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Ask HN: Dealing with Career Mistakes
151 points by throwmeawayapr on April 29, 2022 | hide | past | favorite | 145 comments
Two years ago I had an option to go into the management path. My leadership was supportive and wanted me to take up the opportunity. I chose to pivot into the product management instead. My peer took that role. My role change didn’t go very well. Personally i was unhappy and felt unfulfilled at work. While I was respected at work and my manager very supportive I didn’t enjoy it. I quit and joined another company and pivoted into program management. Since then my work hours have doubled and while I am earning the highest paycheck I could have dreamed of, I am extremely unhappy being an IC. I have 25 years of industry experience and I feel I should mentor people instead of moving JIRA tickets around.

Yesterday I saw my former colleague who grabbed the manager role, got promoted to a director. I was hard working and intelligent than him. I could’ve played my card right and be in that place. Yet here I am being ‘advanced beginner’ in a different role every couple of years doing grunt IC work. How do I turn the wheel of time back and undo my career mistake. I feel incredibly stupid. I am losing confidence in making good decisions.

How do I deal with my feelings? Should I seek professional help?




You have no way of knowing that you would have done well in the manager role and gotten promoted to director like your peer. You claim to be more hard working and intelligent than him but who's to say what you view as hard working and intelligent are objectively true? Who's to say success in those roles is even a function of hard work or intelligence? Who's to say your peer didn't have some third skill relevant to managering and directoring that you lack in comparison? Maybe the thing that led to your peer's promotion was his boss's partner meeting his partner at a holiday party which put him on the radar. Who the heck knows.

If a man in line behind you at the convenience store buys a lottery ticket and wins a million dollars, do you kick yourself for not buying that ticket when it was your turn in line? Life is chaos; pretending things like this are in your control is useless. Punishing yourself for not knowing what you didn't know in the past is cruel.

Your misery comes from your own self-imprisonement. Happiness will not come from a time machine. Rather you should work on keeping your ego out of the driver's seat. A therapist might help, to teach you frameworks around catastrophization. Eastern philosophy has a lot of answers for dealing with ego as well. Alan Watts' The Book is a good way to experiment on that path.

Forget the past and focus on the present. If you don't like the present, focus on the future.


>If a man in line behind you at the convenience store buys a lottery ticket and wins a million dollars, do you kick yourself for not buying that ticket when it was your turn in line?

That's a very nice analogy - is it something you came up with ? (I am going to steal it so I would like to know who I'm stealing from :) )


I think it's an example of the post hoc fallacy and is often presented in terms of a casino slot machine, where a player leaves the machine and the next player wins the jackpot. X is assumed to cause Y, simply because X occurred before Y. With the above example, X is 'not buying the lottery ticket when you had the chance' and Y is 'the next person to buy a lottery ticket wins the prize'.


Slot machines are a much worse example because they have programmed minimum prize percentages, so if one has gone without a win for a while then it's more likely to win than average. With the lottery ticket, there was really no reason to have made that decision.


Isnt this the fallacy? Aren't those minimum prize percentages set in advance? As in, if a machine has a 0.0002% chance jackpot it will have that with each pull and no less (ie minimum prize percentage). Minimum prize percentage just means it never goes below a certain percentage (eg it can't go to zero). Also, the smaller payouts can be higher minimum percent. But over the long term the payout is always less than the cost to play.


My understanding is that the algorithm is something like:

   func doTheyWin():
     if timeSinceLastWin < 10:
       winPercentage = 1
     else if timeSinceLastWin < 100:
       winPercentage = 25
     else:
       winPercentage = 99
     return random(100) < winPercentage
      
That is an algorithm designed to meet people's expectations of the gambler's fallacy, basically.

Other comments say that slot machines in Las Vegas are prohibited from using this algorithm, but nothing is stopping, say, video games from doing this. (Hearthstone has a "pity timer" for giving you legendary cards in card packs, for example. It's random until it feels bad for you, or more likely the data shows that you won't buy any more card packs and they'll go out of business if they don't give you a legendary every 40 card packs or whatever.)


> so if one has gone without a win for a while then it's more likely to win than average.

This isn't true. At least, in Las Vegas, by law every spin must have RNG that is independent of previous spins. They can't be programmed to "go cold" after a jackpot, or guarantee a win after a cold streak.


In roulette they post the last 20 or so results, the reason they do it is because the marble is not self aware of previous results, each marble roll is an independent event.

I'm unsure if slots are like this, I guess it would depend on the quality of the RNG and trust in the casino/machine that it's configured correctly.


