How I tackled a listicle of essential Chicago bars

Financially, I don't recommend it!

By way of preamble: Unlike almost everything else on this lil Substack, I made this post paid. In a way, it’s a cheeky experiment to try to understand what media consumers consider to be of enough value to pay for. For instance, many of you may rely on the occasional listicle to help you decide where to get a topnotch burger or superb cocktail. More than likely you didn’t have to pay to read that bit of service journalism, but instead found it for free on an online food or lifestyle magazine or blog. Aside from relying on the generalized expertise of their authors, many of these listicles don’t undergo a super rigorous vetting process. Hopefully, the writer visited a handful of the spots mentioned within the past year. Others they included because a PR agency representing the place told them about them, or someone they know and trust vouched for them, or another writer covered them beforehand. Because lists get a lot of clicks and engagement, publications keep churning them out. But writers don’t get paid enough or have sufficient time to put in the work to make them truly valuable, rendering them nearly on par with AI-scraping of existing information. I struggle mightily with this disconnect, so today I wanted to share a blueprint for how we as an industry might (slightly) better tackle this service, based on a recent experience I had. Thanks for supporting me and little stories.

I get a fair number of requests to write clichéd Chicago food and drink listicles. A guide to Italian beef! A roundup of the best hot dogs! A tour of Chicago’s mob-style bars! I said no to all three of these in recent months for the following reasons:

1. At the moment, I have nothing left of value to say about Italian beef, not least for $350;

2. Chicago food writer Dennis Lee wrote THE definitive guide to Chicago hot dogs in 2022. I wouldn’t dare attempt to supplant this unless I had sufficient budget to eat at every damn hot dog stand in the city, full stop;

3. I had just finished a massive, on-the-ground wine guide and was too burnt out to take on another listicle on quick turnaround for too little money.

In October I got an email from a national drinks publication editor to write a listicle summing up Chicago’s 10 essential bars. I politely declined at first, saying that I can’t justify writing such a comprehensive guide without ample time and budget to experience a dozen or more places. (Internally, I screamed: Why on earth would I do my hometown the injustice of so woefully underrepresenting its finest watering holes out of roughly 900 total, many of which I’d never even heard of, let alone darkened their doors?) Do I sound like a broken record on the sorry state of freelance service journalism yet? Good.

The truth is, beyond the aforementioned shortcomings of the listicle genre as a whole, I find these sorts of undertakings exhausting in this era of online media.