The Examined Life

I asked AI to roast me. It wasn't pretty. Then it said, “Do you want me to be meaner?” The exchange was testy and agitating. It then asked, if I want it to go “nuclear.” Is this an AI slippery slope? Who owns our memories? Is creativity at risk? And should we let our kids interact with ChatGPT? [Episode 104]References from the show:• Subscribe to Future-Proof your Career with AI newsletter: https://khemaridh.substack.com/• ChatGPT's updated memory changes the game: https://open.substack.com/pub/khemaridh/p/im-finally-ready-to-commit-to-chatgpt—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Should we be avoiding our uncomfortable emotions? Clinical psychologist, Emily Anhalt explores how we consistently avoid feelings like shame, grief, and sadness through work, substances, or disassociation. Emotional fitness isn't about eliminating these emotions but learning to become comfortable with discomfort. [Episode 103]Dr. Emily Anhalt is a clinical psychologist and author.Learn more about Emily:• Emily's Website: https://www.dremilyanhalt.com/• Emily's Book: https://www.dremilyanhalt.com/book• Instagram: https://www.instagram.com/dremilyanhalt/• X/Twitter: https://x.com/dremilyanhalt• LinkedIn: https://www.linkedin.com/in/dremilyanhalt/—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

I left Wall Street 10 years ago. Was it the right decision? What would I have done differently? 10 years is a long time — and comes with a lot of data points to assess the decision. [Episode 102]References from the show:• Walking away from a $2 million salary on Wall Street (with no plan): https://youtu.be/sy4FGaYK_l0• I Left a $2 Million Job. Here's What I Wish People Had Told Me: https://youtu.be/Ypwp4RICGoc?feature=shared• Are you a Post-Achievement Professional?: https://www.khehy.com/post-achievement-professional—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Can you achieve the American Dream by saving half your paycheck? Sam Dogen, founder of Financial Samurai, left Wall Street at 34 with a seven-figure nest egg after a demanding investment banking career. He saved “until it hurts” but would he do it differently? We discuss real estate, generational wealth, and financial freedom. [Episode 101]Sam Dogen is the founder of Financial Samurai, one of the most visited sites on Financial Independence and Early Retirement.Learn more about Sam:• Financial Samurai: https://www.financialsamurai.com/who-is-sam-dogen-founder-of-financial-samurai/• LinkedIn: https://www.linkedin.com/in/sam-dogen-aa2152178/• X/Twitter: https://x.com/financialsamura?lang=en—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What happens when men hit their 40s with all the trappings of success but a gnawing emptiness inside? Greg Scheinman shares his awakening at 47 — the same age his father died — when he realized professional achievement alone wasn't enough. He introduces his "six F's" framework (family, fitness, finance, food, fashion, and fun) as a roadmap for midlife men stuck in the "over-indexing trap" of prioritizing career above all else. Instead of fearing midlife as the beginning of the end, Greg challenges men to embrace this season as their opportunity to rewrite the script and find authentic fulfillment. [Episode 100]Greg Scheinman is the Founder & CEO of Midlife Male Ventures, Bestselling Author, Coach, Speaker, & Entrepreneur.Learn more about Greg:• The Midlife Male: https://midlifemale.com/• Greg's LinkedIn: https://www.linkedin.com/in/greg-scheinman-b442004/• Greg's Instagram: https://www.instagram.com/gregscheinman/?hl=en—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What happens when your world shatters with the unimaginable loss of a child? Mary Anne Keegan shares her raw journey after her healthy 20-year-old son Matthew was suddenly diagnosed with cancer and passed away just ten months later. She discovered that grief doesn't follow a playbook — giving yourself grace becomes essential when navigating between holding tight to memories and building a new life entirely. [Episode 99]Mary Anne Keegan is the CEO of a fractional marketing firm and is involved with the Matthew Keegan Memorial Scholarship Foundation. Learn more about Mary Anne:• LinkedIn: https://www.linkedin.com/in/makeegan/• Matthew Keegan Memorial Scholarship: https://www.asufoundation.org/education-and-scholarship/donor-named-funds/the-matthew-keegan-memorial-scholarship-CA125360.html—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Can capturing untold stories heal decades-old wounds? When Dorothy Chow set up a makeshift podcast studio to record her father's Khmer Rouge survival story, she had no idea what would unfold. What began as a historical preservation project transformed into profound healing for both father and daughter. [Episode 98]Dorothy Chow is the Host of the Death in Cambodia podcast.Learn more about Dorothy:• Death in Cambodia, Life in America Podcast: https://www.deathincambodiapodcast.com/• Dorothy's Instagram: https://www.instagram.com/deathincambodia/?hl=en• Dorothy's LinkedIn: https://www.linkedin.com/in/dschowcapm/—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

