I used this framework to make major career decisions. It takes 5 minutes.

{{first_name|Hey}},

Welcome back. This is Five Prompts, the weekly newsletter where I pull the best AI prompts from the week, break down why they work, and give you the CMO perspective you won't find in a generic prompt list.

This week we're talking about decisions. Specifically, why smart people get stuck making them and a framework that fixes it in about 30 minutes.

Let's get into it.

The Decision-Making Prompt

Here's what nobody tells you about decision paralysis: it's almost never about the decision. It's about not knowing what a good outcome looks like. You're evaluating options against a moving target. No wonder nothing feels right.

Here's the prompt that reframes the whole thing:

"I need to make a decision about [describe the decision]. Here are my options: [list them]. For each option, tell me: What's the best realistic outcome? What's the worst realistic outcome? What's the most likely outcome? Then tell me which option has the best most-likely outcome. Don't optimize for best case. Optimize for expected value."

Why this works: It kills the fantasy. Most people get stuck because they're comparing the best-case scenario of one option against the worst-case scenario of another. Anyone else here a victim of overthinking it? (raises hand) This prompt forces expected value thinking, which is how professional strategists actually make calls.

I ran this exact prompt when deciding whether to leave my last CMO role (just needed some extra confirmation). The expected value answer was obvious in about 4 minutes. I'd been agonizing for 3 months.

Here's a framework I used leading strategy at spots like Disney and Bank of America. It's called "two-way door vs. one-way door" decisions.

A one-way door is irreversible. Signing a lease. Hiring a full-time employee. Taking on debt. These deserve serious analysis.

A two-way door is reversible. Launching a product. Testing a price point. Trying a new content format. Starting a newsletter. These deserve speed.

The unlock: most solopreneurs treat every decision like a one-way door. That's why everything takes forever. Before you analyze your next decision to death, ask one question: can I undo this in 30 days? If yes, stop thinking and start testing.

The people who build fastest aren't smarter. They just know which doors open both ways.

You don't have to read everything — just the right thing. 1440's daily newsletter distills the day's biggest stories from 100+ sources into one quick, 5-minute read. It's the fastest way to stay sharp, sound informed, and actually understand what's happening in the world. Join 4.5 million readers who start their day the smart way.

Join for free today!

Ditching ChatGPT is hot right now. I used ChatGPT for over a year. Tried Claude, bridged conversations between the two for a while. Then last month, I fully switched to Claude and never looked back. And then upgraded to Pro. And now I’m paying for Max - it’s that good.

Not because ChatGPT is bad. It's a solid tool. But Claude thinks differently. It reasons through strategy instead of just generating content. It pushes back when an idea is half-baked. It handles long context without losing the thread -- full documents, transcripts, research, all of it. Claude feels more like a team member than a happy, agreeable servant.

If you've been curious about making the switch, I published a free migration guide that walks you through it step by step. It took me a while, the slow go. But this is to help you go without learning curve. No starting over. Just an upgrade with some translation on what you should use in Claude vs what you might have used in ChatGPT.

It covers what transfers directly from ChatGPT (everything you already know about prompting), what's different about Claude (Projects, Artifacts, longer context), how to move your workflows in about 30 minutes, and the features most people miss.

Grab the free Move to Claude guide here.

The Clarity and Direction Deep Dive has 20 prompt sets built around exactly this kind of strategic thinking. Decision frameworks, quarterly planning, simplifying your business, finding leverage. Each one comes with CMO commentary on why it works and how to apply it.

Next week we're shifting gears. You've got clarity and a decision framework. Now we find where your biggest leverage is hiding. Same effort, bigger results.

BTW, I’m trying to keep this to Wednesdays. This week ran away a bit, but keep an eye out mid-next week. See you then!

Keep building,
Tuck

Follow for daily prompts: X | Threads