Philip Su grew quickly to a Distinguished Engineer at Facebook and OpenAI. We talked about the psychology behind peaking in a tech career and the pressure at the highest levels.

Check out the episode wherever you get your podcasts: YouTube, Spotify, Apple Podcasts.

Timestamps

00:37 - Growth past IC9

05:39 - Motivation changes over his career

11:36 - Asking to not be promoted

17:33 - What made it hard to sustain IC9 performance

22:22 - What motivated him outside of promos

26:21 - Is career advice useless

29:34 - Motivation after you’ve hit FIRE

36:08 - Meaning and fulfillment

38:17 - Top book recommendation

40:14 - What he would change

Transcript

00:37 — Growth past IC9

Ryan:

[00:37] Last time we talked, I focused almost entirely on, you got to a distinguished engineering level. You grew very quickly. How’d you do it? And this time I wanted to focus more on what happens when you hit your terminal level. Or what I mean is there’s this idea of a career asymptote, which is no one can grow forever. And at some point, you’re going to get to a level where you can’t go any further, and you may have 20, 30 years left in the career.

[01:15] So what I wanted to ask you is, when you got promoted to IC9 or distinguished engineer, which is crazy high, that’s like four levels higher than a senior engineer, what was your immediate thought? Were you thinking, “I want to go to IC10? Does that exist?” Or are you thinking something entirely different?

Philip:

[01:36] Yeah, I honestly didn’t think about it when I was earlier in my career. I really just assumed that, oh, yeah, you go for a promotion and once every few years you get promoted. And I never once thought, there’s gotta be an end to this, right? Like everybody, there’s gotta be an end, right? And I think many people might not think that through, right? And so for me, it took many years before I figured out.

[01:59] Even at seven, for instance, I felt like, oh, hey, things have got to slow down. Because it gets harder and harder. The amount of scope that you need becomes tougher. The number of roles that offer the opportunity actually gets smaller because the organization also needs that scope of work, right? So, for instance, at Microsoft, oftentimes when they reorganize, they figure out, hey, your organization should at most have four partners.

[02:25] And that’s just a budgetary sort of thing. That’s a business opportunity thing. So you need the opportunity as well. And so when I was growing to IC9, I think I just didn’t think of going any further as realistic. I was at Facebook when they first created level nine, right? And I remember that three level eights were promoted into nine. And at that point, those three level eights were all universally loved and known throughout the company as obviously super senior technical people.

[02:57] And to me, that felt unreachable. If I’m honest, when I think about those folks and the type of work they were doing, that really felt out of reach for me. So I think definitely by the time I got to IC8 or IC9, it really felt like the end is near.

Ryan:

[03:12] Well, a lot of people might feel that sooner in their career, too. What kept you pushing past the staff level or the senior staff level? 6, 7, 8, 9.

Philip:

[03:24] When I got all the way through to 7, I think, which was at my 12 years at Microsoft, right. I was really personally ambitious for level growth. And I think the reason was, in school, I loved tests. I loved grades because I was good at grades and tests. When I started professional work, there was nothing quantifiable. It wasn’t like once every two months you got a test that told you you were doing well.

[03:48] So for me, promotions became one of the very few quantifiable things, right? It’s sort of like, well, how much money do I make? And there are so few things that are actually numbers, right? So to me, a level was almost like an achievement number. And so throughout my 20s and my early 30s, I was really ambitious to get through all the way to level seven. But I think starting there, I just realized the nature of the work changes with every additional level that you go into.

[04:17] I wasn’t sure that I would like the end of work, first of all. And then the other is I felt things slowing down rightfully, because everybody has a talent limit, right? So for me, as I approached that, I just began to feel like I was no longer ambitious for the further growth. So I would say my growth into 8 and 9, neither of those were things that I was seeking myself. I was, by that point, doing the work I found interesting and trying to do a better job of it, as opposed to.

[04:46] I would characterize my time, especially in my 20s, as mostly focused on how do I grow to the next level. Tell me what I need to do, that sort of thing. By the time I went from 7 to 8, getting to 8 was honestly a surprise for me at Facebook, because getting to 8 was the first time I learned that there were levels at Facebook. When I joined Facebook, it was 500 engineers, right? Everybody was focused on the work itself and did not worry about careers and stuff, which I think is normal for small companies.

