How To Invite AI To Punch You Right In The Task List

My Sunday Scaries tend to hit me on Monday mornings and they are existential. You know those deep-dark forever-empty thoughts, like “Am I enough?” or “Is my life meaningless?” Yep, I get them too.

This Monday’s creeping dread was “Am I making enough money?” and as a business owner, that’s uncomfortably adjacent to “Is my business making enough money?” It gets blurry, separating personal goals from business goals when you’re the head honcho, and it gets me into trouble when I try to solve personal problems with panic sales outreach.

Thanks to Past Dan, he had built a room specifically for these Monday Mumbles. Not a physical room (though a padded one would work🤡), but an AI workspace where I could hash things out.

Introducing the Strategy Room, a persistent AI workspace — a Claude Project, a Gemini Gem — loaded with real context and given one job: advise me like a board of directors I can't afford. Mine is stocked with contracts, forecasts, meeting notes, and standing instructions to argue with me. We’ll come back to that last bit, the standing instructions.

So, Monday morning, I stepped into my Strategy Room to take my back-of-the-napkin revenue projections and my forever-empty fears to probe them for everything I missed.

Here's what it found.

• It found $10,000 in retirement contributions miscoded in my books as a "Bank Fee."
• It found that my read on three "dead" leads was wrong. All three. One had explicitly said reconnect in October and I'd filed her under no. One was on family vacation, and I'd filed her under cold. One said check back later in the year, and not in that “don’t talk to me again” voice.
• It built me a right-sized revenue plan through Halloween. Real tasks, real sequence, and a conference strategy for laying relationship rail into 2027.

To be clear, I could have quieted my own fears without AI, just like I used to almost 7 years ago when I first started Learn to Scale. However, Dan from Many Moons Ago would not have caught the accounting mistake, the dead leads, and would have tried to manhandle an upcoming conference as the only lifeline to meeting my revenue goals, rather than using it to build pipeline for 2027.

You see, the Strategy Room was explicitly designed to be a counterbalance to the worst version of myself. It wasn’t an oracle to tell me where I should focus my business strategy, it wasn’t a sycophant to tell me I’m brilliant, and it wasn’t a hustle-culture guru telling me to fix my grindset and get back to cold calling.

No, my Strategy Room is friction-first because I don’t go in there on Mondays for answers. I go in there for sparring. I’ve done the work to learn that this is what I need: I need to push my own fears against a bean-counting personality to hear myself in the reflection and to force me to answer the detail questions — that I would typically avoid!— that shrink a $75K feeling into a $45K goal for new logos.

And now, I’m going to show you how to make a friction-first Strategy Room in less than 20 minutes.

(This is directly related to the next Show Me Something Cool With AI, so if you are thinking of attending at the end of August, give this a shot!)

However, before you whip out your chatbox, a short safety lecture: prepare to be seduced. We are about to build the most cogent, plausible, and reasonable sycophancy machine. It will tell you things that you will want to believe. It will make assumptions that seem logical. You will fall in love with what it tells you.

Fair warning. Now let’s play with fire.

Part 1: Strategy for What?

We all need perspective. Our human brain meatballs can easily slip into fight or flight mode, or hyperfocus on what’s immediately in front of us, or ruminate on the same traumatic event. In some contexts, that protects us from tigers, but for the modern human, we’d much rather be in control than controlled by cortisol.

The first step in making a Strategy Room is to decide WHAT this Strategy Room is supposed to do for you, the human. Here’s three options to get you inspired, pick one and test it out now:

Chief of Staff (“Leo”)

Relationship Advisor (“The Yenta”)

Career Coach (“Future You”)

You see I added friction rules to each persona? This is where all that self-reflection work you did with your therapist is going to pay off: when you explicitly describe your vulnerable emotional kindling then AI can specifically push you on the things you need to be pushed on the most.

Part 2: The Context

AI needs examples and exemplars of what “good” looks like here. What you feed into your Strategy Room will directly influence how useful this room will be. More isn’t necessarily better (read the last TL;DR on efficient AI use), but precision and quality absolutely matter. Garbage in, garbage out.

There’s also a longevity question here that you need to answer or else this will be awesome next week and subsequently more useless over the next few months. Humans are always changing but this Strategy Room will not change unless you plan for it.

Calling you out: you either will not notice how YOU change or you will not remember to update the Strategy Room.