To understand today's market turmoil we need to take a page out of history. This a deep-dive (and front row perspective) on the global financial crisis from 2008. You'll learn about excess leverage, liquidity crisis, the failure of risk models, and Wall Street impacting Main Street. This will help you decide if you should “do anything.” [Episode 97]JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

The economy is broken and everything is going to sh*t. That's the current narrative. But I attended a FIRE (Financial Independence, Retire Early) conference and discovered a thriving community completely defying this narrative. These professionals, not bankers or FANG engineers were nurses, teachers, IT managers. They save aggressively, embrace frugality without suffering, and build very intentional lives. [Episode 96]References from the show:• Why do people hate on financial independence and early retirement (aka FIRE): https://www.khehy.com/why-do-people-hate-on-financial-independence-and-early-retirement-aka-fire—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What happens when career advancement requires you to be manipulative, bossy, and a bit reckless? Jenny Wood's meteoric rise at Google reveals that success often demands breaking unspoken rules. From strategically meeting your boss's boss to mastering the Monday MiniFesto, Jenny shares how walking the line between authentic boldness and calculated self-promotion propelled her career. But beneath these tactics lies a deeper truth – it's not about becoming cutthroat, but about pushing past the fear of judgment that keeps most people playing small. [Episode 95]Jenny Wood is a former Google Executive, author and entrepreneur.Learn more about Jenny:• Website: https://itsjennywood.com/• LinkedIn: https://www.linkedin.com/in/jennyilles• X/Twitter: https://x.com/itsjennywood?lang=en• Instagram: https://www.instagram.com/itsjennywood/—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Is your identity preventing you from making a necessary change? The golden child, the one who spent decades climbing the corporate ladder, often stays miserable because they can't separate who they are from what they do. Annie Duke reminds us that even the toughest career pivots are surprisingly reversible, and encourages us to imagine what we'd do with those reclaimed 60 hours each week if we finally walked away. [Episode 94]Annie Duke is an Author, Professional Speaker & Decision StrategistLearn more about Annie:• Annie's Website: https://www.annieduke.com/• LinkedIn: https://www.linkedin.com/in/annie-duke/• X/Twitter: https://x.com/annieduke?lang=enReferences from the show:• Your Future Self by Hal Hershfield: https://www.halhershfield.com/yourfutureself• How to Change by Katy Milkman: https://www.katymilkman.com/book• Alliance for Decision Education: https://alliancefordecisioneducation.org/• The Decision Education Podcast: https://alliancefordecisioneducation.org/podcasts/—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Markets are selling off. Quick, how do you react? I've been long (i.e. no selling) since 1999. Yup, 25 years. But that doesn't mean that major sell-offs don't test my resolve. It's particularly hard given our unique financial situation: lots of financial assets, no cash, low income and high spending. So how do we do it? [Episode 93]References from the show:• How to stay calm in a bear market: https://www.khehy.com/how-to-stay-calm-in-a-bear-market—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What happens when you hit a career crossroads and don't know which path to take? Anne-Laure Le Cunff discusses navigating "liminal spaces" – those uncomfortable in-between periods where you've left something behind something familiar but haven't yet found what's next. Instead of rushing to the nearest known thing or following the obvious sequel to your career, she offers pragmatic steps to thrive in the uncertainty. [Episode 92]Anne-Laure Le Cunff is a Neuroscientist, Ex-Googler, Founder and Author.Learn more about Anne-Laure:• LinkedIn: https://www.linkedin.com/in/neuranne/?originalSubdomain=uk• X/Twitter: https://x.com/neuranne• Instagram: https://www.instagram.com/neuranne/?hl=en• YouTube: https://www.youtube.com/@neuranne• Tiny Experiments Book: https://nesslabs.com/book—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What happens when a brain tumor forces you to actually take a break and stop? After decades in management consulting and startups, Steve Mallouk's diagnosis made him confront the difference between chasing "enough" money versus "enough" life experiences. His journey from BCG partner to embracing vulnerability reveals how facing mortality can have unintended consequences. [Episode 91]Steven Mallouk is a happily retired executive living life to the fullest.Learn more about Steven:• LinkedIn: https://www.linkedin.com/in/stevemallouk/References from the show:• My wish this Christmas: More of the gift of life itself.: https://www.linkedin.com/pulse/my-wish-christmas-more-gift-life-itself-steve-mallouk-3hhbc/• My Update, 4 Weeks After Brain Surgery: https://www.linkedin.com/pulse/my-update-4-weeks-after-brain-surgery-steve-mallouk-thszc/—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Is your drive for success killing you? Lou Marchetti was a private equity Master of the Universe until he dropped dead during a CrossFit workout. (Yes, he had a heart attack.) Despite this wake-up call, it took getting fired two years later to finally confront the deeper void his relentless achievement was trying to fill, leading him on a journey from compulsive doing to conscious being. [Episode 90]Learn more about Lou:• LinkedIn: https://www.linkedin.com/in/louis-marchetti-b513612/References from the show:• Living the Questions: https://ltq.kit.com/48ef4c404a—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

