Getting Paid
Thoughts on quitting while you’re still ahead.

Almost since I started working I’ve wanted to quit my job. I’m not talking about the jobs in high school and my early twenties waiting tables, clerking at a copy-shop job, or operating a machine at a bindery — a job that, after two weeks, convinced me to go back to college. I did a stint as a home health aide, which felt like a step up in that I was helping people, if only with light housework and a half hour of conversation. But it, too, was a low-paying job without benefits, one that a white girl with straight A’s wasn’t expected to stay at for long.
The hard-won office jobs are what I’m talking about, the ones that required a navy-blue suit, low-heeled pumps, and earrings that didn’t dangle, tinkle, or shimmer. Wearing such an outfit, I landed a position — at the ripening age of thirty-six — doing what I wanted, writing and editing. Yet within three months, I started looking for a shiny new job with a better commute, a more congenial work environment, and something that felt less like work. It took me five years to get another job, only to realize, three months in, that it was more of a rebound thing than true love.
While I pursued the ideal job tirelessly, I simultaneously plotted my escape from the nine-to-five. I tunneled my way toward freedom as doggedly as a lifer with a spoon under her mattress, turning pennies-earned into pennies-saved, one dollop at a time. It took me twenty-two years, but I finally had my finances in order. And suddenly — perversely — my job as a Marketing Communications writer for a financial services company felt like the dream job I’d been chasing all along.
Unwittingly, I’d grown attached. I told myself I had to stay for the money — after all, I may live well into my nineties — but even that began to feel like an excuse. Like a victim of a mutant strain of the Stockholm syndrome, I’d convinced myself I loved my job and couldn’t get by without it. As long as I kept showing up and doing what was asked of me, the devil I knew would protect me from the consequences of market volatility, a destabilized climate, and the uncertainties of a looming Trump presidency.
This made no sense. I’d been downsized twice over my decades of work. Even now my company was in the middle of a “foundational change journey.” There would be “displacements.” I could hope for a layoff, but I couldn’t volunteer. Which meant I would probably have to leave on my own momentum, without a package. I’d done it before. I’d chosen sanity over security and just walked away. I’d left with another job lined up or simply because I could. In short, I’d had plenty of practice quitting a job. What was stopping me now?
I’d be 58 in a few weeks — not 65, but silver haired and post-menopausal just the same. Why face that I was heading into what, optimistically, would be the final third of my life when every paycheck was a hit of self-esteem? It told me I was needed. I was valued. At the very least, my existence was duly noted. Whether I was psyched about my job or dissatisfied, I had a place to go, people to see. Without a slot on the org chart and a bimonthly direct deposit, my worth as a human being would be under question.

My wake-up call came during a slow workday in the middle of a slow month. Idly, I picked up the receiver, without checking caller ID. It was a guy from Fidelity Investments, asking if I want to schedule an appointment with a financial adviser.
He had the wrong gal.
Though I worked for a firm that managed mutual funds, I was possibly the most risk-averse investor on the planet. Unmoved by statistics showing that women suffered for being more conservative investors than men, my portfolio consisted entirely of 30-year Treasury bonds, cash, and, except for a small portion that had somehow gotten tied up in company stock, the most conservative mutual fund offered in my 401(k) plan.
In theory, I believed that a financial adviser was a good idea. Just not for me. But getting the Fidelity guy off the phone was not the only reason I agreed to let him make an appointment for me with an adviser named Kate. I was curious about what she would say.

