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Chapter 3

You Can Eat Your Dinner or Drink Your Dinner, But You Can’t Do Both

career

For one hot second, being a little chubby paid off. In fact, it was the impetus for career number two.

My battle with my weight started in my mid-twenties. Once I was introduced to the adult world of working all day, the culinary thrill that is New York City, and traveling and therefore eating out on a corporate card, a never-ending war with the scale began. I was a skinny enough kid, but as an adult, my weight could best be described as up and down like a toilet seat at a party. It probably always will be, try as I may to manage that struggle.

I had done some radical diets over the years, but pre-layoff, around 2006 or 2007, I decided to see a registered dietician on a weekly basis. As part of her process, I would write down my food in a journal each week and track my calories, a startling and painfully revealing exercise.

Did you know a Starbucks Vente skim latte has about 130 calories?

A quarter of an avocado has 100.

Each week, when I had my appointment, I had to show the nutritionist what I had been taking in. She had a lot of funny lines, including, after seeing my notes listing margaritas (plural) with a platter of Mexican food, “You can either eat your dinner or drink your dinner, but you can’t do both.”

Translation: If losing weight when you are on the south side of five foot two means consuming 1350 calories per day, not per meal, then using 500 or, okay, 750 of them on three drinks is problematic.

After hearing that particular line, I told her she should write a book. She told me she didn’t know how to write a book, so I trotted down to Barnes & Noble and bought a book on how to write a non-fiction book proposal to see if I could drag a book out of her. We teamed up, found an agent (Maura, still my agent today), and actually sold the proposal for Urban Skinny!

I still had my job at BusinessWeek at the time, so collaborating on a book was just what kids today call a side hustle.

Though I wrote that book while I was still employed, it wouldn’t hit the shelves for years, after I’d been laid off.

Broken and Breaking Free

After the thirty-one job interviews, seven months into my layoff, I did eventually get some challenging, albeit low-paying, full-time freelance work at the Wall Street Journal, developing and launching their live digital programming. It paid less than half of what I was making when I was laid off at BusinessWeek, but it truly was a blast. The people I worked with were clever, young, and entrepreneurial in a way I’d not experienced.

We were a good team, too—Lauren Goode and Kelly Evans and the crack-of-dawn shift that left us delirious. Despite the criminally early call time, we had some seriously good laughs, once with Kelly over my lack of even a basic understanding of how to make an Excel spreadsheet (I still have no clue), and frequently over an obsession Lauren and I had with some moisturizing hand lotion called Glysomed that you can only buy in Canada.

Five months later, a full year after getting laid off, I was finally offered two full-time, semi-interesting jobs, with benefits, in news. One was a continuation of my gig at the Wall Street Journal, and one involved doing something similar at Reuters.

Both were digital programming, not television per se. Of the two jobs, I had to take the Reuters one. It excited me the least but paid the most. It was a financial necessity, not a choice.

Anti-The Secret? Yes.

Pro-avoiding going broke? Also yes.

While I was grateful, and it was a tremendous relief to finally have the illusion of job stability, as I faced starting a new gig in my humbled and traumatized state, I knew it would be difficult. The simple reality was that I was gun-shy; my confidence had been broken. My half-assed vision board had done nothing to change that. I was visualizing the shit out of life, but mostly I was just worried that, no matter where I worked, I wouldn’t succeed.

Starting a new job is hard under any circumstances. It takes months before you know where the photocopier is, who is nice and who is not, how to change the way you work to fit a different culture than you might have experienced at a previous job. It’s hard to hit your stride at any job, let alone one you took out of desperation.

That job, that I had scrambled to land, that I went on thirty-one job interviews to find, was, at the very least, ill-fitting. Not only was it not what I would have chosen, but it didn’t feel like a productive or positive environment for a million reasons. And that added to my overall anxiety.

I knew five days into it that it was a bad fit. It wasn’t actually television. And, while the people I worked with were unquestionably the most dedicated and fun group of journalists I’d ever had the pleasure of working with, the job itself just was not for me.

Which brings me back to the vision board.

Just as I was deep in the throes of hating my new, not even one-year-into-it job, I joined up with a group of creative and like-minded women who had, by choice or by way of the recession, started working for themselves, all while trying to find their way in the murky waters of a new economy. Some had turned a side gig into a full-time gig, and some had been laid off and were trying to make a go of running their own businesses.

A lot of businesses were made that way. Companies still needed the services, but slashing headcounts was also still needed even as the recession slowed, so consulting—executing tasks once done in-house—became a thing. I’m not sure it was the start of the surge in the gig economy, but I suppose it helped, along with the fact that online services like staffing and bookkeeping and business-card-making 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