Dr. Work-love, or How I Learned to Stop Worrying and Love My Job

When my wife and I decided to venture to the Bay Area for six months at the end of 2014, it was far from an impulsive decision. We were both in need of a work-life-balance change, having both lived in New York City since the early aughts; and put off a vacation together for the previous year. The latter was due to the fact that I’d quit my job to become a full-time freelance writer and editor in September 2013, and was far from making a decent enough wage to take an unpaid leave of absence. Swapping coasts seemed like a win-win situation: We could work remotely during the week; and on the weekends, exploit California’s hiking trails, beaches, dog parks, and campgrounds. Not to mention all that great wine and food.

Long before I gave my two-weeks notice to my previous employer, my wife and I had attempted to circumnavigate what her one steady paycheck and my bunch of random ones, spread out over 12 months, looked like on paper. We discussed the sacrifices we’d need to make, financially; and how much money I should be pulling in each month for rent, groceries, and other couples expenses. Needless to say, it was a daunting task. Whereas I’d been earning a highly competitive salary at my last official job, it was clear that once I made the leap to freelance, it’d be months before money would start flowing in (if at all). So my wife drew up a “contract” in Google docs -- a series of promises, and an exit plan, were my business to fail -- and I agreed to all the terms. I closed my eyes, plugged my nose, and jumped into the deep end.

As a full-time freelancer, I was back to eking out a living like the 24-year-old me, who’d shown up in New York City willing to do just about anything to become a professional writer. Two unpaid internships, 10 years of media jobs, and a smattering of part-time freelance writing gigs under my belt, I’d finally been able to make my dream a reality. I didn’t have some ambiguous title dreamed up by an HR rep: I was now running and directing the show, all success achieved under my watchful eye. Sure, money was constantly on my mind, but it came second to the thrill of running my own word- and thought-based business. I also found that with the absence of a commute and an office environment, I immediately felt better. Gone was the anxiety inducing morning rush to get to an office; as well as the daily awkward interactions with half-asleep subway-goers, co-workers, and direct-reports. I was free from toxic office politics, whispers about job security, and that nagging voice inside my head, always wondering how much more everybody else was making than I was. All I had to do was open up a Google spreadsheet, and there it was in plain view.

By the last day of January, my wife and I had sublet our Brooklyn apartment; mailed two bags full of clothing and shoes to our first Airbnb in Berkeley; crammed our 1997 Honda Accord full of everything else -- including our puppy, Es -- and started driving westward. (I’ll never forget: The day we left Greenpoint, it was bitterly cold, and I’d walked Es to the corner to do his business. That’s when I’d noticed a giant fire along the Williamsburg side of the East River, a tangle of firetrucks and other emergency vehicles less than a mile from our place. I snapped an Instagram picture of it. Brooklyn was literally burning as we were leaving.)
For the next 4.5 days, my wife and I shared driving duties pretty much all day, checking in to a series of mediocre La Quinta Inns in strange, stripmall-friendly cities. We took a southerly route to avoid winter weather: Brooklyn to Indiana - Indiana to Oklahoma City - Oklahoma City to Bakersfield (California!) - and Bakersfield to Berkeley. Although we hit some wintery mix in the Chicago area, we basically avoided Mother Nature’s fury for the entire cross-country trip. All inclement weather aside, that car ride was a grueling test of mind, body, and soul; most of it was accomplished in a state of perpetual ennui, each of us hoping that during the longest stretches of highway, the pop country radio station wouldn’t fizzle out into static (neither of us is a big country music fan, but often, Alan Jackson and friends were the only tunes pumping through our ’90s car stereo). When we finally arrived in Berkeley, we were equal parts ecstatic and exhausted -- but immediately had to unpack and set up temporary shop in our small rental house. This was only the first of three Airbnbs. The next place was in a ritzy, hillside neighborhood called Montclair in Oakland, where we spent the entire month of March. Our 200 square-foot, sub-garage-level apartment -- with a motel-sized fridge, hot-plate in place of a stovetop, square of fabric for a bathroom door, closet-like shower stall, and spotty Internet service -- weighed heavily on our psyche. Although our poor Honda Accord did her best to shuttle us over all the speed-humps and around the twists and turns to get to our aerie on Pinehaven Road in Montclair, she finally sprung a leak in her underside -- something to do with the catalytic converter -- and began growling and coughing. We wouldn’t land our costly trade-in until we moved into our third apartment, a hippie pad on the Oakland/Emeryville border, where I’m sitting writing (and editing) this right now.

