It started on a bus. I was killing three hours surfing across BlueSky and following interesting links. One landed me on an article in the Marginalia about a letter from Sol LeWitt (an artist who has always intrigued me) to Eva Hesse, the TL;DR of that letter was if you want to make art, you have to stop overthinking it, and “just DO.” I could write another article about how to apply LeWitt’s advice to the job search — but I’ll save that for another day. It was a note at the very bottom of the article that led me to another about Brian Eno’s “oblique strategies” for overcoming creative block.
I discovered Brian Eno’s music in high school. I may have even written a paper about musique concrete and the origins of ambient electronica in college. I think I may have even encountered his oblique strategies but long ago forgot about them.
Hurtling down I5 on that bus, reading about Eno’s Oblique Strategies — the card deck he and Peter Schmidt built in the 1970s to break creative gridlock in the studio — I had an idea.
What if I created Oblique Strategies for the Job Search?
Job seekers hit the same wall. The motion-not-action version of a stalled search is brutal in its sameness: search for a job, apply for a job, search for a job, apply for a job. Nothing lands. Nobody calls back. A job seeker can get stalled, hitting refresh on a job board, or an email in box. Similar to the way an artist might stare at a blank page, jot a few words, or notes, then delete, and start over. Eno and Schmidt built a set of prompts to knock creatives out of that pattern. To come at the problem sideways. Oblique Strategies.
I did some more searching and found a few websites with the original Oblique Strategies prompts. While some prompts felt applicable to the job seeker, most did not.
So I decided to build a set of prompts.
I started with Claude, feeding it context and asking: what would oblique strategies look like for a stalled career search? We landed on around 35 cards. Then the project sat — that stretch of May and June was swallowed up by the end of the academic year. It wasn’t until I was traveling again, this time on a plane, that I picked it up again.
Once again, using Claude, I developed a PRD, made some edits to it after a quick batch and forth. From there I went to Lovable and shared the PRD describing what I wanted: a site that serves up three cards, no clutter — pick one strategy, decide on an action to take within 24 hours. That’s the whole mechanic. After a little trouble shooting Lovable built a working version. I quickly realized there was no easy way to add, edit, or remove strategies. So I pushed for a second pass: a login authenticated interface where I could add and edit strategies myself instead of being locked into the original set.
That’s the web app now — Oblique Strategies for The Job Search. I’ve shared it with a few of my students, and some other career coaches, and the response has been great.
Often, to break out of a rut in the career search, you just need a little nudge from the side to inspire you.
Check out Oblique Strategies for the Job Search, and let me know what you think!