Issue #183 | February 24th, 2026

Before we dive into this week's newsletter, we’re gathering feedback to help shape future events and conversations around what matters most to you.

Could you take a minute to fill out this quick 5-question survey? Thank you so much in advance!

1→ Which of these best describes you?

A

Hobbyist

B

Creator

C

Influencer

D

Entrepreneur

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Hi, it's Pat!

You’ve probably heard the quote (often attributed to Einstein): “Insanity is doing the same thing over and over again and expecting different results.”

It’s a classic for a reason — most of us get stuck in a loop at some point. We keep tweaking, adjusting, and hoping for a breakthrough, but nothing really changes.

I talk about this in Lean Learning: sometimes, you need more than just another small tweak. You need a bold move. You need to take a risk.

Let’s get unstuck.

Quote of the Week

"If you want something you’ve never had, you must be willing to do something you’ve never done."

—Thomas Jefferson

Story of the Week

Why Playing It Safe Keeps You Stuck

It’s easy to stay comfortable. It’s easy to keep doing what you know, even if it’s not working. But comfort rarely leads to growth.

The biggest breakthroughs in my business — and in the businesses of every successful entrepreneur I know — came from making a bold move, not from playing it safe.

But let’s be real: bold moves are scary. They come with risk. And most of us are wired to avoid risk, especially when things feel “good enough.”

How to Take Smarter Risks (Without Blowing Everything Up)

I’m not saying you should bet the farm or make reckless decisions. Bold doesn’t have to mean foolish. Here’s how to take bigger swings — safely:

1. Do Your Research

Before you leap, learn from others who’ve done something similar. What worked? What didn’t? What would they do differently? The right research can help you avoid obvious pitfalls.

2. Find a Mentor or Guide

Talk to someone who’s already walked the path. A mentor can help you see blind spots, challenge your assumptions, and give you the confidence to move forward.

3. Start with a Pilot or Test

You don’t have to go all in right away. Try a small version of your bold idea — a pilot program, test launch, or limited run. See what happens, learn from it, and then scale up.

4. Build a Safety Net

What’s the worst-case scenario? How can you protect yourself if things don’t go as planned? That might mean keeping your day job while you launch a side hustle or setting a firm budget for your experiment.

5. Get Accountability

Tell someone about your bold move. When you make your commitment public, you’re more likely to follow through — and you’ll have support if things get tough.

What Bold Move Could You Make?

• Launch a new product or service you’ve been thinking about for years
• Pitch yourself for a speaking gig or podcast you don’t feel “ready” for
• Invest in a coach, course, or mastermind that scares you (in a good way)
• Change your business model, pricing, or target audience
• Take a sabbatical to recharge and rethink your direction

Your Challenge

This week, ask yourself:

• What’s one bold move I’ve been avoiding?
• What’s the smallest version of that move I could try, just to see what happens?

Remember: without bold moves, you don’t get bold results. Sometimes, the change you want requires a leap you’ve been too afraid to take.

Here’s to making the leap — safely, and with intention!

RSVP to Tomorrow’s Workshop!

Growing your audience is hard enough.

Managing that audience manually? That's what burns creators out.

If you're struggling to keep up with your email list, it's probably not because you are doing something wrong. It is because you are doing everything yourself instead of building systems that scale.

Tomorrow, February 25th at 12:00 PM PT / 3:00 PM ET, I am hosting a live workshop with Kit’s Creator Educator Shiv Chibber to show you exactly how I use trust-first automation to serve my audience and scale Smart Passive Income without constant hustle.

You’ll walk away knowing:

• How to build two core automations that nurture and engage subscribers automatically
• Why refining your audience matters more than growing your list, and how to do it
• The organizational systems that keep your creator business scalable as you grow

Because I am partnering with Kit on this, anyone who attends live will also get access to exclusive bonuses we are only sharing with attendees.

Cheers,

Pat Flynn

Co-founder, SPI Media

Dad Joke of the Week

Why did the man fall down the well?

…Because he couldn't see that well!