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 useful leadership within a company) and they're generally useful as all-round contributors.

There will be people out there who will mark you down for this. That reflects poorly on those people, but that doesn't mean they won't be in positions of influence where their poor judgement can still impact you negatively.

There will be plenty of other people who get it, and who will respect the choices you have made.

And you can always swing the pendulum back again later.

I know a lot of older workers, myself included, who don't want a seat at that table anymore.

I've also had peers become my manager, and vice versa, and that's the dynamic that seems quite successful.

Now if your manager is so bad that they can't recognize you are an extremely low touch employee...well, it doesn't matter the experience level, you'll be in for a bad time.

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.

Maybe I'm projecting from my own experiences but this usually is because the leadership has a "top down" mentality, "we know better because we are in this role" and your other team members who are likely less experienced than you can't tell the difference between "dissenting with evidence" vs. "being contrary".

Seems like the best plan is to keep your eyes open for other opportunities when it's no longer tolerable.

I work for other people right now

These were not the same roles

and its not an early stage company

I want fresh IC references and thats been successful

I want subsidized health insurance / contribute to an HSA and that's been successful, at least I have COBRA again and can keep contributing to an HSA uninterrupted

I want professional validation on stacks I want to use, get paid to do that

I want structure because doing side projects on my own schedule didn't have the same motivation for me

why does being versed in other parts of the industry dilute the point, need me to log in with an alt to be relatable?

But I think it's fair to say you have to pick a lane. You can't have your cake and eat it too. If you haven't succeeded as a founder, it rings ironic to proclaim "4 year vesting with 1 year cliff is just simulating what FAANGs were doing 10 years ago but out of touch tech wannabes are imagining is normal now" or that "we only took non-dilutive capital, nothing that converts to shares - people need to use their imagination."

Do you think it's fair for someone would to ask whether if you were really serious about succeeding as a founder, you should've invested a little less imagination into the capitalization strategy and a little more imagination towards identifying the ideal customer problem to be solved? After all, it's not like there's any dearth of founders who have built successful businesses with the standard VC backed approach. Especially those who were facing bear markets for what they were building.

Lord knows VC could use some competition. The issue I've observed is that everything else (except bootstrapping for very specific kinds of businesses) is purely worse for a founder who isn't already independently wealthy, which is ultimately just a different kind of bootstrapping.

I'd love to be proven wrong if there is, empirically, an alternative.

okay

following my business successes - which can include passing through profits outright, and or exits - I’ve done “thought leadership” and advisory to other companies, I’ve travelled around Europe for extended periods of time half way doing advisory but mostly living out a dream I wanted and enjoyed, I’ve formed funds and managed capital with great legal counsel, fund administrators, the works. I’ve had periods of illiquidity, even periods where liabilities were greater than assets, right now I like to get paid to do nextjs, and rust, and a couple other stacks.

turns out, you don't have to pick a lane. people take the linkedin and resume I choose to show at face value, which only shows IC roles and an Engineering Manager role.

If we're being frank, if the idea of picking a lane is doing something well, by choosing both lanes, you've actually chosen neither lane.

1. You are clearly not independently wealthy enough to have to never work again; otherwise you wouldn't care about "subsidized health insurance / contribute to an HSA" (both of which are things that the independently wealthy couldn't care less about), so either you are a) making up achieving outsized exits as a financier and you never actually achieved it, or b) worse, you made the outsized exit, became independently wealthy, and due to fiscal irresponsibility lost your position of independent wealth

2. You clearly aren't in a stable career position at a company with a long tenure steadily moving upward seeing as how you ended up having to take a job at a company with incompetent leadership that ultimately ended up firing you for making ultimately a reasonable suggestion

If anything, I think you have proven my point which is that you very much do need to pick a lane. There's the old saying that "startups don't die of starvation, they die because of indigestion" owing to the common and real risk of overly broad scope and dilution of focus. I think that same warning applies equally to careers -- your dilution in long-term focus may have played a role in you not achieving the success you might otherwise have been able to achieve. But I can't tell you for sure. Only you will be able to figure out that answer. And in order to figure out that answer, you have to be willing to be honest with yourself.