As you are collecting your context, lean more into evergreen content or deep existential truths and ignore the Dumpster Fire of the Day— many of these AI tools will populate additional topical context the more that you use it, so it’ll come.

Here’s some things to scrounge up for your Strategy Room

• Leo, the Chief of Staff: Corporate Mission/Values, HR handbook, a Notion/Google Drive of Standard Operating Procedures, a link to a live Org Chart, and your Annual/Quarterly Strategic Plan.
• The Yenta, the Relationship Advisor: A picture of your vision board, your Tinder profile, examples when you were truly yourself, and your style fingerprint.
• Future You, the Career Coach: Your resume, stories of your proudest achievements and most humbling failures, job descriptions of roles you would love to fill, your LinkedIn profile export, and portfolio content of your best work.

Part 3: The Build

Open up your AI tool of choice and create a Project (Claude/ChatGPT) or a Gem (Gemini).

The next part is easy: input your Why from Part 1 as system instructions and upload your context from Part 2. Tada, Strategy Room.

(quick little itty-bitty safety note: for the love of privacy, use a paid AI tool if you are pasting in PII data, details about your past divorce, or your sales pipeline. If you aren’t on a paid plan, be cautious about what context you are uploading to a free AI tool.)

Now the hard part…

Part 4: The Calibration

Don’t just run into your Strategy Room with your deepest darkest fears. Instead, approach your shiny new Strategy Room like a safety inspector and see where it's blowing smoke. Here’s a battery of prompts to see how your Strategy Room performs:

1. Describe your purpose in three ways: as if I am a 7^th grader, as if I am a college student, and as if I am a PhD.
2. What context or information do you lack that would be incredibly helpful to have?
3. What are three ways that you will lead me astray, and how can we prevent that from happening?
4. Here’s a problem I’m grappling with: [describe a problem, fictional or real].
   1. Give me some advice on how to handle this.
   2. Now, give me a completely different opinion.
   3. Now, how are both of those perspectives wrong or based on weak assumptions?

As you go through these test cases, you can either manually update the Project/Gem instructions or simply ask the AI to draft updated instructions based on the conversation.

Part 5: Use What You Built

You just invested some time into building something neat, but it ain’t doing much if you don’t use the thing. Here are a few easy little hacks:

• Pin the Project/Gem so it’s a lot more visible.
• Copy the AI output from another chat and throw it past your Strategy Room with the prompt, “Hey, double check this for me: anything I might be missing or assuming?”
• Set aside a recurring calendar block on Monday (“Mumbletime”) or Friday to plan your week/review your week with your Strategy Room.
• For Leo the Chief of Staff, consider sharing the Project/Gem with other colleagues (be careful that you’re not giving a junior employee access to privileged info in your context) and ask them to test it.
• For those of you readers who are in 25-100 person organizations, this Strategy Room for a leadership team is basically what I build in my governance engagements (➡️ Let’s Talk About That!)

Now, Tell A Friend

This is a very barebones way to give yourself some new perspective, but solely talking to AI instead of real humans is how you become a gremlin. Share what you’ve built, play around with it, and steal great ideas from other people to augment your Strategy Room.

On August 28^th, a whole batch of people will be show-and-telling their Strategy Room projects at Show Me Something Cool With AI. You should come. It’s super fun and casual.

A TL;DR from the CRO

My Strategy Room gets relocated over the summer to the beach and that's all the context I need to make my To-Do list for the week.

-Roman Noodles, Chief Ruff Officer

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My carnivorous terrarium is now complete:

My first carnivorous terrarium involved a Venus Flytrap that slowly but surely rotted away, and since then, I stumbled across this YouTube terrarium creator that has been my featured entertainment while on work trips.

The precision that Tanner uses in designing his hardscape, the substrate, the placement of every little moss-ling: *chef's kiss*

I ended up taking a clay pot, turning it upside down, and then using aquarium-safe silicone to stick some agates onto the pot, covered it with some dried and live sphagnum moss, and centered it all around a Cape Sundew.

A sticky flycatcher.

Will it capture some of the flies that the summer has been sending my way? I dunno, but I'm kinda feeling the jagged agates sticking out of the mossy landscape. Makes me think of a little bog that had a mini cataclysm caused by miniature feuding wizards.

Tapping two Swamps for the black mana,

Dan from Learn to Scale​

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​PS. My gateway drug to SerpaDesign was this mini waterfall inside a jar.​