Best Software Engineering Career Advice of 2025

For the podcast, I've interviewed a bunch of CTOs and distinguished engineers from companies like Enthropic, Google, and Meta. And my favorite question to ask these people is if they could go back to the beginning of their

career and [music] 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

potentially helpful. And so this video is a compilation of all the best answers to that question. So here's the full video. If you could go back to yourself

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

>> I have a few thoughts that I 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

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

want, right? Before you commit to doing these things. I think another thing is I

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. So one decisions were easy then because it was like, well, does this job get me a step closer? Yes, it does. Then I'll take it,

closer? Yes, it does. Then I'll take it, right? But once I caught that car, you

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

terminal level. This might be the highest I ever get in my career. Um, the

problem with peaking early, you know, cuz I hit that level when I was probably, I don't know, 20, you know, 30 years old or or something like this, right? Um,

right? Um, the problem is you're like a child actor. Like the question is what are you

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're you are not going to enjoy the next 40 years of work. And so for me, I I was the dog that caught that car. And

I had no mental model for like once I became the death 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 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

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 in his is in his late 90s. Like, would you want a few

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

want? Like, this is an interesting question, right? So, I think for me now,

question, right? 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

get there? Right? One final thought that I'll leave with you with the sleeping bag business is sometimes you bend the read, sometimes you break the read, right? Sometimes things break and they

right? Sometimes things break and they aren't fixable. So, when I had sleeping

aren't fixable. So, when I had sleeping bags in my office, uh my fiance 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 p.m. when

work ended. That was when I would go see her. So, basically, I got to eat like a

her. So, basically, I got to eat like a late Denny's dinner with her from 11:00 p.m. to like midnight, and that was my

p.m. to like midnight, and that was my plan for my visiting fiance, right? I am

very fortunate and lucky that she is my wife now. But anybody I tell that story

wife now. But anybody I tell that story to, you could bet nine out of 10 times that 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 reads bend and some reads break. and I was clearly bending

reads 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? 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

right? So a be sure that's really what you want. And part B is like,

you want. And part B is like, you know, be sure you're com 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

want. So my advice to my younger self about that period of time would have been, you know, in net getting to level 67, getting to an E7 when you're 30

versus 38 in the big arc doesn't make any difference. Like beyond 38, I still

any difference. Like beyond 38, I still have 30 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

terminal level? Like what's the real plan there versus can I keep a healthy relationship with my spouse, with my kids, right? That's important. And so

kids, right? That's important. And so

that's what I would advise back then.

Maybe saying something around people pleasing, right? you know, in the the

pleasing, right? you know, in the 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

behind, right? So, that relative comparison. Um, but then also after you

comparison. Um, 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. Just being like are is are you

yourself. Just being like are is are you doing what you want to do? Are you doing it because that's the expectation of somebody else? Are you climbing the

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. 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 uh you know, I wasn't going to do so well. And over time, I like built up

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

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 um push

the boundary and try new things. Uh

because a I had a lot of ideas that I felt like I maybe waited a little bit too long because you know I felt like oh am I going to rock the boat too much but um I ended up doing a lot of those

projects that did rock the boat and they were very successful and I wish I just you know trust 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. I'm going to I'm going to 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

of work. Like I'm only just now realizing in the last year and a half or so that like I was underinvested in 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

optimizations were. and you realize that like you spend all this time road mapping, goaling, checking in with yourself about your career progression.

But in terms of like general life progression, I didn't apply nearly that same figure. And so I think that that

same figure. And so I think that that had a negative consequence and only moving to LA now 2 years ago did the shift. And this is because I got pulled

shift. And this is because I got pulled out of the tech bubble. 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

there. But now like I have all these people that I can rely on and like I'm moving apartments right now and 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. I would come back to the don't

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

hey, I'm I'm mediocre at a lot of things. Like I I see my friends I would

things. Like I I see my friends I would look up to my friends who are really good at design and I' like, oh, I wish I could do that, right? Or I look to my other friends who are just better

engineers like I wish I could that could do that. But the thing that I had was

do that. But the thing that I had was ability to negotiate across all those themes. And that's uncomfortable because

themes. And that's uncomfortable because I wasn't sure if that would pan out. And

it turns out that it did. Um, and then the other thing is exactly as we were just discussed, don't like don't don't filter, be be braver about this stuff.

Um, it's it's kind of ironic that later in my career, I part of like my 9 to5 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 I vividly remember those stories. And then it dawned on me later

stories. And then it dawned on me later when I was doing post rank 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 the thing. Uh but I was totally adept and

thing. Uh but I was totally adept and fine when I was pitching uh my product to an audience. And the difference is in one hand I 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 like

enact change in the ecosystem to move it to some new direction. So that turned out to make all the difference for me and uh maybe that's the key thing like

if you told me uh early in my college career that my future holds public speaking I would I don't know what I would do. [laughter] I would say that

would do. [laughter] I would say that you're crazy.

>> 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

high growth. My whole career was in companies that were growing very rapidly. And I compare that, people talk

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 went is because Amazon grew 100fold 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

same. The thing I would change is probably not surprising you. 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

expert. It's great to be right, but build the skills to have the relationships, make the friends, um, 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

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 happen. So build that reputation.

happen. So build that reputation.

>> The thing I'll say is, "Hey Dwayne, I know you like code in, 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 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

to do. And I feel if I had that earlier on in my career, there's a lot of imposttor 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 a keyboard, right? My ideas and the value

keyboard, right? My ideas and the value I derive is is greater and like focus not on being an output machine, but

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

I'd probably say younger self, uh, be be more courageous and less embarrassed.

You're going to fail a lot and it's fine.

>> That's easier said than done. Like I

feel like embarrassment is like you just feel it.

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

it would actually be Brian, you should go to therapy. That might also be good advice. I think it's it's generally

advice. I think it's it's generally helpful to uh 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 onto teams where they're not valued.

>> You're really good at working on front end, right? And then you end up on a

end, right? And then you end up on a backend 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 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 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.

>> Yeah. You're you're trying to lean into your strengths but the 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 >> and you're going to be way happier. It's

going to work much better for you.

>> Just try stuff and don't don't be afraid just because it looks hard or because those other people look much better than you because they may might be better than you. Sure. But but but you can also

than you. Sure. But but but you can also get there. It's not rocket science. It

get there. It's not rocket science. It

is just computers. And if you if you like computers, you're pretty well off if you just keep going with that.

>> Just use common sense. [laughter]

[gasps] I think there's a lot of stuff in a especially in big companies that pulls you away from common sense.

There's a lot of this like organia things are this way because they have been this way. There's a lot of misaligned incentives. There's also a

misaligned incentives. There's also a lot of good things, but there's the these things also. So, it it's just really important to use common sense for this. And you know, early on in my

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

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 and develop your common sense. 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 IC's, there's no wellstudied 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