No. 332 | May 15, 2026
Welcome to Friday Five, a short dose of ideas for your weekend.
How you do anything is how you do everything. Regret often comes from ignoring what genuinely interests you. Curiosity rarely follows a straight path, but it often leads to meaningful work.
If this resonates, forward it to a friend. Most readers discover Friday Five that way.
This Week in Friday Five
🎵 Three songs to start with: Phish
💬 How you do anything is how you do everything
📝 Regret comes from not trying
📚 Bill Gurley on chasing curiosity
🎙️ Jeremy Allen White on film and television
Music of the Week
Phish is a rock band from Vermont formed in the early 1980s, consisting of Trey Anastasio, Mike Gordon, Jon Fishman, and Page McConnell.
Their music blends funk, reggae, rock, folk, country, jazz, blues, bluegrass, electronic, and pop. Somehow, it still sounds unmistakably like Phish.
Start with “Free,” “Back on the Train,” and “Bouncing Around the Room.”
🎵 Phish
Quotes of the Week
How you do anything is how you do everything. Small tasks reveal discipline, standards, and character. These quotes capture that idea:
“We are what we repeatedly do. Excellence, therefore, is not an act but a habit.” — Aristotle
“The only way to do great work is to love what you do.” — Steve Jobs
“In any moment of decision, the best thing you can do is the right thing. The worst thing you can do is nothing.” — Theodore Roosevelt
“Eighty percent of success is showing up.” — Woody Allen
Article of the Week
“I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.” — Jeff Bezos
Jeff Bezos starts an online bookstore with a relentless Day 1 mindset.
An elderly man in Japan rides his bike to work into his 90s because he still has a reason to get up every morning.
Roger Federer learns to control frustration by mastering the mental side of tennis.
Arthur Blank and Bernie Marcus are fired, then build a better hardware store than the one that pushed them out.
The common thread is simple: focus on what’s ahead instead of staring into the rear-view mirror.
These themes run through one of my recent reading lists:
📝 March Reading List: 4 Best Books I Read in March 2026
Book of the Week
Bill Gurley took a tech job after college. On paper, it looked perfect. He hated it. Eventually, he found his way into venture capital instead.
That tension sits at the center of Runnin’ Down a Dream, a book about choosing genuine interest over comfort or convention.
Gurley argues that great careers are built through curiosity, apprenticeship, and decades of compounding effort. He uses stories from people like Danny Meyer and Sam Hinkie to show what enduring success actually looks like.
A few principles that stayed with me:
- Chase subjects you can’t stop thinking about
- Build technical mastery through years of deliberate practice
- Surround yourself with ambitious and talented people
- Put yourself where the best work in your field is happening
- Treat rejection as part of the process
- View your career as a long-term apprenticeship
For more on Gurley and building a meaningful career:
📚 Runnin’ Down a Dream: How to Thrive in a Career You Actually Love
Podcast of the Week
Jeremy Allen White is an actor from New York City who has won both Golden Globe and Primetime Emmy Awards.
He recently starred in one of my favorite shows, The Bear, and portrayed Bruce Springsteen in Deliver Me from Nowhere.
White recently joined the Smartless podcast to discuss acting, dancing, dream roles, and building a career in film and television.
For more on White and his path:
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