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 person, worth it? We hadn’t come out of the recession fully. Jobs and projects were still going away. Things did not feel secure.
Betting on myself meant taking my fate into my own hands. Jump, and all the stuff on my new and improved vision board would form.
Would it, though?
Writing other people’s books had potential, but it was uncertain. But my job was, too. Somewhere in my logic, I considered that, if a single woman with only one mouth to feed couldn’t do it, who could? Strangely, at a time when my confidence tank was depleted and fueling me with only fumes, I had the conviction buried somewhere inside to quit and start my own business.
Sitting by and letting someone else drive was, apparently, not my thing. Reflecting on the machine inside me that turned on when I needed to find a job, I realized that I was a survivor. I was never going down with the ship. If I had learned one thing about myself, that was it.
When I was deep in it, sadly, my job loss seemed like a weakness, and my inability to find a job an indication of my shortcomings. It was only later that I realized all of that was just what was inside my head. Certainly, those thoughts wouldn’t have crossed my mind when witnessing anybody else struggling to find a job.
But, hey, not many of us offer ourselves the same level of dignity and respect we give to others. (I later read that in a self-help book.)
Friends later commented on how impressed they were that I’d tackled that job search like I had, and in a way that they said they would never have been able to. Thinking about those comments, in that moment—both the insanity of it all and the motivation—I decided that I had the strength to cut my losses, and my 401k (gulp), and jump ship to go it alone.
Maybe ego was involved to a certain degree. Maybe I wanted to leave on my own terms. Maybe I could not face being shown the door. Choice is, after all, choice. Maybe being laid off a second time, which was entirely possible, was not how I wanted my story to go. So I rewrote it.
There I was, just two years after a herculean effort to find a job, and I was quitting one. Bold move? Yes. Brave or stupid? Hard to say. Probably both. But once the decision was made, and my parents hesitantly got on board (at least they said they were, but only after telling me that Uncle Burt said it was nearly impossible to make a living as a writer), I did it. Considering the agony of the previous two years and the number of people I knew who had lost work and never quite landed it again, it was a perplexing and audacious move, and I’m sure, to many who had watched me buckle under the pressure of the job search, completely idiotic. But it suddenly felt right—like, the rightest thing. I felt oddly calm in a way I had not previously.
At the very least, I would be in charge of my destiny. No boss or corporation would be the decider in my career. Stephanie, Inc. would call the shots and, as such, I felt confident I would survive. I had learned that much. I was taking my professional destiny into my own hands. As crazy as it was, I knew in my gut it was the right move.
Plus, I had that million-dollar check pinned to my wall, so I was probably going to be good.
Self-Help: Occupational Hazard or Personality Disorder?
Jumping off a cliff and starting my own business writing self-help books for well-known experts meant that it wasn’t just the vision board that got me hooked on finding the fix to all the holes that surely must have existed in my mind, body, and soul. Being obsessed with personal growth and self-help, in fairness, suddenly became my full-time job.
Writing a book for someone is actually writing a book with them. Twenty or more hours of their time is required just to get started—mostly with interviews and talking through their life or their life’s work. It’s intimate in a sense, because they have to open up and trust me with their life story or body of work, their insecurities, and the stories they aren’t certain they want to share.
It gets personal.
An interviewer by trade, I love asking questions. I pride myself on pulling stuff out of them that maybe they didn’t think was important. I often try to make idle chit-chat about seemingly unimportant things, or talk a bit about myself, to spark a conversation unrelated to the specifics of their book. That’s when I can hear how a person talks, their voice, and usually learn more about them than I do when they focus on the topic at hand. In those instances, sometimes, the best stuff comes out—the stuff they wouldn’t have thought important. Sometimes it’s challenging to figure out how to best demonstrate a protocol they may advise in their book, to get it on the page in a way that the masses may best understand. Talking things through helps.
Generally, whenever someone meets with me to write a book, they will tell me the concept of their book in relation to a previous bestseller. The Marie Kondo of love or the Suze Orman of career coaches; the #GirlBoss of whatever or the Phil Knight of blah-blah. In fairness, there is something to be said for banking on previous winners; we see it in movies all the time.
For me, that means a lot of reading and research before I embark on someone’s diet book or career book. If an expert I’m working with offered up a diet plan, I’d do it, measuring food, eating at certain times, and analyzing how I felt along the way. I try to understand how it made me feel, whether something was confusing or simple, so I could best explain it to the reader.
One book I worked on