Oxide's Cantrill Says Promotion Targets Fuel Tech Midlife Crises

Ryan Peterman

Engineers who optimize careers around prestige titles or early retirement face an existential vacuum upon reaching them because external benchmarks cannot supply intrinsic purpose.

AI-assisted summary of Distinguished Eng: Why You Shouldn’t Goal On Promotions | Bryan Cantrill — original source. Check the original for full context.

Source published: 2026-09-26

Key ideas

Bryan Cantrill cautions that optimizing engineering careers solely around promotions like Distinguished Engineer leads to midlife crises rather than genuine fulfillment. (0:00)
Targeting Financial Independence (FIRE) before pursuing meaningful work is flawed, as achieving wealth without an intrinsic mission routinely triggers post-achievement depression. (2:21)
Major engineering milestones can cause emotional crashes or 'engineering postpartum,' even when the completed project is deeply meaningful. (6:28)
Early Yahoo employee 'Web Surfer 1' earned a fortune from initial equity while perpetually complaining, demonstrating that wealth and undemanding work do not prevent dissatisfaction. (8:46)

Detailed notes

## Background This video was published on YouTube by Ryan Peterman on September 25, 2026. It features a conversation with Bryan Cantrill, founder of Oxide Computer Company and former distinguished engineer at Sun Microsystems, discussing career boom-and-bust cycles, competing with Jeff Bezos, and navigating career regrets.

## TL;DR Bryan Cantrill challenges the conventional mindset of chasing engineering promotions and Financial Independence (FIRE), warning that anchoring self-worth to titles like Distinguished Engineer creates an existential vacuum and engineering 'postpartum.' Drawing on his firsthand experience losing paper fortunes in the dot-com bust, Cantrill argues that monetary metrics and empty consumerism fail to provide genuine fulfillment. He underscores the point with the absurd cautionary tale of Yahoo's employee number six—a chronically unmotivated 'Web Surfer 1' whose responsibilities dwindled to curating Northern California snowboarding links despite striking it rich.

## Atmosphere & style The conversation carries an intimate, candid, and collegial vibe, feeling like an unvarnished chat between tech insiders sharing a world-class cup of coffee. Cantrill serves as an energetic, seasoned contrarian, deploying blunt psychological humor and self-deprecating tax anecdotes to puncture conventional corporate climbing tropes. The dynamic is lively and grounded, shifting effortlessly from earnest philosophical reflection on midlife crises to uproarious laughter over early dot-com absurdity.

## Bulletin - [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) Bryan Cantrill cautions that optimizing engineering careers solely around promotions like Distinguished Engineer leads to midlife crises rather than genuine fulfillment. - [02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) Targeting Financial Independence (FIRE) before pursuing meaningful work is flawed, as achieving wealth without an intrinsic mission routinely triggers post-achievement depression. - [06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) Major engineering milestones can cause emotional crashes or 'engineering postpartum,' even when the completed project is deeply meaningful. - [08:46](https://www.youtube.com/watch?v=uLFqnloaL4s&t=526s) Early Yahoo employee 'Web Surfer 1' earned a fortune from initial equity while perpetually complaining, demonstrating that wealth and undemanding work do not prevent dissatisfaction.

