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💯 "I use AI every day but I'm still winging it”

42% of you said AI still feels harder than it should. Here are 3 habits that might help.

Author

Max Haining
September 20, 2026

Happy Sunday! 👋

Last week I gave you AI doom. This week, I thought I’d give you (and myself) a break.

I’ve been reading through your replies and poll responses lately and the same AI frustrations keep showing up. Not existential “will AI replace humanity” frustrations but much more normal ones like:

So I went looking for habits that might relieve some of that friction. Just three things you can stress-test on your own work this week and tell me if any of them helped.

WHAT’S INSIDE 👇

✅ The 3× rule for spotting work worth testing with AI
✅ A better way to teach AI what “good” looks like
✅ The Vacation Test for turning good chats into reusable workflows

+ I put all three prompts into a free PDF you can keep at the end.

THE FUTURE OF WORK WITH AI

I think this is the bit that gets lost when every week brings another model, agent, or terrifying headline. The future of work doesn’t arrive all at once. Mostly, it looks like normal people noticing one annoying bit of their job, trying something different and getting a little better at it. Here are three examples I liked:

1. Use the 3× rule to find the right task

Alice Browne from Brainlabs is a pretty good example of what an AI-active People leader looks like right now. She’s been publicly sharing how she uses AI in her own work while Brainlabs rolls Claude across its ~1,000-person agency.

And the company has a brilliantly simple rule for figuring out what’s worth using AI for:

If you’ve done something more than 3 times, try to automate it.

You don’t need 400 skills but you can pick one thing you’ve already done three times, then paste:

I do this task repeatedly: [TASK].

Here’s how I do it now: [STEPS].

Break the process into:
keep human / AI can help / AI can handle

Then design the smallest reusable workflow I can test today.

Give me:

  • the inputs I need

  • the exact steps

  • a reusable prompt/template

  • what I should check before trusting the result

Ask me max 3 questions if you need more context.

2. Show AI what “good” looks like for better output

Douglas Brundage at Every has a simple fix for one of the most annoying AI problems: you know what you want. AI just keeps missing it.

When he uses AI to build slide decks, he doesn’t start with a giant prompt. He makes a few slides himself first, gives those to AI as the reference, then lets it build the rest. He edits what it gets wrong and asks AI to turn those corrections into rules for next time.

So instead of describing your taste over and over, you’re giving AI evidence of it. You can steal that for basically any kind of work:

Here are 3 examples of work I consider good: [EXAMPLES].

Reverse-engineer them into 5–7 observable rules for:
structure / detail / tone / formatting / what to avoid.

Show me the rules first.

Then create [OUTPUT] using them.

After I edit your version, compare mine with yours and update the rules into a reusable quality brief I can save for next time.

That’s a lot more useful than typing “less corporate” for the seventh time.

3. Run the Vacation Test for reusable workflows

Emily Kramer’s three-person team at MKT1 had built a bunch of useful AI workflows. The problem: too much of it lived inside one person’s laptop, account or chat history. So they started using a very simple Vacation Test:

If this person or computer disappeared tomorrow, could the work still run? Could someone else update it?

If the answer was no, the workflow wasn’t really reusable yet. That’s a useful test even if you’re working solo. Next time you finally get AI doing something well, paste:

This result is good. Assume I disappear for two weeks.

Turn what we just did into a workflow someone else could run without me or this chat.

Include:

  • when to use it

  • required inputs

  • exact steps + prompts

  • what good output looks like

  • what a human must check/approve

  • what to do when something goes wrong

Remove anything from this conversation that didn’t matter.

Finish with a 5-line handoff checklist.

Then save that somewhere you’ll actually find it again. A good chat is nice. A workflow you can reuse is much better.

The models are going to keep getting stupidly good, stupidly fast whether we keep up with every release or not. I’m much more interested in a future where non-technical professionals get better at experimenting with their own work without constantly feeling like they’re behind.

That’s the future of work with AI I want to be part of.

BEFORE YOU GO

Steal this if you feel personally attacked 👇

Be honest: what does AI use at work actually look like for you right now?

Login or Subscribe to participate in polls.

I’ll share where everyone lands next time.

See you next Sunday! ✌

Max