Why reasonable people make reasonable choices that produce ridiculous outcomes.

I’m Jared Heymann. I write, speak, and generally overthink the hidden forces behind how we work, make decisions, create value, and occasionally get ourselves spectacularly stuck.

I’m interested in what happens one question below the obvious one

Why can being good at your job make it harder to leave?
Why does more freedom sometimes make choosing harder?
Why do smart people follow perfectly reasonable advice that doesn’t work for them?
And why do we keep using what someone can do as evidence of what they should do?

My current obsession is Shouldology, a book about getting your career unstuck by understanding the person underneath the résumé.

Out late 2026

shouldology.com

The book

A howwhy-to guide to getting your career unstuck. Sample chapter, the Should-ictionary, and the mixtape.

Read a chapter

Sessions & keynotes

Speaking

Two sessions built for executive MBA programs, and one for people whose careers were rearranged without their input.

See the sessions

Essays & video

The Almanac

An Overthinker’s Almanac. Systems thinking applied to whatever I couldn’t stop thinking about this week.

Start reading

Huh. Why does that happen?

That question is most of my career. I chased it into a chemistry PhD, a few years teaching, fourteen years running R&D at a company known for bleach and cat litter, an MBA, and a startup I co-founded and eventually had to close.

Somewhere in there I noticed I was giving off considerably more game-show host than scientist, which in Ghostbusters is an insult and in my case turned out to be useful information. I just had it filed in the wrong drawer for about twenty years.

The longer version, including the parts that went badly

The ridiculous stuff is the method

Potatoes. Plywood. A koi pond. Star Trek shirt colors. Complicated ideas are easier to carry around when you can picture them, and a scene we have both watched gives us something to examine together without pretending that one person’s success story is a set of instructions. The joke helps the idea stick. Often it also helps you see it.

I like the playground metaphor, and the coke can / slushy machine was memorable. These are already part of our cohort lexicon.
Jimmy, UT Dallas Executive MBA

UT Dallas Executive MBA orientation, August 2026. Fifteen of 23 participants responded. Fourteen rated the sessions 4 or 5 out of 5 and expected to use what they learned. Eleven said they would recommend it to future cohorts at a 9 or 10. One said neither session added value, and that one stays on the page. Aiming at a specific room means missing the people it was not for. A session everybody likes equally is usually a session that said nothing. Full results available to any program considering a booking.

Jared Heymann speaking on stage — On stage, mid-sentence, gesturing at something.