## Key takeaways - [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) Fixating on reaching the Distinguished Engineer level is often a recipe for a midlife crisis because achieving the title leaves an existential vacuum. - [00:45](https://www.youtube.com/watch?v=uLFqnloaL4s&t=45s) Engineers obsessing over prestige and titles should examine their psychological motivations and speak with current, unhappy Distinguished Engineers. - [02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) The sequential mindset of achieving financial independence first and doing meaningful work later ignores the reality of how people find purpose. - [02:58](https://www.youtube.com/watch?v=uLFqnloaL4s&t=178s) Living through the 2001–2003 dot-com crash was a clarifying experience that eliminated mercenary motives and forced engineers to rediscover genuine passion for technology. - [04:15](https://www.youtube.com/watch?v=uLFqnloaL4s&t=255s) Dot-com figures who cashed out in their twenties without a passion for technology often became aimless, filling the void with empty consumerist milestones like buying six houses. - [06:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=360s) Engineers treating high-paying tech jobs purely as an endurance test to escape should leave immediately to pursue what actually fulfills them. - [06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) Hitting major professional or financial goals routinely triggers 'engineering postpartum,' an emotional crash following the completion of an intense, long-term effort. - [07:45](https://www.youtube.com/watch?v=uLFqnloaL4s&t=465s) Some individuals attempt to resolve the post-wealth existential void by detaching from empathy and pursuing endless wealth accumulation for its own sake. - [08:46](https://www.youtube.com/watch?v=uLFqnloaL4s&t=526s) Yahoo's sixth employee held the official title of 'Web Surfer 1' and made a king's ransom purely through early equity without ever advancing. - [09:15](https://www.youtube.com/watch?v=uLFqnloaL4s&t=555s) Before automated search engines like Google or AltaVista existed, the early internet relied on human curation to catalog web directories. - [09:35](https://www.youtube.com/watch?v=uLFqnloaL4s&t=575s) Due to chronic lack of effort, Yahoo's 'Web Surfer 1' had his responsibilities whittled down from the entire directory to curating links solely for snowboarding in Northern California.

## Detailed walkthrough ### [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) The Trap of Goal-Oriented Ladders and the "Third Path"

Ryan Peterman introduces a common dilemma faced by ambitious new engineering graduates navigating career ladders. He outlines two predominant schools of thought: the first is to focus entirely on craft and let promotions follow naturally as a byproduct; the second is to actively manage upward by asking leadership, "Hey, what are those things that the next level needs to do?" and tailoring output to match that exact mold. Bryan Cantrill immediately counters by offering a "third path," questioning the underlying motive altogether: "Why do you want to be a distinguished engineer? Because if that's the goal... you get there. You'll be a distinguished engineer. Now what?"

Cantrill warns that becoming fixated on a title cannot provide genuine personal meaning. When a young engineer declares their ultimate goal is to become a Distinguished Engineer (DE), Cantrill diagnoses it as "a recipe for a midlife crisis." Rather than optimizing for promotion rubrics, he advocates steering individuals toward a path grounded in self-development and internal drive.

When engineers insist that the title itself is what matters, Cantrill suggests they need to be put "on the couch a little bit" to uncover the psychological root of their ambition—asking bluntly if they were "not loved enough as a child" to examine their reliance on external validation. His antidote to prestige-seeking is exposure to reality: - Introducing ambitious engineers to current Distinguished Engineers who attained the title and are completely miserable. - Connecting wealth-obsessed people with deeply unhappy millionaires to prove that financial metrics do not solve existential fulfillment. - Identifying what serves as the true "fuel in that furnace" so that impactful work and promotions emerge organically rather than through synthetic posturing.