Best of luck.

so I did in fact put a target on myself for asking anything

all happened at the end of yesterday, thought I was in the clear but they were conferring. My weekend post and reflection ironically turned out to be foreshadowing.

(hm all the time stamps are wrong, I originally posted the observation two days ago. I posted this sunday or so and got fired on monday afternoon)

We’ll see.

That tells you much about the culture of the place. The other ICs know that you can't ask questions like that - they know that not only is the place dysfunctional as far as the sprint cycle, but it's vengefully dysfunctional - management will get you if you point out their dysfunction.

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, and went hunting for a dev job - this was 2015 so not too shabby.

There were a lot of things about this move I regret. The pay cut, the fact that my office in London got shut down as a consequence of my quitting meaning nearly everyone was made redundant, the fact that at my new role I was kind of resented a fair bit by other engineers.

But I was a lot happier and settled in my life. And nobody else can do that for me. I had to own the actions to make my short life on this planet better.

I’ve done management work since, and I’m now back to being an IC at a FAANG, but not as a software dev. I am now thinking about getting back into dev but it’ll get harder for me now I’m in my mid-40s.

I say if you aren’t happy, do it, but realise there will be some pain points. Ride that out, keep your head down and stay focused and you could be a lot happier.

Only bad thing about age is that in many organisations you will deal with people that don't have that much experience as yourself and they are not aware when they are making a mistake doing something, because they read about solution on some happy clappy blog or something. Less experience people tend to go into arguments more easily to defend their position and you have all seen this many times over. Unfortunately there is no easy way to get around this. Typically you get to explain things over and over and it may get really boring, as new cohorts come in. In most places the problems to solve are all the same. Take data from one place, transform it and put in another. Progression to management in that sense is where you get people to do all the boring stuff, that is still fun for them and you keep an eye so they don't screw things too much while yourself taking care of the big picture.

Probably best way is at that point to start own business. More fun and reward.

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

No, people won't really understand.

Is it a bad move? There are no bad moves, only bad reasons?

I was not CTO, but I was basically doing that job without the title. My company was slowly failing (although no-one would admit that at the time, it did go bankrupt 9 months after I quit). We'd moved to NYC for the company, on a company-sponsored visa. My partner and I had just had our first child. Like your "friend", I was pretty tired of management, politics, the constant scramble, and trying to fit some actual building stuff in between.

So I quit, moved back to my home country, took a few contracting gigs for a while, and then went full-time as a software engineer at a medium-sized company.

It was absolutely a backwards step, career-wise. Less pay, disconnected from the startup scene, outside the networks I'd spent years building. It easily put me back 5 years, probably more like 10, in terms of career.

OTOH, I was working from home, with heaps of flexibility, which was perfect when my kid was little. For a while, we both worked 4 days, one weekday off each at home just hanging out with the kid. Work was fine, but I kicked the obsession that it had just about become.

10 years later, I haven't tried to climb back. I do 5 days full-time now, but I'm just a senior engineer. I miss the challenges, but not enough to want to go back. I get paid less, but I'll probably live longer, and certainly better, this way.

Everyone's different. Some people leave tech, and make furniture in the woods. Some people just pull back a bit. You can pause and then have another tilt at it once you've recovered a bit. There's no rule book, really. Do what feels right and good.

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.

The weakest part is usually the human factor and the need to bucket someone into a few categories like "rock star" or "loser" or "slightly better than unskilled labor" or "nerd engineer".

Have been in a similar situation and sadly found unless your peers have truly understood what you've done and how, they'll filter your suggestions or insight through whatever bucket they've placed you in.

They key is that you can’t just stop doing what you hate but you have to be able to lean into what gives you some satisfaction.

Example: I made a trade from a key role to a dev role in one job change. In dev role I was working with a technology I had significant experience with in my prior "key" role. In the new role, when the topic came up, I suggested we avoid certain vendors since in my prior role I was responsible for the technology vetting and I determined the chosen vendor was not forthcoming with some important limitations. My feedback (constructively and succintly presented) was completely ignored since I was "just a developer" and I ended up having to make the sub-par technology actually work.