> In roulette they post the last 20 or so results, the reason they do it is because the marble is not self aware of previous results, each marble roll is an independent event.

The reason they do this is the above, but actually because people are dumb and think they can see patterns that dont exist ("look the same number came up twice in a row! i better place a bet")


There was a time when you could infer a wooden roulette wheel's bias by collecting enough samples.

I think now the casinos track this and retire biased wheels, which is why they have the data feed in the first place. And then yeah, why not publish it to make more types of gamblers interested in the game!


its basically a gamblers fallacy, another one is people will get angry if they were playing a slot machine, losing - got up and the next person immediately won a jackpot. they think it was their jackpot. when in reality it is just RNG at its finest.


Actually that does beg the question - does the randomiser seed for autopicked lotto numbers use a time stamp? Ie, would you have actually gotten the same numbers he would have gotten if you didn’t buy it?


You could replace it with a scratch-off ticket to dodge the problem


Agreed 100%. I had an opportunity for a managerial role, I took it, I thought it would make my career better.

It didn't. I crashed, burned, couldn't write as much code as I wanted and managing people is an entirely other and opposite skill than writing code. I quit, I took a break and I'm now planning on writing code as an engineer for the rest of my career. I'll leave herding cats^H^Hdealing with people to more suited candidates.

You can't know that your current choice is a mistake. That's an unproductive attitude to have in life.


Unfortunately, at many places, going into management is considered as career advancement instead of parallel path, and this is reflect in terms of compensation as well (a huge mistake).


At tech companies, this is starting to change. They'll have an IC path and a management path.

But at a non-tech company that happens to have engineering roles (Bank, healthcare, etc.), yeah that's not happening. If you want to write code, you might end up being promoted to "Senior Software Engineer", but you'll stall there and your compensation will fall even farther behind the curve than it already is. You might cap at 150K/year if you're lucky.


Well said. OP is making the classic mistake of comparing them with others and assuming that Grass is greener on the other side. Never compare yourself with others, never. Always compare yourself with YOURSELF. I keep saying this and hoping it helps others.


> Life is chaos; pretending things like this are in your control is useless.

Yes, I've been thinking a lot about this and if free will is just an illusion. I sorta like to think it is just an illusion. It does make it easier to deal with "wrong" decisions.


(Not OP but) This quote most likely is not about free will. But how life is random/chaotic. Two people in same situation doing exactly same thing might end up with different end results.

In professional poker there is a rule/saying, "you can do everything right and still loose" (due to chaos). The trick is to not over-think your mistakes, if you made a stupid decision reflect why, if you didnt make stupid decision it might not have been a bad decision, just unlucky.

You cannot control the chaos only adapt and look ahead, instead of if only i did this or that i would be better off. You cannot know for sure if something would happened or not.

You absolutely have free will to do something about your situation, but you cannot guaranteed outcome.


Think of a situation where you think you could have done something better than someone else.

It is likely that you could have using your mind, body and life experience.

Do you think that you could have done the situation better if you were using their mind, body and you had their life experience? I believe that we would all have the same outcome. If that is the case, then free will is an illusion.


Free will is an illusion, but it doesn't change anything.

Lives go on as we cannot predict/simulate our world to 100% predict human reactions and decisions.

> I believe that we would all have the same outcome.

We are not talking about impossible hypothetical situations. We are talking about Bob and Alice, where Bob thinks to himself that only if he followed same career choices as Alice he would be in the same place as her. Since he is smarter and harder working than her. And that is simply not true due to life being chaotic, unfair and luck plays its part. He would have a chance but not guarantee to have same outcome as Alice.


that kind of thinking could result in repeating your mistakes.


I often see this reaction when people suggests that you should care too much about your past decisions since you can't ever imagine control everything.

It's about _past_ decisions, nobody says you shouldn't care about doing the best for you in the present. You can't be sure if your decisions are the best, but you surely have to avoid the bad one if you can !


Don't repeat the same mistakes, it is boring. Make new mistakes, much more learning happens that way. There's probably a Yodaism in there.

The meta level is to recognize classes of mistakes and create a process around preventing them to help avoid future mistakes.


If free will isn't an illusion.


what benefit is gleaned from thinking free will is an illusion?


Not beating yourself up over past mistakes.


but you are saying you dont have a choice about that

i dont really see how you can say free will is an illusion so you shouldnt do something.

Thats a direct contradiction


> Thats a direct contradiction

No, if free will is an illision, then even "choosing" to believe in it and "choosing" to let things go is an illusion. It would apply to every "choice" we make.


if only it were so simple to side step personal responsibility. just call it illusory. to what effect?


