How freelancing is like sales…or dating

 “It’s only been one day, honey.”

—my girlfriend Victoria, on Jan. 2, 2018

As many or most of you know, I opted to leave my staff newspaper job late last year.  The reasons for this were numerous and perhaps uninteresting to go into here (though I may indeed expound upon this at some later date), and it was an absolute leap into the unknown.  It was the third time in my career that I left a job without another lined up, but unlike my two previous sallies into the void, another full-time job did not avail itself readily.

It was a huge risk, and I basically put all of my chips down.  Nothing ventured, nothing gained.  No guts, no glory.  Fortune favors the bold.  Audentes Fortuna iuvat (thank you Google translate).  I gave up health insurance, a steady income and the access to entertainers and various other cool shit I’d worked on curating over three years as a culture and entertainment editor.

I had to move on.  I was unappreciated, underpaid, insulted and basically doing the jobs of three people for the price of one.  I had a month’s worth of vacation that I was paid out for and some savings.  I took December off to travel to California and spend a leisurely time in New Jersey for Christmas with my family and girlfriend and friends and loved ones.

Then the bills started piling up as my savings dwindled.  The District of Columbia decreed I did not meet the minimum standard for unemployment compensation.  In short, I couldn’t afford to just loaf around on the couch all day catching up on “Game of Thrones” (which I swear I’ll get to at some point, Chris). 

Sink, swim or weep. 

I write now as the first month of 2018 has come and gone.  It’s the first month since June 2016 that I haven’t been on an airplane, although I have in fact been to the airport many times in January to pick up the lost luggage stuck at the Delta counter as one of my side jobs.  For those who don’t know me well, and have seen photos and Facebook posts of me traveling the world over, it might seem ostensibly that I have a perfect life.  Actually, I cannot deny that I’ve been privileged to do some really amazing things in my nearly four decades on this planet, much of it thanks to being a member of the press corps.  I could have been content to be a copy editor on the night desk of a Top 10 market newspaper with a “side job” as the Lifestyle editor.  But I wanted more.  Ambition has always been my albatross and my north star.  No rest when there’s more to be done. 

That said, I have done pretty much every menial job you can imagine over the years—and I say this to illustrate that in January 2018, I’ve had to put back on my hustling cap to get whatever income I can while simultaneously chasing the ephemera of freelance writing.  I gave myself December off with the vow that come January, I’d hit it hard, send out tons of resumes and try my damndest to get articles published in as many outlets as possible.

While, if not paying the bills, bringing in at least a little bit to eat and help Victoria with the rent and groceries.  (That she believes in me is a miracle, and that she is patient with the intermittent remuneration is once again proves she is the greatest woman in the world.)  Thirty-one days hath January, and in the past month I’ve hit it day in and day out, giving as little shrift as possible to self-pity and angst that I’m on the edge of 40 and more or less in the exact same spot I was at at ages 23, 24, 25, 27, 32, 33, 34 and 35. 

I’ll admit, I thought I’d be farther along by now.  Maybe with an Oscar or two or a book published.  Maybe on talk shows.  Or at least maybe, just maybe, not being once again in the gig economy.

But it’s OK.  I can do it.  In the past 31 days I’ve driven around once again delivering people’s lunches and dinners for DoorDash and Postmates (whom I stopped driving for in 2016 when they only revealed the commission after the job was completed, but hey, times are tough), gotten back on the church singing circuit, worked a daylong gig interviewing people at the National Archives courtesy of an old buddy and, thankfully, gotten in a few bylines.

I’m gonna pause here to say that for anyone who wants to be a writer or thinks “gee, I got stuff to say, I can do this, why can’t I make it as a scribe?” let me be the first to dissuade you against any notions of easiness.  In the past month I have sent out hundreds of queries to editors seeking to get into their stable of writers.  Fortunately, thanks to persistence and luck and a rather hefty backlog of bylines from my Times portfolio, at least a few of them were willing to give me the time of day.  In January I got two bylines for a subsidiary of the Los Angeles Times with more to come, as well as a few other publications that have said yes, they’ll take me.

But being a freelance writer in the 21st century is not what it once was.  I recall the glory days (they’ll pass you by) of $1 per word or more.  Now I’m lucky if I get $150 per article.  Some still will give you a byline “for credit” or building up your portfolio.  It’s fortunate that writing gives me a thrill, and more or less during my Times days I was basically an unpaid freelancer.  There’s nothing more thrilling and invigorating than when you find the lede and when you discover an in and a way to make what is interesting to you not only palatable but exciting to an audience.  Martin Scorsese once said “Your job is to get your audience to care about your obsessions.” 

