Scott Monday's Newsletter

2023: The Nightmare - Part 4

Don't discount your intuition; it's decades of experience in the form of a whisper.

Nov 8 • 

Scott Monday

Reflection on My EO Presidency

A year of leading, losing, and learning: why I don’t regret the hardest role I’ve ever taken.

Nov 1 • 

Scott Monday

October 2025

How to Build a 2026 Playbook

A step-by-step guide to generate your 2026 Playbook and set up a year of domination.

Oct 25 • 

Scott Monday

The Three Types of Think Weeks That Changed How I Lead

Nine years, nearly twenty Think Weeks, and three distinct formats later: here’s what worked, what didn’t, and how you can design your own version of…

Oct 18 • 

Scott Monday

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Parenting in the Age of AI

There's a new kid in school. His name is AI. And he's going to beat up your kid and steal his lunch if you don't make friends. Right away.

Oct 11 • 

Scott Monday

3

The 5-Year Vision That Makes Tough Decisions Easy

One document was a seismic shift in my decision-making process. Here's how you can create yours in just an hour or two.

Oct 4 • 

Scott Monday

September 2025

Launching a New Business: Month 33 Update, Part 2

Four lessons from the messy middle of building a business.

Sep 27 • 

Scott Monday

1

Launching a New Business: Month 33 Update, Part 1

Three years of risk, losses, and lessons: How a new business is finally turning a corner.

Sep 20 • 

Scott Monday

1

The Exit Mirage: What They Don't Tell You About Stepping Away

The hidden cost of walking away: without purpose on the other side, an exit becomes regret.

Sep 13 • 

Scott Monday

Through the Eyes of an Executive Assistant

What I learned by flipping the script and asking the EA, not the executive.

Sep 6 • 

Scott Monday

August 2025

Trapped by Commitment

Why sticking it out isn’t always the right move, and how to know when to quit, commit, or endure.

Aug 30 • 

Scott Monday

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The 5-Star Review Formula

Here's how one of my businesses generated 364 5-star reviews and one pesky little 4-star that keeps us humble.

Aug 23 • 

Scott Monday

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