Best Software Engineering Career Advice of 2025

Hi all, it's been such a fun project for me this year launching this podcast and trying my best to make the content as helpful as possibleAppreciate everyone who has taken the time to watch my videos and give feedback on how to make it betterIt wouldn't be the same without your support! Next year I plan to work hard to keep improving the content, see you in 2026 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 00:00 - Intro 00:50 - Meta Distinguished Eng (Philip Su) 05:23 - Amazon Principal Eng (Steve Huynh) 06:23 - Google Staff Eng by 28 (Ricky Lee) 07:30 - Meta Staff Eng by 25 (Evan King) 08:51 - Shopify Distinguished Eng (Ilya Grigorik) 10:49 - Amazon VP (Ethan Evans) 12:24 - Meta Senior Staff Eng (Dwayne Reeves) 13:14 - CloudKitchens CTO, Ex Uber Senior Staff (Brian Attwell) 13:55 - Instagram Principal Eng (Jake Bolam) 14:42 - Uber Distinguished Eng (Joakim Recht) 15:03 - Creator of Claude Code, Ex Meta Principal (Boris Cherny) 15:45 - Outro

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Peterman?

  For the podcast, I've interviewed a bunch of CTOs and distinguished engineers from companies like Anthropic, Google, and Meta. And my favorite question to ask these people is if they could go back to the beginning of their career and give themselves some advice, what would it be? And this is my favorite question to ask because these people have so much experience. I'm always curious, what is that thing that they wish they knew earlier that we could learn from? And so before you do any New Year's planning, I thought it would be helpful if I curated all of the top answers to that question. And so I went through every single episode that I've done so far, and I watched the answers to that question to pick the ones that I felt were most authentic or potentially helpful. And so this video is a compilation of all the best answers to that question. So here's the full video.

• 0:44Ryan Peterman?

  If you could go back to yourself when you just entered the industry and give yourself some advice, what would you say?

• 0:50Speaker 01

  I have a few thoughts that I'll share. One, Roy Disney said, "Decisions are easy when your values are clear to you." Right? Decisions for me, a lot of times were hard because I didn't have clear values. If you know exactly where you're going, decisions toward getting there become a lot easier. So one advice I would give my younger self is spend a little more time thinking about what you actually want, right? Before you commit to doing these things. I think another thing is I often feel like I was the dog that caught the car, you know? Like, I was convinced when I joined Microsoft that what I wanted to be was a dev manager. Okay? And so for my first eight years or so, I would take any job that would get me a step toward that.

• 1:31Speaker 01

  So, one, decisions were easy then because you're like, well, does this job get me a step closer? Yes, it does, then I'll take it, right? But once I caught that car, you know, once I hit that level, once I recognized that, hey, E7 might be my terminal level. This might be the highest I ever get in my career. The problem with peaking early, you know, because I hit that level when I was probably, I don't know, 20, you know, 30 years old or something like this. The problem is, you're like a child actor. Like, the question is, what are you going to do with the rest of your life? Like, if your whole plan is acting, and if nobody hires you for acting, you're going to be in a world of hurt. Like, you are not going to enjoy the next 40 years of work.

• 2:14Speaker 01

  And so for me, I was the dog that caught that car. And I had no mental model for like, once I became the dev manager, which I did become, right, at a very young age, once I became a Level 67, and I became that at a relatively young age, it was sort of like, well...

• 2:30Speaker 01

  Like what happens next? And I really went through a period of pretty serious depression because I felt like I had lost a purpose to life. Like, life seemed to have so much meaning and direction when I had a clear goal. But I caught the car, right? And then it was like, what to do? So the other thing I would caution my young self about is to just be sure you actually want the thing you want. You know what I mean? Like, one thing I tell people now is, you know, would you want to be Warren Buffett? You know? So, many people love the billions of dollars, but he also is in his late 90s. Like, would you want a few billion dollars and be in your late 90s? Like, is that worth it? Is that what you want? Like, this is an interesting question, right?

• 3:11Speaker 01

  So I think for me now, I think a lot more about, um, am I even going a direction I want to be at when I get there? Right? One final thought that I'll leave with you with the sleeping bag business is, sometimes you bend the reed, sometimes you break the reed, right? Sometimes things break and they aren't fixable. So when I had sleeping bags in my office, uh, my fiancee came out to Seattle to visit me. During that time, when she visited me in Seattle from Maryland, during that time, I would see her every evening at 11:00 PM when work ended. That was when I would go see her. So basically, I got to eat like a late Denny's dinner with her from 11:00 PM to like midnight.

• 3:54Speaker 01

  And that was my plan for my visiting fiancee, right? I am very fortunate and lucky that she is my wife now. But anybody I tell that story to, you could bet nine out of 10 times, that's the story that ends with, that's how I got the engagement ring back, right? Is how that story ends, right? I did not realize that some reeds bend and some reeds break. And I was clearly bending something to an extreme that most things would have broken, right? And so I do think that in one's life, back to your point of like, what should a diehard person who only cares about career do? Like, what is the absolute fastest way to like get there, right? I would say, A, be sure that's what you want, right?

