Work Less Wednesday: September 24

👋 Hey Reader!

This is issue #173 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. Big Announcement - I’m Shutting Down How To Work Less​

On October 1st, I am shutting down 🏖️How To Work Less for good.

Over the last 3 years, hundreds of entrepreneurs have transformed their businesses as a result of the program.

But it’s time is over.

Why?

To make room for something new.

(More on that soon.)

​As a farewell gift (until October 1st), I’m offering the ENTIRE How To Work Less product for $500 (retail: $3,000).​

On top of that, you will get the next new Work Less product I release FOR FREE when it drops.

Want to learn more? See the next story. ⬇️

P.S. If you’re reading this and have bought HTWL in the past, we are not removing access to the course materials (and have something special in store for you next launch) - don’t worry!

🎧 2. New Podcast - Shutting Down HTWL - Business Update Q4 2025​

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If you want to hear more about my decision to shut down How To Work Less, I’ve got you covered!

This is my first business update in over 18 months, and I cover:

• Exactly WHY I’m shutting down How To Work Less, and what’s coming to replace it.
• How working closely with 75+ entrepreneurs over the last 2 years led to my businesses’ new mission.
• Why I’m excited about creating entrepreneurial tools for internal and external growth.
• Announcing the launch of my new Substack called “inner entrepreneur.”
• How I’m finding alignment between my mission → business → ideal day.
• Why I’m moving from focusing on leverage to scale this year.
• Finally, how you can get your hands on How To Work Less AND my next new product for just $500!

​You can watch the video version here.​

​Or catch the audio-only version here.​

📝 3. Marc Andreeson on How To Get Stuff Done - To-Do List/Watch List/Later List​

Simple, solid, evergreen advice for moving the needle on the things you actually care about.

​Full post here.​

🔵 4. Is This OpenAI Brand Exploration A Joke? - Case Study by Area Technology​

I shared this case study with my clients last week and got very mixed reviews.

Had to open it up to discussion here.

This company worked with OpenAI in 2023 and created these logos:

Area @areatechnology_ Brand exploration for OpenAI with Sam Altman, February 2023 Two logo concepts – Circle and Monogram – alongside broader exploration for ChatGPT across brand and product. More details and link below. 11:54 AM • Sep 17, 2025 102 Retweets 2151 Likes Read 194 replies

​

I’m kind of mindblown.

I don’t know how to feel about it.

It very 2000s.

At least it’s different, lol.

What do you think?

Good? Bad? Genius?

You can see the full project breakdown here: https://www.area.tech/openai.​

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

🎧 What I’m Listening To - Santana Live at Tanglewood - Full Concert(1970)​

📚 Graphic Novel I Just Bought - Regression (The Complete Collection)​

🧱 LEGO I Just Finished (Recommended!) - Tranquil Garden​

🎙️ New Recording Gear I Just Picked Up - DJI Mic Mini​

💬 Quote I’m Pondering…

How we can work together

When you’re ready, here a free way 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.

And 2 paid engagements:

1. LAST CHANCE: 🏖 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. (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.