rw-book-cover

Metadata

Highlights

  • Before AI, knowledge set you apart. Knowing more meant earning more. Accumulating skills, developing expertise, and mastering frameworks got you ahead. (View Highlight)
  • Today, as models swallow entire fields overnight, wisdom—skills like emotional clarity, discernment, and connection—is what keeps you indispensable. As CEO of Microsoft, Satya Nadella made it a priority to instill these capacities throughout his organization. In eight years, the company’s market capitalization climbed from 3 trillion. (View Highlight)
  • They are building the technology that will make their own skills obsolete. In the not-too-distant future, AGI will be able to do what they can do today—faster, cheaper, and at scale. (View Highlight)
  • My job is to help these leaders develop their abilities in areas that AI cannot replicate. I help them lead not from fear, ego, or having something to prove, but from a deeper place of wisdom. (View Highlight)
  • AI models don’t sleep or burn out; they can absorb entire fields of study in days. One highly trained model will soon be able to outperform an expert in physics, law, and engineering—simultaneously, at any hour. Facts, skills, and expertise will be increasingly commoditized, and even the smartest of us will be replaceable*.* (View Highlight)
  • Our entire society is built around knowledge as a scarce, precious resource. School systems, standardized tests, Ivy League pipelines, job interviews, LinkedIn profiles are all mechanisms to measure, prove, and reward how much you know. Hence the rise of over 1 billion knowledge workers: professionals valued for what they knew and could do, like lawyers, engineers, consultants, and programmers. (View Highlight)
  • Now, imagine a world where all that is irrelevant, akin to the ability to build a fire today—occasionally useful, but mostly unnecessary in a world with light bulbs, central heating, and stove tops. (View Highlight)
  • extraordinary knowledge or skill created a protective moat around bad behavior; people muttered, “That’s just how they are,” and kept the peace. But when a model can draft the brief, diagnose the anomaly, or optimize the market strategy in seconds—and do it politely—why keep paying the emotional tax of a brilliant jerk? (View Highlight)
  • And when knowledge is no longer scarce, what remains valuable? Wisdom. You can get answers from AI, but how you use those answers takes wisdom. (View Highlight)
  • Wisdom is how to live. It is the residue of mistakes, metabolized by time and reflection. It can’t be rushed, and it can’t be copy-pasted. It is an embodied—as in felt in the body—experience, guidance from the inside. (View Highlight)
  • No matter how intelligent AI becomes, it can’t live your life for you. It can’t feel your body’s signal in a high-stakes negotiation, sense the hidden fear in a boardroom, or hear the unspoken “no” behind a client’s polite words. (View Highlight)
  • That’s why tomorrow’s economy will prize wisdom workers. Let’s dive into their three core skills: emotional clarity, discernment, and connection. (View Highlight)
  • Most people think emotional work is about becoming more “regulated” or less reactive. Two of the main strategies I see today are:
    1. Emotional repression. We numb, distract, stay busy, avoid certain topics, or intellectualize. We tell ourselves we’ve “moved on” or “let go” when, in fact, we’ve buried something alive inside of us.
    2. Emotional management. The well-meaning attempt to “handle” feelings. We try to breathe through them, exorcise them by writing in a journal, reframe them, or meditate until they pass. (View Highlight)
  • Whether repressed or managed, avoided emotions don’t go away. They return in a pattern I call the “golden algorithm.” It goes like this:
    1. Name an unwanted emotion in your life.
    2. List the ways you try to avoid it.
    3. Notice that every way you try to avoid it, you actually create it. For example: I don’t want to feel like a failure —> I play it safe —> I feel like a failure. (View Highlight)
  • With emotional clarity, on the other hand, you take your emotions seriously, but not literally. It is the ability to recognize your emotions, feel them, and move forward unobstructed—the difference between being caught in the storm and becoming the sky that holds it. Surveys show that this kind of emotional intelligence is already the number-one criteria for managers when considering a team member for a promotion or salary increase. (View Highlight)
  • Obsessing over pros and cons lists? Finding yourself in a recurring pattern? Ruminating at night about how to avoid a company setback? These aren’t thinking problems; they’re feeling problems. In fact, studies show that when the emotional center of your brain is impaired, your IQ stays the same, but it takes hours to make a simple decision—like where to eat or what pen color to choose. Neurologically speaking—and contrary to popular belief—we don’t make logical decisions. We make emotional ones. And emotional avoidance clouds our decision-making. (View Highlight)
  • Psychologists echo this: Chronic procrastination shows up less as a time-management failure and more as an emotional struggle—we delay to dodge anxiety, self-doubt, or fear of failure. (View Highlight)
  • Some of the most brilliant founders, executives, and creative professionals I’ve worked with weren’t stuck because they lacked intelligence or strategy. They were stuck because they didn’t know how to deal with their emotions. They avoided discomfort or bypassed fear. And they made reactive choices—ones that felt smart in the moment but cost them deeply in the long run. Sometimes it meant burning out their team or walking away from an opportunity too soon, and other times it meant chasing the wrong metric for years. (View Highlight)