[05:15] When you’re on a big mission, you’re just trying to get the mission done. So I didn’t even learn I had a level until my boss, who was Boz, said, “Hey, congratulations, you’ve been promoted to level eight.” And I was like, “What? There’s a level here? That’s kind of amazing. Thank you.” So I think I stopped focusing on the level itself, and my promotions became more a consequence of the work that was being done.

05:39 — Motivation changes over his career

Ryan:

[05:39] Early in your career, it sounds like you were constantly maybe harping your manager and saying, how can I get promoted? What’s the next thing? And later you transitioned into doing meaningful work and getting promoted as a byproduct. What was it that changed in your mind where you went from that mentality to promos don’t matter anymore?

Philip:

[06:02] Yeah. I think there were two things that come to mind. One was that the thrill of the promotion itself was no longer the same as when I was younger. So I think when I was younger, because I sought after those grades, those measurable metrics, I very much felt great every time I got promoted. This was wonderful, right? I think as I got promoted even into level seven, I started to honestly become a little bit.

[06:27] Not ambivalent about it, but I guess it wasn’t all roses to me anymore, the idea of getting promoted, because I realized that each promotion also came with much higher expectations. Expectations that I was no longer positive that I was going to deliver. When I went from a four to a five, I was confident that I could do this work. It’ll be great, right? And when I got to seven, I felt like.

[06:52] Like this is pretty much nearing the boundary of my capability. And so I felt a lot more comfortable saying, hey, if they keep me here perpetually, it is still work I enjoy a lot. I think the second thing that really changed for me is realizing also that asymptote, right. Realizing that, you know what? Maybe this ultimately is my final level. I was so humbled many years ago when I had this lifelong mentor throughout much of my adult life that was one of my best managers at Microsoft.

[07:26] And I recently, just in the last few years, thought, you know, there was this one conversation where he promoted me into level seven. And I said to him, “That’s great. Thank you. Let’s talk about how to get to eight, right?” And his first response to me was like, “Philip, can we just take at least one one-on-one to celebrate the fact that you’ve actually reached this tremendous level at Microsoft?”

[07:46] And I honestly felt like, no, we can’t. I’ve got to keep going. But years later, I realized he himself was probably 15 years more in industry than I was at the time. And he himself, in hindsight, had to be a level seven. He was not a partner at Microsoft. And so for me to come across sort of so naively without considering, for instance, his feelings or considering just realistically, this is a guy I look up to a lot, and he’s giving me mentoring advice all the time.

[08:15] And he himself is level seven. And so for me to be pushing so hard, I think just the humility of realizing that people do tremendous work at those levels, and I should just appreciate that if I can even keep up with the expectations, that’s already kind of a big accomplishment.

Ryan:

[08:33] If I were to think from when I was at my youngest, the beginning of my career, my thought would have been keep pushing. And the thoughts that you just said are noble, but let’s go to eight. Let’s go. Yes, this person’s at that level, but I want more. I want more. What calmed the, I guess, the crazy energy of I want more, even if it’s not realistic?

Philip:

[09:04] I think some of it might be as simple as age, to be honest. And I think society is designed to work this way, right? Like young people go to war, right, traditionally. And there needs to be this ambition of, I’m going to build great things, I’m going to do great things. I think that energy from the young is super powerful. And I definitely don’t want to sit here and say, let’s quell all of that.

[09:25] Like, let’s make sure when a person is 23 and they start work, they’re like, E3 is fine, right? So I definitely want people to have that ambition. I think maybe some of it is the natural aging process, but I do think, at least for myself, a lot of it was the shifting nature of the job itself. I would say for me, up until, let’s say, an IC6 level of work, it just felt like doing the same stuff, but grander, if that makes sense.

[09:53] You’re still coding all day. You’re meeting with engineers primarily and product managers, sometimes designers, but it’s just about doing it at a much higher amplitude. I’m now gonna do much bigger refactors. I’m gonna participate in longer-range projects. Oh, we should do this new service that does X. But I think beyond that the nature really changes to where just doing more better is typically not how people get there.

[10:19] You will find very rare cases, for instance, where people can do more better, but they are preternaturally gifted for super fast coding or whatever. I was definitely not that person because I was much more a generalist. And so for a generalist going beyond six, I think it does change the nature of the work such that you’re doing maybe less direct coding, for instance, maybe even less direct architecture stuff, but much more things like team direction.

