If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071

Modern Wisdom

Chris Williamson

Society & Culture, Health & Fitness

4.6 • 5.9K Ratings

🗓️ 14 March 2026

⏱️ 117 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 Sponsors: See discounts for all the products I use and recommend: ⁠https://chriswillx.com/deals⁠ New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom Get up to $350 off the Pod 5 at https://eightsleep.com/modernwisdom 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 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 - Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	What got you into thinking about the idea of career regret as somebody that's had a very
0:05.2	seemingly successful and fun career? Why did you think about it? I used to, so I spent 25 years
0:13.6	as a venture capitalist and the four years before that as a sell side analyst on Wall Street.
0:18.6	And through that process, I started writing as a way to
0:22.0	differentiate myself. And so I was an early blogger. It was actually a fax. That's how old I am
0:27.6	when I started. And I got in the habit of when I had ideas jotting them down. And then, you know,
0:35.9	either developing them, a lot of them ended up just undeveloped.
0:39.5	But if I developed them, they would become a blog post. And there was a period in my career where I was
0:44.4	reading a ton of biographies. And I finished this third one and saw a through line with these other two
0:50.6	from people that were in wildly different fields, and I jotted those notes down.
0:55.5	And that thing kind of simmered and breathed and took on a little bit of a life.
1:00.7	And I got asked by the dean of the business school here in Austin University of Texas to
1:06.0	talk to the NBA class one day.
1:08.2	And I was like, can I do this?
1:10.2	And he said, sure. So I pulled it out
1:12.4	and developed it a little bit as a PowerPoint presentation. Anyway, they posted that on YouTube.
1:19.6	A few people noticed some people that have been on your show, James Clear noticed. And he posted it
1:24.9	on his website. And people started prodding me to develop it as a book.
1:29.1	And a few years ago, I decided to begin retirement as a venture capitalist.
1:34.4	It actually takes a while, unfortunately.
1:36.5	And in that window, I thought about doing this.
1:40.3	I thought about doing a book.
	...

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