---

[02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) Deconstructing Financial Independence and the Dot-Com Reality Check

```mermaid flowchart TD accTitle: The Cycle of Goal-Obsessed Career Motivation accDescr: A diagram illustrating the hollow pursuit of arbitrary goals leading to post-achievement existential crises.

subgraph Pursuit["The Extrinsic Pursuit"] A["External Goal\n(Distinguished Engineer / FIRE)"] --> B["Relentless Grinding\n(Sacrificing Meaning for Metrics)"] B --> C["Goal Attained\n(Paper Wealth / Promotion)"] end

subgraph Reality["The Aftermath"] C --> D["The 'Now What?' Vacuum\n(Midlife Crisis / Engineering Postpartum)"] D --> E{"Two Common Reactions"} E --> F["Extreme Consumerism / Disillusionment\n(Buying 6 houses, finding no peace)"] E --> G["Endless Accumulation Loop\n('Snip the wires' like Larry Ellison)"] end ```

When Peterman pushes back by arguing that many mentees prioritize promotions primarily to achieve Financial Independence (FIRE)—reaching a point where they never have to work for money again—Cantrill questions the premise of that benchmark within the technology industry. He notes that tech is already an extraordinarily well-compensated domain where basic material luxuries are universally accessible. Sitting in San Francisco's Mission District, he points out that anyone in the field can easily afford a $6 cup of world-class Ethiopian coffee.

When Peterman asks what happens if a person's true passion does not earn any income, Cantrill rejects the sequential mindset of "I'm going to achieve financial independence and then I'm going to do the thing that is meaningful to me." He reflects on living through the dot-com bubble as a formative educational experience: - Cantrill, like most tech workers in the late 1990s, made substantial paper wealth during the boom and subsequently "lost every penny of it." - He accumulated an IRS capital loss carryover so large that he carried it forward across countless tax years, eventually losing track of it after repeatedly claiming the standard $3,000 annual deduction against regular income. - The 2001–2003 dot-com bust created an economic "nuclear winter" that purged purely mercenary motivations, forcing survivors to rediscover why they loved technology outside of monetary rewards. - The few people who successfully cashed out in late 1999 or 2000 were often those who had never cared about technology in the first place, leaving them rich in their twenties but completely adrift.

Cantrill recounts that those early dot-com winners struggled profoundly over the ensuing decade. Bereft of a compelling mission, they experimented with empty consumerist milestones like buying six houses, only to realize that managing real estate is a logistical headache: "Am I just like proving that I can buy six... So like why do I want six houses?" While acknowledging that individuals must reliably provide for themselves and their families, Cantrill warns against treating tech as an endurance test to be escaped. He jokes that people plotting an exit strategy should leave immediately: "Quit your job at Meta and become a podcaster"—which prompts laughter from Peterman, who did exactly that.

---

[06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) Engineering "Postpartum" and the Yahoo Surfer

Peterman notes that online FIRE communities frequently feature posts from people who finally hit their target net worth only to panic, asking, "Guys, I did it and I don't know what to do now." Cantrill relates this directly to a phenomenon he calls "postpartum in engineering." Even when a team's objective is profoundly meaningful, hyper-focusing on a single milestone creates an emotional crash once the goal is reached: - When Oxide Computer Company shipped its first commercial rack, Cantrill actively worried about team-wide postpartum depression after years of relentless collective effort. - Achieving purely financial milestones yields an even shallower payoff, leaving people bewildered once they realize they can purchase anything they want but have no driving purpose. - Some individuals resolve this existential vacuum by completely detaching from empathy or self-reflection—"snip all the wires"—and pursuing endless wealth accumulation for its own sake, citing figures like Larry Ellison.

Peterman questions this philosophy by presenting the counter-example of a friend who is genuinely content doing absolutely "nothing"—sleeping in, watching shows, and relaxing with friends, perfectly suited for an idle life if handed a billion dollars. Cantrill responds by recalling an acquaintance from the early internet era: an early employee at Yahoo who was neither deeply technical nor exceptionally sharp, but got hired in the company's infancy simply because Yahoo was looking for a "web surfer," a low-stress job that perfectly matched the lifestyle of an unhurried pothead.

