All right, we're gonna start our first question block with something we've been excited about for a while now, a live caller, so I can actually talk to someone back and forth. We have video on the live caller too, so if you're a YouTube listener, youtube.com/counterpartmedia, you can actually see both of us on the screen.

Our first live caller is Spiros, who has questions about lifestyle-centric career planning and concerns about falling into the second control trap with his current career that may be going too well, and because of that, it is steering him, the pressures of that are perhaps steering him away from a deeper life.

All right, so let's go to our phone line and talk with Spiros. All right, we have our next caller here. Spiros, thank you for calling into the Deep Questions podcast. Now, from what I understand, you actually have a case study you wanna share with us of some of the principles I talk about actually put into action.

- Yep, exactly, yeah. So what I would like to do is I would like to talk about how I've been applying So Good They Can't Ignore You since I read it like a long time ago, actually. But then I feel like I kind of messed up somewhere along the way, so after I kind of summarize, I would like us to go into kind of like, where did I go wrong and where do I go from here?

- Sounds good. - All right, so I moved to the US from Greece in 2012, like literally 10 years ago to do a PhD in robotics. And I read your book a couple of years later, so in 2014. And I was like, whoa, okay, I see what I'm supposed to do.

So I started applying it first to research, but then I got the opportunity to participate in the 2015 DARPA Robotics Challenge. So then I started applying the principles to robotics software as opposed to just robotics research. That went pretty well. I got really into kind of like the more the software side of robotics.

I decided to take a little bit of absence to join a robotic startup, ended up dropping out of the PhD program with a master's, did really well in that startup. I was the first software engineer. I hired a team eventually, followed the startup to Austin, Texas in 2016, then moved to San Francisco in 2017 to work for another robotic startup.

Again, did really well, got promoted, got to travel to Hong Kong and China for manufacturing purposes. And now since 2018, I've been working for one of the top three, perhaps the top self-driving car company here in San Francisco. Again, I've been doing really well. I've gotten very high performance reviews.

I've gotten promoted. I'm on track to get promoted again. I'm considered a very reliable, high performer, all of the good stuff you would expect from somebody following these principles. I have tons of options. I don't mean to like sound, I don't mean to brag, but like I get so much recruiter email these days that it's almost like spam.

So I do have options. Now, the reason, now this is where this is turning from a case study more to a question. I feel like to put it in terms of your book, I think I fell for the second control trap. I think I got too excited about the performance and the promotions and the compensation and the recognition that I've kind of become too busy, I have too many responsibilities, I'm too busy.

My compensation is too good to ignore, if you will. So that's kind of where I would like to focus the question part. - Excellent, excellent. Well, let me first, I'm gonna back you up to the beginning of your case study just for the edification of our audience. I wanna go back to you as a PhD student, you read so good, they can't ignore you.

Now you glossed over a little bit, oh, I put those principles into play and started becoming very successful in my studies. Let's go back and try to make that concrete. So like, can you identify what did you start doing that let's say other students in your cohort who weren't as successful or you, the password yourself weren't doing?

Let's try to do some differential analysis here. 'Cause I'm curious in this beginning point first and then we'll get to you now. - Yeah, yeah, for sure. So because of your own case study in the book, you were also a PhD student and eventually a postdoc, et cetera. I was like, oh, I'm just gonna do exactly what Kyle talks about here.

Kyle talks about getting a very fundamental research paper and kind of like going deep into the research paper, trying to understand the proofs, trying to understand the results. So that's something that I did, I scheduled some time every week to go through either fundamental papers in my field. So I was in formal methods in robotics, which is like formal verification, formal synthesis.

Anyway. - Yeah. Which by the way, I'm happy to geek out with you about that. We can talk about your improvers and we would lose all of our audience. But just let you know, I'm restraining myself right now. - I'm tiptoeing around it on purpose. 'Cause this can be a rabbit hole, yeah.

So that's one thing that I remember very distinctly doing. Then once I got the opportunity though, to participate in the DARPA Robotics Challenge, I was like, okay, I can apply this here as well. So then it shifted from like reading research papers as my deliberate practice, let's say, to learning C++, learning Python, which are like some fundamental languages for this kind of thing.