[10:45] Is this even the right product to be building right now, given where the industry is moving? Maybe trying to influence even another organization that’s on a collision path, right? Maybe trying to find a mutually useful way to land both sides. So I think that also, pragmatically, as you go up higher in levels, it’s almost definitely true that you will have more meetings, just period. Whether you’re an IC, whether you’re a manager.

[11:10] That’s just what it is. And plenty of people, for whom directors, as an example, every single hour’s meetings and half of the hours are double booked. And so they’re just choosing which one to go to for that, right? That’s typically how, one small example of how the nature of the work changes. And so for me, as the nature of work changed, I was less enthused about how it might continue to change if I continued getting higher level.

11:36 — Asking to not be promoted

Ryan:

[11:36] You mentioned that you sought out a demotion from IC9 to IC7, or distinguished to senior staff. Did you ever consider saying to your manager, I don’t want to get promoted?

Philip:

[11:48] Past IC7 from going to 7 to 8? Not really, because I didn’t know levels had existed at that point. So that promotion was sort of like a surprise, right? But I think if I’m honest, Facebook was also so small even back then. I was promoted into eight maybe one year at Facebook. I was a seven at Microsoft for probably three years. So you figure, like, let’s say four years, right? One year into Facebook, I get promoted to eight.

[12:14] Facebook was still, I want to say back then, 800 engineers globally. So the company was much smaller. And I think when a company is that size, the work doesn’t include as much meta work. The work is mostly the work. So you’re doing the code, you’re doing the actual. Whereas I would say my even at Facebook many years later, when I came back to Facebook Seattle, when I joined, I was the second person who joined, right?

[12:41] So the office was four desks. When I went to Facebook London for five years and I came back, the office was more than 2,000 people. And so just like that, mind-blowing. Size means that the typical senior job when an organization is tens of thousands of people is a lot more people wrangling, I guess, and a lot less technical. I think one of the struggles I’ve had throughout my career is so many higher level jobs, including a solid IC6, quote unquote.

[13:13] Just coding has to do with how well they work with others. And in some environments I just don’t work very well with people like others do. I would say objectively when I was leading the Facebook London site, I was good at the job. It was a very people-focused job. But for me, the happy parts were people like welcome to the team or, like, hey, going to do this collaboration with Menlo Park and all this stuff.

[13:37] I think there’s another type of people-oriented thing that happens at large companies, which is a lot of what people might call politics, but a lot of work that has nothing to do with the actual software deliverable but has everything to do with the fact that when three or more people are somewhere, there’s politics. Just figuring out the people thing. Dealing with unhappy people, for instance, is something I’m very bad at.

[14:03] Giving people constructive feedback is something that I am fairly bad at. And so more jobs at those levels just require even an IC7. Minding your own business is probably regularly supposed to be giving pretty helpful feedback to other engineers. They’re not their managers, but still you should be improving those around you. And I am much less good at that.

Ryan:

[14:26] When you sought out the demotion from IC9 to IC7, I’m just thinking for someone who’s thinking that the success criteria is going up in levels, it would be very difficult to accept going down from, you know, kind of like undoing all that hard work, quote unquote. What was that process like?

Philip:

[14:50] I think it was hard. I think it was Will Smith or someone else famous said getting famous is amazing. Being famous is a mixed bag, and then getting not famous is horrible. And I think that’s human nature, not just about fame but about anything, right? When we are growing in anything. Let’s suppose you first get into auto repair, right? The first big job you do beyond an oil change feels like success.

[15:15] Right. Eventually you’ve removed an engine, you’ve done clutches, and at some point, like my age right now, I literally just started giving away some of my auto repair gear because I’m realizing I’m not doing this as much. Physically, I’m not as capable of doing it. And that feels a little bit sad. And I think the same thing happened to me in my software career, which is on the way.

[15:40] Rising up, it always felt great, right? Other than the rising expectations and the worries around that. But the general thing felt like, oh, I’m progressing. Being at the top was a mixed bag. There were some amazing things. There were some very hard things. And then I think coming down, I feel like there were a few things that were hard about it. One was that I think I knew I could do more because I had done more before.

[16:09] But part of it was the feeling of being exhausted, running at that pace, and always having the Eye of Sauron, like roving the land looking for people.

