You won’t find my name anymore on the list of IWOC members. After a dozen years of freelancing and IWOC (including a couple of terms as president), and about 30 years in newspapers before that, I have decided to retire. This won’t be a semi-retirement of doing a few projects here and there to keep my hand in. It’s walking away from everything all at once. 

You see, I reached the point where I want all of my time to be my own. This past spring my wife and I took a bird-watching trip to the border country of southeastern Arizona, someplace neither of us had ever visited. Of course I had a deadline overlapping the trip, had to ask for flexibility from an editor, had to push to get ahead before we left, and had to push to finish the assignment when we returned. I decided I’d had enough of jamming my pleasures into the spaces between work. In addition, my journalism work has become more difficult in the last few years. People aren’t as cooperative — when they bother responding to interview requests at all. I don’t know why that is, and while I could speculate about the reasons, ultimately reasons don’t matter. Only the effect on my work matters.

I will miss IWOC very much. It was invaluable in helping me master the mechanics of freelancing, but the greatest benefit was finding a group of friendly, helpful, and supportive people, and it is all of you that I will particularly miss. I don’t recognize as many member names as I used to, but that’s good because organizations need to change if they are to survive. IWOC especially needs to do that as writers face the age of artificial intelligence (as true a moniker as it could be since what it produces has little to do with actual intelligence) and business “thought leaders” (a term much like “artificial intelligence”) who see it as an easy way to generate their “content” (meaning clusters of words that have the appearance of being substantive).

I found IWOC through a friend who worked at a Sun-Times suburban newspaper and became one of the many casualties of the post-recession newspaper economy. She saw an ad for a freelance bootcamp by this Chicago writers organization, and she wanted to go but not alone. So I took a day off from my newspaper job, and we went. What I found was people who had made a successful living from freelance writing for years. Not too long after that, when the idiocy at my corporation grew beyond my tolerance, I remembered IWOC and thought, “If they can do it, so can I.” 

I’ll miss trips downtown for IWOC meetings, too, because downtown is downtown and always stimulating and interesting. I haven’t attended in person recently because, pandemic aside, I moved from southeastern Wisconsin to Madison where my wife has a job with an actual office. (I was walking to the train station with George Becht one night soon after joining IWOC, and he told me that after a few years of freelancing I wouldn’t want to return to an office job. He was right.) Reaching downtown Chicago is now a minor expedition — driving to Milwaukee to catch Amtrak to Union Station — instead of an easy ride on the Metra North Line. 

You may be curious to know what my retirement plans are, other than watching birds. Well, my plan is to figure out tomorrow when tomorrow arrives. It’s another lesson learned from freelancing: adaptability. If something doesn’t work, no big deal; you do something else. It’s time for me to find something else. 

I hope you all fare well. 

-- David Steinkraus