And then something called the robot operating system, which is like a middleware for robotics applications. So I knew that these things existed and I knew some programming of course already, but I was like, okay, these are the three fundamental things I need to know if I wanna write robotics software and like get the robot to actually do something.

By the way, we got to work, like my team for the DARPA Robotics Challenge got to work with those like Atlas humanoid robots from Boston Dynamics. So yeah, pretty crazy platform to be working on. - Also terrifying, but yeah, go on. - Yeah. And so that's another way I applied that.

So like I was, for example, I remember very distinctly scheduling blocks at the very beginning of my day, like before I even went into the grad student cubicles or whatever, like I would, let's say, go to a coffee shop or something like that. And I would spend like, let's say two hours just going through tutorials, writing code, just deliberate practice.

- Okay, so just to clarify for the audience, the first thing you did was, it's hard to understand these fundamental papers. Having that knowledge will be useful. Quick follow-up here, because I get this question a lot. How did you actually structure the reading of hard papers without a formal forcing function?

Like I need this for a project I'm working on. You just had a system, a quota? How did you do that? - So yeah, so the way I motivated myself was that, hey, I'm seeing that I'm having a hard time with like the very formal aspect of writing. So I was able to write research papers, but they were kind of like, they weren't going very deep on the math, on the proof side of things.

So I was like, okay, I'm gonna motivate myself by saying that by understanding the fundamental papers and how these proofs work, I will be able to do that myself eventually. Then in terms of like how I structured that, I think it was something like, kick off a note in Evernote, pick one of these papers and then schedule time within the week.

You know, as a grad student, I kind of like reminisce about the flexibility I had in my schedule as a grad student. - I reminisce about that. Yeah, once a month, at least once a month, I have a moment where I just insanely nostalgic for that. But anyways, go on.

- Yeah, yeah. And so I was, if I recall correctly, this was like eight years ago at this point, I was scheduling time like on a weekly basis to make sure I get in at least a couple of hours. So it's kind of like go over the paper. And then the other thing I was doing, which I think you also mentioned in the book is, when I was reading like papers around what I was writing, around like papers I wanted to reference and I wanted to cite in my own paper, I wouldn't just like skim through them or read them and then forget about them on a pile.

I would actually take notes. Like I would take digital, I would take notes on the paper and digital notes and I would kind of sketch out what this paper is trying to do and how it proves the results. - Yeah, right. Well, okay, so just to summarize that before we jump now to the current moment, just to summarize that for the listener, what Spiros is doing here, which is straight out of "So Good They Can't Ignore You" is identifying the thing that is actually valuable in the field where you are, not what you want that answer to be, not what matches how you want your day to go, but what is actually valuable.

So first off for him, that was understanding how to do this more fundamental theoretical work. And then later on, okay, understanding how to use all the different programming language tools that are relevant to the DARPA Robotics Challenge so I can be as useful as possible. And in both cases, what you did, which I think is right, is said, okay, that's the reality of what matters.

What do I actually have to do to learn that? Oh, it's hard. I have to read these hard papers and I'm in the same place. Theoretical computer science is the same as early in your grad student career. Understanding papers is how you advance. Understanding papers is incredibly hard. And those two things are true at the same time.

And it was a big differentiating factor when I was coming up, those who would wrangle papers and those who would just look for what's easy. So I think that's a great example of the principles in action. And it worked, okay. So it worked too well. So now we jump ahead.

You're suffering from the second control trap. So for people who haven't read that book, the first control trap is trying to get a lot of autonomy in your career before you built up the skills to actually justify it. That's where you are 23 and you quit to start your nonprofit that's gonna change the world, but you don't know what you're doing.

The second control trap is when you get enough leverage and skills and power in the marketplace to actually have control of your career is exactly when all of the pressure in the marketplace is gonna be to stay, to move up to the next level, to take the higher salary.