[08:46](https://www.youtube.com/watch?v=uLFqnloaL4s&t=526s) The Tale of Yahoo Employee Number Six: "Web Surfer 1"

Bryan Cantrill shares an illustrative story from the early days of the dot-com boom about a friend or acquaintance who joined Yahoo as a single-digit employee—roughly employee number six—with the official job title of "Web Surfer 1." Coming in so early, the employee received an initial equity grant that ultimately made him "a king's ransom" as Yahoo exploded in value. Despite striking gold, he never received another equity grant and never advanced beyond the entry-level surfer rank. To the bewilderment of everyone around him, he spent his days constantly complaining about how terrible his job was. As Cantrill points out with incredulous humor, the man had essentially won an unbelievable lottery where he was paid a fortune to do virtually nothing: "You surf the web for a living."

To explain how such a role even existed, Cantrill reminds the audience that this was the era before search engines existed—predating not just Google, but Lycos, HotBot, and AltaVista. At the time, Yahoo was not an algorithmic search engine but a human-curated directory of links, requiring staff to manually browse the nascent internet, discover pages, and categorize them. When the employee first started, his remit covered the entirety of Yahoo's link directory. However, because he was unmotivated, not particularly good at it, and "stoned all the time," management progressively carved away his responsibilities to keep the directory functioning.

By the time he finally left the company, his purview had been whittled down to a comically narrow slice of the web: curating links exclusively for "snowboarding in Northern California." Cantrill laughs at the sheer absurdity of that being a viable, lucrative job, concluding with the hope that the person eventually found something genuinely fulfilling in life, because it was abundantly clear that work—and the curation work itself—meant nothing to him.

- **Role and Compensation**: Hired as an entry-level "Web Surfer 1" as roughly employee number six at Yahoo; never promoted and never received a refresher equity grant, yet became wealthy purely through the original equity grant. - **The Pre-Search Web**: Yahoo originated as a manually maintained web directory in an era before automated search engines like Google, AltaVista, Lycos, or HotBot existed. - **Shrinking Scope**: Began by overseeing the entire Yahoo directory, but due to chronic lack of effort and energy, his scope was repeatedly reduced until he was solely responsible for the "snowboarding in Northern California" category.

## Notable quotes > [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) Why do you want to be a distinguished engineer? Because if that's the goal... you get there. You'll be a distinguished engineer. Now what? — Bryan Cantrill

> [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) a recipe for a midlife crisis. — Bryan Cantrill

> [00:00](https://www.youtube.com/watch?v=uLFqnloaL4s&t=0s) Hey, what are those things that the next level needs to do? — Ryan Peterman

> [02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) I'm going to achieve financial independence and then I'm going to do the thing that is meaningful to me. — Bryan Cantrill

> [02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) Am I just like proving that I can buy six... So like why do I want six houses? — Bryan Cantrill

> [02:21](https://www.youtube.com/watch?v=uLFqnloaL4s&t=141s) Quit your job at Meta and become a podcaster — Bryan Cantrill

> [06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) Guys, I did it and I don't know what to do now. — Ryan Peterman

> [06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) postpartum in engineering. — Bryan Cantrill

> [06:28](https://www.youtube.com/watch?v=uLFqnloaL4s&t=388s) snip all the wires — Bryan Cantrill

> [08:46](https://www.youtube.com/watch?v=uLFqnloaL4s&t=526s) You surf the web for a living. — Bryan Cantrill

> [08:46](https://www.youtube.com/watch?v=uLFqnloaL4s&t=526s) snowboarding in Northern California. — Bryan Cantrill

## Mentioned AltaVista, Bryan Cantrill, FIRE movement, Google, HotBot, Larry Ellison, Lycos, Meta, Oxide Computer Company, Ryan Peterman, Sun Microsystems, Yahoo

## Video description Bryan Cantrill was a distinguished engineer at Sun Microsystems and has now founded his own company called Oxide Computer Company. We discussed his career experiences through boom/busts, what competing with Bezos was like, and career regrets.

Watch the full conversation: https://www.youtube.com/watch?v=qhSL-5GtmQM

