websites eventually made it super easy to launch and run a small operation on one’s own from anywhere—no pricey office rental required.
Either way, there were eight or so of us there to gather and boost each other over eggs and coffee; we called our meetings the Break Free Club.
I hadn’t exactly broken free. I still had a day job, but my side gig had picked up steam.
When I worked in television, I really loved it, and I thought I was good at what I did. Plus, I had done only that for so long that I didn’t know if I was good at anything else. When I first got laid off, I was certain I was not. My confidence eroded at a rate I’d never previously experienced. While my initial conclusion was that, as a TV producer, I had no real or tangible skills, I started remembering that big win with Urban Skinny.
As a producer, I read the newspaper every morning. I made sure everyone else could do their jobs on a shoot. I wrote copy for the prompter in incomplete sentences…with lots of…for pausing on air…and routinely fit stories into ninety seconds. I lived and died by the clock. I told the truth. I got the facts straight. I could ask a long stream of questions and still find more to ask. I drank with the crew. None of those things seemed like actual professional skills. Outside of work, I was an excellent parallel-parker, derived from seven years living in Hoboken, New Jersey (the Mile-Square City), where I learned to cram my car into the tiniest spot, even if it meant a little bumper-nudging of other cars to make mine fit. I can open a wine bottle with great speed and precision because, during summers at university, I worked in a fancy restaurant in Niagara-on-the-Lake, Ontario, with white linens and expensive food.
I didn’t see any of those things as translatable into corporate-America-type jobs, but collaborating on books, that started to seem doable. In fact, that first book led to ghostwriting a second book. And a second led to a third. I was working around the clock, and the potential to ghostwrite self-help books full-time became real.
The Break Free Club would meet once a month to talk through our new roles as freelancers and balance the dream versus the reality of professional life. We’d systematically go around the table and report on the wins, the challenges, and the commitments to ourselves for the month ahead. I liked this process, and it inspired me enough to think I could maybe tackle the writing thing full-time.
Having said that, there was some hocus-pocus involved, philosophically speaking, as our group was led by an aspiring life coach. She told us that the Universe was definitely going to play a role in our breaking free. I liked what this coach had to say. Plus, we were all deeply hoping that this new ability to be free and be our own deciders would allow us to flourish. The life coach had us write checks to ourselves for a million dollars, and once, during a weekend meeting, we spent a full afternoon making vision boards.
This vision board was a real vision board, much more upscale and specific, with cut-out words too, like an old-school ransom note. My dreams were taped to colorful construction paper, which probably increased their odds over that old magnetic board in Harlem.
I started to believe.
Looking back now though, I’d like to poll the most successful people in the world and find out if they had vision boards.
Hey, Barack Obama: Did you have a vision board?
What about you, Lady Gaga?
Serena Williams—did you cut out a silver Wimbledon tray and tape it to your wall, or did you go out and practice your sport and put in the hard work needed to be a champion?
I suppose I could have continued to put in hard work both working in the news by day and writing books by night, but instead I cut out pictures and taped them to construction paper. And then I stared at it. For some reason, that made more sense at the time than, say, going back to school or networking. Or writing more.
Plus, at these meetings, there was a constant drumbeat of “Don’t return to a job…it will hamper your ability to build a business.” The prevailing wisdom was to hold out at any cost to preserve the time to make your writing or design or filmmaking business work. To an extent, I understood this notion. The words resonated while, at the same time, they tugged at the practical side of my brain.
I didn’t want to short myself and miss out on that damn potential I wasn’t living up to, but I also wanted to pay my bills at any cost first.
There was also a slight undercurrent—when we talked about what we did to earn money that wasn’t exactly in line with the mission of breaking free and doing what we loved—we needed to apologize for, or at least rationalize, why we did it. There was a theory that all work had to feed your soul. But some work simply had to feed my mortgage.
This noise eventually put me at a professional crossroads. Though nothing in my life to that point had led me to believe I was an entrepreneur, I was disillusioned with what had become of the news business, or at least what it had become for me. I wasn’t working anywhere near where I wanted to. I was still broken from the trauma of getting laid off, and as I tried to look ahead at my prospects, they didn’t feel so bright. But I had worked so insanely hard to find another job, the thought of quitting to start a business seemed downright moronic. Still, as the self-help ghostwriting work trickled in, so did the thoughts of spending more time on that line of work.
The Grappa Epiphany
Two years after I was laid off, I was sitting at the bar in a restaurant where my neighbor Doug and I used to meet weekly. It was a full hundred blocks from our Harlem apartments. We jokingly called it our local hangout, as we both dreamed of living much further downtown than we were, though I doubt Doug had a vision board anywhere but in his head. I always ordered the exact same thing: an endive salad and the Bolognese pasta
(I like what I like). And I had a crush on the bartender, Tommy (I like what I like). As such, Tommy would often convince me to buy a more expensive wine than I should have.
One night while waiting for Doug (and drooling over Tommy), I mulled over the horror show that had become my day job and how I could build a business on my own and control my own destiny, rather than wait for someone in some office somewhere to crunch some numbers and lay me off again. Plus, I had been watching the show House of Lies, about a consulting firm, so while I didn’t have an MBA to guide me as I attempted to run a business, I felt I had learned a lot about billing and such, though in a less ruthless and racy manner than theirs.
Regardless of my inexperience or ability to break free, it was officially, glaringly apparent that my job was not for me, and if I had any potential, I was never going to realize it or live up to it there. So that night, at my wannabe local-local, I found myself staring at a row of grappa bottles up on the wall. I don’t even like grappa, but the bottles were fascinating to look at. And there were tons of them—twenty or so—all beautiful odd and varied shapes, glass-and-clear-liquid art. I was mesmerized by how pretty they were, wondering how many varieties of grappa there could be and whether they all tasted the same amount of gross. As I pondered them, I had a strange and unfamiliar feeling of confidence wash over me.
Lost in thought, I metaphorically stumbled across a message in the bottle. Well, one in the form of a wall of grappa.
It read: Bet on you.
Bet on you.
The Universe was speaking. Or was it my long-lost confidence?
Either way, it was strangely loud, and it formulated rather quickly in my brain. Was I going to continue to work at what felt like a dead-end job? Was the anxiety of living on high alert, wondering when the hammer would next come down on my fate at the hands of another human resources