So it's when you're most able to be autonomous is when it's hardest. And that's what you're hitting now. So why don't you explain to us a little bit more, what is your job like now? What is your day-to-day like now? Is it managerial? Is it technical? Let's get a sense of where you are.

- Yeah, so my title is Staff Software Engineer. So it sounds like I'm a software engineer, like I'm writing code every day, but I'm not actually writing code every day because at a certain level in the individual contributor, like a real ladder, as we call it, you kind of like fork into different archetypes.

So there is the software engineer archetype, and this is the person that like writes really good code. There is the domain expert archetype. This is the person who has like three PhDs in convex optimization or machine learning or whatever. So domain expert. And then there is the archetype that I think I better fit into, which is kind of like high level tech lead, is what we call it.

And so this is the person who is able to kind of understand how the system works end to end and kind of coordinate this team with this other team and this other person over here and get this other subsystem to do the right thing. And then you get the entire project or the entire effort to do the right thing just by understanding the system end to end and leading the integration effort.

So to put it more concretely, I do everything from analyzing kind of like metrics to see kind of like where we have gaps, writing project proposals, writing design documents. And then once we kind of move into the execution part of the project, I'm usually maybe I'm running some meetings or not, depending on whether we have a program manager support or not.

I'm coordinating all of these different individuals, software engineers, systems engineers, test engineers, sometimes operations teams that are like handling the self-driving cars on the road. - So what's a day look like? Is it how much of it is Slack and email? How much of it is- - That's exactly what I do.

You hit the nail on the head. It's very much hyperactive, hive mind mode all the way. I have to fight really hard just to block out like two hours at the beginning of my day. And maybe if I'm lucky, I will actually get to actually do the work in those two hours.

Like today I'm on call, for example. So like for all I know, once my on-call shift starts, I will be completely derailed by like an issue coming in on pager duty. There is a lot of activity on Slack. I've done all sorts of really tips and tricks, applying some of the stuff from your books and your podcast to minimize that.

I only check email like, I try to check only once a day. I once experimented with going a week without checking work email and nothing terribly happened. So I'm very much inclined to keep doing that again, yeah. But like email is okay. Slack is where most of the hyperactive, hyperactive mind is kind of like operating.

There are lots of meetings. It got much worse, you know, during the lockdown. So I'm sure others are saying the same. Like sometimes I feel like, when am I supposed to like use the restroom and like make coffee? Like there is no time in between these meetings. - Yeah, which is a first.

- So there is a lot of that. Yeah, exactly. There is a lot of that. One of the things I talk to with my manager the most often is like, hey, we need to figure out a way for me. I need to carve out time to do proactive work as opposed to waiting for a problem to arise and then doing reactive work and then fixing the problem.

Like the reactive work, part of the problem is that reactive work is actually gets recognized a lot. So there is like, it's really hard to motivate proactive work when there is tons of reactive work to do and it gets recognized too. So that's one challenge. - But why do you care about it being recognized?

- Ooh, wow. I was not expecting that question. When I say recognized, I mean, okay, there is a recognition in terms of like, like performance reviews and stuff, but there is also the like doing what the company, the business thinks is most valuable. Right now, this quarter, this month, this year, whatever.

And it's often the case that what, the business priorities are to deal with the reactive problems. They are not to go and do proactive work. - Yeah. All right, well, I'm gonna give, I'm gonna give a two-part answer here and I'm gonna be terse because the second part of this answer is something that's probably gonna take you weeks of actual thinking to do right.

So you'll have to check back in. I'm gonna give you a short-term, a short-term thing to try and a long-term thing to consider. The short-term thing to try is, I think this might be a good setup for a deep to shallow work ratio conversation with your manager. So I talked about this some in deep work, but then got a lot of feedback from people after that book came out about this particular strategy working well.

So it's pretty well road tested. And it's where you have a conversation like the type you're already having with your manager, but it's a little more quantitative, right? You say, okay, this is what deep work is. This is what like reactive work is. You're in a tech company in San Francisco.

So they probably know the term already. And you say, what ratio of this sort of reactive, shallow to deep proactive do you think is optimal for my position? Like what ratio of those two is going to produce the most value net for the organization? So we got to get a number on it.