What I’ve left out of the above paragraph is the stretch of time when my freelance business went belly up. I must’ve sent off hundreds of pitches to editors between when we touched down in Berkeley and by the time we arrived on Ocean Avenue in Oakland (our third place) and literally got zero new gigs. All rejections or non-answers. Despite living in California’s near-rainless, cusp-of-summertime conditions -- 65-75 degrees, blue skies, sunny, happy/chill people everywhere -- I was at my darkest, mentally. I would sit for hours in front of my HD monitor, with nothing to write about and no new ideas springing into my head. Was this really the end? I kept telling myself, peppered with a bunch of F-bombs. I started to obsessively troll the job pages on Mediabistro and Indeed -- like a stiff shot of Jameson and its Heineken chaser -- using broad search terms like “freelance,” “writer,” and “editor” to look for the perfect escape from the freelance doldrums: a real job.

I finally hit rock bottom on a Skype call with my parents in early March, when my retired English professor father asked me for the umpteenth time if a feature I’d filed right before the previous Thanksgiving had published yet. What my dad and many of my non-writer friends don’t understand is that print publications often work on incredibly long lead times. So even if I’d endured months of hell to get that feature written on deadline, it might be months -- if not more -- before it hit newsstands. Actually, there was a chance that it might never see the light of day. When writers sign work-for-hire contracts with publications, there’s a lot of legal jargon that explains why your piece might get killed -- i.e. left in editorial limbo, unpublished -- and a “kill fee” paid out that’s a drastic amount less than what you would’ve gotten had your piece made it to print. Most of the (print) publications I write for don’t pay until the piece publishes, too, so often when the check finally arrives in the mail, I’m like, “Oh yeah, that one.” Indeed, the feature hadn’t been published yet, and having not published much more than a few web listicles by the time of that Skype call, something inside me snapped. I went absolutely bonkers with rage. I don’t remember what I shouted at the two stunned people behind my computer screen, but it was completely inappropriate. After I apologized and disconnected, I felt like a total asshole. My wife, who had been standing behind me the entire time, suggested I find someone to talk to. I took her advice.

***

Over the next few weeks, I placed several phone calls to psychologists in the Oakland area, finally landing on a Montclair-based PhD, who was an accomplished author himself and ran a successful practice and consultancy. Let me preface this by saying that one of the most difficult things to do in life is to describe to a perfect stranger on an answering machine why you need mental help. Despite the message I’d left him being an incoherent ramble, he returned my call, and we ended up having a spirited discussion about why I was seeking his advice and what he might be able to offer me. We then set a date to meet, and I soon found myself in the waiting room outside his office. The door opened, and I was offered a firm handshake.

Not surprisingly, as soon as I had a neutral, knowledgeable person to converse with about the tangle of thoughts in my brain -- and the way I was feeling about them on any given week -- the writing gigs began to appear. I was hired to do a piece by Refinery29 and then Esquire.com, both new publications to add to my LinkedIn portfolio. A third publication hired me to write a pair of features; two newbies showed interest in my work; and even Playboy joined in, hiring me to write a piece for its July/August issue. (Since beginning a draft of this piece, I was hired to write yet another feature by a new publication.) Suddenly, all of the seemingly half-baked nonsense that I’d jotted down (and pitched, unsuccessfully) throughout those psychologically poisonous months in Berkeley and Montclair seemed to take on a new form. They were all actually good ideas that had been rendered shit by my dust with the Dark Side.