What the heck is happening to the internet? Why does everything feel so different now? Between algorithmic feeds optimizing for outrage, AI-generated content flooding our feeds, and the commodification of our attention, we're watching the entire digital landscape transform in real-time. What does this mean for connection, authenticity and truly expressing our human-ness? [Episode 89]Here's how I'm learning how to code using AI (affiliate):https://buildyourownapps.com?affiliate_code=86e5a8—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:

Is the 40-hour work week dead? Elle Griffin's research shows that 70% of salaried workers clock less than 40 hours. But here's the twist: as AI and automation make us more efficient, we're not necessarily working less – we're choosing to create more. From remote software engineers to newsletter writers, the future isn't about less work, it's about having the freedom to choose how we spend our time. [Episode 88] Elle Griffin is the founder of the media cooperative The Elysian. Learn more about Elle: • Elle's Website • Elle's LinkedIn • The Elysian Substack • The Elysian YouTube channel References from the show: • Are 20-hour workweeks on their way? • How many hours do you actually work at your salary job? • Is your company wasting your time? • Is it for work or for pleasure? • You'd still work if you didn't have to • Will we return to craftwork? —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Are solopreneurs destined to be stuck trading time for money? Serial entrepreneur Bart Egnal breaks down the traps of scaling a service business — where more revenue often leads to lower profits and bigger headaches. As entrepreneurs hit different revenue breakpoints, they face crucial decisions about hiring, systematizing their IP, and most importantly, whether scaling aligns with their deeper motivations beyond just watching "the numbers go up.” [Episode 87] Bart Egnal is the CEO at The Humphrey Group and Chairman at the Niagara Institute. Learn more about Bart: • Bart's LinkedIn • The Inspire Podcast • The Humphrey Group Blog —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

What happens when a founder walks away from $60 million after selling his company? Post-achievement entrepreneurs often find themselves chasing bigger highs yet nothing fills the void of being without a rudder. Loom co-founder Vinay Hiramath's candid story reveals a deeper truth about conditional love and validation that many children of immigrants face: the crushing fear of being ordinary [Episode 86] References from the show: • I am rich and have no idea what to do with my life —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

What happens when your spouse's startup explodes and you're suddenly worth $20 million? The anonymous spouse of a successful founder shares the real truth about identity earthquakes, unconscious power shifts, and the loneliness of being the "hidden partner" in entrepreneurial marriages. She candidly reveals how couples navigate the psychological whiplash of going from breadwinner to background character and why entrepreneurs get divorced when they finally "make it.” [Episode 85] Photo by Kiwihug on Unsplash —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

What if we've been thinking about retirement planning all wrong? Christine Benz, Morningstar's personal finance expert, breaks down how our obsession with the financial aspects of retirement often overshadows other priorities like relationships and purpose. Drawing from her new book "How to Retire," she challenges the conventional wisdom that you'll spend the same in retirement as during your peak earning years, revealing how real retiree spending follows a surprising "smile" pattern. [Episode 84] Christine Benz is the Director of Personal Finance and Retirement Planning at Morningstar. Learn more about Christine: • Connect with Christine on X/Twitter • Connect with Christine on LinkedIn • Christine at Morningstar • Read Christine's Book: How to Retire —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

