How My Crappy Day Jobs Made Me a High-Earning Freelancer

Ever worked a day job you couldn’t stand?

Me, too.

For years, I worked as a legal secretary for movie studios and talent agents. Before that, I scooped ice cream, worked at McDonald’s, and even sold aluminum patio awnings over the phone.

Every minute I worked these mind-deadening jobs, I thought it was a complete waste of time. I felt like I was using about three brain cells.

Most importantly, I was making no progress on my dream of writing for a living!

These jobs were just a necessary evil, a way to pay bills. Or so I thought.

Once I became a freelancer and started building my business, I realized I had learned a lot from those supposedly time-killing day jobs. I’d acquired useful abilities that helped me build a six-figure freelancing career.

Here are the skills I gained working day jobs that help me as a freelancer today:

How to cope with difficult people.

Talent agents are not known for their sweet personalities — one agent famously used to call his assistant and then, before he could reach the desk, toss his files on the floor and exclaim, “That’s for you!”

Being around raging jerks all day helped me learn to keep my cool, smile, crack a joke even, and in any case never let them rattle me. Later, when I got assignments to interview some prickly CEOs of major corporations as a freelance writer, I wasn’t intimidated by them.

How to warm people up.

If you can sell aluminum awnings to people over the phone, you can pretty much talk anyone into telling you anything. That phone-sales job helped me hone my people skills and learn how to quickly create rapport with nearly anyone. This skill became invaluable when I did investigative reporting and needed to convince people to talk to me, even if they really didn’t want to.

That ability helped me land some top-dollar assignments, including a contract to write my first print book, for which I needed to track down many big-company founders and get them to open up.

How to meet deadlines.

When I worked as a legal secretary at MGM, we wrote contracts for auditioning TV actors. If the actor got cast in a show, we’d have to track their contract and make sure the studio renewed the contract each year, before the option expired. Otherwise, the actor — now a big TV star — would renegotiate for vastly more money.

A missed deadline could get you fired and cost the studio millions. After developing the discipline as a legal secretary to never miss deadlines, it was no problem for me to make article deadlines I was assigned as a freelancer.

How to talk to celebrities.

At one point, I worked at the William Morris Agency (now William Morris Endeavor). Stars and famous movie directors were everywhere, constantly coming in for meetings. You’d go out to the lunch truck and find yourself in line with someone from the hot TV show of the moment. I spent enough time with famous people to discover they’re human beings, just like me.

When I started my first freelance business — as a script typist — I once got a gig to go to Barbra Streisand’s house in Malibu and work on an event script she was putting together. The fact that I’d worked with celebs before helped me land the gig, and helped me to stay cool and professional around the diva. This led to more lucrative gigs typing scripts for name TV stars and movie directors. Later, as a writer, I would interview celebs for lucrative articles, too.

How to negotiate.

Listening to lawyers hammer out actors’ contracts for hours on end, I realize now, was a terrific learning opportunity for a budding freelancer. Today, I’m completely comfortable negotiating with my clients, where I know many low-earning freelancers who are afraid to make a counter offer and always jump at the first rate they’re offered.

How to set boundaries.

One night when I was making evening phone calls, the owner of the aluminum-awning company came in drunk, and started drooling over me. I was about 16 at the time, and he was my boss. But I peeled him off me and got the heck out of there.

As a freelancer, you’re constantly dealing with prospective clients who’d like to take advantage of you, getting more work out of you than they paid for. I’ve never had trouble drawing the line with them, thanks to my day-job experiences.

Working for others gave me a lot of experience dealing with the business world. And that all paid off once I began running a freelance business of my own.

What lessons have you learned from your day jobs? How have these lessons helped you in your freelance work?

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