[16:20] And I think the higher level you are, the more that you feel that intensity all the time, and rightfully so. You’re getting paid the big bucks. And so it’s right for a company to constantly question whether or not they’re getting their value out of you. So I think it’s only fair. But I felt that struggle. And I think the other thing that was hard for me about getting demoted down to seven was more that feeling that as I saw other people who used to be below me rise above me beyond that level, that was very difficult.

[16:52] I don’t begrudge them their success. So I’m not at all saying I’d rather go out there and make sure this person never succeeds. What I mean is more that I felt wistful, I guess is the right word, which is like, I was not crushed that someone else was doing better, but I did feel a little bit like I once could do that work. And part of me wonders if I could again.

[17:12] It’s like when Beowulf, at age 70, is asked to slay the dragon one last time. He gets out of his old house, and he slays the dragon one last time. Part of me wishes that I had that in me, that when I’m 70, I can be called upon one last time to do this thing. And I’m able to deliver at that level, but I know that maybe that’s not it for me. Right.

17:33 — What made it hard to sustain IC9 performance

Ryan:

[17:33] You mentioned that you used to be able to do it, and then you couldn’t. What changed that made it hard to perform at that level?

Philip:

[17:40] I think if I were to bucket it into a few categories, one is my environment changed. So as Facebook, the company grew, right? Senior ICs do a lot better, I think, in larger companies if they are domain experts. So you’re great at, let’s say, SQL optimization, right? And you’re helping SQL move on to SSD and you’re moving SQL into the cloud. That sort of IC does best in a large company. In a tiny company, a generalist does best because when I first started on video calling, I also negotiated the contracts with Skype with a third-party tester, with all sorts of things.

[18:18] So I’m negotiating contracts, I’m doing crazy things, but I’m also coding the thing, and then when the press release goes out, I’m talking to the press. So I’m literally meeting the press about the video calling feature, right? That is what a generalist excels at. And I could only do that because Facebook was small. By the time I came back to Facebook Seattle, and the Seattle office itself was 2,000-plus people, and the company was maybe, I don’t know, 30,000 people.

[18:40] There’s no way you would send me out to negotiate a contract with Microsoft. That would be ridiculous, right? And so for me as a generalist, my environment shifted to where specialists would survive better. And for me as a generalist, I was honestly just not as useful, right? For one whole six-month period, the team that I was on, the only mission for the ICs for that entire six months was to fix the bugs on this internal tool.

[19:02] So I spent six months fixing the bugs, which I’m happy to do, but I am not especially skilled at that. Right. And so I think one thing was my environment changed. I think the other thing that changed for me was I did tire a little bit of feeling like there was always so much pressure just to meet expectations, if that makes sense. So up until I would say IC6, I never felt the Eye of Sauron. Like I was never at any point in my career feeling like, oh, if I just fall a little below right now, maybe they’re going to can me.

[19:36] Right. But I think regularly at IC7 and beyond, once in a while I would feel like, oh, I feel like my own performance this half, I don’t know, things aren’t looking great, you know what I mean? And I think in a way it’s like when I was super ambitious, being like the slowest member of a team. But catching up and rising was exciting to me as I accomplished more in my career and I felt my happy places.

[20:03] I no longer liked the feeling of being the slowest on a team or feeling like I was potentially going to have a talking to at some point because I wasn’t performing to expectations. So I think that sort of pressure also was something that I no longer enjoyed in reality.

Ryan:

[20:20] That Eye of Sauron, though, was in your head rather than reality. Given that you got promoted from 7 to 8 and 8 to 9, right?

Philip:

[20:28] Yes. Maybe some of it is imposter syndrome, but I think a lot of it is actually just an honest look at myself and reality. So when I was an IC4 looking to go to IC5, right, there were plenty of IC5s where I felt like I could totally do that work. Just give me two years and I’ll be just as good.

[20:47] At IC7, I could see many IC7s where I’m like, honestly, if you put me on that guy’s team, I could not do that work. Right. I know I can’t.

[20:57] And so I think my realistic appraisal of my own abilities was more accurate to what they actually were.

Ryan:

[21:07] Right.

Philip:

[21:08] And also maybe some of it, if I riff on your theme a little bit, maybe some of it also is that as you get more and more senior, not only are the expectations higher, but the number of business roles where you are the perfect guy for the role actually is far, far less. When you’re an IC6, almost any team would welcome one. It’s like, great. Like, just pick up a keyboard and we’ll get going.

