Redefining "Gainful Employment"

Fixing Work for the Independent Worker

In 2016 I left the startup I co-founded and supported for 10 years, which had been acquired, to pursue … I wasn’t sure what.

I held several advisory roles with promising startups and was enjoying my time with founders, but I also experienced my share of frustrations and discussions with companies more interested in picking my brain than formalizing a working relationship. And I wasn’t sure how to translate my years building startups into a fulfilling corporate role.

Adding more complexity to this time of transition, my nanny had abruptly quit after years of support, and I struggled to find another sustained caregiver. I became the chauffeur and aftercare provider, finding unexpected moments of enjoyment watching my kids at soccer practice, taking them to the park after school, waiting in the car during violin lessons, often while scrolling through client emails and exploring new roles. 

This period of blended work and life would last another year before I went into a new, more-than-full-time global role that was chaotic and intense and yet carried a much more familiar kind of stress than I had experienced the year before. 

While I now look back on this transitional period fondly I make a point of remembering how unsettling it all felt.

I was flexing new muscles as a parent and advisor, without the incessant travel, the overwork, the Proof of Existence I received biweekly in the form of a W2 pay stub. I had felt more grounded and closer to my family, but identityless at the same time, perhaps a bit like an impostor. I felt guilty for work and parenting infractions, taking work calls from park benches and always forgetting to pack snacks.

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Even my family, who sometimes complained of my workaholic tendencies, weren’t sure what to make of this period of seeming downtime. My husband’s grandfather, Pops, a fiercely loving man but not known to pull any punches, took me aside during a visit, one of the last we would have with him before he passed and asked me with true concern: “Jory, what are you doing? Shouldn’t you be working?”

The irony behind my perceived post-acquisition “leisure pursuit” is that I never actually stopped working. I just worked differently, and for less.

Leaving the company that had acquired mine meant leaving my subsidized health insurance, matching retirement contributions, life insurance policy, and expense account; I now paid for all of these things out of pocket, with the added insult of outrageously high insurance premiums and deductibles. 

Perhaps, this is what Pops was talking about when he thought I’d lost my marbles: Why would I purposely inflict myself with the uncertainty and expense of a 1099 life, no matter how unfulfilling full-time work may be?

I don’t blame Pops for his belief that something was wrong with my decision. He was a relic of the “work for 40-50 years then retire” model. His son, my father in law, took a job out of medical school and worked for the same organization for 40 years, growing his role in management responsibility until the company’s enforced retirement age of 65. And even now, years later, he still works regularly as a per-diem physician in the emergency room three days a week. He continues his daily runs and garden work, integrating painting and piano lessons into his now expanded weekly routine. 

This more traditional working model suggests that, after 45 years of full-time loyalty, workers deserve to pursue other interests, have a pension, and retire comfortably. 

It also suggests that those of us who did not pursue this model, or who lost full-time jobs, don’t.

A longtime professional friend who worked at Meta for 10 years lost his job last year, as well as his premium health insurance. He counted himself lucky, however, when stricken with a life-threatening illness after his layoff, he managed to get sick while still under the company health plan benefit, which was extended as part of his severance. His family would have been financially ruined without it. 

In the U.S., there is a fundamental contradiction in the promise of the American Dream: We are encouraged to pursue any enterprising pursuit, work hard, and thrive. But 1099s do so at our own risk.

We can’t secure car loans or mortgages without years of proven self-employment income. 

We can’t be insured, trained, or trusted without the validation of a full-time employer. 

I’ve transitioned in and out of solopreneur work since the 1990s; I know this drill and accept it. I’ve always justified the mental and financial expense of 1099 status as the tax I pay for occupational self-sovereignty. 

But why should I have to?

Fortunately more and more of you are joining me:

This year approximately 17% of U.S. workers reported 1099 income, up from 10.1% of workers in 2015, reflecting the growing trend of independent contracting and gig work in the U.S. labor market, but also of part-time specialized knowledge work. About 11% of workers report 1099 income of $100,000 or more annually, suggesting that a significant percentage of workers are not just side-hustling but deriving a living from non-W2 work. (TaxAct Blog)​ (Advisor Perspectives).

Communities, platforms, and marketplaces abound that help workers de-risk portfolio careers, by surfacing fractional, contract, interim, advisory, and full-time opportunities for people who may not have trod a traditional corporate path but sure know how to grow a business. Some give access to better benefits for soloists, to corporate-grade executive AI education, and to tools, resources, and advice from those who are navigating independent work lives and thriving. 

Some of us are writing about our pursuit of self-directed, solo careers. 

How about you? Care to share a resource, or personal story of your own experience with independent work? Don’t be shy. The more we share, the more we know about and can support each other. Selfishly, I want us all to win.