Ask HN: Going from CTO to Developer? • Hacker News Board

Re: Ask HN: Going from CTO to Developer?

#21

Post by erkmene » Sat, Mar 30, 2024, 7:34 PM UTC

convolvatron wrote: post #16

simonw wrote: post #10

I've done this. I have friends who have done this. I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum... Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide use…

the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC

This is an exceptionally profound observation. IMO not having a strong ego helps and if it goes right, everyone benefits from this.

Re: Ask HN: Going from CTO to Developer?

#22

Post by [deleted] » Sat, Mar 30, 2024, 7:34 PM UTC

convolvatron wrote: post #16

simonw wrote: post #10

I've done this. I have friends who have done this. I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum... Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide use…

the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC

[deleted]

Re: Ask HN: Going from CTO to Developer?

#23

Post by ilc » Sat, Mar 30, 2024, 7:36 PM UTC

PaulRobinson wrote: post #14

I did this from a hands-on CTO role at a 20-person startup to a senior engineer at a 200 person e-commerce outfit known nationally in the UK. I was miserable for a long time, and sat down one day and made a list of all the things I liked about the job and all the things I hated. Everything in the “like” column was dev work. Everything in the “hate” column was the management work. So I slept on it for one night, quit,…

Don't let age stop you, people make a big deal out of age discrimination.

There is some, but there are good dev roles out there for those of us closer to the AARP card than the college ID ;).

Re: Ask HN: Going from CTO to Developer?

#24

Post by tylerrobinson » Sat, Mar 30, 2024, 7:36 PM UTC

convolvatron wrote: post #16

simonw wrote: post #10

I've done this. I have friends who have done this. I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum... Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide use…

the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC

This is true, and it’s also true when you’re a manager. You always need to manage up and down.

Re: Ask HN: Going from CTO to Developer?

#25

Post by tptacek » Sat, Mar 30, 2024, 7:37 PM UTC

I flinch whenever I see people talking about "being a CTO", because there's really no such thing. The title doesn't really mean anything. In startupland, three possible (and possibly overlapping) meanings of the title are:

1. The corporate officer title a founder that isn't the CEO gets because they're on the board, purely as recognition of their seniority ("why is this person on the board?" "because they're the CTO.")

2. The consolation prize a founder or early employee gets when the mature engineering organization takes away their commit privileges.

3. The fluffy title a founder or senior employee gets when they transition to a customer-facing role so that prospects are (ostensibly) impressed.

These are all situational and don't really describe a "role". Excepting case (1), I would be a little alarmed if a company I worked at asked me to assume a "CTO" role. Either way: having been a "CTO" says basically nothing at all about whether you're lateral to software developers.

Your question makes more sense if you consider the move from VP/Engineering to developer. Either way, you're completely fine from a signaling perspective, but you're especially OK if your title was "CTO" and not "VP/E". The last thing in the world you should want is a career trajectory defined by "CTO-hood". Yikes!

Re: Ask HN: Going from CTO to Developer?

#26

Post by ldjkfkdsjnv » Sat, Mar 30, 2024, 7:38 PM UTC

convolvatron wrote: post #16

simonw wrote: post #10

I've done this. I have friends who have done this. I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum... Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide use…

the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC

This is partly why ageism exists. The longer you have worked, the more obvious the failings of your superiors are. Older workers are harder to trick into working on some project that will fail/produce no business value.

Re: Ask HN: Going from CTO to Developer?

#27

Post by excto » Sat, Mar 30, 2024, 7:39 PM UTC

I'm an ex CTO. I ran the company as basically 2ic for 5 years before I quit.

Before I quit they offered me profit share which was stupid because profit can easily change.

I do not regret leaving at all from a mental health perspective. I was losing my friends, family and myself.

I do regret leaving because afterwards I'm just a loser developer, lumped in with the guy that moves the button left a bit, when before I was orchestrating tech strategies and winning.

I think I'd have been better off staying as CTO, not because "profit share" was attractive to me, when I had no say in expenses, but because I was good at making a business succesful. Sitting here pushing pixels and spreadsheets sucks.

Every situation is different though. The only lesson I learned was that every job is hard but in different ways. Going back to dev felt demeaning. Watching inexperienced sales people ignoring what matters to people buying services. Trying to have an opinion but being told in no uncertain terms they don't care because I'm a nerd and people don't buy from nerds.

Seriously it's been difficult going backwards. I think I would have been way happier still being in charge.

Re: Ask HN: Going from CTO to Developer?

#28

Post by yieldcrv » Sat, Mar 30, 2024, 7:42 PM UTC

convolvatron wrote: post #16

simonw wrote: post #10

I've done this. I have friends who have done this. I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum... Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide use…

the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC

hm, that might be happening to me, I'm an IC right now

I make it pretty clear during hiring that I don't have aspirations beyond IC anymore. Been there done that kind of vibes, I like to build. I say my value add is that I can add a vote for whatever policy or method would improve an org, people seem to like that.

But I'm currently on a team where leadership is doing everything outside of the sprint cycle, random demos in the middle of the week that nobody ever heard of before that day and so we must have all these features ready for right then, so I asked - I thought - a light question in the middle of the standup "are we using the sprint cycle?" because we have 2 week sprints and standups. and that was the.biggest.deal I've ever seen, all the leadership was convulsing amongst each other because they all have to show face to each other, instead of addressing their incompetence. "We- we- we'll take this offline!"

the meeting offline never happens. leadership can't be reached throughout the day. and the other IC's I do talk to (who don't know I've been in other non-IC roles before) act like I asked the biggest boat rocking question ever and I'm putting a target on myself.

To me, thats funny because the biggest boat rocking question would have been "why don't you do a demo from the staging branch that you're supposed to merge from dev in a schedule that's parallel and independent of the sprint" "why don't we have a staging branch, do you know what you're doing?" "why are you merging our pull requests in any order, not knowing the code base, and then yelling at us when there are merge conflicts, we should be reviewing each other's PRs"

Its actually a tolerable position,

but maybe there is a reality that I do have other jobs and maybe more comfortable about my prospects than other ICs there, and also have management experience that is impossible to hide.

Re: Ask HN: Going from CTO to Developer?

#29

Post by michaelt » Sat, Mar 30, 2024, 7:43 PM UTC

> Will this be perceived as a stupid career move or will people understand?

Most people in tech know everyone who founds a startup immediately grants themselves a grand-sounding title, it's traditional.

Nobody will think it strange if a 22-year old startup CTO with 4 reports switches to being an IC at a big corporation.

Re: Ask HN: Going from CTO to Developer?

#30

Post by KingOfCoders » Sat, Mar 30, 2024, 7:43 PM UTC

(CTO coach here) Several of my clients have gone that way. Though I would ask people to just write code. Look at DHH, you define the CTO role and you can delegate stuff, not go to meetings and write some code.