• 4:37Speaker 01

  Don't be the dog that caught that thing and then you regret catching the thing, right? So, A, be sure that's really what you want. And part B is like, You know, be sure you're comfortable with other things breaking, you know, because like that is what it will take to get there if that's truly what you want. So my advice to my younger self about that period of time would have been, you know, in net, getting to level sixty seven, getting to an E seven when you're thirty versus thirty eight in the big arc, doesn't make any difference. Like beyond thirty eight, I still have thirty years of work to go, right? So it's like, how fast do I want to be at my terminal level? Like, what's the real plan there? Versus can I keep a healthy relationship with my spouse,

• 5:19Speaker 01

  with my kids, right? That's important. And so that's what I would advise back then.

• 5:24Speaker 02

  Maybe saying something around people pleasing, right? You know, in the culture that I was raised in and, you know, there are these tracks that you get on. And it's like, okay, we'll do well in school and then go get a job and then go get married. And like, you know, you have this feeling of being ahead or behind, right? So that relative comparison. But then also, after you do a thing, after you make some sort of achievement, you're kind of looking for, to someone else for validation. I don't know if my younger self would have like listened, to be quite honest with you, but you know, just if I could somehow learn this lesson that like, the person that you really need to please is yourself.

• 6:08Speaker 02

  Just being like, are you doing what you want to do? Are you doing it because that's the expectation of somebody else? Are you climbing the ladder because you want to get to the top? Or are you climbing a ladder because the ladder was put in front of you? Just examining that.

• 6:23Speaker 03

  I think to my younger self, I would just tell him to trust himself a little bit more. Because I think for a very long time, I just had so much imposter syndrome. I was so anxious that, you know, I wasn't gonna do so well. And over time, I like built up that confidence, like through projects, my projects succeeding and working well with others and getting good feedback. But I think I was like really unsure of myself. And I actually feel like I could have done more if I was willing to trust my judgment a little bit more, or Have more of almost like audacity to push the boundary and try new things. Because I had a lot of ideas that I felt like I maybe waited a little bit too long because,

• 7:08Speaker 03

  you know, I felt like, oh, am I gonna rock the boat too much? But I ended up doing a lot of those projects that did rock the boat and they're very successful. And I wish I just, you know, trusted myself a little bit more to do it earlier. So I'd be less anxious and stressed all the time and be fretting less over imposter syndrome in the beginning of my career.

• 7:29Speaker 04

  I'm gonna, I'm gonna take a more maybe emotional angle on this as opposed to technical or career oriented. But like, I think the advice to me would be to really invest in relationships and the aspects outside of work. Like, I'm only just now realizing in the last year and a half or so that like I was under invested in friendships and romantic relationships and things of this nature. And it was largely because I was putting so much effort into work. Even if it wasn't in hours wise, like that's where my optimizations were. And you realize that like you spend all this time roadmapping, goaling, checking in with yourself about your career progression. But in terms of like general life progression, I didn't apply nearly that same vigor. And so I think that that had a negative consequence and only moving to LA now two years ago did the shift. And this is because I got pulled out of the tech bubble.

• 8:15Speaker 04

  Now, a lot of my friends don't work in tech and we invest a lot more in each other, both financially and from a time perspective. And I have found that my life is so much more fulfilled because of this. And so work continues to be a focus, it continues to grow, things are great there. But now like I have all these people that I can rely on and like I'm moving apartments right now. And I have any number of people that I can call to help me move. And these small things are like, you know, like I said, it's a bit sentimental, but they're, they're really what matter in life. More so than your quick career progression. So I wish I had learned to more fairly allocate time between those two and effort.

• 8:51Speaker 05

  I would come back to the don't be the best, be the only. I think early in my career had a lot of fear of.

• 9:01Speaker 05

  Hey, I'm mediocre at a lot of things. Like, I see my friends, I would look up to my friends who are really good at design. And I'd be like, "Oh, I wish I could do that." Right? Or I'd look to my other friends who are just better engineers. Like, "I wish I could do that." But the thing that I had was the ability to negotiate across all those themes. And that's uncomfortable, because I wasn't sure if that would pan out. And it turns out that it did.

• 9:30Speaker 05

  And then the other thing is, exactly as we were just discussed, don't filter, be braver about the stuff. It's kind of ironic that later in my career, I, part of like my nine-to-five effectively became public speaking. Going through high school, I was deathly afraid of public speaking. I would run away from class to avoid it, right? Like I say, I vividly remember those stories. And then it dawned on me later, when I was doing post-trank, that, "Hey, why is it that I was, even through university, like, I had cold sweats, standing out in front of a class, trying to explain a thing?

