# Use regret and curiosity to decide when to change paths

Markdown copy of https://realalpha.app/s/use-regret-and-curiosity-to-decide-when-to-change-paths/ on Real Alpha, the best minutes from long interviews with the people building AI. Cite and link the page, not this copy.

- Speaker: [Bill Gurley](https://realalpha.app/people/bill-gurley/) · Bill Gurley is general partner at Benchmark and author of Runnin’ Down a Dream. · Backed and sat on the boards of Uber, Zillow, OpenTable and Stitch Fix.
- Host: [Tim Ferriss](https://realalpha.app/people/tim-ferriss/) · Host, The Tim Ferriss Show · Wrote The 4-Hour Workweek; an early investor or advisor in Uber and Shopify.
- Show: The Tim Ferriss Show
- Episode: [Bill Gurley — The AI Era, 10 Days in China, & Life Lessons from Bob Dylan, Jerry Seinfeld,, and More](https://realalpha.app/v/rjSesMsQTxk/), Dec 17, 2025
- Moment: 1:31:37 to 1:37:11 of the episode (6 min), playing on https://realalpha.app/s/use-regret-and-curiosity-to-decide-when-to-change-paths/; the episode from there: https://realalpha.app/v/rjSesMsQTxk/?t=5497

## Quote

> “over time, we are as much more likely to **regret the chances we didn't take** than the chances we did.”
> — [Bill Gurley](https://realalpha.app/people/bill-gurley/) at [1:35:39](https://realalpha.app/v/rjSesMsQTxk/?t=5739) · The Tim Ferriss Show

## Takeaways

1. Ask whether you want to keep doing this for the rest of your life.
2. Use trusted peers to assess whether a setback is surmountable.
3. Regret can be a useful prompt to take a considered risk.

## About this segment

Bill Gurley says hard stretches are normal, but persistent reluctance to continue can be a signal to pivot. He describes leaving two careers and explains why people often regret chances they never took.

From “Bill Gurley — The AI Era, 10 Days in China, & Life Lessons from Bob Dylan, Jerry Seinfeld,, and More”, Dec 17, 2025. [Watch the full episode](https://realalpha.app/v/rjSesMsQTxk/)

## Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

[1:31:50](https://realalpha.app/v/rjSesMsQTxk/?t=5510) give you five answers on how to deal with it or to get around but by the way one thing that's important when we're talking about this is daniel pink has this great book on regret and he talks about it as a valid motivator to get you to make good decisions and there is a reality that that anxiety may feel may mean you're not in the right lane and so when you were at that sales job you got to the point where you're like holy shit i don't want to be doing this anymore and i had two careers before i became a vc one as an engineer and one as a cell site analyst i enjoyed both i think i was good at both but i reached a point about three years in with each where i was like i don't want to do this the rest of my life and so i would say equally with like don't give up too early but if the signal is really telling you i don't want to do this the rest of my life

[1:32:46](https://realalpha.app/v/rjSesMsQTxk/?t=5566) jump out that's the precise moment to move on and try something new and i spend a ton of time in the early chapters, trying to get people to understand that's okay. Most people don't end up in a career that their major was. Like, I think one of the reasons people grind too long is because they think they're supposed to. They just think they're supposed to stay in this lane they're in. How did you conclude it was time to hop in those cases? We don't have to go into tons of the background because we talked about so much of your history and decisions and so on, including, I don't want to say stealing Palm Pilots, but it's a pretty good story about getting a Palm Pilot. But was it just a gut feeling? Was it like a disquiet that you felt in your system or was it more than that? I'm sure I've overplayed it in my brain,

[1:33:37](https://realalpha.app/v/rjSesMsQTxk/?t=5617) but they feel like very concrete moments where I had almost near certainty. The first one was I started my third project at compact computer corporation where I was an engineer and the projects were these computers we were releasing. And the third one was another computer with a little faster clock speed and a better Intel chip. But the rest of it was all the same and we were going to do it again.

[1:34:05](https://realalpha.app/v/rjSesMsQTxk/?t=5645) And I'm like, that doesn't seem that interesting to me. And I'd become curious about other things. So when I was doing external learning, which is what I refer to as this kind of spare time learning, it wasn't that, you know, it was something else. I was reading Peter Lynch's book on stocks and stuff like that. Right, segue to the sell-side analyst. Yes. The thing that happened as a sell-side analyst, and this gets into, and I may parlay this into something from the Daniel Pink book, but this notion of do you want to do this the rest of your life?

[1:34:42](https://realalpha.app/v/rjSesMsQTxk/?t=5682) the sell side job is wonderful you get access so early in your life to so many amazing people but you have to work really hard and you know this classic thing where you're in your 20s and you're working on wall street you know they serve dinner at the office like the cafeteria is open that'll tell you something and it was like 10 30 or 11 p.m and the entire research department was on the 36th floor of Park Avenue Plaza. And I did a loop. The four corner offices were the most senior analysts. And for whatever reason, I popped my head in each of their office and they were career sell side analysts. I said, do I want to be this person when I'm 60? It just stuck in my head. I went to the next one, went to the next one. Hopefully I don't know who those people were, But I was like, no, I don't.

[1:35:34](https://realalpha.app/v/rjSesMsQTxk/?t=5734) Like that night, that night, I made the decision that I got to go do something else. In Daniel Pink's book, he talks a lot about boldness regrets. And this is where I say, do you want to do this the rest of your life? He says, one of the most robust findings in the academic research and my own is that over time, we are as much more likely to regret the chances we didn't take than the chances we did.

[1:35:58](https://realalpha.app/v/rjSesMsQTxk/?t=5758) What haunts us is the inaction itself. Foregone opportunities all linger in the same way. And he says that they've studied this across China, Russia, Japan. It's common across all of them. And you may have heard of this YouTube video where Bezos talks about his regret minimization framework. And so he had the same thing. He's walking around Central Park. Should I stay in this incredible job at D.E. Shaw where he's making tons of money?

[1:36:24](https://realalpha.app/v/rjSesMsQTxk/?t=5784) or should i take this flyer on this online bookstore i want to do and he put it in his mind that test which is when i'm 80 and looking back am i going to regret not doing this you know well it makes me think of and this is also no dicey proposition quoting niccolo machiavelli but make mistakes of ambition not mistakes of sloth yes right the same thing and i do think about that a lot myself i mean i'm at a point where i'm trying to figure out my next chapters too because this podcasting game's getting pretty crowded and i still enjoy doing it but that's