This week’s prompt will teach you how to play with AI.
Don't rush to ROI. Creative breakthrough solutions cannot happen until we develop creativity.
Your Prompt
You are my slightly chaotic AI intern.
Give me a mini-project I can complete in under 30 minutes that is:
useful a little ridiculous low stakes designed to make me more comfortable experimenting with AI
For each project include:
1. The goal
2. The exact first prompt to try
3. What skill this is secretly teaching me
Mix business and personal ideas together.
Optimize for curiosity and experimentation, not productivity.
I’m trying to become more adaptable... not more polished.
Against The Grain
When’s the last time you started a hobby and stuck with it... even though you were bad at it for the first six months?
Here’s a challenge we're facing right now...
It’s becoming easier to train a smart 22-year-old to perform a professional service than it is to convince a seasoned professional to try AI at all.
And the gap where that’s okay is closing quickly.
For years, experience compounded. The people with 20 years in the industry had the advantage because they’d seen more patterns, made more mistakes, and developed better judgment.
And we still need those skills.
But AI changed one critical variable: The willingness to be bad at something again.
Not at pickleball. Not at pottery. Inside the very expertise that built your career.
A college graduate expects incompetence. It’s built into the deal. They ask dumb questions, break workflows, test random ideas, and accidentally automate half the marketing department because nobody told them they weren’t supposed to.
A seasoned professional often has the opposite instinct.
They’ve spent 25 years learning how to stop looking inexperienced.
Don’t ask obvious questions. Don’t look uncertain. Don’t fumble publicly. Don’t admit you don’t know.
Professionalism, in many industries, became the art of growing out of appearing ignorant.
Then AI showed up and said: “Cool. Become a beginner again.”
That’s a brutal psychological transition.
Especially for high performers.
Because the resistance usually isn’t technical... it’s identity-based.
If your entire career was built on being “the answer guy,” AI can feel less like a tool and more like a threat to your status.
So instead of experimenting, many experienced professionals do something far more dangerous...
They wait.
Meanwhile, business owners are building accounting departments with three people instead of ten.
College grads are building internal marketing automations with Claude Code and Zapier tutorials.
General ledger platforms are moving into tax prep.
Software companies are finding holes in professional workflows much faster than most firms expected.
Yes, those systems still have problems.
But the holes are getting patched faster than the skeptics are learning the tools.
That’s the part a lot of experienced professionals are underestimating.
The future probably does not belong to “young people.”
It belongs to adaptable people.
One of the biggest mindset shifts inside our firms will be creating environments where experienced people can learn publicly again.
Without demanding ROI. Without expecting perfection on the first iteration. Without treating play like unprofessionalism.
The most valuable employee over the next decade may not be the person who knows the most...
It may be the person with deep judgment who is still willing to look stupid while learning something new.
That combination is terrifyingly powerful.
