Honestly... probably not. I'm super specialized and haven't had to deal with that a ton. I've worked with Flume and Sawmill and other things that process stuff really fucking fast and if it turned out that I still had to make it 10% faster I would have no idea where to start beyond "uh... maybe we could parallelize some of it?"
How’d you decide to go from manager back to IC?
Part of it was that I had done a really good job and justified growing my team a lot and it got way too big for me to do a good job with. Part was COVID and having a family was really hard with the meeting load I had. But I've made that switch a few times in my career and in general the reason is that being a manager trades solving fun puzzles as an IC for having to deal with underperformers and convincing other teams to do what you want and it doesn't really pay that much more. The parts I liked were the mentoring and project planning and I can still do that as a sufficiently senior IC.
Is there any plan to retire?
Someday maybe? I get paid a lot and I have two kids in private school and I actually like my job, so I'm not in a hurry to give up work. I'm sure I could find a way to get enough passive income to do okay, but I'm super specialized in my job and I like thinking about these things and I don't want to go learn about real estate investing instead. I don't even take enough vacation as it is.
As you mentioned you get paid a lot, cannot help but ask. How much ?
Does it get difficult with exp to stay in core tech and not move to management but still be able to improve on TC?
at Square there's very little difference between IC and EM comp, so here, no. In general, once you get to very senior engineer you're definitely priced out of a lot of jobs, and if I wanted to leave to get a raise I'd either have to go to a FAANG again or take a CTO role somewhere that I had faith in the company's chances. So... Maybe? I've had a couple offers recently where if I was a little less risk averse they'd probably pay much better than this in the very long run but I don't know if I can really do that right now with my family depending on me.
Tell me more about your experience with switching companies. When is a good time to switch? Is job hopping the only way to avoid cliff? Tell me more about your experience with company that haven't IPO and then it IPOed.
In my experience you should switch jobs either if you feel like you're not learning anything new and not growing into your next role (at that company or elsewhere) or if you get fired. It's worked for me! I'm hitting my cliff at Square now and they definitely gave me more than a normal raise to soften the blow, and I'm probably getting paid competitively, but it's still a lot less than I was getting. I just have to keep reminding myself that I didn't entirely deserve how much I made the last few years (or would have if I'd held more stock, sigh). I don't know what to say with the last part. I got pretty lucky with the companies I worked at early in my career. At this point I've gotten so accustomed to being at big companies that I'm having trouble assessing offers from startups - I don't know how to value 20% of a company with three other people that's only taken a seed round.
At this point, what are you working for? More money? Passion? To avoid boredom?
The first two. I have a family with an occasionally working wife and kids in private school, so the money is still useful. We burned through a lot of my savings a few years ago (have kids early if you're going to, IVF and egg donation get expensive as hell). But I also really like my job. I'm very specialized and what I do is pretty important and I got to design myself a role here where I decide what I'm going to work on and I have good enough judgment that they keep letting me do it. So I like working and I really ought to take more vacation but I'm not in any hurry to stop for good.
Is Square worth the hype? I have an L6 offer. Trying to decide between few others and this.
I really like it. Been here about four years. Stock obviously doesn't hurt, but more than a lot of companies I've been at, there's room to find your own path. I've had a lot of success here telling people what we ought to do and if I'm convincing enough, we do it. And if you have any thoughts of trying management, Square is great at letting people become managers and then switch back if they don't like it and there's really no stigma of failure about it. I know at least ten people that I work with pretty regularly who have all done that and I'm sure there's a lot more than that
Do you think you’re a winner?
Hm. Never thought about it that bluntly. Yes? I get paid a ton to do a job I wrote the job description for and people are interested in my opinions. There's always something that could be better, and I'm very conscious of the fact that there are a bunch of people who are more successful than me and some of those are even younger than I am, but that just means there's a lot of winners, right?
Guys I think this thread might blow up and up might not be able to answer everything. Let's like the comments which we want the answers for
We'll see where it is when I wake up tomorrow :p
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How is work at Square and why is that your stop after 25 years?
I really like it here. Square has been great and letting me try new roles - I was an IC, then a manager, then back to an IC role that I pretty much designed for myself. I have a lot of flexibility in what I do on a day to day basis. I can't say that everyone will have this experience, but it's worked well for me. That said, who knows how long I'll be here. I'm not in any hurry to leave but I'm still taking to recruiters. I just get to be pickier now