[21:35] But I think once you get to a certain level, it’s like, well, we need someone who’s good at marketing. And then this person has to also be somewhat technical, or the shapes become very specific.

[21:46] And I think that just realizing that my shape wasn’t right for many, many roles also made me realistically feel like maybe this isn’t the right long-term place for me.

Ryan:

[21:55] It sounds like over the course of your career, you worked an extraordinary amount. I mean, you mentioned last time we talked that you bring a sleeping bag to work. And I think early in your career it makes a lot of sense because you were so gung ho and you’re pursuing the promos, but then when you were at Facebook and you weren’t pursuing the promos, you’re just getting them because you were doing awesome work.

22:22 — What motivated him outside of promos

[22:22] What was your motivation to work so crazy hours at that time?

Philip:

[22:27] One of the most intense work periods of my life was shipping the first version of Facebook video calling. I had worked with Denise, with Chago, with maybe one or two others, with Vijay. That first version, when we went out, I think I went about six weeks down in Menlo Park, where I literally got up out of bed, went straight to work and worked all the way until I drove back to the apartment and went to sleep.

[22:55] I was eating junk food the whole day. It was like SunChips and whatever. But despite that, I lost ten pounds in those six weeks. It goes to show how intense brain-related work can be, but I had no idea there were levels. So obviously, a promotion was nowhere on my mind when I was doing this work. But I tell you, it was one of the most fun periods of my life because it felt so thrilling that I was directly impacting real users because Facebook was so tiny back then.

[23:25] You could see the users having errors right away. I was patching errors every day. It felt missional, right? It felt like this was the first time video calling was going to be easy for people without installing any software. WebRTC was relatively new back then. We still had to get some software with the first version out. And so I felt like this strong sense of mission, and being on a tiny team of three people also felt like, wow, I owe it to the other folks too, who are working equally hard to pull forward.

[23:55] So I think that was still in it for me, but no longer based on promotions as a thing, but more because I believed in what I was doing, and I felt that direct customer contact with people I could actually see getting positively impacted by the fixes.

Ryan:

[24:13] When you look back on a career of working so many hours, would you say that it’s worth it, and would you recommend it to others?

Philip:

[24:21] I think it’s become popular for successful people to tell people not to push as hard, and for wealthy people to tell people not to push as hard. And it’s understandable that people who aren’t as late in their career or aren’t as wealthy would say, well, it’s easy for you to say that, right? Because you’ve already gotten there. Like, I once had a guy say to me, “Well, it’s easy for you to say that because you’ve already been there, done that.”

[24:44] And I think at some level, yes. But I also think that there is sometimes wisdom that can only be gotten when you live a certain thing yourself. This is why when someone tells you money can’t buy happiness, nobody believes it, right? Everybody thinks there’ll be the one exception. And I think the thing is, you have to have lived a certain life before to really objectively be able to say whether it’s better or not.

[25:14] And I think for me, given my personality, the really much higher level roles that require broad impact and feel like a lot of pressure for me, just for my own personality over time, is not the right thing. But I would, at the same time, say, well, I don’t want to look a gift horse in the mouth. The freedom for me to, for instance, work on my own software right now, it only comes from having had a career where I got paid enough that I could save enough money that I can go two years writing my own software, right?

[25:46] And I don’t want to look a gift horse in the mouth and say, “Oh no, I totally shouldn’t have done that.” That’s not true at all. I think what it is for me is I would have appreciated, when I was younger, being more cognizant of the trade-offs that I was making. You know, like, hey, if I dig in really hard right now and I really work hard, then this will buy me the freedom when I’m 50 to work two years on my own software.

[26:11] I wish I knew that was the trade-off. Whereas I think at the time I was just blindly pushing forward, like, hey, I’m just ambitious. I want to do all this stuff.

26:21 — Is career advice useless

Ryan:

[26:21] And in your career and your life in general, you must have mentored so many people. And like you said, if you give someone advice and then they can’t really take it until they actually experience it, is all advice useless? Then what’s the point?

Philip:

[26:43] I think there is still a point, which is there’s a massive difference between you ignoring advice and you not knowing the advice was even there. And I think the difference is two things. One is when you have the advice in the back of your head but you’re ignoring it, when eventually some consequence comes about, it actually will reinforce for you why the advice was given and you’re much more likely to take more immediate action because it rings true, right?