And when you have to get quantitative about it, they're not gonna come back with the answer. I want you to do a hundred percent reactive shallow, right? Because you have this other value, you have this training, you can produce new things. So when you get a number that they agree to, this often leads to the dissolving of ossification in business culture.

So it lets loose a lot of innovations. They might say, okay, maybe it should be 50/50. So what we're gonna do is, mornings now are for you to do proactive work. No calls start till, you're not on call till the afternoon. We tell the whole team, don't expect responses.

That's just an example. I don't know your exact situation. It might be Tuesdays and Fridays. You work from not at the office and maybe from somewhere else and you're just doing proactive. The quantitative nature of that really makes a difference. And the positive orientation makes a difference. So it's you coming to your manager saying, how do I produce more for the company?

Not you coming to the manager and saying, I'm fed up with you slacking me all the time. You know, you're terrible. The latter conversation doesn't go well. The former conversation I have report after report of that working. This though is a short-term solution. Try that, see how it helps.

And that might be it. My long-term solution, I'm gonna ask that you, you probably are at a good point. And let me actually ask you, how old are you if you don't mind sharing? - Yeah, I'm 34. - Okay, so you're in this sort of heart of the millennial generation, approaching middle age.

It's a perfect time to start thinking through these questions of, okay, let me step back. How are things going in my life? What reconfigurations are looming on the horizon? It's a good time to go through a serious lifestyle centric career planning exercise where you really look out. I would look at 40 and 50 as age targets.

And like we talk about on the show, have this really clear vision of all aspects of your life in an ideal world at that point. Not just work, but where you live, what you're doing with your time, who you're around, see it, smell it, taste it, we like to say.

Get that vision for 40, get that vision for 50. And then look backwards and say, how do I get there? And in answering that question, you may end up saying, okay, my current career trajectory, that's fine. I just have to do this deep to shallow work ratio, maybe do a lateral move at some point into more, you could maybe figure it out.

Or you might end up with an answer. You say, I have a lot of skills. I am an ML robotics expert engineer. Okay, why don't I take that out for a spin? And I can actually maybe do something drastically different. I'm on contract. I work six months out of the year.

I live on Vancouver Island. I mean, you have a lot of flexibility. So short term, I would do that ratio conversation. Long term, I would say, let's go through that exercise in detail. And just see where it leads you. And don't be afraid if it leads you to, I'm more or less close, I see to make some tweaks, or if it leads you to, I'm about to buy a ranch outside of Austin.

It could lead you in a lot of different directions to be open to all of that. How does those as a one-two punch, how does that sound as a potential way forward? - I'm glad the conversation went there 'cause I kind of anticipated this and I've already done the first draft of what you just described.

- All right, tell us. - It could come up. - Should I actually go into it? - Yeah, okay, give us the brief summary of the ideal lifestyle picture you're playing with. - So the brief summary is that, so I'm originally from Greece, right? So I wanna get to a point where I can spend more or less every summer in Greece.

Working, not working, doesn't really matter. Spend about six months out of the year in the US and then spend another quarter just working from somewhere else. Other things I wanna be doing, I wanna be able to be near the water. I love swimming, I love water sports and whatnot, so I wanna be able to do that.

I want to start writing. I wrote a few blog posts and articles back in grad school and I really enjoyed that, but I gave that up later on to focus on my career. So I wanna get back into writing, maybe eventually actually write a book, we'll see about that.

I want to, so I'm currently single, so eventually I wanna be able to meet somebody. Now I feel like I'm so busy or so exhausted that I don't even make enough time in my schedule for dating, so I definitely wanna, the connection back with the suffering, essentially, to put it in deep life terms.

Other things in there, funny you mentioned Austin. It's actually Austin is on that roadmap because I figured that if I were to move to Austin, which is central time, but I work Pacific time hours, then I get two extra hours in the morning when I still have energy and willpower to do things like deep work, to do things like writing before I engage with the hyperactive hive mind.