I was having this conversation two days ago. I believe free will is an illusion, everything is ruled by causality beyond our comprehension.

But even as I say write it, in a couple of minutes my brain will jump back into thinking I'm in control. It's very strange.



I agree with everything you say. However,I think this argument is overused. Sure , luck is important and there is always incomplete information but it doesn’t mean you can’t differentiate between good decisions and bad decisions. It also doesn’t mean you can’t improve yourself by improving your decision making skills. For example , there is a lot of luck involved in poker games , but experienced player who can make consistently good decisions are going outperform those who are not making good decisions.


I completely agree. I’m a pretty good software developer but I’m pretty sure that I would be only an average manager at best, that kind of job is not for me.

https://en.m.wikipedia.org/wiki/Peter_principle


>> Happiness will not come from a time machine

This needs to be framed.


Well said though I be a bit more soft in the words.


My apologies. It takes me way more effort to write that way, so I don't bother for anonymous comments. But I know you're right and I agree with you.


I was hard working and [more] intelligent than him.

Being more hard working and more intelligent than the competition won't get you very far in anything except purely practical work.

Those definitely aren't things that make a manager successful. Being approachable, being on the side of the people you're managing, willing to pass on the credit for wins and take responsibility for failures, being willing to make hard calls and tell people 'no' when they're unreasonable etc are the nice things that make a manager a good manager. Being selfish, ruthless, and willing to burn bridges to get further up the ladder are often useful skills too, albeit from a slightly nastier perspective.

Management is psychology and politics. Those things don't require much hard work or intelligence. (I'm not calling all managers stupid; managers need 'street knowledge' and savvy judgement.)


Upvoting this. In my many roles I've had an opportunity to observe and work quite close with executives at several Fortune 100 companies - VPs, CEOs, etc.

I would not rank "hard work" or "intelligence" very high when it comes to common traits of these folks. In fact, I would say maybe half of these folks really stood out in terms of raw intelligence - people who make you say "wow, that person is bright". And we're not talking "Field's medal" smart.

The same characteristics that make for successful politicians makes for successful executive - emotional intelligence, ability to connect with people, confidence, ability to communicate clearly and drive the organization forward. There is a bit of force of personality here - their actions push decision making forward. And that doesn't require a big ego are a silver tongue. I've met quiet, reserved leaders who just have a style that says "I see it like X, so we need to do Y" and everyone else says "of course!" and off they go to do Y.

It's a common trope but "big picture" thinking is a big deal - don't get mired in trivial details, focus on what important, stop people from wasting time on unimportant things. Basically keep the machine well-oiled and moving forward - keep people happy and focused.


I've found that having strong individual contributor skills and having written most of the foundational codebase myself are a dangerous trap as a manager. It's very easy to put yourself on the critical path for delivery, which is really bad for your team. You need to build up those skills on the team instead, trust people who you think might not be ready, and be willing to take the heat when they fail. To the extent I still use my IC skillset, it's to fill in the gaps where I don't have a seasoned developer to lean on. I review a lot of patches. That, and I blow off steam by working on non-critical features.


>Being more hard working and more intelligent than the competition won't get you very far in anything except purely practical work.

Ouch, I really felt that.


It's true. I'm objectively more intelligent than my cofounder. He knows it, I know it. He's the far better manager than I am and grew to lead half the company, almost 5x more reports than me.

It's really all about empathy, structure, but first and foremost the ability to pass on the work to _someone else_ and make them succeed at it.

I tend to nerd snipe myself much more often because I like the technical challenges.


Sounds like you are both smart enough to realize and appreciate that while you each have strengths, you compliment each other.

Many would become envious of each other or allow their egos to get in the way, so good on you.


Everyone thinks they are more intelligent and hardworking than the people around them.


Not really, lots of people know they aren't the "smartest guy in the room", or "the most specialised" or whatever, but trust their people skills, family connections, visions or simply brute force their way up.

The point is that social skills and networking will get you much much further than being the semi silent, guarded and "honourable" person sitting in the corner of the room - even if you are actually way "smarter" than the socialites or the people with a flair for marketing, social games, politics etc.


Building excellence will always require you following the old adage of "if you're the smartest person in the room, you're in the wrong room". There is exactly one person in the world to whom that doesn't apply in any given field.

Being "quietly smarter than everybody" is a huge alarm signal that you're stuck at your current level and won't grow much further unless you change circumstances.


