If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071
Modern Wisdom
03/14/26
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Bill Gurley is a venture capitalist, general partner at Benchmark, and a former Wall Street analyst.
How do you find work you actually enjoy? So many people warn about the jobs they hate and the dreams they never chased. But turning passion into a career is harder than it sounds. So how do you reinvent yourself and build a life where work feels meaningful instead of miserable?
Expect to learn why most people end up having careers they regret, how to build a framework for regret minimisation, what people do that achieve success in their dream career, how to know when you’re plateauing versus when you’re just bored, what great mentors actually do that books and podcasts can’t, if someone can learn to love the grind or if it is something that’s innate, how you know if you’re in the wrong field versus just in the hard phase of the right field and much more...
Timestamps:
(0:00) What Career Regret Really Means (4:44) Why Uncertainty is So Uncomfortable (9:41) Why We Feel Obligated to Stick to One Career (15:05) Is Life Really “Use It or Lose It”? (23:04) How Some Of Us Successfully Pivot Careers (30:14) The Real Risk of Starting Over in Your 30s (38:42) Do Discipline, Motivation and Obsession Work Together? (41:54) Signs It’s Time to Change Your Career (48:30) Plateau or Boredom: How to Tell the Difference (50:12) Can You Upgrade Your Circle Without Losing Yourself? (54:49) Do Mentors Actually Make a Difference? (01:00:53) Can You Learn to Love the Grind? (01:07:37) The Pains and Pleasures of Reinventing Yourself (01:25:21) What Investors Look For in Founders (01:30:34) Founder vs Company: What Matters More? (01:42:01) Why You Should Lean into AI When Honing Your Craft (01:47:13) Which Careers Will AI Replace? (01:49:11) The Best Way to Start Your Career in Your 20s (01:50:56) Why Career Switchers Become Innovators (01:55:43) Where to Find Bill
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Extra Stuff:
Get my free reading list of 100 books to read before you die: https://chriswillx.com/books
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Episodes You Might Enjoy:
#577 - David Goggins - This Is How To Master Your Life: lnkfi.re/SN-Goggins
#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: lnkfi.re/SN-Peterson
#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: lnkfi.re/SN-Huberman
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Previous Episode
Louis Theroux is a journalist, documentary filmmaker, broadcaster, and author.
What is it really like inside the Manosphere? Online spaces for men have exploded in influence, shaping how millions of young men think about success, relationships, and masculinity. Supporters say it helps men improve their lives. Critics say it’s dangerous and toxic. So what’s the truth, and is the manosphere as harmful as mainstream media says it is?
Expect to learn why Louis is so interested in investigating the Manosphere and what’s driving the growing trend, if it’s possible to speak to issues that men face without being a part of the Manosphere, if Louis agrees to anything that Manosphere has to offer, why looksmaxxing is becoming a growing trend in the Manosphere, if more traditional gender roles are actually desired by women, what the future of the Manosphere and the route young men are going and much more...
Timestamps:
(0:00) Why Louis is Exploring the Manosphere (8:33) The Danger in Blurring Entertainment and Real Life (14:16) Why Men’s Issues Are Suddenly Everywhere (21:03) What the Manosphere is Really Trying To Do (34:40) How Childhood Shapes Manosphere Beliefs (40:36) How Algorithms are Influencing Young Men (51:36) The Pressure of Living on Camera (57:43) Can Men’s Issues Be Discussed Outside the Manosphere? (01:09:00) Is Looksmaxxing the New Red Pill? (01:16:13) Where Does Louis Agree With the Manosphere? (01:22:23) Why Men’s Issues Deserve More Empathy (01:40:07) Where to Find Louis
Sponsors:
See discounts for all the products I use and recommend: https://chriswillx.com/deals
Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom
Get up to 20% off the leading longevity and cellular health supplement at https://timeline.com/modernwisdom
New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom
Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom
Extra Stuff:
Get my free reading list of 100 books to read before you die: https://chriswillx.com/books
Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom
Episodes You Might Enjoy:
#577 - David Goggins - This Is How To Master Your Life: lnkfi.re/SN-Goggins
#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: lnkfi.re/SN-Peterson
#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: lnkfi.re/SN-Huberman
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Get In Touch:
Instagram: https://www.instagram.com/chriswillx
Twitter: https://www.twitter.com/chriswillx
YouTube: https://www.youtube.com/modernwisdompodcast
Email: https://chriswillx.com/contact
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Next Episode
Dr Debra Soh is a neuroscientist, sex researcher, political commentator, and author.
Why are we more connected than ever—but having less sex? Technology promised endless connection, but many people feel more isolated than ever. With sexlessness increasing, what’s causing the modern “sex recession,” and what can be done about it?
Expect to learn if people having less sex is a big deal or not, what the current state of modern sexual activity is, when the sex recession started and if rising hypergamy was a factor, if the role of porn attributed to the sex recession and the shocking new neuroscience of porn use, why looksmaxxing and plastic surgery are on the rise, the role of social media and smartphones had in growing sexlessness, what can be done top-down to fix the sex recession and much more...
Timestamps:
(0:00) Is Sex Really Declining? (4:13) When Did the Sex Recession Start? (7:24) Why Hypergamy Is Changing (16:26) Is Hypergamy Reshaping the Dating Market? (22:39) How the Pill Changed Female Sexual Choice (32:01) Life As a Romance Novel Model (33:27) How Modern Environments Disrupt Our Hormones (37:05) Porn’s Devastating Impact on Men (46:42) How Porn is Impacting Women (51:38) Is Porn Making Sex More Aggressive? (01:08:25) How Social Media is Rewriting Sexual Norms (01:14:10) The Beauty Standards Porn is Creating (01:25:04) Is Looksmaxxing Backfiring? (01:29:11) Is Sexlessness Destroying Marriages? (01:38:25) Is the Sex Doll Revolution Coming? (01:45:52) Why Connection Feels Harder Than Ever (01:47:48) Are We Opting Out of Having Children? (02:01:50) Can the Sex Recession Be Reversed? (02:05:36) Where to Find Debra
Sponsors:
See discounts for all the products I use and recommend: https://chriswillx.com/deals
Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom
Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom
Get a free bottle of D3K2, an AG1 Welcome Kit, and more when you first subscribe at https://ag1.info/modernwisdom
New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom
Extra Stuff:
Get my free reading list of 100 books to read before you die: https://chriswillx.com/books
Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom
Episodes You Might Enjoy:
#577 - David Goggins - This Is How To Master Your Life: lnkfi.re/SN-Goggins
#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: lnkfi.re/SN-Peterson
#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: lnkfi.re/SN-Huberman
-
Get In Touch:
Instagram: https://www.instagram.com/chriswillx
Twitter: https://www.twitter.com/chriswillx
YouTube: https://www.youtube.com/modernwisdompodcast
Email: https://chriswillx.com/contact
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