  • Companies are increasingly adopting AI into their workflows—Moderna just plugged more than 3,000 custom GPT agents into every corner of the company, for example. As models handle more and more tasks of execution, people’s jobs will be more focused on decision-making, and emotional clarity will be even more valued than it is today. Indeed, 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. (View Highlight)
  • Too much choice stalls action. In the famous “jam study,” shoppers presented with 24 flavors bought jam 3 percent of the time, while those offered just six flavors purchased 30 percent of the time—a 10-fold jump. • Information overload erodes well-being. Two-thirds of managers report that constant data flow lowers job satisfaction, and one-third believes it harms their health. • Analysis paralysis kills action. Research by Deloitte in 2024 showed data overload is the number-one source of “analysis paralysis” in the C-suite. (View Highlight)
  • What most people don’t realize is that your relationship with yourself sets the tone for everything else. If you don’t trust yourself, you won’t trust your team. If you shut down your own desires, you’ll feel resentful of others’ wants. If you’re judging other people, you’ll judge yourself even more. (View Highlight)
  • I’ve worked closely with some of the most accomplished people in the world—people leading multi-billion-dollar companies, building cutting-edge AI tools, or running high-stakes creative teams. The biggest barrier to their growth is almost always the way they relate to themselves when things get hard—or even when they are great. (View Highlight)
  • Here’s an experiment you can try: For 20 minutes every day for a week, listen to the critical voice in your head*.
    1. Every time it is mean, say “ouch.”
    2. Every time it tells you that you messed up, say “ouch.”
    3. Every time it tries to make you feel small, say “ouch.”
    4. Every time it tells you you can’t do something that other people can do, say “ouch.”
    5. Every time it nags you to do something, say “ouch.” (View Highlight)
  • The majority of us have been taught that connection is earned through achievement. We believe that once we become successful, smart, or generous enough, we’ll be worthy of connection. (View Highlight)
  • But people don’t want you to be perfect. They want to be connected to you. This doesn’t mean charisma in the traditional sense; instead, it’s deep relational presence—the ability to attune to others, see and be seen, and create safety even when pressure is high. The foundation of my coaching is built on connection. I teach it through a framework called VIEW: Vulnerability, Impartiality, Empathy, and Wonder. (View Highlight)
  • When you stop performing and start relating from a place of vulnerability and openness, people can feel you. And that feeling is what builds trust, safety, and deep connection. (View Highlight)
  • This skill will matter more than ever when knowing things is no longer primary to being effective. Studies show that teams whose members feel safe to speak up learn faster and hit their targets more often. Google’s Project Aristotle, which set out to understand what made teams successful, found that of all variables studied, psychological safety was the number-one predictor of high-performing teams. (View Highlight)
  • While people do grow attached to chatbots and develop bonds that soothe loneliness, these connections are fundamentally parasocial and transactional: The flow of care moves in one direction; AI has no skin in the game. Deep connection demands mutual, embodied relational presence—nervous systems coregulating through micro-expressions, tone shifts, and even subtle changes in breathing. AI can model supportive language, but it cannot feel surprise when you walk into the room, nor does its pulse quicken when you share bad news. (View Highlight)
  • The Harvard Study of Adult Development—the world’s longest-running longitudinal study, tracking people since 1938—found that the single strongest predictor of both happiness and physical health in old age was the warmth of participants’ close relationships. In fact, quality of connection at age 50 predicted health at 80 better than cholesterol levels did. (View Highlight)
  • No matter how powerful AI becomes, if you want to feel fulfilled, you’ll still need to be deeply connected with other humans. If you want to change the world, you’ll need to be deeply connected with other humans. If you want to be a part of a high-performing team, you’ll need to be deeply connected with other humans. (View Highlight)
  • How you answer these questions will set you apart: What do I want and how do I own it? What kind of leader do I want to be? What’s the most effective thing for me to be doing at this moment? What does “effective” even mean to me? These are not problems of knowledge or information. They are a matter of wisdom. (View Highlight)
  • It’s clear to many that we’re already stepping into the age of wisdom work. Every CEO Dan Shipper points to the rise of the allocation economy, where the advent of AI means everyone will become a manager: “You won’t be judged on how much you know, but instead on how well you can allocate and manage the resources to get work done.” Being a great manager requires all three of the skills I’ve described. (View Highlight)