Deep Thoughts on 'Deep Thoughts with Jack Handey'
warning: this is a very, very deep post.
“People think it would be fun to be a bird because you could fly. But they forget the negative side, which is the preening.”
I was (still am?) a bit of an odd child. I was obsessed with rock and roll from the 60’s and 70’s and somehow got hold of a karaoke machine to record songs, then dub over my radio host voice between the songs. It was called “talk show runnels.” I wish I were making this up, but I have one of the tapes somewhere up in my attic. One day when Apple creates a cassette tape-to-lightning port I’ll provide the receipts.
My friends and I were inseparable, creative and a bit.. against the grain. And most of us still are, which I am grateful for every day. We didn’t play a ton of video games, and we didn’t have the money to buy the hottest beanie baby out. Instead, we jerry-rigged some contraption I found at Radio Shack in the early 2000’s and made recorded prank calls to honor our hero, Roy D. Mercer. Our hard rules: no actual food orders and no “bad words.”
On weekends, we scavenged local garage sales (and sometimes dumpsters!) to build “trash art.” My best friend’s dad was not too happy about the slightly-used computer chair from the early 80’s that was further collecting dust in his garage.. so sorry, Mr. Lloyd. We even managed to acquire some scrap metal from a family member which we fabricated into a fully functional trailer that could be pulled behind my mountain bike. It fit a lawn mower, a weed-eater, an edger and a can of gas. With access to the library’s printer for flyers, basic grassroots marketing efforts, knocking on strangers’ doors, this “neighborhood lawn business on bikes” helped fund said contraption for prank calls, the karaoke machine and even a few physical copies of SNL skits we were inevitably too young to watch or comprehend.
That brings me to another hero of ours at the time: Jack Handey. What 12 year old at the time even cared to watch these, let alone found the skits funny? Well, we did and.. it kind of explains a lot in how I try to show up each day. ‘Deep Thoughts with Jack Handey’ was one of my favorite recurring bits. Simple, silly, timeless.. though I am not sure the slow, introspective tone would trend on tiktok today.
(If you’re still with me, I think this will make sense)
“Deep Thoughts on a Career Pivot, a mid-life crisis and life, in general... in 2026” doesn’t exactly have a flashy name, but here we are.
This is the first time since graduating from college back in... checks watch.. a long time ago... that I am purposely and selectively searching for my next act. In 2010, I was the first person from my family to graduate college. I didn’t have a job or internship lined up. I had minimal responsibilities. But I had been to ACL a few times in Austin and loved the city.. so I packed up and moved there. In retrospect, it was an uncertain time, a bit reckless, and perfect.
I found an internship working in Minor League Baseball, as marketing & promo manager by day, and stadium emcee + general wild man, “Ballpark Rob,” by night. It was a dream job and the perfect place to start my career. I was featured on the local news as “Rain Dancer” in the brutal summer drought. I was even one of the “celebrity judges” of a local news station’s ‘Annual Belly Flop Competition’. AND my starting salary was just a tad more than I made tugging around a lawnmower on a 10 speed bike a few years prior.
Searching for purpose, a career, a safe place to build feels a bit heavier in 2026. We live in a time where accessibility to incredible tools is a default. Life-changing product releases are buried behind wild world news stories. There are so many ways to go about finding your calling, your pivot, your meaning, and so little time. Strike that, reverse it. Am I qualified, am I overqualified? Am I fluent in Claude Code, Spanish and water cooler talk? Just how much value have I provided to the relentlessly underserved shareholders? Finding a next step at mid-life doesn’t feel logical. It’s actually kind of a shit show and it’s also kind of exciting.
“Slow news day in Austin… Let’s get that rain dancer on Nightbeat.”
I tend to minimize my accomplishments with self-deprecating humor. I’d rather let my work, my background, my instinct speak for itself. I’ve never been one to pretend that I have all the answers, nor do I believe I’m always right. My opinion or viewpoint is a single data point, which can be valid.. and it could not be. I think it’s more a snapshot in time, of lived experiences, career arc, trauma, education and love.
That sometimes sounds better on paper, or with a friend you’ve known your whole life, your closest coworker, or even with your favorite ai tool-turned-brainstorm-partner-turned- therapist/life coach.
But in today’s world, where we are competing with thousands of applicants for a lateral move, or slogging through linkedin feeds full of self-absorbed slop.. can confidence, humility and truthfulness coexist?
I think they can. Or at least in my head at this particular snapshot in time they can. That is sometimes easier said than done, but I am choosing to believe that.
It would be selfish to not share my deepest, darkest thoughts on career pivots in 2026, the year of our Lord. Here are some thoughts on mid-life-identity-crisis-on-the-precipice-of-an-ai-renaissance after drinking way too much coffee this morning.
Ten Deep Thoughts from this Thursday morning, June 4th after ~200 mg of caffeine:
It is possible to have 10-15 years of experience in generative AI if your default measurement of time is in dog years.
The difference between your current “dream job” and recent “job dream” is a good sign on if you should be looking or not.
If your team’s culture says “we are a family here,” your “real family’s culture” is probably missing an important teammate. Or, you are dining at the Olive Garden.
How does AI even know the keyboard combination to create an em dash — yet can’t identify which one of those objects are a crosswalk
Instead of doing actual work in AI, I simply burn all of my tokens being over-complimentary of its human-like nature, its all-encompassing knowledge and general, perfect omnipresence. It’s a small investment that will pay dividends when they’re finally able to identify the crosswalk, and subsequently take over.
“You are what you eat” became “you are what you tweet,” which eventually became X, and now is just a graveyard feed of content slop and political chaos.
Did anyone even check in with shareholders to confirm they are in fact feeling valued?
When asked to explain the “gap” in my cv, sharing my experience shopping at the Gap in 2026 has not landed well on multiple levels.
Why is it acceptable for a boss to schedule a meeting over your lunch, but when you schedule a lunch over your boss’ meeting, you get a PIP?
Do you ever think about that one engineer at copilot or claude that is reading through you and your ai bot’s chat history? I hope they are ok.
These “deep thoughts” are just a small sample-size of what my brain is trying to comprehend on this journey to finding my next perfect fit. If you are in the same shoes, have gone through something similar or just want to connect.. let’s chat.
Also, I’ve had fun building a little beta version of a chatbot me - ROB-ot - in an attempt to learn new tools and further build out AI fluency. But with a bit of my personality, authenticity and general shenanigans. You can test it at the bottom-right of this page! It’s better on desktop right now and I’ll share more when I get the mobile gremlins worked out.
God bless you, friends. Hang in there. Don’t forget to smile because you have a nice smile and someone needs to see it.
-rob (ot?)