Running Away from Home (Again)

Writing has always been my friend. Now uncertain about the direction to take it, I’ve been feeling a little lost. I became aware of this when Alberta discovered my high school yearbook while searching for papers she needed for a book chapter she was preparing.

It had been sixty years since I last opened the white book with “Hewlett High School Class of 1963” imprinted in dark blue across the cover. Slowly turning the pages, I became nostalgic reading the comments friends made alongside their postage stamp pictures. I found myself staring for a long while at the future Frankie Berlin envisioned for me: “Hey Abe, I look forward to seeing you spouting your bombast in the sports section of the New York Times.”

Well, I never quite made it to the Times, but not long after I arrived at college I found a part-time job as a sportswriter for the Skokie News, a suburban newspaper covering a small upscale city northwest of Chicago. Serendipity had shined on me, but I was too young and immature to appreciate it.

The editor liked my first few articles on the high school football team, but I balked when he suggested I attend all the road games and interview at least one player after each game. I didn’t quit outright, but I became an unreliable reporter.

I invented final exams as an excuse for my dalliance, but was fired by a no-nonsense boss. Apparently, the real world was not going to be as forgiving as my parents. Humiliated and enraged, I retaliated by changing my major from journalism to psychology. As my father said during Christmas break, “Stevie, you just may have bitten off your nose to spite your face.”

For each of us, a turning point comes when we must choose one career path and leave or set aside the other. I became a psychologist but never abandoned my writing. In academia, I published furiously and ghostwrote my colleagues’ research reports. But I became alienated from the bureaucratic excesses and interpersonal politics of university life and soon departed.

No longer stultified by the dictates of academic writing, I plunged headlong into magazine freelancing. The highlight of this endeavor was a “promising” rejection of my article, “How to Sabotage Your Affair,” by Penthouse.

Without the structure of a defined job, I took refuge in my family’s real estate business and immersed myself in a new passion—the challenge, math and money promised by the stock market. But whatever future this interest had was waylaid by a series of family crises that included a suicide, a homicide and, soon after, my midlife depression. The illness was debilitating and for twenty years my writing languished.

A little over two years ago, I accompanied Alberta to a writer’s workshop in Aspen. Whether by curiosity or a twinge of competitiveness, I decided to search for personal finance magazines and sites that accepted articles from writers outside their own editorial staff. One popped out at me because of an unusual focus on placing financial issues in the context of personal experience—that was, of course, Humble Dollar. After reading a few articles, I thought I might have a shot.

After Alberta left the next day for an early morning seminar, I planted myself in a coffee shop and began to write an article on the resurgence of interest in the option-income fund, where an investor sacrifices considerable upside potential in return for a monstrous dividend. Later in the day, I submitted the draft to Jonathan who, after a series of edits to which I have become familiar, accepted it.

I was ecstatic and emboldened to follow-up with more pieces. Over the last two years, I have contributed many articles to Humble Dollar, basking in the grit and joy of writing and the acceptance of the community of readers. I confess I was also gratified by having Jonathan’s approval, something I never got from my father.

But there has been a shift. The site now has a special place for traditional domains of personal finance like how to navigate the labyrinths of Social Security and Medicare, as well as education in how to navigate the money landmines of retirement. But I am woefully uninformed about the nuances of many of those domains, fluent only in the basics. Investing for many readers is a means to a coveted end–to lay back hands-free, travel, enjoy the grandkids and prepare for the possibility of a heath catastrophe. But it’s not necessarily a devoted pastime by itself, as it is for me. It’s that 10% of retirement assets in which I give myself permission to roam.

Why am I so stubborn, always trying to force my square peg into a round hole? I feel like the guy who left the party early, a misfit, just like I felt in my family. Are my fellow contributors the brother and sister my parents preferred? I feel like the quarterback flushed out of the pocket. I need to move my MO closer to the investment needs of readers desiring to be educated in how to cope with the often daunting and unexpected financial demands of the senior years.

Apparently, I was not ready to surrender. Out of curiosity, I submitted a manuscript to an online site that educates doctors and dentists in how to invest their prodigious cash flow responsibly without being fleeced by financial advisors. I was a great fit, a shoo-in, or so I thought—a psychologist who worked at a medical school and as a maverick investment advisor for Charles Schwab.

Enthused, I rifled off an article. A positive response would come in three weeks. Of course, spoiled by Jonathan’s whirlwind response time, I figured I would hear in a day or two. Well, it’s been over six weeks and I’ve stopped expectantly scouring my emails.

In the meantime, I have been orienting myself to benefit from areas of personal finance in Humble Dollar outside of mutual funds and ETFs. One article in particular was eerily timely. I came across DrLefty’s thoughtful post on making final arrangements just as Alberta and I were about to depart for purchasing two burial plots about 500 miles from where we live.

Running away from home with $44 was no picnic, and my journalistic adventures were no walk in the park. So good to come back home, fresh and chastised.