So Austin is actually on the trajectory, potentially. - Well, okay. I mean, it sounds like to me, you're heading down the path towards changing your career situation. If that lifestyle sounds like either a greatly reconfigured job at your current employer or a different setup altogether that's maybe more freelancer contractor based, is that a scary thought for you or is that where you've led yourself already?

- Exactly, you're spot on again. What is scary is I don't wanna, in my attempt to escape the second control trap, I don't want to accidentally veer all the way to the first control trap 'cause it'd be easy to say, screw all this, I have enough money in the bank to last me X many years, I'm just gonna quit.

I'm just gonna say, screw Silicon Valley, I'm gonna go to Mexico and work on my book or whatever. But then I would be probably falling for the first control trap if I go so extreme. So the scary challenge is bridging the gap between where I am right now and kind of this vision for when I'm 40 or when I'm 50.

- Yeah, well, okay, this is great. So in the first answer, I gotta give some generic advice about deep to shallow ratios as a first step and lifestyle-centered career planning. Now we get an example of lifestyle-centered career planning. So I can give you a piece of advanced advice that goes to lifestyle-centered career planning and implementation and you're spot on about you don't wanna fall back into the first control trap.

You're not gonna be happy if you say, I'm gonna go to rent a house in Cabo and just work on my book. That'll last a month before you start to get antsy. So what I'm always looking for in this situation is concrete exemplars. I'll often talk about the rule of three.

So you wanna find a real person who has your background, who has a professional setup that resonates. Hey, that works. Okay, here's how they did it. Oh, they're a contractor that works on this type of ML project or whatever. Like it's concrete. This is someone and it's a job that they do.

It's a six month a year job. It's a flexible enough job that they take summers off. They go up to New England in the summer. So real people doing with your skillset, what you wanna do. Rule of three is if you wanna be really secure, find three different people doing something like that.

So now you know it's not a one-off, it's actually a viable path, but have a specific target that you're working backwards from. This guy, her and him did this setup with my type of skillset. How do I move there? I mean, I will say I'm doing that in some of my own lifestyle centric midlife career planning I've been doing.

I don't share a lot of details about exactly what I'm thinking about because there's a lot of stakeholders involved, but this has been my approach is what I'm seeking is examples. I am seeking people with similar backgrounds who have already figured out a configuration that seems to work. That's how I think you can avoid the first career trap.

I think you're there right now, the seeking stage. Go seek out these examples, meet the people. Also, by the way, say, can I call you? Can I take you out for coffee? If they're local, people are happy to share details of their experience and get concrete with them. How did you make this change?

What are the hard parts? What advice do you have? I don't know if you ever talked, you probably didn't, but in that top performer course I did with Scott Young, we talked a lot about this, this journalistic approach to career development where it's like-- - I know of that course, but I haven't taken it.

- We have students actually go through this. It's like you're writing an article on how this specific type of job transition works. You're out there doing research, gathering real information, always concrete, always like this is something that people are actually doing. And I think you are ready to start looking for those exemplars, which is also an exciting part of the process because you get all the aspiration without actually having to yet do anything that's scary.

So, good for you. I think you're in the fun part. But I would, no reason why you can't start just trying to find people right now who come out of your background, who have a setup where they work eight months a year, they work six months a year, they're location independent.

I'm sure they're out there in your field. There may be an academic affiliation, there may be a nonprofit affiliation, maybe they're a fellow at the OpenAI, whatever. And there's so many options out there for your field. I think you're ready to start looking for concrete examples. - This makes a lot of sense and really resonates.

Yeah, you've mentioned this before, but I never pieced it together. You're right, yeah, that's what I need to do. - Excellent. Well, Spiros, keep me posted. I wanna know what you end up doing and maybe we'll follow up and we'll share that with the audience. But in the meantime, thanks for the case study.

Thanks for the questions and also an excuse for me to go through a lot of different advice. So I find that useful as well. - Yeah. - All right, so good luck for you. Thanks very much. - Thank you, Kyle and Jesse. Bye. (upbeat music) (upbeat music) (upbeat music) (upbeat music) (upbeat music)