One of the final interviews I conducted as the entertainment editor of The Washington Times was with the great Aaron Sorkin, whose directorial debut, “Molly’s Game,” is still making the awards circuit.  It’s a fine line, I’ve found, between fawning over an interview subject while also bringing in the atypical questions.  As a writer, I can’t help but worship at the altar of Sorkin’s brilliance, but as a professional journalist, when I got to sit down with him in a hotel conference room in DC back in November (with another journo, so we had to take turns on questions), I found I had to ask the “right” questions.  I could have inquired of his writing process for hours, and maybe when I was in my twenties I would have fawned over his success and his awards.  But I found, over the course of several years on the celeb interview circuit, that it was best to approach my subjects—even those whom I came into wide-eyed—with the right combination of admiration and inquisition.  (Sure, I had nerdy questions about who “asked” William Sadler to do his kata naked in “Die Hard 2,” but all of these I leavened with inquiries about the craft.)

So back to Aaron Sorkin.  I got in questions about shooting in Washington thanks to the film adaptation of “A Few Good Men” and if Paddy Chayevsky was one of his influences (it was!), but towards the end of our chat, he gave I believe the single greatest bromide about writing in a succinct axiom that bears repeating:

“When I’m writing, I don’t try to get a show of hands to see what everyone wants and then try to give it to them. I write what I like, I write what I think my friends would like, I write what I think my father would like, and then I keep my fingers crossed that enough other people will like it that I can keep doing it.”

This is an Oscar and Emmy winner basically saying he writes to please himself, his friends and his pop.  It just so happens that his work has had the fortune to be recognized by the greater public and his colleagues.  Oh, and millions of dollars.

But back to earth.  I may fancy myself a writer—and I do—but I find in Mr. Sorkin’s humble assertions an object lesson: Don’t write like you’re out for awards and fame.  Write because you must and you have no other choice.

It’s nice to get paid to write, I assure you.  And I’m fortunate that at least a few outlets are giving me a shot at it, even if the pay is not what it once was.  But I’ve also found that, inasmuch as the byline is the reward, the chase can also be the thrill.

Remember “Wall Street,” that ‘80s flick with Charlie Sheen and Michael Douglas where Gordon Gekko basically says it’s not about what he does with his money but more that he “wins”?  On a far lesser scale, writing as a freelancer is similar: You pitch and pitch and hope someone bites.  You make a “sale.” 

This is just like dating.  Now, I’m in a loving, happy relationship, the best of my life, but I wasn’t always a man off the market.  I remember well my time “on the scene.”  I was using three different apps to “meet” people.  Occasionally you’d meet someone in person.  And of all those in-person meetups, some would end successfully.

It’s about the game.  Just like freelancing.  Pitch, pitch, pitch until someone—or more than one someones—says yes, we’ll pay you for your words, kid.  When I drive around now as a delivery boy, I use DoorDash, Postmates and Roadie simultaneously.  Jobs come in and I grab them or let them pass by.  The more I work, the more I make.  It’s a numbers game.

You hear sales guys talk about chasing the high.  When I was doing standup comedy, you heard about comics talking about chasing those laughs.  I remember the best audience I ever had, who were eating up my jokes like they were cocaine candy.  It was never that good again (truth be told, I wasn’t that good anyway), but I always hoped it would be.  That’s the little bit of positive reinforcement that keeps you going: in dating, in sales, in comedy, in the gig economy.

There’s one more pile of gold just over the hills.

But in my current “occupation,” it’s also the way to stay afloat.  Because, invariably, then comes the pitfall.  Earlier this week I took my car into the shop for some routine maintenance, only to discover that my Scion tC needed a ton of work—so much, in fact, that it would cost me more than I made freelancing and hustling the entire month of January.  (I’ll spare you the numbers because it’s both uncouth to discuss and because they’ll make me cry.)

So why do it?  Why keep at the game?  Why not go back to being a full-timer in Corporerica?  Because, frankly, I like it.  Because it’s fun.  Because it’s adventurous.  And, most of all, because I’m a writer.  This is what I do.  I have things to say and stories to tell and the lives and projects of the famous to distill into 1,000 words or less.  I could be selling insurance or back being an office drone.  I could be struggling less.  I could be less in the red.  

It’s fun chasing the “win,” just like in dating or in life.  The world will not come to you.  I’d love for it to be not so and for fortune and success to fall into my lap.  But I know better. 

And so I continue on.  Through struggles and trials and tribulations and setbacks and low bank accounts and rejections and, more often, hearing nothing at all after hundreds of inquiries.  Don’t get into this business if you can’t take rejection, McFly.  Do it because you love it.

Persistence is key.  In life, in love, in the professional world.  Don’t give up and keep going.  Allow for epic self-pity but then toss the drink aside and move on.  The world needs good stories and great journalism more than ever now.  People want to buy it; I want to supply it.

I’ve always said I’m the world’s worst salesman.  I can’t sell anything I don’t believe in and wouldn’t presume to push it upon you.  I was the world’s most insecure teenager and twentysomething, but finally in my thirties I found a product I could believe in: myself.  I’ll sell the shit out of it and be the professional writer editors dream of.  I was on the other side of that table as an editor and now I’m here selling.  But I wouldn’t presuppose to sell you anything you wouldn’t want.  I’ll only bring the gold.  I’ll only bring a good job. 

I bring only the stories that need to be told.  Fuck all the rest. 

I am a writer.  This is my gift I share with you.