No. 347 | August 28, 2026
Welcome to Friday Five, a short collection of ideas to take into your weekend.
This week’s themes: putting up with the rain, the urgency of doing, swallowing the frog, learning from others’ mistakes, and playing the long game.
If this resonates, forward it to a friend. Most readers discover Friday Five because someone they trust shared it with them.
Music of the Week
“The way I see it, if you want the rainbow, you gotta put up with the rain.” — Dolly Parton
Dolly Parton was an American singer, songwriter, actress, and businesswoman who became one of the most recognizable faces in country music.
Widely revered as the “Queen of Country,” Parton earned 11 Grammy Awards, sold more than 100 million records, and became one of the most successful songwriters in popular music.
She wrote her first song when she was five and has spent more than seven decades writing and performing across country, bluegrass, gospel, pop, and rock.
She’s one of the country GOATS.
Start with “Jolene,” “9 to 5,” and “I Will Always Love You” to get a feel for her music catalog.
Quotes of the Week
“Thinking is easy, acting is difficult, and to put one’s thoughts into action is the most difficult thing in the world.” — Johann Wolfgang von Goethe
“We suffer more often in imagination than in reality.” — Seneca
“Well done is better than well said.” — Benjamin Franklin
Article of the Week
“If you have to swallow a frog, don’t look at it too long.” — Jim Clayton, quoting his grandfather
Adversity breeds resilience. Howard Schultz learned that early, watching his father struggle to make ends meet. Jim Clayton learned it growing up on a farm in Tennessee.
Play the long game. Jeff Bezos stayed focused on the customer and long-term growth despite pressure for short-term results. Clayton took a similar approach, learning to defer instant gratification once he had enough to live on.
The journey, not the destination, is the point. Stewart Butterfield learned this while building a video game called Glitch that ultimately failed. The team’s internal communication tool became Slack. Clayton embraced the same long-term mindset, spending years planning for succession and recognizing that he would eventually need to hand over leadership.
The takeaway from these four leaders: use adversity to your advantage, think in decades, not quarters, and stay present during your journey.
For more on how Schultz, Bezos, Butterfield, and Clayton thought about these principles, read:
📝 3 Business Lessons from Jim Clayton’s First, a Dream
Podcast of the Week
“Doing always beats thinking, the end.” — Gary Vaynerchuk
Gary Vaynerchuk is a busy guy. He runs multiple businesses spanning media, sports, wine, and venture capital.
He recently joined My First Million to talk about how he runs them.
Vaynerchuk also covers investing in yourself, being long-term greedy, the efficiency of 15-minute meetings, how to pick projects, the five-year bets he’s making, and removing toxic people from your life.
For more on Vaynerchuk, his businesses, and how he thinks about entrepreneurship, listen:
🎙️ How GaryVee Runs 7 Businesses
Book of the Week
“Failing is scary. Wasting your life is dangerous.” — Guy Raz
How I Built This shares lessons from successful entrepreneurs on how they turned ideas into enduring businesses.
The book is full of stories. Lots of them. Raz interviewed more than 200 successful entrepreneurs to learn about their journeys.
How did they come up with their idea? What’s the best way to raise money and recruit people to join you? How do you fend off competitors? And when do you start paying yourself?
These are the questions the book answers.
Core lessons from the book I can’t stop thinking about:
- Successful founders research and test their ideas before fully committing.
- Study other founders’ mistakes to find shortcuts and avoid mistakes of your own.
- True resilience requires shedding your ego when a crisis hits.
- Standing out requires storytelling and creative product positioning.
- Lean on mentors, friends, and family for advice and support.
- Purpose-driven businesses that solve real problems create lasting value.
For more on Raz, entrepreneurship, and learning from successful founders, read:
📚 How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs
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