It has occurred to me that it might finally be time to write a book or something more longform about my time at Chicagoist. The site launched in 2004 and I joined in 2005, remaining the only constant on the staff masthead (aside from our New York-based leadership) until we were abruptly shuttered in 2017. This writing might never see the pubic light of day, but it seems like an endeavor worth undertaking for a number of reasons.
I imagine there aren't a lot of people out there who managed to be in a leadership position at a single digital media outlet during that period, and even fewer who simultaneously had a full career in the marketing and advertising sector, giving me a unique vantage point into all the changes journalism underwent during that time. And I think I can do it in a mostly positive way that highlights some of the difficulties we encountered without applying blame—which is a nice byproduct of the passage of time and the bigger picture of all that happened coming into clearer focus devoid of the emotions that might have been present at the time.
It also seems like a more compact and focused unit of time to explore, and it might even unlock the ability to write about other periods of my life that have so far stymied me.
Anyhoo, just putting these thoughts here in hopes that sharing them publicly will hold me accountable and actually spur me to accomplish this task.
We'll see if it works, but I thank you for reading this far even if it doesn't.