• 10:09Speaker 05

  But I was totally adept and fine when I was pitching my product to an audience." And the difference is, on one hand, I was trying to describe a thing that, you know, I didn't have any particular investment in. It was a test of my knowledge. Versus, "Here's a thing I'm passionate about, and I want to enact change in the ecosystem, to move it to some new direction." So, that turned out to make all the difference for me. And maybe that's the key thing. Like, if you told me, early in my college career, that my future holds public speaking, I would, I don't know what I would do. I would say that you're crazy.

• 10:50Speaker 06

  So I'll answer in two ways. One of them I did, and one of them I really didn't. The thing I would do is always prefer high growth. My whole career was in companies that were growing very rapidly. And I compare that, people talk about a career ladder. Well, my ladder was always an escalator. I could climb, but it was also moving up for me. And so the reason I got where I I went is because Amazon grew 100 fold while I was there from 10,000 people to a million. Revenue grew like 80 times. The escalator went up and I rode it. I also climbed. So that part I would keep the same. The thing I would change is probably not surprising you.

• 11:29Speaker 06

  I would wake up much sooner to jobs are still with other humans. It's great to be an expert. It's great to be right, but build the skills to have the relationships, make the friends.

• 11:45Speaker 06

  Get to know lots of people and you don't have to be an extrovert to do that. I was a classic introvert. I've certainly learned to be more extroverted. But with online tools like LinkedIn or pick your tool. You can make a reputation and build connections from the safety of your keyboard in your darkened room. All by yourself. And so do do whatever works for you, but get known. Because it works so much better. You know, Amazon called me for the job. Not the other way around and you want that happening. So build that reputation.

• 12:24Speaker 07

  The thing I'll say is, hey, Dwayne, I know you like coding. But the thing you should realize, right, is when someone goes and tells you, hey, can you write some code to do this? You should stop and think, how do they know that's the right code to write? You should aim to be the person who's making those decisions around what's the right thing to do. And I feel if I had that earlier on in my career. There's a lot of imposter syndrome and other stuff I dealt with early in my career. That having this clarity is like, you know, I'm more than what I can type on the keyboard. Right? My ideas and the value I derive is is greater and like focus not on being an output machine.

• 13:08Speaker 07

  But really being the one and focus like, can I be in those rooms that's deciding what's the right thing to do?

• 13:15Speaker 06

  I'd probably say younger self, be be more courageous and less embarrassed. You're gonna fail a lot and it's.

• 13:23Speaker 05

  Fine.

• 13:24Ryan Peterman?

  That's easier said than done. Like, I feel like embarrassment is like, you just feel it.

• 13:30Speaker 05

  Yeah, I know. I mean, but this would be the opening two sentences before a larger conversation about how to assert your own feelings and understand them.

• 13:43Speaker 05

  Maybe it would actually be, Brian, you should go to therapy. That might also be good advice. I think it's generally helpful to be more in touch with your own emotions for your own sake, and it helps you relate with other people better. Go where you're valued. I've seen lots of people go on to teams where they're not valued. You're really good at working on front end, right? And then you end up on a back end team and all of a sudden your performance is crap. Or like, you like working on framework things and you're on a product team and you're like constantly tweaking the frameworks and making them better. And then you get a really bad rating at the end of the year, even though you landed like 500 diffs or something. Yeah, yeah. Like, go into the environment in which like you're valued. And maybe you end up being in an environment you're not valued in for a year, but just like recognize that and get out of it. Right. Right. So I think. So like lean into your strengths, basically.

• 14:27Speaker 05

  Yeah. You're trying to lean into your strengths, but your management chain or your team around you doesn't care about your strengths, right? Go and find a team that likes your strengths and go there. Right. And you're gonna be way happier. It's gonna work much better for you.

• 14:43Speaker 06

  Just try stuff. And don't be afraid just because it looks hard or because those other people look much better than you, because they might be better than you. Sure. But you can also get there. It's not rocket science. It is just computers. If you like computers, you're pretty well off if you just keep going with that.

• 15:05Speaker 04

  Just use common sense.

• 15:08Speaker 04

  I think there's a lot of stuff in, especially in big companies, that pulls you away from common sense. There's a lot of this like organarcia. Things are this way because they have been this way. There's a lot of misaligned incentives. There's also a lot of good things, but there's these things also. So it's just really important to use common sense for this. And, you know, early on in my career, I was kind of starting a bunch of startups and worked at a lot of startups. And I think there too, it's the same thing. Kind of use common sense to figure out what the market wants and what users want to build it. So, yeah, just like trust yourself and develop your common sense.

• 15:45Ryan Peterman?

  Thanks for listening to the podcast. I don't sell anything or do sponsorships, but if you want to help out with the podcast, you can support by engaging with the content on YouTube or on Spotify. If you want to drop a review, that'll be super helpful. And if there's any guests that you want to bring on to, please let me know. I feel like sourcing very senior ICs. There's no well-studied list out there on Google that I can just search this up. So if there's someone in your org or at your company who you really look up to and you want to hear their career story, let me know and I'll reach out to them.