👋 Work Less Wednesday — July 30, 2025


Work Less Wednesday: July 30

👋 Hey Reader!

This is issue #165 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. I’m Hosting A Virtual Retreat On Friday & Saturday - Last Chance To Join Us!

ICYMI: This Friday & Saturday I’m hosting a virtual retreat.

Here’s what’s going down:

  • 🎤 I’m going to be speaking & leading workshops.
  • 👥 I’ve got some incredible (special!) guests booked.
  • 📈 You’ll get a chance to zoom out and think holistically about your business for two days.

If you want in, here’s the deal:

You’ve got to be one of my clients.

When you sign up, here’s what will happen:

  1. 🎟️ You’ll join us live for the virtual event.
  2. 🤝 You’ll have your 1:1 deep dive onboarding with me ON YOUR CALENDAR for early August.
  3. 🧠 And the best thing? You’ll get me as a “co-founder without the shares” for your business for the next year.

If you’re a creative solopreneur earning $10k/m, click here and I’ll give you all the details.


🧠 2. "How I Practice At What I Do" - Blog by Economist Tyler Cowen

This blog post was resurfaced by Tim Ferriss in his newsletter last week.

It was written in 2019, but still hits.

It all came about when the author (Tyler Cowen) said this:

“Athletes train. Musicians train. Performers train.

But knowledge workers don’t.

Knowledge workers should train like LeBron.”

In response to this somewhat controversial statement, someone in the comments section of his blog asked him:

How do you train?

This is his response:

  1. I write every day. I also write to relax.
  2. Much of my writing time is devoted to laying out points of view which are not my own. I recommend this for most of you.
  3. I do serious reading every day.
  4. After a talk, Q&A session, podcast — whatever — I review what I thought were my weaker answers or interventions and think about how I could improve them. I rehearse in my mind what I should have said. Larry Summers does something similar.
  5. I spent an enormous amount of time and energy trying to crack cultural codes. I view this as a comparative advantage, and one which few other people in my fields are trying to replicate. For one thing, it makes me useful in a wide variety of situations where I have little background knowledge. This also helps me invest in skills which will age relatively well, as I age. For me, this is perhaps the most importantly novel item on this list.
  6. I listen often to highly complex music, partly because I enjoy it but also in the (silly?) hope that it will forestall mental laziness.
  7. I have regular interactions with very smart people who will challenge me and be very willing to disagree, including “GMU lunch.”
  8. Every day I ask myself “what did I learn today?”, a question I picked up from Amihai Glazer. I feel bad if I don’t have a clear answer, while recognizing the days without a clear answer are often the days where I am learning the most (at least in the equilibrium where I am asking myself this question).
  9. One factor behind my choice of friends is what kind of approbational sway they will exercise over me. You should want to hang around people who are good influences, including on your mental abilities. Peer effects really are quite strong.
  10. I watch very little television. And no drugs and no alcohol should go without saying.
  11. In addition to being a “product” in its own right, I also consider doing Conversations with Tyler — with many of the very smartest people out there — to be a form of practice. It is a practice for speed, accuracy in understanding written writings, and the ability to crack the cultural codes of my guests.
  12. I teach — a big one.

You can read the full article here.


💼 3. Entrepreneurship Is Personal Development - Video From Jay Cohen

Last week I shared this bit of writing on the topic of entrepreneurship as self development.

It resonated with my friend Jay Cohen enough that he made a whole YouTube video about it ⬇️

video preview

Jay’s a cool dude and has lived many lives:

Former drug addict, Marine, father, entrepreneur, gym owner.

He has a lot of wisdom to share.

In the video, he shares how he took his business from $5k/month to $88k/month, then back down to -$15k/month, what he learned from it, (plus much more).

It’s a really great 16 minute breakdown, I recommend you check it out here.


🦘 4. Taking A Leap At 31: Could This Pivot Cost Me Everything? - Substack From Vanessa Lau

If you’ve been following Vanessa Lau’s entrepreneurial journey, you know that she shut down her 7 figure business and took a big sabbatical a few years ago.

When she came back (much stronger, I might add) - she had two businesses going on:

  1. Her 1M subscriber YouTube channel (funded by sponsorship deals)
  2. Superboba - her boba tea startup

This Substack breaks down a decision I figured was coming at some point (because I had to make it).

See, it’s really hard to focus on two important businesses at once.

It’s why I shut down my agency even though that business, and this business, were both making money.

Eventually, you realize that every hour you spend on one thing is taking an hour away from something else that's more important.

So for Vanessa, she’s stepping into her full role as co-founder at Superboba (and dialing back YouTube).

I HIGHLY recommend reading the full Substack breakdown here, I think most entrepreneurs would benefit from hearing this lesson from her.

video preview

Or you can watch the full 82 minute YouTube version here.


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

🎧 Awesome Music Game I’m Playing With Some Entrepreneur Friends (Thanks Claire Perkins!) - Music League

🤑 How An 8-Figure CEO Uses AI To Get Clients (Spoiler: He Doesn’t) - Podcast by Jon Courtney

📕 Elden Ring Art + Lore Book I’m Pre-Ordering - Grace Given: The Mythology of Elden Ring

🧘 New Meditation Practice I’m Experimenting With (Thanks Jay Cohen!) - Ziva Meditation

💬 Quote I’m Pondering…

“If you are like most people, you’re trying to do everything. You’re trying to be everything. Well, you’re never going to be great if that is the case. Figure out that one thing that you were put here to do, focus on it, and you will be happy, fulfilled, and energized.”

From The EOS Life by Gino Wickman



😊 Have a great week - Rich

P.S. Did someone forward this to you? Subscribe here.

P.P.S. Thank you for trusting me with your time. If these emails ever turn into a burden, I encourage you to unsubscribe from Work Less Wednesday.

702 N 3RD ST PMB 868, PHILADELPHIA, PA 19123
Unsubscribe · Preferences

Rich Webster

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

Read more from Rich Webster
Phish tour

Work Less Wednesday: July 22 👋 Hey Reader! This is issue #164 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. I’m Hosting A Virtual Retreat On August 1/2 - Here's How To Come On August 1st and 2nd I’m hosting a virtual retreat. It’s going to be epic. I’m going to be speaking on a variety of topics, and I’ve got some (special!) guests booked. But here’s the thing…there’s only one way...

 ?Now-Time? & ?Inventory Press

Work Less Wednesday: July 9 👋 Hey Reader! This is issue #163 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. This Week’s Video - Why "Work-Life Balance" Is Killing Your Business On May 18th, my good friend Zander Howard-Scott invited me to come speak to a group of artists and entrepreneurs at his Creative Sovereignty event in Montreal. Today I’m excited to share the replay of one of...

video preview

Work Less Wednesday: July 2 👋 Hey Reader! This is issue #162 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. Podcast with Chris Do - Quit Client Work & Work Less for More Money A couple months ago I sat down with one of my mentors Chris Do to catch up. Lucky for you, the conversation was recorded. And this week the podcast dropped. Here are a few quotes to set the stage: “The more...