The last time a Fidelity representative gave me advice it was the mid-1990s, when the association I worked for introduced a 403(b) retirement-savings plan — the nonprofit equivalent of a 401(k). We employees gathered in the cafeteria to hear his presentation, which convinced me I was late to the game. I had wasted at least ten good investing years. Now I had to catch up, if I could — if I wanted to avoid an impoverished old age.
“It’s the only way,” the Fidelity guy said.
You would think that the first hefty, pre-tax transfer from my paycheck into a growth mutual fund would inspire happiness — or at least a sense of relief. After all, I was on my way. But doubts gnawed at me. How could I afford to keep investing so aggressively? What if my mutual fund tanked and I lost all that money? What if the stock market collapsed? Investing was supposed to provide a sense of security. Instead it fed a frenzy of fear.
Over the next few weeks, the Fidelity guy’s warning wormed ghoulishly through my thoughts. The only way. The only way! By the time the second pre-tax transfer came out of my take-home pay, I was looking for another way.
I found it in the 1992 book that, for the next fifteen years, became my Bible. Your Money or Your Life, by Joe Dominguez and Vicki Robin, laid out an eight-step path to financial independence — or FI, as it was known to the initiated — designed to help readers achieve deceptively simple results. Spend less, without feeling deprived. Save enough to build a six-month cushion. Invest the rest in ultra-conservative government bonds. Keep this up until your investment income covered your expenses, and then some. Finally, quit your job.
Except for the investment piece, nothing about FI struck me as radical. Any financial adviser worth her salt would tell you that tracking expenses and keeping an emergency fund just made sense. But scrutinizing cash outflow turns out to be a lot of work. I attempted to track every penny and, at the end of the month, assessed each spending category in terms of life energy spent, how well each purchase aligned with my values, and how my spending might change if I didn’t have a job. I developed a newfound respect for accountants, as my tallies of individual expenditures defied my efforts to reconcile total output. Even so, I got a pretty good sense of where my money was going, how much I actually needed, and how to avoid ugly surprises about purchases made just to blow off steam.
Though never the tightwad Dominguez and Robin were, I got out of debt, paying off my credit cards, and student loans. My partner and I paid off the mortgage on a condo two blocks from the commuter rail and close to three bus lines, making it possible to share one car. Well, at least we have only one car, we would reassure each other after a vacation or restaurant splurge. Despite my many lapses I was able to max out my retirement plan. I invested additional funds according to the book — or the Bible — in long-term Treasury bonds.
I’m not recommending this investment approach. When I started buying 30-year Treasury bonds, interest rates were around 5% instead of the 12% Dominguez enjoyed in the early 1980s. Now you’re lucky to get 3%. Treasury bonds were also supposed to be the safest investment around. They were backed by the “full faith and credit” of the U.S. government. Dominguez, who died in 1997, could not have foreseen the age of government shutdowns, Congressional gridlock, and a president who has declared personal bankruptcy four times. In this new normal, I had to admit that there was wisdom in diversifying — or investing instead in freeze-dried food packets, bottled water, and a generator.
Following Your Money or Your Life also had the unintended consequence of helping me rationalize my corporate jobs. I worked to save enough money to quit so that I could write without being derailed by economic necessity. But a paycheck to fall back on was, for me, a double-edged sword. While it cushioned the inevitable rejections and attendant money anxieties of a full-time writing life, it also afforded me the luxury of being complacent. And not just about writing.

In the temperate offices of the Fidelity Investment Center, Kate gave me a firm handshake and ushered me into her office. She put me at ease with small talk, looked up my account, perused the sheet I’d made for her of my other assets, and asked me to ball-park my expenses. After running scenarios, she turned her screen toward me and walked me through her calculations of my income and expenses over the next four decades or so. Then she looked meaningfully at me.
I didn’t get her meaning.
“So, do you think I can quit my job?” I asked.
She said I could, if my expenses were as low as I’d told her they were.
It turned out that they weren’t.
The changes in my balance sheet over the past two decades had all come at a cost: high-speed Wi-Fi, cellphone plans, rising real-estate taxes, Netflix, and one-click shopping at Amazon. On my Quicken reports I found plenty of purchases Your Money or Your Life dubbed “gazingus pins” — items that call out to you from the shelves and you just have to have, for reasons you may never understand. I had some classic ones.
Unworn clothes. Pristine art supplies. Escape from Cubicle Nation and six more books on my Kindle with unheeded advice about making a living without a job. Dinners out, drinks with coworkers, coffees to-go, and eight pairs of prescription eyeglasses and sunglasses I’d acquired over the years, thanks to my vision plan. I hadn’t questioned my expenditures in years, and it showed. I harbored no regrets about gifts to charity and subscriptions to literary magazines. But if I was going to quit my job, I’d have to realign my spending with my new situation.
I gave myself a year to get my ducks in order. And then, I got cold feet.

