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Lessons learned in the dating game also apply to freelance writing

Learn how to apply the rules of dating to your freelance writing career.

Freelance writing is like dating
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Dating and writing tend to breed unattainable visions. We expect passionate kisses during a rainstorm. Instead, we get stilted conversation over slowly congealing appetizers. We think our piece can change the world. Instead, it’s “this isn’t the right fit for us” or “the structure is off” or “can you turn this 2,000-word, multiple-sourced feature into a 750-word listicle?”

For both, the silence – that awful, endless stretch of uncertainty – can crush your self-esteem to dust.

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I spent a healthy portion of my twenties dating. I was spectacularly mediocre – my dad once referred to my travails as 50 First Dates, after the Drew Barrymore-Adam Sandler movie. But what I learned in coffee shops and restaurants has segued nicely into freelancing, where remaining open to joy while protecting yourself against the inevitable emotional crotch-kick is required.

Nearly 12 years into my freelance life, striking that balance remains challenging. I’ve come up with a few rules so my enthusiasm stays strong.


Keep your options open 

It’s OK to have dream publications but not at the expense of your portfolio or your bills. Pinning your hopes on one publication is foolish, especially if the editor ignores you. Find an outlet that cares about you as much as you care about them. If you make writing for Slate or The New Yorker your one goal, you’ll neglect other worthy outlets. Those clips may entice editors at your dream publication to work with you.

Similarly, abandon the notion of “one pitch for one publication.” Each pitch can be tailored for another outlet, ensuring you’re writing instead of waiting for an email that will never arrive.

(As for those unreturned emails, editors are swamped. Answering your eloquent plea can get neglected when they’re proofreading, organizing a staff meeting, writing three blog posts, comforting advertisers, and holding a writer’s hand through rewrites before the issue closes.)


Don’t take rejection to heart

I can’t tell you how many times I had a great time on a date and then that young lady would either vanish or coldly reject me as if I was a telemarketer calling at dinner. It hurt. After the 10th time, I became immune. It is exhausting to star in your own mopey tragedy night after night.

Some outlets will take a chance on you. You may have felt that you did a wonderful job, but the editor may be less enthusiastic. Sometimes there’s a lack of chemistry. For example, I lack a rhythm with regional magazines. Maybe my sensibilities are too broad or my style rubs editors the wrong way. That disagreement does not define my ability as a writer. I do.

Know when to walk away

Rejection runs both ways. Keeping your heart and soul protected from how a client treats you makes it easy to leave if things turn ugly. There’s such a tendency to get enchanted by the attention – I’m getting paid $1 a word! My piece is all over Twitter! – that we forgive editors who use their position as a cudgel. That’s a bad relationship. Anybody who treats you poorly as payment for appearing in their publication provides ample justification to leave.


Play it cool

Should your relationship with an editor sour in the middle of a job, complete the assignment, file your invoice, and move on. If you’re asked to contribute later, politely decline. Repeat if necessary. Eventually, they’ll get the hint and leave you alone.

Maintaining composure on the stinging side of rejection requires restraint mixed with common sense. It is so tempting to bestow a parting shot that can be seen from space. Sometimes an editor’s behavior is so egregious that decorum erodes and glorious, cathartic anger erupts. I have gone nuclear as a last resort. Editors share stories – or post the correspondence on social media as a scarecrow. For rejected pitches, I like to use “Thank you for considering my idea. I’ll try again in the future.” Then I commence bitching about the injustice with a friend who doesn’t dictate my future employment.

If you end up striking a rapport with an editor, remember that desperation and enthusiasm are closely related. It’s a major advantage when an editor follows you on social media or urges you to keep pitching. (I’ve gotten more than a few gigs those ways.) Since she’s following you for a previously established reason, holster the pithy comments to her vacation photos. Take it from someone who played that role for far too long: the person who tries too hard is a recurring character in bad first dates – and the writer who elicits eye rolls when their name appears in an editor’s inbox.


Have friends and family play matchmaker

When I was single, my friends occasionally set me up on dates with their friends. I was thrilled for the help with my love life then. And I’m thrilled for the help with my professional life now.

I wrote a newsletter for my father-in-law’s company for a few years. My best friend set me up with editing gigs that brought in more than $11,000 over two years. I occasionally edit copy for the mother of my wife’s former piano student.

Parents remain the best PR agents. Several years ago, my dad visited a friend who casually mentioned that his neighbor wrote for the New York Times’ sports section. My dad immediately turned into my agent. “Wait, your neighbor writes for the Times? What’s his name? Do you think he could help Peter?”


Dad’s curiosity has led to four bylines in a dream publication.

Be confident…enough to step back

My brother provided a keen lesson during a dating dry spell: “Nobody wants to buy from a salesman who doesn’t believe in his own product.” You want to exude confidence whether you’re pitching a feature or asking someone out for dinner. I met my wife after I reached the point where I knew I would be great on my own.

Being relaxed allowed me to demystify dating. Nothing is a be-all, end-all, including writing. When you lower the intensity, you see avenues previously obscured by the mania of the single-minded. Practice pragmatism when you’re looking for the gig, then pour your passion into the writing.



Regular contributor Pete Croatto (Twitter: @PeteCroatto) is working on his first book for Atria Books, a division of Simon & Schuster.