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Celebrating 30 Years at the Grindstone | by Jeff Steele

29 Jan 2021 1:20 PM | Cynthia Tomusiak (Administrator)

Back in 1991, February 7th fell on a Thursday. That morning, the phone rang in my tiny studio apartment in Lakeview. I likely snatched the receiver before the second ring. In that halcyon age, freelance writing assignments were dispensed by phone.

The voice on the other end of the line announced itself as that of Judy Hevrdejs, then editor of the Chicago Tribune's Tempo Northwest section. Would I be interested in writing an article about an upscale billiards parlor newly opened in Schaumburg?

Would I!

It'd be my very first gig for the World's Greatest Newspaper, even if it were for a regional section read only in the Northwest 'burbs. I asked Judy to forward details asap. Why recall in February 2021 the moments leading up to that assignment 30 years ago this month?

It was the last time I was without work.

In a business notorious for feast-or-famine cycles, I've since always had at least one assignment, and more often a baker's dozen. So, you're asking, how does a guy of very average intelligence and talent – okay, okay, below average – manage to stay consistently employed for three decades in one of earth's most difficult professional fields? Answer: Fairly early on, I stumbled over a few keys to success. I share them with you here.

  • Join the team. Freelance clients don't want to hire antagonists. They want people pulling in the same direction. Convince your editor or client you've got her best interests top of mind, and she's likely to keep you on speed dial.
  • Embrace professionalism. People who hire writers are all too familiar with scribes who simply aren't professional. So show up on time, file clean copy not on deadline but the day before, and act, speak and dress professionally. You'll stand out from the hordes clinging to amateur status.
  • Seek relationships. You've got a choice between building big fees and building relationships. Choose the latter. Freelancing is easier if you've got four or six or 10 great relationships with regular clients or editors who call on you weekly or monthly. Steadily hitting singles and doubles is better than swinging for fences in this game.
  • Always prospect. After I started writing for the Tribune, I figured I had it made. The paper sucked up freelance like the 1990s' leading vacuum, the Oreck®. Then came the Internet, and newspapers' decline. I'd joined IWOC as an insurance policy, and it paid off with clients who called more often as Tribune editors began calling less.
  • Expect no hosannas. Editors and clients aren't going to toss bouquets and shout your praises from rooftops. Doing so would only invite demands for more cash. So look not for love or admiration but steady work from clients. Start earning regularly as a freelancer and you'll merit the greatest respect of all. Your own.

  • That's about all on this 30th anniversary of my last morning that dawned gig-free. But, you ask, what of that very first article that saw me lurking around a pool hall? Click here. Not a very auspicious beginning, I admit. But even Minnesota Fats had to start somewhere.

    - Jeff Steele


    Photo: Jeff Steele with legendary Chicago photographer Art Shay, 

    American Writers Museum, Fall 2017. (Photo credit: Laura Stigler).


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