👋 Work Less Wednesday — September 03, 2025


Work Less Wednesday: September 03

👋 Hey Reader!

This is issue #170 of Work Less Wednesday, where I share with you 5 things you should know about, in 5 minutes or less. That leaves you with 10,075 other minutes this week.


🎾 1. Book I’m Re-Reading - The Inner Game of Tennis

A few weeks ago, I got back into playing tennis.

On the court, I was discussing the psychology of tennis and was reminded of a book I read over a decade ago:
The Inner Game of Tennis.”

The book digs into “the mental side of peak performance.”

Not only is it an exceptional book about tennis, it provides lessons that we can apply to life and business.

Here’s the big idea:

There’s the outer game, which is the mechanical part—how you hold the racket, keep your arm level on your backhand, and so on. It’s the part that most coaches and players tend to focus on. Gallwey acknowledged the importance of the outer game, but what he was really interested in, and what he thought was missing from most people’s approach, was the Inner Game. “This is the game that takes place in the mind of the player.”

He goes on to say:

The Inner Game “is played against such obstacles as lapses in concentration, nervousness, self-doubt, and self-condemnation. In short, it is played to overcome all habits of mind which inhibit excellence in performance.”

Our “Inner Game” is going on 24/7, not just on the court.

Here are 3 insights from the book:

  • Focus on process, not outcome. You can’t control “winning”; but you can execute the swing. Focus on the actions that are in your control, let the outcomes come naturally.
  • Relaxed concentration. Peak performance is a combination of calm attention plus challenge. Create the conditions for deep work in your business: clear priorities, fewer simultaneous projects, protected focus time.
  • Visualize desired outcomes and cues. Mental rehearsal primes action. Visualize the day that you want to have, the meeting you want to go well, the writing session you want to focus during.

Check out the book here.


🧱 2. Interesting Concept I Learned About This Week - Chesterton’s Fence

Learned about this from David Goudet’s article, “You Were Born Into a Turning Point in History. What Will You Do With It?

Here’s the excerpt:

There’s an interesting phenomenon often referred to as the “Chesterton’s Fence” principle:

It comes from G.K. Chesterton’s idea:

If you find a fence in the middle of nowhere and don’t know why it’s there, you shouldn’t remove it until you understand the reason it was put up in the first place.

Humans repeat this cycle many times:

  • We create solutions for problems
  • We forget about those problems
  • Some years later, we wonder why that solution is in place
  • We remove the solution
  • We bring the problem back again

I think it’s pretty clear this is playing out in a wide variety of ways in our modern life.

📚 3. The Ultimate Classics Curriculum - St. John’s College Great Books Reading List

This image went viral on social media recently and allegedly drove a ton of applications to St. John’s College.

Turns out people are still interested in reading great books.

You can get the whole curriculum in PDF form here.

And here’s more info about the philosophy behind it.


😆 4. This Made Me Laugh - South Park Clip About ChatGPT

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SMB Attorney
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@SMB_Attorney
8:10 PM • Aug 26, 2025
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“Just because something kisses your ass doesn’t mean it actually thinks you have good ideas.”


🖐 5. More Things I'm Into This Week...

🎧 Deep Work Album I’m Listening To - Music For Writers by Steve Gunn

📰 Great Article - How To Tell If Something Is AI Written

📌 12 Great Lessons – Charlie Munger On Making Mistakes

⚙️ Crazy Popular Mechanics Article – Your “Gut Feelings” Are Memories From The Future, Scientists Say

💬 Quote I’m Pondering…

“The first skill to learn is the art of letting go the human inclination to judge ourselves and our performance as either good or bad.”
From The Inner Game of Tennis


How we can work together

When you’re ready, here are 2 free ways I can help you:

  1. 🎧 My Podcast. Listen to or watch my free podcast The Rich Webster Show. It is an unfiltered look behind the scenes at my life and work.
  2. 🛠️ 6-Figure Solopreneur Systems. Free email course. Steal the exact systems I used to run TWO multi-six-figure solo businesses in under 20 hours a week.

And 2 paid engagements:

  1. 🏖 How To Work Less. From 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. 🏖How To Work Less gives the playbook. Enrolling now. (400+ past students. 5 stars)
  2. 🧪 The Lab. I advise and mentor 6-7 figure Creative Solopreneurs. If you want to work closely with me (i.e. we speak 1-2 times a week), watch this video, the follow the instructions.

😊 Have a great week - Rich

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Rich Webster

13 years in recovery. Two $500k/y businesses. Creator of 🏖️How To Work Less. 32k read my newsletter. ⬇️

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