If you're looking to ditch anxiety, overwhelm and comparison — this episode's for you. Executive coach Joe Hudson put out a list of steps to develop your emotional resilience and Khe reacts to the entire list. I promise you'll find a handful that resonate. [Episode 83] And if you have a Big Decision to make in 2025 check out Joe Hudson's Great Decisions course. RadReaders will receive a $300 discount using discount code RADREADS. Sign up at: https://view.life/radreads (code: RADREADS) —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Is searching for your life's purpose causing more anxiety than fulfillment? Jordan Grumet, a former doctor turned author and podcaster, discovered that chasing "Big P" purpose – those audacious, society-approved goals – often leads to burnout and emptiness. Instead, he advocates for embracing "Little P" purpose: the small, joy-filled activities that light us up, which paradoxically can create deeper impact and meaning than grand aspirations ever could. [Episode 82] Jordan Grumet is an author, hospice doctor, and financial expert who explores the intersection of medicine, wealth, and meaningful living through his writing and podcasting. Learn more about Jordan: • Jordan's Substack • Earn & Invest Podcast • Jordan's Books • Jordan's LinkedIn • Jordan's X/Twitter References from the show: • Breaking free from a life that doesn't fit • Becoming a millionaire won't solve this problem. —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

We would love to live in another country with my kids. But there's inertia, logistics and — let's be honest — a baked in view (for Americans) that despite its warts, life is pretty good here. I'm inspired by families who challenge conventions and blow things up a bit — especially if they have kids. Tiago Forte and Lauren Valdez left comfy Southern California for Valle Del Bravo in Mexico. [Episode 81] Tiago and Lauren are the co-founders of Forte Labs and the Building a Second Brain franchise. Learn more about Tiago and Lauren: Forte Labs: https://fortelabs.com/blog/why-were-moving-to-valle-de-bravo-mexico/ Substack: https://laurenvaldez.substack.com/ X/Twitter: https://x.com/fortelabs YouTube: https://www.youtube.com/@TiagoForte Instagram: https://www.instagram.com/fortelabsco/profilecard/?igsh=MTkzZWdtbnh3NWxoOQ== —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Modern life doesn't allow us to take a pause, zoom out and reflect on our lives. We're always putting out the latest fire drill or reacting to an endless stream of work messages — but how do we know if we're doing life right? Follow along with this 16-part interactive Q&A. [Episode 80] —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Are our kids buckling under the pressure of academics and sports? Achievement culture flows downstream from ambitious parents who are looking to “future proof” their kids. It comes from a place of love, but comes at the steep cost of mental health challenges. [Episode 79] Jennifer Wallace is a journalist, mother and author of the book Never Enough: When Achievement Culture Becomes Toxic-and What We Can Do About It. Learn more about Jennifer: Jennifer's Book, "Never Enough": https://www.amazon.com/Never-Enough-Achievement-Culture-Toxic/dp/0593191862 Jennifer's Website: https://www.jenniferbwallace.com/articles Jennifer's Instagram: https://www.instagram.com/jenniferbrehenywallace/?hl=en —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

I often joke that my love language is simple. “No thank you.” After all, if you don't put yourself out there — you can't get hurt. How much does a marriage suffer when your love languages talk right past each other? [Episode 78] Sunil Arora is an executive coach, father and husband. Learn more about Sunil: Sunil's LinkedIn: https://www.linkedin.com/in/sunil-arora-1b7a905/ Sunil's X/Twitter: https://x.com/sdotarora?lang=en —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