It was frustrating and painful, not because of ego, but going into the task knowing it would suck since the wrong decision was made and now I was the guy having to make broken pieces meet some demanding requirements because "a developer" couldn't possibly know more than an "architect".

I don't know about other developers & engineers but I've already learned quite a few lessons the hard way and don't need to burn my evenings and weekends knowingly doing something the wrong way.

You might say "That's OK, that's what they're paying you for" but if you've been in this situation, usually someone less knowledgable, bordering on clueless will draft a schedule and you'll be the guy to make it happen. So a bad technical decision turns into a pressure cooker which then turns into more stress. Which is similar to another poster who said (I'm paraphrasing) "each job will suck in different ways".

People overestimate the importance of titles.

Anyone can start a company and call themselves a CTO. Plenty of line managers at big tech companies have more responsibilities than CTOs at start ups.

As long as you're not 5+ years into people management and have a team of less than ~50 it shouldn't raise any flags with most interviewers. People switch between manager and IC all the time.

Just have a good story ready, be humble, and demonstrate good self-awareness and you'll be fine.

Of course, I then ended up being CTO again!

A small start up CTO is nothing like a CTO of a big successful company.

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.

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!

The CTO is the chief engineer he or she sets technical direction for the company. VP of Engineering is the top manager for that division and executes the CEO’s vision using technical choices made by the CTO.

In many companies these are the same person, but not always. In my last startup they were separate people. The best chief engineer (CTO) isn’t always a good people person (VP).

Software companies that differentiate by some metric other than core technology might not need a CTO, which would explain your confusion if that’s your background.

I worry that a lot of HN "CTO discourse" is really wishcasting, about what an "if I was monarch of all the developers" role would be (and then about what it's like to aspire to such a role). No healthy engineering team has such a person!

What industry are you in? In deep-tech / hardware the role of chief engineer is well understood. In biotech it is sometimes called chief scientist.

Since you asked: I'm one of the principals at Fly.io. Before that, I was one of the founders of Latacora, which embeds directly inside of startups for years at a time running their security teams full time. Before that, I founded Matasano Security. Before that, I was a Product Manager at Arbor Networks, after being the lead developer on their DOS product for a couple years. I'll stop there (I'm older than the median HN commenter).

Later

For what it's worth, for companies literally chartered to do scientific exploration --- drug discovery chemistry, for example --- I completely buy that there is a real "Chief Scientist" role, though I can't claim to understand that role well enough to defend it. But that doesn't describe any software company anywhere. Regardless, "CTO" is something different.

Recently watched a relatively young person parley a position at a small company with a VP title that resulted in a slot at a regionally well known organization as a director and then president of a much larger startup.

Over about 4 years he went from front line sales to running a sizeable company with the key step being the VP title at the small company that rocketed him up.

I also recall a former co-worker that was denied promotion and generally failing to progress in his career. He took a slot at a tiny company explicitly for the title. I think it was director. He managed to parlay that into very positive career moves.

Personally, I don't care as much about titles these days. I just don't want to work for places making terrible tech decisions and forcing me to work within that. I'm happiest making the decisions and really don't want to stop, whatever it's called.

But I have found often startup CEOs look for CTOs for a few tactical and myopic reasons. They cannot code (or worse cannot design beyond copy-pasta from stackoverflow) or just to bolster their "look we have a faang-er as CTO" creds. Just as often the CEO has very little business or product sense (not to mention any leadership) but just needs a coder to build out their ideas (usually half baked ones in a very reactive fashion). Here you will also find that there is a new direction each week based on what a lead told them in passing.

Worst of all you will have very little resources (are you the sole coder/CTO?) but will be blamed for all the wrong choices (dont worry about writing tests - we dont have time ===> why are things breaking?).

The pendulum in this case is not a bad choice. Typically after you are burnt by one startup it doesnt meant all startups are bad. Just that you could use that big-co IC role as a charging station. Or if you actually like management (and there are lots of reason to) you could always switch to management in a big co and then go back to a startup more worthy of you. Now obviously you are the mercy of the hiring committee/team/market so a better story for why the switch definitely helps.