In March 2016 — the month I had planned to quit — I received the best performance review of my career. I liked my boss — a lot. He was the best manager and advocate I’d ever had. I had a sweet commute: a twelve-minute train ride two blocks from my house followed by scenic walk through historic Boston neighborhoods, from Beacon Hill to the Back Bay. I was paid well. I enjoyed my colleagues. I felt competent and appreciated.
How could I leave now?
One mild Tuesday morning, I walked from the train station to the office, as I’d done almost every workday for more than ten years. The route — like so many of my work routines — was a deeply grooved habit, as hard to break as my addiction to caffeine. Passing by the dogs racing after each other in the Boston Commons, I indulged in a wave of nostalgia for my own place in the pack. What would take the place of the striving, the ritual morning coffee run, the outbreaks of hilarity on Friday afternoon? Then, waving my badge in front of the door that led to my cubicle, I experienced a familiar wave of despair.
It will pass, I reassured myself.
At my desk, two screens came up consecutively, each asking for an ID and a password. I checked to see who else was online. Their little boxes were green. Next to the names of those who’d recently moved on (voluntarily or otherwise) was a string of zzz’s. Rest in peace, I thought, morbidly, imagining the zzz’s taking the place of my little green box. I checked email, sipping coffee from a refillable plastic cup. At that very moment, wastebaskets across America were heaped with paper cups, plastic lids, and cardboard sleeves. The thought depressed me. Dread deepened as I read the headlines.
Remind me, I said to myself. What was it about this routine I would miss?
I swiveled around to the 19th-floor window. Rooftop HVAC fans, the weeping willows around the duck pond in the Public Gardens, the gold dome of the statehouse: this view comprised my well-appointed boredom. From the other side of my cubicle wall, a colleague’s disembodied voice rose up. “Who’s on the line?” he asked, kicking off a conference call.
The corporate environment gave me some comfort. In contrast to, say, a personal essay, writing marketing copy offered anonymity. Each word was a collaborative effort. And I liked collaborating. My boss and I made a great team, brainstorming headlines, putting together presentation slides. Many designers, writers, and editors — the “creatives” — were, like me, doing work on the side. Two stand-up comics, a short-story writer, a visual artist, several musicians, and a poet were all among my colleagues. They would understand if I left to write.
But would I write? I wasn’t going to sit in an Adirondack chair by the beach, like a retiree on a Fidelity brochure. For one thing, I couldn’t afford it, especially not if I quit now. I didn’t have a pension. And I was too young (I loved that phrase, too young) to collect Social Security. I was aiming for what Yeats described as “a life of order and of labor, where all outward things were the image of an inward life.” This was the payoff — the promise — of FI.
In mid-June, the company unveiled a new organizational chart. I got a new boss. On July 8, I turned in my laptop, my badge, and my Blackberry. And just like that, my fantasies of destitution fell away.
Since the presidential election, I worry more than ever about global mayhem and financial collapse. I have to wonder though what made me think a paycheck would protect me. Over the fifteen months between deciding to quit and actually quitting, I must have been like the guy in the Buddhist parable who’s chased by a tiger over a cliff. He catches onto a vine. He can’t hang on forever. He’s completely screwed. But what he does is instructive: he reaches out to pluck a strawberry growing nearby. It tastes so sweet. Like my job, it’s sweeter than any strawberry he’s ever tasted. It’s because he knows it’s his last.
Alisa Wolf has worked as a writer and editor for consumer and trade magazines and, more recently, as a marketing communications writer. Her work has appeared in Agni Online, the Agni Blog, Calyx, Cimarron Review, Concho River Review, Fjords Review, The Legendary, Pisgah Review, Red Cedar Review, and Schuylkill Valley Journal as well as The Prentice Hall Reader, 11th and 12th editions.
Support The Billfold
The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by making a monthly pledge on Patreon or a one-time-only contribution through PayPal.
Comments