WORK LESS WEDNESDAY

WLW #196

April 01, 2026

👋 Hey Reader!

This is issue #196 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. How To Charge More Cohort 2 Starts In 1 Month! – Get On The Waitlist!

ANNOUNCEMENT: We are kicking off our 2nd cohort of 💸How To Charge More at the end of April!

HTCM is my cohort-based program designed to teach you one thing:

How to raise your prices. By a lot.

It will be a 4 week program, taught live with me covering 8 lessons including:

  • How to craft a $10k-250k offer (how to structure, price, and sell)
  • How to calculate the true value you create for clients (tangible and intangible)
  • How to find clients who pay more money (and get them to do it!)
  • How to raise your prices with current clients (exactly what to say and how to frame it)
  • How to sell outcomes instead of deliverables (and work less hours for more money as a result)

Click here to join our waitlist for Cohort 2.

(P.S. I take special care of my clients who take early action so make sure to hop on there if you’re interested! 🤫)


🌎 2. Great Mini Article From Derek Sivers – I Was Inconsiderate But Now I’m Everywhere

Quick read from Derek Sivers about meeting people where they are.

Can be summed up with this quote:

“If you have something worth spreading, it’s considerate to spread it widely, to reach people through their favorite medium.”

Read the full thing here.

P.S. Found the one on Sublime.


🤖 3. Why It Feels Like Your AI Sucks – Why AI Companies Lied About Context Windows

Have you noticed that when you upload a bunch of long files to AI, it feels like it didn’t read it?

Well, you’re right. It didn’t.

If you want to know why, this is a great explanation from Tiago Forte on YouTube.

As we continue to use AI, I believe 2 things are going to be big issues:

  1. How do we structure our workspaces so that AI can easily access and understand the data?
  2. What tools are incentivized to actually read everything? (ex. subscription vs. credit-based LLMs)

I discuss this concept in detail (and what to do about it) in my paid-Substack only workshop “How I’m Using AI In My Business) → You can sign up for $15/month to get access to it.

🎶 4. Music I’m Listening To – The Sagegazers On YouTube

Sometimes the algorithm gives you something good.

A few days ago, I came across this YouTube channel devoted to uploading cassettes of 80s new age and ambient music, and my mind has been blown.

There is so much awesome stuff here.

Ideal for deep work, meditation, and relaxation.

I have been working my way through the releases, but here are 4 that I’ve liked so far:

📼 Sérénité by Paul Sauvanet (1989)

📼 Where Rivers Run Free by Daniel Perret and Alap Jetzer (1988)

📼 Elysian Fields by Rocco Notte & Richard Bush (1984)

📼 Taoasis by Mathias Grassow (1987)

Check out the channel here.!

🖐 5. More Things I’m Into This Week…

📜 Great Article About The Hidden Scripts We Have About Work – “What Are the Scripts You Grew Up With About Work?”

📘 Book I’m Reading – The Language of Emotions by Karla McLaren

🥚 Anime Film I Watched This Week – Angel’s Egg (1985)

💉 Article I Enjoyed – The Ozempicization of the Economy by Kyla Scanlon

💬 Quote I’m Pondering…

“You are a success to the degree that you grow, and you grow to the degree that you become a wiser, more useful, and more secure person. In other words, we live to learn, and by this very process, we learn to live.” – Manly P. Hall


How we can work together

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

  • 👤 My Substack. My weekly Substack inner entrepreneur discusses the internal side of entrepreneurship – mindset & growth.
  • 🎧 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.

And two paid engagements:

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