What does it mean to truly surrender into love? It means putting yourself out there and being vulnerable. And also that you could get hurt. I went on my second psychedelic journey to understand why I am scared to love my wife in the deepest and most sincere way. [Episode 77] References from the show: My first psychedelic journey was a chaotic and insightful mess.: https://youtu.be/vANnWVQ9hcE —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Jack was going through the motions during his investment banking job. He was told that this was his dream job, but it was soul-less. Plus, he didn't want what the folks ten years older than him had. But then a side project researching crypto led to a dream opportunity. But was it really a dream job? [Episode 76] Jack Purdy is the Director of Sales at Messari, Web 3 research firm. Learn more about Jack: Jack's X/Twitter: https://x.com/jpurd17 Jack's Website: https://www.jackpurdy.io/about Jack's Substack: https://examininglife.substack.com/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Carrie Sun went down the high-earning finance path and walked away. She attended Wharton's MBA program and dropped out to pursue a writing career which led her to one of the world's largest hedge funds as the CIO's executive assistant. This was meant to serve as a bridge to her creative career, but instead led her to burn out spectacularly. [Episode 75] Carrie Sun is the author of Private Equity. She started her career in financial services. Learn more about Carrie: Carrie's Website: https://www.carriesun.com/ Carrie's Book: Private Equity : https://www.penguinrandomhouse.com/books/727375/private-equity-by-carrie-sun/ Carrie's Instagram: https://www.instagram.com/carrieyisun/?hl=en —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Imagine going from 60-hour weeks to a semi-retired life of leisure. But if you give up goals and the relentless pursuit of ambition, what is left? Are you a dilettante, who grazes at ideas without putting anything into action? [Episode 74] —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

It's rare to see someone leave the McKinsey/BCG track to become a writer. This involves financial sacrifices and an “Identity Earthquake.” But what do you gain? The right to creatively express yourself and to know that you are living in alignment. And that you're doing your Good Work. [Episode 73] Paul Millerd is the author of Good Work and The Pathless Path. Links: Paul's Website: https://pmillerd.com/ Paul's YouTube: https://www.youtube.com/c/PaulMillerd Paul's LinkedIn: https://www.linkedin.com/in/paulmillerd/ Paul's Instagram: https://www.instagram.com/pathlesspaul/?hl=en Paul's Substack: https://substack.com/@paulmillerd Good Work Book: https://pmillerd.com/goodwork/ The Pathless Path Book: https://pathlesspath.com/ The Pathless Path Podcast: https://pathlesspath.com/podcast/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Midlife, it's more of a mindset than a specific age, right? Well, it's also that wide age range of 40-60 when you start questioning your financial reality, career decisions and — the big kahuna — your own mortality. What role do relationships, shame and vulnerability play in navigating mid-life? [Episode 72] Erin Cochran is the co-founder of the Midlife conference and the branding agency Iced Coffee, Please. Learn more about Erin: Instagram: https://www.instagram.com/ciderhouseroadie/ LinkedIn: https://www.linkedin.com/in/eskinner/ What Madeleine Albright taught me about work-life balance: https://www.washingtonpost.com/news/parenting/wp/2018/02/22/what-madeleine-albright-taught-me-about-career-choices/ The Midlife Conference: https://www.themidlifeconference.com/ References from the show:—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

I left a high-paying job on Wall Street to become a *checks notes* influencer? This wasn't a planned career choice, yet here we are nearly a decade later. I discuss my history as a thought leader, how I would do things if I were starting today and how it's really hard to crack $250,000. [Episode 71] References from the show: The $645,099 business pivot: https://radreads.co/pivot/ Quitting Wall Street to become a creator: https://www.youtube.com/watch?v=-n_HlDRQXI8 —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER:  ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career. ⁠⁠⁠⁠⁠

Who wouldn't pursue financial independence and early retirement (aka FIRE)? The path to get there includes frugality and investing. But what happens when you hit the “number?” And are there more realistic ways of getting the benefits of FIRE? [Episode 70] Learn more about Diania: Diania's LinkedIn: https://www.linkedin.com/in/dianiamerriam/ EconoMe Conference: https://economeconference.com/our-schedule/ References from the show: CNBC article: This 35-year-old has a net worth of $470,000... https://www.cnbc.com/2022/09/22/diania-merriam-semi-retired-in-her-30s-now-she-works-7point5-hours-per-week.html NYT article: Your Neighbors are Retiring in their 30s. Why can't you?https://www.nytimes.com/2024/05/07/magazine/retire-early-saving.html  Why do people hate on financial independence and early retirement (aka FIRE): https://radreads.co/why-do-people-hate-on-financial-independence-and-early-retirement-aka-fire/ The dubious promise of financial independence: https://radreads.co/the-dubious-promise-of-financial-independence/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Being a part of an IPO is a dream. Especially when you're the 6th employee. Rick Foerster played the long game and 12 years later left a $2.25 billion company with the freedom to make many new choices. But he struggled with the loss of identity, purpose and meaning. [Episode 69] Rick Foerster is a former healthcare executive and writes at The Way of Work.Learn more about Rick: Rick's LinkedIn: https://www.linkedin.com/in/richardfoerster/ Rick's X/Twitter: https://twitter.com/rickfoe Rick's Substack: https://substack.com/@rickfoerster The Way of Work: https://www.thewayofwork.com/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