[Source](https://www.youtube.com/watch?v=uLFqnloaL4s)

中文简报

Oxide的Cantrill称晋升目标引发科技人中年危机围绕显赫头衔或提早退休来规划职业生涯的工程师在达成目标后会面临存在主义虚空，因为外部衡量标准无法提供内在意义。 Bryan Cantrill对盲目追求工程晋升和财务自由（FIRE）的传统思维提出质疑，警告称将自我价值锚定在杰出工程师（Distinguished Engineer）等头衔上，会造成存在主义虚空和工程“产后抑郁”。结合自己在互联网泡沫破裂中痛失纸面财富的亲身经历，Cantrill指出金钱指标和空虚的消费主义无法带来真正的满足感。他还以雅虎第六号员工荒诞的警示故事印证了这一点——这位挂着“Web Surfer 1”头衔的员工长期缺乏动力，尽管一夜暴富，其职责最终却缩水到仅仅负责维护北加州滑雪链接。 Bryan Cantrill告诫称，单纯围绕杰出工程师等晋升目标来规划工程职业生涯，会导致中年危机而非真正的满足感。 (0:00) 在从事有意义的工作之前先追求财务自由（FIRE）存在逻辑缺陷，因为在缺乏内在使命感的情况下实现财富，往往会引发成就达标后的抑郁。 (2:21) 即使完成的项目极具意义，重大的工程里程碑也可能导致情绪崩溃或所谓的工程“产后抑郁”。 (6:28) 雅虎早期员工“Web Surfer 1”凭借原始股权发了大财，却始终牢骚满腹，这表明财富与轻松的工作并不能消除不满。 (8:46)

Reading summary

Engineer and executive Bryan Cantrill argues that treating promotions or financial exit numbers as primary career goals is an existential trap, advising technologists to anchor their careers in intrinsic curiosity rather than titles or sequential retirement plans. The Psychological Trap of Chasing Prestigious Titles (0:00) When early-career engineers fixate on reaching top-tier ranks such as Distinguished Engineer (DE), Cantrill diagnoses the mindset as a direct path to a midlife crisis. While career discussions often debate whether to focus purely on craft or optimize upward against performance rubrics, Cantrill suggests a third perspective by questioning what happens after the title is attained. He contends that an obsession with external milestones frequently masks a need for psychological validation rather than genuine engagement with technical problems. The Illusion of Sequential Financial Independence (2:21) In response to Ryan Peterman's observation that many engineers chase promotions to achieve Financial Independence, Retire Early (FIRE), Cantrill rejects the premise that workers should endure unfulfilling tech roles solely to fund future passions. He points out that compensation in software engineering already affords substantial daily comforts, such as premium coffee in San Francisco's Mission District, without requiring complete financial independence. Treating technical work merely as an endurance test to be escaped, Cantrill suggests, is counterproductive when compared to directly pursuing meaningful work. Dot-Com Lessons on Wealth and Post-Achievement Voids (2:21) Drawing on his experience during the late-1990s dot-com era, Cantrill describes how the subsequent 2001–2003 market crash eliminated vast paper fortunes, leaving him with an IRS capital loss carryover so large he eventually lost track of the recurring $3,000 annual deductions. He observed that the few who managed to cash out in their twenties without a passion for technology became deeply aimless, occasionally attempting to fill the void through empty consumerism like purchasing six houses only to be burdened by their maintenance. Engineering Postpartum and the Reality of Directionless Wealth (6:28) Reaching a monumental milestone often triggers what Cantrill calls 'engineering postpartum'—an emotional drop that can occur even after deeply fulfilling projects, such as Oxide Computer Company delivering its first commercial rack. For those who optimize purely for financial independence, the post-achievement vacuum is even more severe, occasionally driving individuals to detach from self-reflection entirely and pursue endless wealth accumulation for its own sake. The Pre-Search Web and Yahoo's 'Web Surfer 1' (8:46) To demonstrate that high wealth and low effort do not produce personal satisfaction, Cantrill cites an early acquaintance who joined Yahoo around employee number six as 'Web Surfer 1.' In the era preceding automated engines such as Google, AltaVista, Lycos, and HotBot, Yahoo was a manually curated directory of web links. Despite winning a financial windfall from initial equity without ever earning promotions or refresher grants, the unmotivated employee spent his days complaining, even as management steadily shrank his responsibility from the entire web directory down to a single category: Northern California snowboarding. Cantrill concludes that neither titles nor windfall liquidity resolve the fundamental challenge of existential fulfillment, leaving open the question of how engineers can reliably identify the work that genuinely motivates them before committing years to climbing synthetic corporate ladders.

Source quotes