[27:10] And so when someone tells you money won’t buy happiness and, let’s say, a brick of $2 million falls on your forehead, right? And then you go out and you buy something and you realize it’s not a happy thing. One of the things that I splurged on for myself when I felt like I have financial security is I bought a $50 pen, okay, because New York Magazine said this is the best pen out of the 100 they reviewed, and it was this Baron Fig pen out of machined aluminum or something.

[27:36] And I bought that pen, and after using it for a while, I realized this is not my favorite pen. There’s a Pilot G2 or whatever that’s much better than this, and it’s like a buck fifty, right? It took me buying that machined aluminum pen before I was like, actually, if you mill a pen exactly round, no matter what surface you put it on, it’s about to roll off, right? And it’s hard to grip onto because it’s slippery.

[28:01] It takes getting there. So I think part of the advice is when you finally do buy that pen and you’re disappointed by it, you realize, hey, people used to tell me that this thing might happen, right? So I think that recognition is helpful. I think the other thing, however, is even if you don’t take someone’s advice right away, I do think, at least for me, when I next face a decision where that advice might apply, it makes me think a little more hard about it. I may not take the advice, but I’ll at least think, several very smart people have told me this thing.

[28:35] Maybe there’s a reason they say that.

29:34 — Motivation after you’ve hit FIRE

Ryan:

[29:34] Obviously part of career and what motivates people at some point is the financial earnings. And I’m curious to explore the topic of the motivation after those more objective things because, for instance, there’s this subreddit and this movement on financial independence and all of that.

[30:11] And I remember when I used to look at that subreddit, there would be a recurring post of someone saying, “Hey, I finally did it. I finally hit my retirement number, and I’m depressed,” or “I don’t know what to do,” because they’ve been on this money-making hamster wheel for such a long time that their happiness was kind of tied to that. And so at some point in your career, you broke out of that needing to be on that wheel.

[30:40] What did you look to that gave you meaning and fulfillment in your day-to-day outside of needing to be in this capitalist machine?

Philip:

[30:50] I feel like, to your point about the FIRE movement, there are two types of personalities. There’s one type that, when retired, will be happy, and they will be happy for years. This is the type of person that is happy to sit on a beach, read a book, and if they are doing that two months from now, they are still happy. It’s like, oh, this is the best, right? There’s another type of personality, which is mine, which is the first week on the beach is amazing.

[31:15] And then once I’m there for two weeks, I’m like, what’s going on? What am I doing here? For me, four months on a beach feels like, quote unquote, a waste. And I know that that offends many people. For the type of personality for whom lifelong beach them is amazing, they will feel like what I’m saying is nonsensical. But I think there’s a type of personality that understands exactly what I’m saying.

[31:37] Which is like that sort of person feels like the rat in the cage that pushes the dopamine button and then dies pushing it because it can’t even bother to eat because it feels the pleasure is so great that it can’t eat. When I see that, I feel like that’s sad. That to me is sad. That is not dying in bliss. There’s a type of personality that says, “What more could you want? Like if you could feel a sensation that is more desirable than even food when you’re starving.”

[32:02] Like, wouldn’t that be the epitome of happiness? And in my mind, that is just a travesty. Like, to me, it feels like this rat could have been so much more, right? So that’s how I feel about myself. So I would say of the FIRE movement, for someone like me, the best parts of the FIRE movement, if I were to embrace it myself, which I never did, but if I were to embrace it, the best part would have been before I retired because it gave me such a strong sense of purpose.

[32:28] I am going to save up until I have $1.5 million. That’s the goal. And every two months I can remeasure how the investments are doing. Right? That is the excitement. The moment I reach the R in FIRE, then that’s actually probably the dangerous spot for me. So I think, in my particular case, for my personality, always having that sense of a goal is good. And that is what I’ve struggled with when I have been in periods of unemployment.

[32:55] I’ve really struggled with what, quote unquote, should I be doing?

Ryan:

[33:00] So then I guess the question is, you can think of getting promoted and all this stuff in engineering as this game that you’re playing, and you’ve got a goal, and you’re kind of going up, and you’re excited. Oh, I want to go to that next one. Oh, I want to go to the next one. I’m going to grow the skills. Do you think that you’d be happier if you got promoted slower and the game lasted your whole career? So let’s say whenever it is you actually want to retire, say, I don’t know, 65 or whatever the age is.