I cannot afford to buy the house I rent. Is that a feature or a bug? A deep-dive on the under-discussed variables of home ownership. [Episode 68] References from the show: I spent $1,140,000 on rent. Here's everything I learned: https://youtu.be/L5ZEk3rtCbw?si=-W_m7fxpH8Y6X999 The hidden benefits of renting (over buying): https://radreads.co/the-hidden-benefits-of-renting-over-buying/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

You're reading the wrong books. The pop-psy self-improvement cannon is rife with recycled takeaways that don't actually change you. However, many professionals resist reading fiction. It feels indulgent, pointless and definitely doesn't give you new marketable skills — but that might be missing the bigger picture. [Episode 67] Anna is a founder and community builder. She's a voracious reader and polymath.Learn more about Anna: Anna's Website: https://www.annagat.com/ X/Twitter: https://x.com/TheAnnaGat Interintellect: https://interintellect.com/ —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career. ⁠⁠⁠⁠⁠

We've been thinking about networking wrong this entire time. Let's flip the script and focus instead on adding value, deepening connection and staying in touch. These strategies can then help you change careers, improve your “business development” and increasing your surface of luck. Mo Bunnell is the founder and CEO of Bunnell Idea Group (BIG), a consulting and training company that specializes in helping professionals improve their business development and client relationship skills. He's the author of Give to Grow and The Snowball System. [Episode 66] Links: Real Relationships, Real Revenue Podcast: https://bunnellideagroup.com/podcast/ Give to Grow Book: https://bunnellideagroup.com/givetogrow/ X/Twitter: https://x.com/MoBunnell LinkedIn: https://www.linkedin.com/in/mobunnell —-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠—-BECOME A RADREADER: ⁠⁠⁠⁠⁠Join 50,000+ ambitious professionals⁠⁠⁠⁠⁠ for our weekly essays on productivity, money and career.⁠⁠⁠⁠⁠

Is working 100 hours a week as an investment banker worth it? You'll sacrifice your health, relationships and passions — but will get paid well. I share my experience at Broadview/Jefferies covering how I survived, what the pivot was like and if I'd do it all over again. [Episode 65] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Should you walk away from your dream job (during your prime years)? If you've been grinding for over a decade to establish yourself in your career, you've probably made some sacrifices along the way. And a sabbatical can be a useful career tool to reprioritize family time, your physical health and hobbies — without burning all the ships. [Episode 64] Rachel Feintzeig is a work and life columnist at the Wall Street Journal. Learn more about Rachel: • X/Twitter • LinkedIn • The Wall Street Journal References from the show: • Ever Dream of Taking a Sabbatical? Here's How Our Columnist Did It • My Dream Break From Work Wasn't What I Expected —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Could the secret to success be embracing your envy? Joe Hudson reveals how comparison breeds misery and stifles growth and how you can transform self-abuse into self-acceptance while maintaining your ambition. [Episode 63] Joe Hudson is coaches executives in Silicon Valley. Learn more about Joe: • Joe's X/Twitter • The Art of Accomplishment Website • The Art of Accomplishment Podcast —- Use code RADREADS for $300 off Joe Hudson's Connection Course: https://view.life/radreads —- BECOME A RADREADER:

A common struggle for high-achievers is the need to make every moment productive. As a result, rest and leisure are accompanied by guilt. Internal Family Systems (or "IFS") is a therapy approach that will help you navigate perfectionism, relentless drive and obsession with optimizing everything. [Episode 62] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Meditation is good for you. Like eating your broccoli, we get it. But beyond stress-relief and cognitive clarity, how can the practice bring you closer to truly enjoying your life? We discuss how to get started, getting to know your insecurities and how “spiritual bypass” can undo some of the benefits. [Episode 61] Cara Lai is a meditation teacher. Learn more about Cara: • Cara's Website —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Many people dream of making millions as a hedge fund manager on Wall Street. But it's an absolute grind. Ben Jasper did this for 20 years at some of the world's largest hedge funds before saying, “Enough.” At 40 years old, Ben bought an unsexy business and started his second career. He had to borrow a ton of money from the SBA and put up a personal guarantee on his house, all to wake up at 4am to go to the factory and turn on the machines. But to Ben, it's an incredible opportunity. In this episode, we'll cover how you only need to put 5% down to buy a business, the steep learning curve of unsexy businesses, when is the right time to leave a high paying job on Wall Street and if entrepreneurship or Wall Street is the best ways to compound wealth. [Episode 60] Learn more about Ben: • References from the show: • How to Buy a Manufacturer with $1m in Cash Flow —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

I just turned 45 years old, which means I've lived 60.3% of my actuarial lifespan. I have way less hair, but at least I've held on to my six pack. I left Wall Street so that I could have time freedom, raise my kids and surf every day, and I learned a few lessons along the way. I'll share 45 of them on workaholism, borderline alcoholism, how to cope with long hours, taking a huge pay cut and what to do when you find your favorite t shirt. [Episode 59] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Imagine you're about to have your first kid. But your career is muddling along and you don't have a dependable source of income. You need a plan to grow your wealth. Quickly. And it happens to be the start the pandemic where ALL crypto projects are going gangbusters. Writer and serial entrepreneur Nat Eliason saw an opportunity to get rich and hatched a plan. What followed was a wild ride involving anonymous crypto accounts, millions of (paper) dollars, hacks and crashes. [Episode 57] Learn more about Nat: • Nat's Website • X/Twitter • Instagram • YouTube —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

There's a simple playbook for happiness. One we've been taught since we were kids. Study hard, get a good job, climb the ladder, make a bunch of money and then you'll be happy. So why do so many of us feel unfulfilled, lost and rudderless? This week we speak with Stephanie Harrison, an expert on the psychology of happiness and the author of New Happy. We discuss our rugged individualism, obsession with money, emptiness and disconnection, helping others and understanding our emotional pain. [Episode 56] Learn more about Stephanie: • Stephanie's Instagram • The New Happy on Instagram • New Happy book —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

IQ gets all the attention. It's the raw brain power that wows us. But EQ, or emotional intelligence, might be even more powerful. It provides the finesse to interact with peers, confidence to pitch new investors and charisma to recruit top talent. IQ is something we're born with. But what about EQ? In this episode, we'll discuss seven ways to develop your social intelligence, covering strategies like active listening, understanding decision-making and how to be vulnerable without cringey oversharing. [Episode 55] References from the show: • I networked 5,192 times. Here's everything I learned. • The (simple) secrets of superconnectors • A simple habit to let luck find you —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

From playing online poker to pay for college, to starting a gardening lifestyle business that turned into a $40 million empire, Kevin Espiritu's journey is jaw-dropping. He provides a candid look at his obsessive personality trait that fueled his success, and discusses his changing relationship with money as his business scaled. We cover following your passion, playing "the game" and finding fulfillment beyond just financial rewards. [Episode 54] Learn more about Kevin: • Kevin's Website • Epic Gardening • X/Twitter • LinkedIn • Instagram —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER:

Author Geraldine DeRuiter reached the dizzying heights of publishing her first book, then experienced the more muted satisfaction of her second. She's grappled with the realization that external achievements can't resolve core belief of not being "good enough." We contemplate the limitations of external accomplishments in solving our deepest insecurities and the importance of recognizing and appreciating moments of success, even as the goalposts continually move. We cover the profound impact of childhood experiences on our adult drives and fears, the double-edged sword of ambition and the transformative power of vulnerability and human connection. [Episode 53] Learn more about Geraldine: • Geraldine's Website • X/Twitter • Instagram • Meta Threads References from the show: • ⁠All Over the Place: Adventures in Travel, True Love, and Petty Theft⁠ • ⁠If You Can't Take the Heat: Tales of Food, Feminism, and Fury —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers) ⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠ —- BECOME A RADREADER: