WORK LESS WEDNESDAY
WLW #202
👋 Hey Reader!
This is issue #202 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. Actually Helpful Advice For 2026 Grads – The Old World Is Dying by Jasmine Sun
You’ve probably seen the numerous graduation speeches this year where the speaker mentioned AI and was loudly booed by the crowd.
There’s a reason for that.
Most students don’t want to hear that they wasted the last four years of their lives, are now in a bunch of student debt, and have to “get on board with AI” (with no job prospects in sight.)
Well, I’ve got good news, and bad news.
- The bad news is the world is changing.
- The good news is the world is changing.
This article from Jasmine Sun is a practical, and actually useful, set of advice on how to succeed as a new graduate (and more importantly, as a person) in 2026 and beyond.
Here are a few points I flagged agree with (and have seen playing out in my consulting work):
- People skills: “Relationships are how you earn the trust to make the sale, because even the biggest rationality bros are vibes-based decision-makers.”
- Self-awareness: “Why would anyone hire a 22-year-old with Claude Code when they could just use Claude Code? The AI tools are undifferentiated and everyone has them. Your comparative advantage has to be about you.”
- Flexibility: “There is no such thing as a fifty-year career anymore. At maximum, plan for five.”
♻️ 2. How To Get The Most Out Of Your Advisors – The Progress Loop
Interesting article from Sharran Srivatsaa about The Progress Loop, which is a framework for getting the most out of your mentors, advisors, or investors.
It is a short update email you send every 2 weeks that actually keeps them updated (and able to help you!)
Here are the 6 components of The Progress Loop:
- ✅ 1. Activities – Write down what you ACTUALLY did.
- 🏆 2. Wins – Show your progress.
- 🧠 3. Learnings – The format: “We used to think X was true. By doing Y, we found out X was wrong. What is actually true for our business is Z.”
- 🛑 4. Stuck – Specific questions you are stuck on… “How do we…?”
- 🎯 5. Focus for the Next 2 Weeks – This creates commitment (when people you respect know what you have committed to, you organize your week differently.)
- 🙏 6. Help Us With – Your ask should connect directly to something already in the update.
Read the full breakdown here.
🏙️ 3. Article I’m Revisiting – Cities & Ambition by Paul Graham
Resurfaced this interesting piece from Paul Graham written in 2008 (18 years ago)!
The places we live send messages to us, whether we know it or not.
- New York says, “you should make more money.”
- Silicon Valley says, “you should be more powerful.”
- Los Angeles says, “you should be more beautiful.”
“No matter how determined you are, it’s hard not to be influenced by the people around you. It’s not so much that you do whatever a city expects of you, but that you get discouraged when no one around you cares about the same things you do.”
As someone who made the choice to move to an artist city in the mountains 4 years ago, I’ve been thinking a lot about what message I’m receiving here.
🌐 4. Berkshire Hathaway’s Website Footer – Is Awesome
If you know Warren Buffett and his company Berkshire Hathaway, it might not come as a surprise that their website looks straight out of 1995. ⬇️
But one little Easter egg I came across this week is in the footer of their site. Here’s what it says:
If you have any comments about our WEB page, you can write us at the address shown above. However, due to the limited number of personnel in our corporate office, we are unable to provide a direct response.
Beautiful.
🖐 5. More Things I’m Into This Week…
📙 Book I’m (Re)Reading – Hollow by Brian Catling
🍵 Sparkling Tea I’ve Been Enjoying – Copenhagen Sparkling Tea
🗞️ Article I Read This Week – Just Send The Fucking Email
🤖 Short Story I’m Re-reading – The Last Question by Isaac Asimov
💬 Quote I’m Pondering…
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:
- 💸 How To Charge More (COHORT 2 – MAY 4). Live cohort for entrepreneurs who want to scale their business by charging higher prices.
- 🤝 Creative Partnership (1:1). I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.