conversations are lively and fluid. On crew everyone does everything and duties shift each hour. The work’s a blast; the work’s a drag. You might relish building the perfect apple pyramid, or delight in chatting with neighbor customers … or you might groan at spending another hour bagging groceries, or spot someone from your past life and sort of hide behind your Covid mask.

At home, writing deadlines come and go while family life evolves. My wife and I recently picked up our daughter at college for summer break. We left our dog with M — my former reliable editor and now trusted pet-sitter. When we all got home, the pooch went berserk, delighted to see us under one roof again. We’re swelling with vicarious pride as our daughter lays groundwork for her own career and for grand travel plans in the post-vac world.

Some of my workmates have become running buddies, and I’m gearing up for a run with one in his mid-20s. Like me, he’s a singer-songwriter (with many more listeners). Like my younger self, he’s an ectomorph with running talent to burn. He’s got more speed than experience; I’m the other way around. He’s training for his first marathon; I finished a slew of them back in the day. We’ll soon run on one of his “easy” days, and I told him that he could ditch me and then go do a real workout.

I’m reminded of what the poet Max Ehrmann wrote in 1927: “Take kindly the counsel of the years, gracefully surrendering the things of youth.”

I have another friend, a former marathoner, avid traveler, and fellow writer now well into his 60s. He recently wrote to say he had acquired a guitar and is taking “baby steps” to learn it. “Good luck with the six-stringer,” I replied. “I’ve been playing it for decades and I’m still trying to learn how.”

But it’s a good idea — they say working on something like music helps to keep you younger in heart and mind as you mature. As a wise writer (now an octogenarian) once sang: “He not busy being born is busy dying.”



Jack Crager

Jack Crager is a writer and editor based in New York City (