I was reading a LinkedIn post by an airline pilot who, grounded and unemployed during the Pandemic, found myriad ways to pay the bills, from grocery delivery to a stint as a bike messenger, before returning to his original profession.

The pilot’s story resonated with many people, as did the concept he demonstrated so aptly of the bridge job, or a temporary role one takes to pay the bills, train for a new career, or prepare for a more permanent future role. During the height of the Pandemic the concept of a bridge job became a state of mind, for more than just those who turned to Door Dash or Uber to make ends meet. Even those fortunate enough to stay employed and work at home found themselves evaluating where they worked, how they worked, and what they did as their work. Even perhaps daring to ask: What am I meant to do?

We collectively became side-hustlers.

I loved the pilot’s spirit. He didn’t report his past year of odd jobs with any self-pity but rather with pride in his tour of personal growth. He reminds me of a close friend of mine who unemployed after decades at marketing agencies, took on home repairs for friends during the Pandemic. His bridge job has since blossomed into a considerable contractor business, and he’s had to apply for a builder’s license to take on more clients. His struggle became his opportunity.

For some, these transitions could never be possible, not because they are incapable of doing the work, but because of the mindset required to take a career pause—chosen or otherwise—and make it part of one’s narrative of self-discovery. More times than not, the only reward for it is personal. Future employers don’t give preference to candidates who took time to rethink their careers. They unreasonably expect career decisions to be deliberate and consistent, starting with the first job we take. There’s no preset in LinkedIn for exploring or being in-between roles. If this is your situation, it’s up to you to game the system, put creases in this unstructured time and present it as completely intentional. 

Some of us are really good at off-roading and can even build it into our professional brand. At its best, career off-roading takes us on adventures we didn’t think we were capable of that define the rest of our lives. But for the majority of us, it’s an unwelcome detour we endure until we can find a job with health insurance benefits. We drop into and out of our life’s work, ideally getting better acquainted with it over time. 

The first time I off-roaded was in my mid-20s, before I had any real business skills to offer as a contractor. All I knew how to do was write, and I figured, now while I still have just myself to feed, I should invest in a writing career. I had followed a series in Inc Magazine written by Harriet Rubin, a former publishing executive who had left her career at its height to become, as she called it, a career Soloist. Later I bought her book expounding on her subject, Soloing. I recall thinking it was not very relevant at the time. She talked about negotiating a severance and taking in consulting fees for single projects that exceeded the annual salary of my previous full-time job. I had just wanted to make sure I could cover my $477 share of a rent-controlled two-bedroom apartment in Brooklyn. Ensuring I wasn’t dipping into my retirement wasn’t really a thing, nor was buying a volume of groceries beyond what I could physically carry four blocks and up the stairs of my walkup. That summer, when I had a good month, I invested in an air conditioner and only used it when I could afford the electricity to run it. 

But today is different. And the head game that Rubin navigated through the soloing process is more relevant to me. The trick to soloing isn’t just about keeping the lights on, but about constant reinvention while keeping one’s identity intact.

And the career journey becomes less about building a resume, a reputation, and more about nailing what that 26-year-old living in the Brooklyn walkup wanted: Career Self-Actualization. The inherent knowledge that she had done what she was uniquely meant to do, in a way only she could.

The longest tenure I’ve had at a company was at my own. And even here I saw that ten-year journey as an experiment in discovering what I can do differently than anyone else. I had just enough time and autonomy to run the experiments. 

I recently Googled Harriet Rubin to check in on her life of soloing, now over 20 years into her experiment. I wanted to see if she’d fulfilled herself, or if she’d drifted off somewhere unrecognizable. I was encouraged to see she’d written more books and become an executive coach. I also happened upon an undated interview she did with the business guru Tom Peters. She described the reason for relinquishing her role leading a publishing imprint:

“…I had become the person to whom everyone went to with questions in this particular arena in corporate America. I had no questions myself which means I was learning nothing. In addition, my responsibility was far outstripping my authority, which often happens in corporate America. Phrases like intellectual capital were very popular in those days but I felt my own intellectual capital was going bankrupt. Because I kept giving and giving from what I had learned and discovering very little to nothing.”

It’s a better explanation than the one I’ve given to friends I’ve met for coffee, who’ve looked kindly quizzical as I described my latest incarnation into decentralized systems, serverless technology, holocracies, and other things I didn’t know existed six months before. But when I left the company I co-founded, I recall feeling frustrated by the recognizable opportunities that came my way.

Others presumed I was who I was previously, but I knew that she had run her course.  

And so I explored, advising companies who taught me things. I developed my 50/50 rule of working with companies where I could integrate 50 percent of my previous work experience with 50 percent of something totally new. For instance, I worked with a digital ad platform (which I knew cold) in Augmented Reality (a totally new platform for me at the time). When the founder pivoted to a tokenized business model, and I was now 85% out of my depth, all the better. In fact, it led to me taking a role at a crypto venture studio, applying my experience scaling startups to yet another new realm of tech.

Some of these bets paid off into deeper roles. Some didn’t. I recall a family member, known for telling it like it is, pulling me over in the midst of one of my latest explorations, to tell me it was time to get serious, and—you know—get a job job. Get back on the grid.

I didn’t feel defensive, but helpless. He didn’t know I was as serious about my exploration as a heart attack. Exploring had become my job. I didn’t know how else to work.

My older sister, who has been a special ed teacher and held the same job for nearly 30 years, uses a friendly euphemism for my transitions.

“You’ve always got something going on,” she says. I suppose that’s true. Her comment is the closest thing to describing the forever in-between. 

A good friend who navigated her own career transition a few years back reached out to me recently to ask if I would share insights with her consulting firm on the challenges and opportunities of being a tech startup CMO. I was going to be stepping away from my latest role, I told her.  Would my take still be relevant?

“Of course!” she said. 

It was a great conversation. The kind that I like to have, when I talk without knowing what I’m going to talk about. Bits of recent and past experience uploaded into the teleprompter in my brain. This is what happens when I’m in flow. These reminders that I’ve lived multiple career lives and continually reincarnated into roles emerge like notifications. And somehow they harmonize. My words are reflexive. 

I think of those conversations that would have been squashed, that would never have existed, had I not been a professional shape-shifter. 

The interviewer pulled on a long thread that started early in my career and lengthened before stopping abruptly for a career switch into emerging tech. It was picked up again recently: the future of digital advertising. 

“You’ve really provided some great insights into what is happening now,” he said. “I now have to ask: What do you think will happen next?”

I thought of those mini-eras I spent being an expert, sounding off on the future of things. Sometimes the future felt so close it seemed I was making it. But really I was chasing it; and I accept I always will be. The chase, so uncomfortable, has become so familiar. Life in pursuit of the other side. I’m plugged not into answers, but back into discovery. I’m 26 again, just crepe-ier in the knees. 

I stared at him for a moment on Zoom, “You know…” I said, “…I really don’t know.”

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