Wisereads Vol. 94 — Second Act by Henry Oliver, Cate Hall on cringe, and more
Last week, we featured an excerpt of Elizabeth Weingarten's debut, How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty. This week, we're sharing a special preview of Henry Oliver's recent release, Second Act: What Late Bloomers Can Tell You About Success and Reinventing Your Life.
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Most highlighted Articles of the week
If you are useful, it doesn’t mean you are valued
An anonymous data leader reflects on what it looks like to be valuable to an organization, rather than just useful. "Being useful means that you are good at getting things done in a specific area, so that people above you can delegate that completely. You are reliable, efficient, maybe even indispensable in the short term. But you are seen primarily as a gap-filler... Being valued, on the other hand, means that you are brought into more conversations, not just to execute, but to help shape the direction."
Knowledge Work Is Dying—Here’s What Comes Next
In yet another take on what skills truly matter in an AI-driven world, Joe Hudson—founder of the Art of Accomplishment and executive coach—zeroes in on three that will set knowledge workers apart: emotional clarity, discernment, and connection. "The two building blocks of a company are (1) decisions and (2) relationships. Emotional clarity underpins both of these. It’s why people like Altman hire me, because they see emotional clarity as '[o]ne of the most critical skills in a post-AGI world.' Promotions in the age of wisdom won’t go to the people with the most impeccable spreadsheet, but to those who can transform a team’s silent anxiety into aligned action."
My AI Skeptic Friends Are All Nuts
Security researcher and software developer Thomas Ptacek makes a compelling case to his smartest, most skeptical friends who dismiss AI as a passing fad. His take: AI writes mediocre code. But mediocre code often gets the job done. "Professional software developers are in the business of solving practical problems for people with code. We are not, in our day jobs, artisans. Steve Jobs was wrong: we do not need to carve the unseen feet in the sculpture. Nobody cares if the logic board traces are pleasingly routed. If anything we build endures, it won’t be because the codebase was beautiful."
Most highlighted YouTube Video of the week
Crossing the Cringe Minefield with Cate Hall
In Packy McCormick’s latest interview, he sits down with Cate Hall—lawyer, poker player, composer, and COO—whose first Substack post, How to be More Agentic, went viral last year. Now, she’s back to explore a new idea: how chasing cringe can reveal personal growth opportunities. "The places where you feel that existential cringe, that's really uncomfortable, are actually the places where you can probably make the most progress as a person really quickly. It's a hard one to hear, but it's probably true."
Most highlighted Twitter Thread of the week
Taste
Clear error messages, intuitive UI, and features users didn’t ask for—but ended up needing—share a common thread: taste. It’s a quality startup investor Sara Guo has observed firsthand. "Think of it like running a restaurant. Anyone can follow recipes, source ingredients, and serve food. But the difference between a forgettable meal and a Michelin star isn't just technique—it's the chef's palate. Their ability to know when something needs more acid, when a dish has one element too many, when to stop plating. Software is the same. The best products aren't just feature-complete; they're composed."
Most highlighted PDF of the week
The Memory Paradox: Why Our Brains Need Knowledge In An Age Of AI
Experts in neuroscience, cognitive psychology, and learning theory join forces to explore the overlooked costs of separating knowledge from cognition. Think memorization is obsolete in the age of AI? Think again. "At the heart of effective learning are our brain's dual memory systems: one for explicit facts and concepts we consciously recall (declarative memory), and another for skills and routines that become second nature (procedural memory). Building genuine expertise often involves moving knowledge from the declarative system to the procedural system—practicing a fact or skill until it embeds deeply in the subconscious circuits that support intuition and fluent thinking. This is why a chess master can instantly recognize strategic patterns, or a novelist effortlessly deploy a rich vocabulary—countless hours of internalizing information have reshaped their neural networks."
Hand-picked book of the week
Second Act
Julia Child didn’t discover her passion for cooking until thirty-seven. Vera Wang launched her design business at forty. And Michelangelo painted The Last Judgment in his sixties.
In Second Act, Henry Oliver shifts our attention from child prodigies to late bloomers—both famous and forgotten—offering blueprints for reinvention through vivid case studies. Among them is Antonie van Leeuwenhoek, a former cloth trade apprentice who turned his fresh perspective toward the microscopic world:
"And so, aged forty-two, he looked at a drop of water from a lake and saw 'an abundance of little animals.' This was the foundation of microbiology. Two years later, he discovered bacteria, describing them as 'so small in my eye, that I judged, that if 100 of them lay one by another, they would not equal the length of a grain of sand.'"
We're thrilled that Henry is sharing this special preview of Second Act with Wisereads readers. If you enjoy his chapter on how networks can help launch your second act, the full book is available now—UK paperback, UK ebook, and all US formats.
Handpicked RSS feed of the week
Always happy; never satisfied
Pelion partner Tyler Hogge, formerly a product leader at Divvy and Wealthfront, shares insights on product, leadership, investing, and venture capital on his blog. From Pattern Matching 20 Habits of Exceptional Startups: "Just like startups don’t have distribution to cover up product deficiencies, they also don’t have time. Startups are dead by default. Every day the clock ticks, and every day a company burns money is one more day marched towards the cliff. As a result, exceptional startups have created cultures of intense, maniacal speed."