[33:33] And we could set up that game so that you are constantly searching for that next goal, and you get IC9 at 65, and you get a nice little hit of dopamine all along the way, and you’re constantly growing. Do you think you’d be happier in that case versus you speed-run everything and you get to IC9 in the first third of the game.

Philip:

[33:59] I feel like titrating it out would have been better for me. Maybe not all the way till 65, let’s say, right? But take from E3 to E9 is about six levels, right? If you work about 42 years in your career, that’s one level promo every seven years. When I imagine myself taking seven years to go from three to four, I’d feel like, oh man, I’d feel like I was so behind in the sense that it’s not a competition, but I would feel like, am I really progressing?

[34:26] Because seven years, you could get a PhD at Stanford in seven years. So I’m like, dude, what’s going on? Right. But the lemma or the corollary of what I’m saying then is let’s suppose you get from three to five or six within, let’s say, seven years, which is a leisurely, not superstar pace, but not terrible pace. You go from E3 to 6 in, let’s say, seven or eight years. Right. The remaining three levels, let’s say you would need about 12 years between each of them for the math to work.

[34:54] And when I think about 12 years, I also feel like, oh, that feels so long. I worked at Microsoft 12 years, and that was on six different teams.

[35:02] So on one hand, I feel like it would be better if it came sooner, but on the other hand, I do feel like you’d have to recognize if it came sooner that you might be 25 years in your career without a promotion. And for me, I think I would have to. If I were in my 20s and you told me that I would have to have shifted my intrinsic motivation to something beyond career levels. In my 20s, I didn’t have other intrinsic motivations, so that would have been disappointing for me.

[35:32] I’ll throw in one last thought, though. The median age of a Corvette owner in America is 64. And that’s a median, meaning half the people are above that. Right, right. I personally imagine by the time I’m 64, owning a Corvette would be not half as interesting as when I was 38, you know what I mean? And so, in a sense, I mean, is reaching E9 at 62, like, as good? Is that like getting a Corvette at 64?

[35:59] I don’t know. I feel like in a way maybe that progress is wasted on someone that’s that late in career. So I’m torn about it.

36:08 — Meaning and fulfillment

Ryan:

[36:08] You mentioned in between jobs or when you were, yeah, when you’re in between jobs, the motivation or the goals were harder. Did you ever discover meaning or fulfillment outside of an immediate goal? Do you have any advice on finding meaning in your work?

Philip:

[36:28] Yeah, very personality dependent. But for me, the thing I learned about myself is that I need to do more stuff with people. When I got out of work, a big part of it was the socialization. You show up, it’s like they mandatorily have to show up. Whereas when I throw a party, nobody mandatorily has to show up. So work is like mandatory socialization. But when I first quit Facebook and I took six months off, I thought this would be amazing.

[36:54] I’m gonna reach out to all sorts of long-lost former coworker friends for coffee and whatnot. But the problem is everybody else was busy working. So when I wrote them like, hey, can you grab a coffee, whatever, it’s like, well, I can’t, maybe next week. Right. And so what I figured out there was that, wow, I thought I would have all this socialization, but I didn’t. The best time being without work was I had about a six- or nine-month period where two other former coworkers of mine also were between jobs.

[37:21] And that was amazing. We went skiing three times a week on weekdays. Right. We did all sorts of stuff together. We ate dinner out. And I imagine that’s what I would like to think British aristocrats in the 1800s, like the same men that dug up the bones from the Jurassic period and that’s why it’s called the Jurassic era. Right? Those people, right? The gentleman scientists. Right.

[37:43] I would like to think that part of the secret to the happiness of the aristocracy is actually that there were other aristocrats also looking to do something together. It was fun because Mr. Darcy had no job, but you have no job either. So you and Mr. Darcy get together three times a week to whatever, play bocce ball. So I feel like that is the secret for me.

[38:05] And realizing that has made me feel like whether I’m working or not working, being in a situation where I can find regular socialization is probably key to me being happier.

38:17 — Top book recommendation

Ryan:

[38:17] Do you have any book recommendations? Something that you’ve read that gave you perspective on life that you recommend to someone who may be earlier in their career or are still figuring out how they want to plan things out?

Philip:

[38:29] Yes. I love the book Four Thousand Weeks. I’m not sure if you’ve read it.

Ryan:

[38:33] Haven’t. What’s it about?