[0:00] Bryan Cantrill: Why do you want to be a distinguished engineer? Because if that's the goal... you get there. You'll be a distinguished engineer. Now what? [0:00] Bryan Cantrill: a recipe for a midlife crisis. [0:00] Ryan Peterman: Hey, what are those things that the next level needs to do? [2:21] Bryan Cantrill: I'm going to achieve financial independence and then I'm going to do the thing that is meaningful to me. [2:21] Bryan Cantrill: Am I just like proving that I can buy six... So like why do I want six houses? [2:21] Bryan Cantrill: Quit your job at Meta and become a podcaster [6:28] Ryan Peterman: Guys, I did it and I don't know what to do now. [6:28] Bryan Cantrill: postpartum in engineering. [6:28] Bryan Cantrill: snip all the wires [8:46] Bryan Cantrill: You surf the web for a living. [8:46] Bryan Cantrill: snowboarding in Northern California.

Original transcript

[0:00] I I think there's two schools of [0:01] thoughts on on you know, how people [0:02] structure their careers within these I [0:04] guess ladders. [0:06] If a really ambitious new graduate [0:08] engineer comes to you and they say, [0:10] "Hey, I want to be a distinguished [0:11] engineer one day." [0:13] I have two ideas. One idea is I'm going [0:16] to just focus on the work and just [0:20] you know, promotions will be a [0:21] byproduct. Or I'm going to do the other [0:24] thing where you know, I talk to my [0:26] manager and I'm like, "Hey, how do I get [0:27] to that next level?" And "Hey, what are [0:29] those things that the next level needs [0:31] to do?" And then I will do work that [0:34] molds to that mold. [0:37] >> Yeah, I would try to to steer someone [0:39] with a third path. [0:40] >> What's the third path? [0:41] >> Like what why? Why do you want to be [0:42] What What is it Why do you want to be [0:44] distinguished engineer? Because [0:46] if that's the goal, if the goal is to be [0:48] a distinguished engineer, [0:49] you get there. You'll be a distinguished [0:50] engineer. Now what? [0:53] I I mean, do you I do [0:54] you know, you you it you can be so [0:56] fixated on that. It's like it does at [1:00] some level it doesn't that doesn't [1:02] actually that's not the thing that [1:04] matters. [1:05] That's That doesn't give you meaning. [1:07] And to me, if I had a young engineer [1:09] who's like, "I'm I want to be a [1:10] distinguished engineer." I'm like, [1:11] "That's a recipe for a midlife crisis." [1:13] So, what what what let's try to dial you [1:15] differently. [1:17] And I think that what I think what you [1:19] would what I would steer someone to is [1:21] what what's get you on a path [1:24] that has meaning where you're going to [1:26] be [1:26] developing and what drives meaning for [1:29] you. What's important to you? [1:31] And it's like, "Well, what's what's [1:32] important to me is to be a distinguished [1:33] engineer." I'll be like, "Okay." Well, I [1:35] mean, you you would want to tease it [1:36] apart. Get them on the couch a little [1:37] bit. Like, why I mean, are you not you [1:39] know, loved enough as a child? Like, [1:40] what's going on? Like, you know, you're [1:41] you're you're [1:42] and and you know, kind of work through [1:44] some of these issues because you don't [1:46] want to be dependent on that kind of [1:48] external validation. [1:50] You I would want to be like, "Let me [1:52] introduce you to people who have [1:53] achieved what you are reputedly setting [1:55] out as your goal and are miserable. [1:58] Like let me introduce you to some [1:59] miserable DEs. You want to be wealthy? [2:01] Let me introduce you to some miserable [2:02] wealthy people. So you know that it's [2:05] like that's [2:06] that can't be it. It's [2:09] there's got to be something else that [2:11] that is that the fuel in that furnace. [2:14] And like let's go find that thing. And [2:16] and and then we then then the like the [2:18] promotions will happen and the work will [2:20] happen. [2:21] >> Okay, but let's say okay, mentee comes [2:23] to you and says [2:25] >> you have a good point. I want financial [2:27] independence. A lot of people I think [2:29] want that is they [2:31] they want to [2:31] >> Yeah, what's financial independence [2:32] though? I mean because like we are in [2:34] such a well compensated domain. It's [2:36] like you and I right now could go out [2:38] and get a cup of coffee [2:41] that is the best cup of coffee in the [2:43] world. Or in San Francisco, we're in the [2:44] mission. We can get some coffee that is [2:46] like some Ethiopian coffee, some amazing [2:48] coffee that is like the and that is [2:51] attainable to you and me and and [2:54] basically everyone else. It's like a $6 [2:56] cup of coffee. [2:58] Right? [2:59] >> Yeah, yeah. Well, okay, well let's say [3:01] you define it as you don't need to work [3:03] for money ever again. [3:05] >> But then what? [3:06] I mean this is like okay, you don't need [3:08] to work for money ever again. Like okay, [3:09] I get that. But but so you can go off [3:11] and do the thing that actually motivates [3:13] you. Well, then go off and do the thing [3:14] that actually motivates you. [3:15] >> But what if it doesn't make money? [3:17] >> Well, I think it and I [3:18] Well, this is where I you want to take [3:19] apart. And so like you want to find a [3:22] way I mean certainly you're going to [3:23] have things like [3:25] the the the the difference that you want [3:27] to make, the meaning that you're going [3:28] to find is going to be something that's [3:30] like yeah, this is this is just not a [3:32] career path at all. Like I can't [3:33] actually sustain myself at all. So then [3:36] you need to find a way to balance that I [3:38] would say with your career. [3:40] And you want to keep that balanced. I [3:41] think it I also think it's a mistake to [3:42] be like I'm going to achieve financial [3:44] independence and then I'm going to do [3:45] the thing that is meaningful to me. It's [3:47] like and again you just and I I [3:49] definitely had the blessing of no most [3:53] people were like me. Made a lot of money [3:55] on paper in the dot-com boom and just [3:58] lost every penny of it. I mean, I had a [4:00] I had a loss carry forward for so many [4:02] years that I actually like one year I [4:04] lost track of my loss carry forward. I'm [4:06] like I don't know and I just so but I [4:07] had a loss carry forward I that [4:09] >> [laughter] [4:09] >> and I was like you know I had like fond [4:11] memories of the dot-com bubble when I [4:12] would take my whatever it was $3,000 a [4:14] year against my from a loss carry [4:15] forward. Um the that was most people [4:18] around here. Most people kind of like [4:21] lost it all but also were fine. And they [4:24] think this is the other thing. Like the [4:25] dot-com bust was super helpful because [4:28] if you had geared yourself to be really [4:30] economically motivated [4:33] in '99, 2000, '98, '99, 2000 which would [4:35] have been easy. [4:37] 2001, 2002, 2003 like you that was not [4:39] why you were here. [4:40] Because this place was nuclear winter [4:44] and and you had to had to find something [4:47] else and I I knew like so the funny [4:50] thing I knew like lots of people that [4:51] like had to remind themselves why they [4:54] got in this and it wasn't money. I also [4:56] knew people I didn't know people that [4:58] made a bunch of money in the dot-com [4:59] boom. The people that made a bunch of [5:00] money in the dot-com boom weren't that [5:02] interested in tech to begin with. So [5:04] when it went up in you know late '99, [5:07] 2000 they're like I'm selling it all. [5:10] Like I actually don't want to do this. [5:12] And those people and there are a couple [5:14] of them that I knew and some of them [5:16] really really struggled in the next [5:18] decade cuz they didn't have to work for [5:20] the rest of their lives. But now what? [5:22] Like you don't have to work so like now [5:24] what do you do? And and they were on [5:25] their own search for meaning and like [5:27] not easy and going through periods of [5:30] like oh like I'll buy six houses then [5:31] you realize like six houses are kind of [5:33] like a pain in the ass. It's like you [5:35] and I could go drink six cups of coffee [5:37] concurrently but you're just like what [5:39] am I doing here? Am I just like proving [5:40] that I can buy six So like why do I want [5:42] six houses? So like then I then then you [5:44] you scale that way back. I mean it gives [5:46] you like it really opens your eyes about [5:49] what matters and what doesn't matter. [5:52] What doesn't matter as much. Certainly, [5:54] you need to be able to provide for [5:55] yourself and provide for for a family. [5:58] You want to be able to raise a family [5:59] and so on. [6:00] So, you want to be able to have that [6:02] But, you want to do that in a way that's [6:03] honestly sustainable. I think that that [6:05] too many folks are focused on like, "I'm [6:06] going to do this so I can leave." It's [6:07] like, then maybe you shouldn't be in [6:09] this industry at all. Like, go do [6:10] something Go do the thing you would do [6:11] when you left and find a way to do that [6:14] in a way that like and go pursue that [6:17] dream. And cuz you'll be you'll be [6:19] happier. You'll you'll have meaning [6:21] doing that. Quit your job at Meta and [6:23] become a podcaster, you know? [6:25] >> Oh, well. I did [6:27] >> [laughter] [6:28] >> Well, um [6:29] yeah, it's it's [6:31] It's interesting you say that because [6:32] there's this [6:34] There's this subreddit, this community [6:35] that's all about financial independence, [6:38] earning enough, and [6:39] >> Yeah. [6:39] >> Oh, Jesus. [6:40] >> I'll see [6:41] a very regular post that says, [6:44] "Guys, I did it and I don't know what to [6:47] do