Went back to IC roles, no regrets, much happier with what I am doing. Money isn't everything, as long as you have enough to live well, you don't need to make 7 figures, just make sure you are working toward a couple million in investments for retirement if you are in the US.

If you have solid team members who are secure in what they know and their position they'll appreciate your broad(er) skillset and will want to work with you and it will be a non-issue. If anything they'll respect you tried something "beyond" what a normal senior engineer might do or get to do.

If you have one or more people who are insecure or "not an A-player" they'll likely view you as a threat to their career progression and you'll have to be cautious around these people.

A good / great manager wants people of diverse backgrounds and experiences, a mediocre manager might feel threatened by you because your insight might challenge his authority or the concept of it.

If you're interviewing with a team they'll likely know your background, but if it doesn't come up I wouldn't go out of my way to discuss your CTO role, just stick to the technology parts you've worked with.

The problem you have in a failing startup is you don’t have any scope for bringing in help for yourself. Can you hire a VPEng or Head of Engineering to take on a lot of the day to day management and delivery responsibilities? You can move yourself into a much more technical/R&D role.

Another thing to remember is that “CTO” can encompass many different things depending on the size of a company.

Very small early stage startups - the CTO is generally the most prolific IC. It may be that this the sweet spot for you.

Businesses often require different CTOs for different stages and there’s nothing wrong with being a particular type of CTO. You can say - “the role has evolved and I’m no longer the right person”. Or “my strengths are in these areas, I need people to fill in these gaps”.

If nothing else I think I am a much better engineer as a result of several years of being a manager because now I know the "other side of the coin" and won't shy away from the people-parts of engineering. I am much happier and way, way, way less stressed. I think other engineers respect the decisions and you have greater impact and influence since you are a great engineer AND you can also do the management dance so others look to you as a natural leader.

I'd recommend a few years as an engineering manager for any aspiring engineer.

If you are tired of "all the responsibilities, management, etc" then you will probably not follow that path anymore, you tried and it's not for you.

However, if you ever decide to follow that path again, be advised, boards/founders want to hire C-level people who have a proven track of building successful organizations through good and bad times. Having even a single occurence that signals you were "tired of all the responsibilities, management, etc" will disqualify you.

In my opinion, it’s great because ex-CTO types know what their managers need and are typically very easy to manage.

Now he enjoys private life while creating a super-cool Ghostty terminal in Zig [0], currently in private beta.

[0] https://mitchellh.com/

One scenario I could see working is moving from CTO to founding IC for another startup, but that conserves a number of things your friend might be tired of. Like long hours, and sitting under the Sword of Damocles 24/7.

It sets a strange precedent sometimes too if not well communicated and managed.

Make sure your own management know that you are interested in this path.

The book The Manager's path has excellent advice on ways you can prepare yourself for management positions: https://www.amazon.com/Managers-Path-Leaders-Navigating-Grow...

This I have been successful with at multiple companies. Often bringing a complete shift in development practices / headcount allocation strategies. I've setup multiple teams and initiatives at my current FAANG employer as an L3/L4. My most recent one was a library which is being used by extremely high priority projects with VP-level visibility.

> Make sure your own management know that you are interested in this path.

This is where I have been extremely unsuccessful. I explained that at some point in the future I wanted to be at the Director or VP level. One of the higher level employees that I was discussing this with laughed at me (she also did the same about my library and other initiatives only later to applaud when our VP thanked me for landing them).

My manager and skip level manager are advising to "take your time" and "you may not actually want that" and similar things. They say to focus on L+1 which I do understand as a priority but what I am really trying to communicate is:

1. Long term I'd like to be higher level leadership

2. I don't know if the skills I am learning right now will put me on this path

3. I want to in the short term work on high impact projects and in the long term build the muscles needed so that when I say "I'd like to be a director" no one laughs at those ambitions

That's what matters.

Life is much bigger than careers.

Good luck.