> Those things don't require much hard work or intelligence

They really do. It's different from the work or intelligence you apply to technical problems, but it's there. What you call 'street knowledge' and savvy judgment is commonly known as 'emotional intelligence'. (Your terms are way cooler, though ;)

The "hard work" part is also often on the emotional side. Everything you need to do includes a "how will that make the person feel, and do I want that" component.


> Yesterday I saw my former colleague who grabbed the manager role, got promoted to a director. I was hard working and intelligent than him. I could’ve played my card right and be in that place.

The key to happiness is not to compare yourself to others.

My friend tried to convince me to mine bitcoin. I was worried my GPU would die, so I didn’t. He’s a millionaire now, and works a lot less than I do. If I played my cards right, we’d be on a boat together.

But I’ll be on a boat next week, because a fat paycheck has some benefits. Like yours.

I suggest a long vacation, followed by a dramatic reduction in the number of hours you’re putting in. Forget about work entirely while you’re there. When you’re back, spend every day job hunting.

I have to believe that ageism doesn’t exist, and that you can always change careers. Unfortunately I know it does exist, and that it’s not so easy. But if you fail, your next best option is to embrace the mentality of “do less.” You’re putting in more than your job requires; stop that.


Alternatively, if you really can't stop comparing, pick a different reference point until you can stop comparing.

When I compare myself against my peers from when I was a child, I end up horribly depressed because I have no PhD, no company, etc.

On the other hand, if I compare myself to the average in other categories, I'm doing really well. The employment rate for those with MS is around 30%, and I'm a single gay woman from an abusive household (so no parental support) on top of that. From THAT perspective, the fact that I'm a breadwinner for a middle-class home means I'm doing REALLY well.


> How do I deal with my feelings? Should I seek professional help?

Yes. If you’re at the point where you need to anonymously seek advice/share on HN, I definitely think it would be a good idea to talk to someone. And please don’t read that as me being flippant. I’m a strong believer in therapy and think it is beneficial for every single person.

I would also suggest talking to some sort of career coach. I used to dismiss executive coaches because I thought a lot of the practitioners were just con artists hawking their wares, but I’ve found real value in executive coaching and have good friends who have as well. Finding a good coach is probably just as hard as finding a good therapist (and the roles are similar), but if you don’t want to talk to someone about the residual anger and resentment you have, you should at the very least talk to someone who can help you make sense of making some sort of game plan to get back on the management track, if that’s what you want, or to find something more fulfilling to do.

The thing is, the grass isn’t always greener. There is no guarantee that you’d be happier or made director if you’d gone the management route. Your work hours would also probably be double. But you can’t change the past and hyper-focusing on that won’t help you feel any better.

You need to move forward and you need a plan. Good luck.

Also, go easy on yourself.


While I'm on board the therapy train, I think the career coach would be the far more appropriate professional help in this case.


It sounds like you don't like being a manager. I don't either, which is why I've remained an engineer since 1996.

Your career takes up a HUGE chunk of your days, so you have to decide: Is more money and status important enough to burn out doing a job you hate, day in, day out?

When you finally retire, nobody's going to care what you were in your past life, and engineers make plenty. So why not optimize for the long game?


Honestly, sounds like they don't like being an IC either, based on the "grunt ic work" comment.

They also haven't figured out that IC and Management are different career paths, since they think IC work is just moving around jira tickets.


> they think IC work is just moving around jira tickets.

I really don't think OP thinks this. It was just a way of expressing how unfulfilling they find the current role to be. Thats how i read it.


I disagree. It speaks to a broader belief. Tie that in with the "I'm smarter and work harder" comment, and it paints a bit of a theme about the poster. Moving JIRA tickets, cleaning up boards and doing various other admin are powerful tools to team organization whatever the tool/process used. A smart person and hard-worker shouldn't have any problem picking that up and moving the team forward.

Likewise a savvy "street smart" person that wants to go into the managerial track needs to understand how to convey to the right people that they moved the team forward or they need to get help from a Scrum Master / BA / PM that should be doing that instead. Maybe convincing their report that there is a gap to grow the team, and that their time could better be utilized.

At first you do tech and coding. Then you get to a phase where coordination is key, that includes admin and processes. After that, only then do you get to the "leadership" or "strategy" and other nebulous parts where you have to drive things forward not by doing work yourself but by putting the right people on the right tasks and enabling them.


I transitioned from being a tech lead to a manager. I hated it.

I had an awkward conversation with my manager and we figured it was possible to switch back.

Once I did that, I found I missed parts of management. I had an even more awkward conversation and was able to switch back, but keeping some technical aspects.

Later I switched to a new area and found myself a beginner again, and had to build up the skills, successes and then the recognition that comes with them. Now maybe in the future I’ll be using those old skills and contacts once more!

