A Decade of Self-Employment: My Top 10 List

Today marks the 10th anniversary of my last day as an employee.

After eight years at The Courier News in Elgin, Ill. (then a Copley Newspaper), I resigned on March 26, 1999 to pursue a freelance marketing and writing path. Over the past decade, I’ve been most fortunate, with encouragement and all manners of support from my fantastic wife, Bridgett, to be able to maintain my self-employed status.

Things haven’t always worked out as I planned. In fact, it’s usually turned out even better.

Oftentimes, that is because I was willing to listen to the marketplace when it told me that it wasn’t interested in my ideas. Then, the marketplace would add, “But, hey, if you might be able to do XYZ, would you be interested?”

Almost always, whether it’s providing marketing services for a couple looking to adopt a baby girl or helping a restaurant boost its sales, my answer has been, “You bet!”

I have never applied for a job, and I have never seriously thought of doing so. My entrepreneurial streak is too strong, and the wide-ranging work has just been too fun to ever look back.

Here, then, is a Top 10 List of Self-Employment Memories, listed in no particular order, over the past 10 years.

1. From 2000 to 2004, roving around the Midwest for Time magazine in pursuit of interviews with the likes of Tiger Woods, The Smiley Face Bomber’s college buddies and basketball phenom LeBron James (as a high school senior and later during his rookie season in the NBA).

2. Covering a variety of towns and cities for the Chicago Tribune (1999-2005, with a little work thereafter). After the August 2003 birth of my twin children, Zachary and Maggie Rose, I would often type up my reports with one of them sleeping in my lap.

3. Moving my office from the living room to the second bedroom to Panera and, then, in June 2007, to my current “real office” location a few miles from home.

4. Joining the Oak Park-River Forest Chamber of Commerce in October 2005 to promote my personalized story service, Your Front Page.

While the service has not quite captured the public’s imagination (yet), that first Chamber meeting led to a great six-month gig as community relations liaison for Boston Market’s healthier-food prototype experiment in River Forest.

5. In the summer of 2006, joining Oak Park Partners, a chapter of Business Networking International (BNI) whose purpose is to provide client referrals to one another.

The affiliation has surrounded me with top individuals who have not only referred numerous clients to me, but have also inspired me to develop myself professionally.

6. Realizing in late 2006 that, OK, I guess it was all right to call myself a publicist. After more than 20 years as a diehard journalist, this was no simple step. Of course, my entire Inside Edge philosophy revolves around the journalistic information-gathering and story-telling style.

7. Following a suggestion by a former editor, Scott Stone (now a Daily Herald VP) and creating a math literacy seminar for journalists, Go Figure: Making Numbers Count.

That move has sent me all around the country since 2001, training the media (usually at state press association conventions) as I share my passion for telling stories skillfully, ethically and responsibly. My next training is in eight days, at the New York Press Association convention in Saratoga Springs.

8. In October 1999, getting published in Sports Illustrated, the fulfillment of a lifelong dream. The brief item on the Home Run Power Ratio, a baseball statistic I created, provided me with a much-needed confidence boost.

9. In January 2007, catching on with Five Seasons Family Sports Club as the publicist for its Northbrook and Burr Ridge clubs, and immediately helping secure global coverage for a Guinness World Record attempt.

10. Delivering phone books one day in November 1999. I got a bonus for being extra-diligent in securing signatures from recipients!

I have certainly overlooked dozens of other worthy candidates. But there’s always my Top 20 list, due for release on March 26, 2019.

4 thoughts on “A Decade of Self-Employment: My Top 10 List

  1. That’s a terrific list, Matt. I should do the same, even if I’d be a little late (I’m in my 12th year as a self-employed person). And that’s hilarious that you delivered phone books once. Why do I find that funny? Because I did the same thing. I think I was between college semesters — whatever the case, it was one of hardest jobs (even if it was just a few hours) that I’ve ever done. Those phone books are heavy.

  2. Congrats to you, Geoff! You served as the vital connection for the Five Seasons engagement, so you are embedded in this list, big-time, as I mentioned to another great friend, mentor and influence, Joe Takash. A phone book now serves to prop up the laptop on my office desk 🙂

  3. Congrats…. I’m sure this is only the beginning! Can’t wait to see what the next top 10 highlights will be.

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