Brain Food: How Steve Jobs Learned to Lead
FS | BRAIN FOOD
Sept 6th, 2026 - #697 - read online - Free Version
Welcome to Brain Food, your weekly signal in a world full of noise.
Tiny Thoughts
*
Whatever pattern is repeating in your life has one common variable: you.
**
One of the worst qualities a person can have is the need to show how smart they are by catching others' mistakes. In some areas, this may be useful, but in general life, it's a disaster.
***
We tend to think the people who get ahead have more talent, better connections, greater opportunities, or better luck. Sometimes they do. But some of the strongest advantages aren't things you're given. They're things you do. Most people already know what they should do. The hard part is doing it when it’s boring, the payoff is far away, or no one is watching. That’s where your advantage comes from.
Insights
*
Computer scientist Sara Hooker on underestimating difficulty:
“The first step of any meaningful pursuit is to severely underestimate its difficulty.”
**
Coach Mike Tomlin on what you choose to do:
“It’s not what you are capable of; it’s what you are willing to do. Plenty of people are capable. Fewer people are willing.”
***
Charlie Munger on the Wooden Lesson:
“I think the great lesson of these careers is what I call The Wooden Lesson. And Wooden had the best basketball coaching record in the world, and nobody else was even close. How did he do it? The answer was, he concentrated almost 100% of the playing time on his top seven players. And of course, they got better and better during all the extra playing time. And that's what happens when you give so much power to a Wooden or a Buffett or something. You're doing the Wooden system, and it works like gangbusters, and as an investor, if you can find somebody, even as a mini-Wooden or a mini-Singleton or a mini-Buffett, and play them, and when they have a hell of a run, certainly that can be a very good way to invest.”
The Knowledge Project
Steve Jobs almost disappeared from history.
After Apple pushed him out, he spent the next 12 years fumbling and failing. NeXT lost money for nine straight years. All five of his co-founders left. He stubbornly walked away from deals that would have saved the company. His investors stopped answering his emails. Fortune wrote that Steve Jobs might be a “snake oil salesman.”
Jobs had the vision to change the world. What he did not yet have was the discipline to make that vision real.
By 1993, NeXT was one weekend from shutting down, and Jobs was nearly out of money. That's when everything changed. Those years taught him how to focus, trust talented people, and pragmatically compromise. They turned the founder Apple rejected into the leader Apple would eventually need.
I sat down with biographer Geoffrey Cain to reconstruct Jobs’s lost decade and unpack how to tell conviction from self-deception, when a leader should hold the line, when they must let go, and why resilience without discipline is not enough.
This is how Steve Jobs became Steve Jobs.
+ Listen and Learn: YouTube | Spotify | Apple | Web/Transcript
+ Members have access to an extended version of the conversation.
SPONSOR
Stay hydrated this summer without the sugar, food dye, and other dodgy ingredients found in popular electrolyte and sports drinks. LMNT is a science-backed, zero-sugar electrolyte drink mix that supports active hydration and a healthy lifestyle. They now have Lemonade Iced Tea, which offers their science-backed electrolyte formulation plus naturally occurring caffeine (50mg), L-Theanine, and polyphenols for a powerful blend of antioxidants. It tastes amazing! Brain Food Readers get a special deal. Visit https://drinklmnt.com/FarnamStreet for a free sample pack with any drink mix purchase!
Thanks for reading. I'll see you next week.
— Shane Parrish
P.S. Is this really how people in Scotland got dressed more than 500 years ago?
Want to share this edition with a friend? Use this link: https://fs.blog/brain-food/september-6-2026/
Upgrade Yourself
Members get access to my reading highlights, ad-free newsletters and podcasts, hand-edited transcripts, early access, AMAs, and so much more. Join us → here.
