I don’t have a job, which means the world has been turned upside down.
Not just mine, but everyone’s.
The last time I was in this spot, we were entering a global pandemic that would shut down daily life for more than a year and reorder almost every aspect of the planet.
Six years later, I can’t surf LinkedIn without seeing a single post that are either:
AI will leave everyone without a job by 2028 and the only recourse anyone has for relevance and survival is to buy a paid subscription to Claude.
AI is all hype and victorious human beings will soon return to a life of harmony in the woods, valleys and deserts from whence we came.
The debate has been so omnipresent I’ve wanted to write about it for the past few weeks. I’ve tried to figure out a rock-solid stance a few times for this newsletter, but have experienced false starts every time I sat down.
Hence no newsletter for the last two weeks.
I’ve finally landed on a spot where I’m comfortable not taking a position on February 27, 2026 for what AI’s full impact will ultimately be.
It does my mental state and job search no favors to buy into all the doomsayers, nor will it improve my chances to not continue adapting to an ever-changing industry by using a powerful toolset never before available.
The truth, as always, lies somewhere in the middle.
If I’m asked how I’ve been able to stay in media for the last 25 years, it’s an easy answer.
I like looking down the road at what’s next and am open to change sooner than others.
When it became clear that the future of news would not always be a physical paper landing in someone’s driveway, I started looking toward blogs and digital media.
When it became easier to distribute audio and video, I took to podcasts and VODs.
When social media algorithms became unpredictable, I took advantage of newsletter audience building tools to make sure my work was being seen.
My last stop at ALLCITY was really a culmination of all those disciplines converging in one spot, a confluence that made it possible for us to take on longstanding Chicago media franchises without a lot of runway.
But now it’s changing again.
And it might be the biggest change yet.
I like to think that digital media is a little more AI-proof than other industries.
There’s no doubt it’s helped us achieve the mission over the last couple of years, whether it’s with automatically generated score graphics for social* or email copy that converts for memberships and merch.
*A previously thankless task in a postgame spot where every second counts.
I’ve also spent some of the last month tinkering with AI ideas I’ve had to make media production more efficient and complete, something I’m sure will remain a part of the job description for the rest of my career.
But as I’ve said, AI can’t show up to a tailgate to share a drink with a fan.
It can’t answer a question from a member in a video Q&A on Discord.
It certainly can’t ever know the feelings every Bears fan felt when DJ Moore reeled in that overtime pass from Caleb Williams a few days before Christmas.
While everyone will soon have tools to automatically flood feeds with the same “Happy 63rd Birthday Michael Jordan” graphics and game summaries — tactics that will help visibility and distribution dramatically — the battles will be won in between with the creativity and adaptability.
So no, I don’t think humans are getting completely phased out.
Last year, I took the time to re-read “Division Street,” the legendary Studs Terkel oral history that compiled the hopes, dreams and fears of Chicagoans from all walks of life.
The occasion was the release of “Division Street Revisited,” a great podcast by Mary Schmich that caught up with the descendants of those profiled in Terkel’s book.
I’d recommend listening to the podcast … but only after reading the book, which came out in 1967 yet contains themes identical to the ones facing us today.
Subject after subject discussed things like wealth inequality, racial, religious and gender discord and a politically divided society.
But what stood out the most to me in 2025 was how much automation came up in almost every conversation and with how much dread each word carried.
Discussed then, it seemed as if there’d be no use for humans by the end of the ‘60s.
Blessed with more than 50 years of hindsight, I knew that wasn’t the case. All of those worries, then, stuck out as reminders for me to navigate the coming AI age with a level head and a plan.
Not every person or neighborhood survived automation and the shipping of jobs overseas, of course. It’s part of the reason we’re in some of our current messes.
But the economy and the population adapted to a new world and reality, just as all of us will have to do going forward, whether we currently have a job or not.
Notes 🙌 🦖
That’s an optimistic essay, because I’m coming off a great week.
I connected with a lot of good people this week.
Confirmed my spot in consideration for a couple of interesting jobs
Was introduced to a fantastic Venezuelan spot by one new friend who treated me to lunch in Wrigleyville.
Attended a cool networking event put on by Kit on Goose Island.
Tonight it’s off to the Field Museum for my second round of Dozin’ With The Dinos, this time with my older daughter and friends from the neighborhood.
Things I’m Currently Enjoying 🥇
• My friend Jerry Brewer’s column on USA Hockey winning gold, then losing the room.
• Pope Bob telling priests to not use ChatGPT when writing sermons.
Like all the muscles in the body, if we do not use them, if we do not move them, they die. The brain needs to be used, so our intelligence must also be exercised a little so as not to lose this capacity.”
• My decluttered home office and a slight furniture rearrangement. It’s something I’ve been putting off for at least a year, but damn if I don’t feel like I have space to breathe again.
Have a great weekend everyone!
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