Philip:

[38:34] Oh, highly recommended by Oliver. Oh man, I’m going to pull out the last name, but Four Thousand Weeks, his idea is that the average one of us probably has about 4,000 weeks. And you’ve probably seen the Tim Urban cartoon where he draws out a single box for every week of his whole life. Right. When you think about a life as 4,000 weeks, it actually feels a lot more precious and every week feels much more consequential.

[38:57] So reading that book really helped me take a broader look around. Decisions were often hard for me because my values weren’t clear. But what I would say to the average person, if they’re willing to hear the advice, would be something like, first, visualize today’s biggest goal for yourself in the next whatever many years. Maybe you want to retire by the time you’re 36, or whatever the FIRE movement people want, right?

[39:18] Visualize that goal. Then I would say, now pretend you’ve just reached it. What do you do next? If you have a good answer for that, then you’re fine. Then you’ll be just fine. I did not have an answer for that. And being that person, not having that ready answer really left me in a place where I was like, is it Michael Phelps or whoever? There’s so many athletes for whom, once you reach that career peak, they realize, wait, what’s after football or what’s after swimming?

[39:45] And the answer is nothing, because they’ve built no other skills in any other domain. And once they’re not a famous football player, it’s like, well, how many people really want to see them and for what reasons other than to ask them for money? And so I feel like many people have that big goal. I’m going to get in the NFL. I’m going to get in the NBA, right? But they don’t know what they’re going to do the day after.

[40:04] And so if I could give one piece of advice to people, it would be: think about the day after and what you’re going to do. And I think the book Four Thousand Weeks really helps a person think about that.

40:14 — What he would change

Ryan:

[40:14] And I guess, last question. If you could go all the way back to the beginning and do it over again, is there anything that you would change?

Philip:

[40:22] I think there were a few times in my career where I biased too much toward being maximally available for my employer and not available at all for friends or family. I think there are a few incidents, and if I could change things again, I would have played those periods of my life differently. Funny enough, one of them was not when I lost ten pounds working six weeks at Facebook, because my kids were very young back then, right?

[40:52] My kids were very young back then, right? Probably three and one or something. But what was great was I told my wife back then, hey, after we ship, it’s probably going to be nuts. And so what we did was we just moved the whole family down to California. My wife took the kids to the library every day. I could see them for 14 minutes before I went to sleep, right. And having family with me and just treating it more like, hey, everybody, we’re just going to go on a big trip.

[41:16] That actually made it all right. Whereas I think there were other times in my career where my wife was the primary one taking the kids to and from school. I had very little conversation with them. It felt like I was doing important things, quote, unquote, for the family.

Ryan:

[41:30] Right.

Philip:

[41:30] But at the same time, I wasn’t with the family. And so there are times like that where I do think there were a few periods where I would have played that differently.

Ryan:

[41:40] Everything in life, we have limited time, so everything in life, there’s trade-offs. If you did, let’s just say you went back to those times and you prioritized family, would that have made a material difference in your career success?

Philip:

[41:55] I think it might have. And I think the tradeoff is, in my case, definitely worth it. I say I think it might have because it’s very hard to tell. I’ll throw out examples where it’s hard to tell. How sometimes there’s the type of engineer who works super long hours, but you can tell that as they work longer and longer, they’re actually creating more and more regressions and they’re getting worse and worse.

[42:19] Right. For that sort of person, a break would actually improve their performance. So there’s no telling. Maybe sometimes taking a break would have made me perform even better. Right. So I don’t want to say that that’s definitely not true. But I also feel for the type of person who constantly tells other people, relax, work a 40-hour work week, you’ll do just as well and even better than other people.

[42:43] I don’t think that’s generally true. I think, at face value, it doesn’t seem like it could be true if two people were at the same skill level, but one just worked 10 hours more per week over a period of time. I think anybody would feel it was grossly unfair if that person wasn’t rewarded any differently. It would feel like, what? What sort of crazy company do you work for where these two people get compensated the identical amount over multiple years, but one guy’s working 40% more?

Ryan:

[43:11] Right.

Philip:

[43:11] It makes no sense. So I do suspect it would have impacted career, but I think also that I would have gladly taken that tradeoff.

Ryan:

[43:20] Awesome. Well, thank you so much for your time, Philip. I really appreciate it.

Philip:

[43:23] Yeah, thanks for having me again.