now." [6:47] >> Exactly. [laughter] [6:49] Yeah. I did it. I did And also like I [6:51] gear I mean, I think this is like this [6:53] is a problem by the way in engineering, [6:54] not even in [6:57] even when the goal is has meaning, this [6:59] is a problem. This is what I This is [7:00] what I call postpartum in engineering. [7:02] When you are really focused on shipping [7:04] something and you're just like, [7:06] "Shipping this thing is just the lens [7:07] through which you're doing everything." [7:09] And when we shipped our first rocket [7:10] Oxide, I was very concerned about like, [7:13] "We are going to have postpartum." And [7:15] there are going to be people who are [7:15] like, "I was working so hard and pulling [7:18] so hard for so long." And now we shipped [7:20] it and I'm like, "Now what?" And I'm I [7:22] So, even when the thing you've done is [7:24] obviously meaningful and you've achieved [7:26] something extraordinary, you're going to [7:27] have that. When the thing you've also [7:29] achieved is like, well, I can like buy [7:32] any cup of coffee I want. It's like the [7:33] the thing I want like now I'm not even I [7:34] got like What am I supposed to do? I [7:37] It's just easy to see [7:39] how you people be wonder what the [7:43] meaning of it really is. And then there [7:44] are some people that just like snip all [7:46] the wires and they're like, well, the [7:47] meaning of it is to get even more. And [7:48] then just like, you know, [7:50] then you get like Larry Ellison or [7:51] whatever. But like [7:52] that's also not something that people [7:54] should aspire to. [7:54] >> Right. [7:55] I Well, what would you say cuz I I do [7:57] know someone who is genuinely happy [8:01] just doing nothing. [8:03] By doing nothing, I just mean like [8:06] relaxing in bed, you know, watching [8:08] their shows, you know, playing hanging [8:11] out with friends and stuff. I mean I [8:12] think if they had the billion dollars, [8:13] they'd just do that every day. [8:15] >> Yeah. [8:16] >> But [8:16] what you said doesn't work in that case [8:18] cuz that doesn't earn anything. [8:21] >> I You know, I actually did know a guy [8:23] I knew a guy who I actually did know a [8:24] guy who did this who I was thinking [8:26] about people who made money that don't [8:27] have them. I knew one of I I believe one [8:31] of Yahoo's like first employees, but not [8:34] because he was like crazy sharp or [8:36] anything. Because he like they they [8:38] wanted to hire a web surfer. [8:40] And he was like a pothead who was like [8:42] this like this sounds like the level of [8:44] work that I'm a So, he gets a job as [8:46] like a web surfer one at Yahoo, but as [8:49] like employee number like single digit. [8:51] He gets the equity grant as part of like [8:54] joining the company. Never gets another [8:55] equity grant, but makes a king's ransom [8:59] because he's very early at Yahoo. [9:01] Never promoted above like web server [9:03] rank one or whatever and was complaining [9:05] to everybody about how much his job [9:07] sucked. And it was like, you surf the [9:09] web for a living. Like you've somehow [9:11] managed to like win this insane lottery [9:14] where you're getting paid to do like [9:16] very close to nothing. And he's like at [9:18] when it started, he owned like all of [9:20] Yahoo in terms of like surfing cuz the [9:22] way Yahoo worked. You were you may be [9:23] wondering what the hell I'm even talking [9:24] about. Yahoo was a curated directory of [9:27] links. Like this is again where I sound [9:28] like [9:28] >> Uh pre-Google. [9:29] >> Very much pre-Google. This is like [9:31] pre-Google This is not just pre-Google. [9:32] This is like pre-Lycos, pre-HotBot, [9:35] pre-Altavista. This is this is [9:37] basically pre the ability to search the [9:40] internet. [9:41] You [snorts] would have these curated [9:43] directory of links. And someone needs to [9:45] go like find this content. And it was [9:47] like this guy, Yahoo employee number six [9:49] or whatever he was. [9:50] And so he originally like owned the [9:52] entire directory, but he's like not very [9:54] good and not very energetic. He was [9:55] like, you know, stoned all all the time. [9:57] So they kind of like carved it So [9:59] finally he I I believe at the end before [10:01] he finally quit, he owned only like [10:03] snowboarding in Northern California. [10:06] That's what it was his like [10:07] responsibility [10:09] to It's like, this is a job? And [10:12] So that is the kind of person who was [10:13] And you would like to think that that he [10:15] found something that was actually [10:16] meaningful to him, but clearly it was [10:17] not the work or work for that matter.