Which leads me to the point of this piece: I’ve come to believe that every writer should attempt therapy at least once in his or her career. In a conversation with a fellow freelancer in the days before I left for California, we both agreed that inspiration was an indefinable, haphazard “thing,” something that showed up on some days and not on others. On the days when it wasn’t around, it was a slog, a weight on our respective minds, a wall to creativity. Therapy immediately put those weekly trials into perspective, and my therapist offered me a variety of alternative methods to keeping the wellspring of inspiration full. Sure, it wasn’t immediately puppies and rainbows, but the therapeutic input was unequivocally helpful. For example, after several sessions, I was leant a book by ABC News correspondent and anchor Dan Harris called 10% Happier, which has been like reading my own ghost-written autobiography and helped put my career goals into perspective (I’m just finishing it now). It’s like an invisible hand patting me on the back, saying, “It’s OK, dude. Journalists all go through the same shit. Soldier on. Happiness is just around the corner.” I’ve also become interested in Buddhism and meditation, things that I’d dabbled in in the past but never too effectively.

Now if you’re the type of person who worries about the social stigma attached to things like meditation or being “in therapy,” remember that you don’t have to grab a web-aphone like I have here: Keep it to yourself and harness its power behind the closed doors of your office or cubicle or home. In fact, it took me a long time -- years -- before I felt comfortable saying “I’m in therapy” out loud. Sometimes the most difficult subjects to bring up in public are those related to one’s own fallacies, professionally and personally.

To put this all into perspective, I’m going to end by quoting two entrepreneurs I’ve come across in my daily research, who I think best embody why therapy can be such a boon for writers (or any professional, for that matter). The first is music producer Rick Rubin, who is known for his tremendous run of successful albums and work with seemingly incongruous musicians like the Beastie Boys, Slayer, the Avett Brothers, and country legend Johnny Cash. In a podcast hosted by Tim Ferriss (in a steamy barrel sauna of all places), Rubin said that to be a successful entrepreneur and remain successful, one had to find happiness in his or her life. That’s the single most important thing, he said. Sit with that idea for a moment. If you let darkness overtake you -- the Berkeley or Montclair Will, so to speak -- and are in a constant state of pissed-off rage, your work and everything around it will suffer. Now imagine what the opposite looks like. (Oakland: Part Deux.) By nature, some people are happier than others, but there are ways everyone can bring happiness into his or her life more often. Smiling helps. So does regular meditation. For me, my regimen also includes going on adventures with my wife, grabbing a drink or barbecue with my buddies, free-writing, dog-walking, and buying baseball cards. It’s different for everybody.

The second quote is from an English business consultant and entrepreneur, Cindy Gallop, who said in an interview on simpleweb that one-third of being a successful entrepreneur was “the ability to manage your own mind.” Gallop knows quite a bit about this: In 2009, she stood up in front of a TED audience and did a talk on her newly launched sex-based web platform, MakeLoveNotPorn.com, talking nonchalantly about her proclivity for dating younger men and using words that no TED audience had probably ever heard spoken in public before. In that short talk, you can see Gallop’s mind-management skills in full effect. She never once lets demon doubt work its way into her voice or presentation; she’s one with her idea, her concept, and at the end, she calmly exits the stage to a rousing ovation. Public-speaking engagements aren’t the only place where mind-management skills come in handy; you can also be in the middle of an intense meditation session, where clearing your mind is the objective. Effective mind-management skills can even come into play when using that narrative voice in which you’re writing or reporting every day (read Harris’ book for more on this). After all, it’s your mind that’s creating that voice, spilling its contents onto your page or out of your mouth, one word at a time. Wouldn’t it be great if you were in complete control of it?

If you’re lost in a constant state of stream-of-consciousness like I am, I’d like to suggest that therapy can act as a catalyst to bigger and better things. What those things are is ultimately up to you to find out. Certainly, managing your mind and being happier are two tremendous leaps forward. So is 5-10 minutes of meditation every day. Or giving up your seat to a pregnant woman on the subway or any number of other unprompted, kind things you could do throughout a given day. Because, if you end up avoiding stuff like that, you will find yourself on an endless, sisyphean road trip to California, never quite able to enjoy the jacket-less weather.