It’s ok to feel discontent and do something about it. It’s ok to have second thoughts and course-correct. It’s better to take an active interest in your career progression than sit and hope someone does something for you.

Practical advice:

1. Good line managers often have some latitude and will to help you; you just need to discuss it openly.

2. As an individual contributor I feel you have a lot of control over your hours. Stop working so many. It’s ok to tell people no, that can only be done by X date; they don’t know anyway, they’re not the IC.

3. You don’t need to turn back time. You have learned a lot and this will make you more valuable as a future manager. Including about yourself. Tell your reporting chain you have learned enough about this side of the business and want to move back to management. Apply for management roles internally and externally. Get over your pride and hit up your old friend and see if they have a position for you. Relationships matter more than smarts.

Edit: send me a DM if you want to talk, happy to help someone else through this. It was a difficult time for me for sure. Handle is in my about page.


I see this as a positive thing. You now know what you don't like and don't want to do. Does that get you closer to what you want to do? You only have one life. You failed and learned something about yourself. Now move forward.

Turn envy and jealously into a positive emotion like motivation or inspiration. A therapist can only help and if you want to make tremendous career progress I would suggest seeing one. Focus on yourself and what you can change and control in you.

I bet if you learn about your former colleagues life (who is now a director) and work that you would probably not want the job. There's a reason you turned it down right?

You wanted to see if product management was a better fit. But for whatever reason you were wrong. This is not a bad thing. Did you quit too hastily when maybe you could have found another role at your previous company? What made you choose program management after product management?

Ask yourself the deep questions and you will be enlightened.


> You now know what you don't like and don't want to do.

Edison's "10,000 ways that don't work" is a terrible way to invent a lightbulb, but a great way to live your life from my perspective.


You should seek professional help.

I’m sorry if this comes off as mean but from what you wrote it doesn’t sound like you’re someone I would actually like to work with in any capacity. You sound like the lead character of Clerks - “I’m not even supposed to be here today”.

Not knowing anymore than you wrote I’m pretty sure with that attitude if you took that other path you would be in exactly the same spot you are today: thinking about that other guy.

I hope you find some inner peace and career fulfillment.


I wanted to write what you wrote, but yours is on point and way more eloquent. I agree with this comment 100%.

To OP: please, do look for professional help. It's impossible to play dr. House online, but if I pair my experience of dealing with people with the problem you described, I would guess that you're not happy to begin with - and that spilled over to your career life.

Explore whether there's a root problem, if yes - solve that problem. Then the symptoms will go away.


> it doesn’t sound like you’re someone I would actually like to work with in any capacity.

How are your feelings about what kind of people you don't want to work with are relevant here ?


This is a "public forum" where people have "conversations" and "discuss ideas". When people have a "conversation" it is sometimes helpful to express an "opinion".


I was asking gp how it ties to what OP is talking about. I wasn't implying shouldn't have said that.


OP is expressing dissatisfaction with their career progress. My implication is that this lack of progress might have something to do with how well they work with others. Grumpy, unhappy, unpleasant or difficult people are often unaware of how they come off to others.


>Should I seek professional help?

Perhaps. It might help you focus on what's in your control.

>I have 25 years of industry experience and I feel I should mentor people instead of moving JIRA tickets around.

I'd advise show, don't tell. What I've tended to notice about people who get trusted with more responsibility in any dimension is that they tend to do two things:

1) take responsibility without being asked. 2) find higher and higher leverage things to work on. They don't do everything perfect, but find out what their boss/employer truly values and double down.

Judging by the fact that you were offered a promotion choice in the first place (albeit you think you chose the wrong door), it seems might have just forgotten how to do what you've already known in the past.


> I have 25 years of industry experience and I feel I should mentor people instead of moving JIRA tickets around.

Managers don't mentor in the same way that you want to mentor.

I suggest targeting roles like "lead developer" or "architect." These are the kinds of roles where you're writing designs, and mentoring other developers.

When you change roles, (either within your company or with a new employer,) be explicit that you're targeting a lead / architect role. If they push you towards a novice role, walk away. Expect that it will take you longer to find a lead / architect role than to find an entry-level role.


> I have 25 years of industry experience and I feel I should mentor people instead of moving JIRA tickets around.

The roles that people have on paper aren't what make them mentors. In my experience the management path is a tradeoff between stress and income. The higher up the ladder, the more stress, more income.

You can be a great mentor as an IC. TBH the best mentors I've had were not my "boss" but a peer or more senior IC.

My advice would be to definitely seek help to organize your feelings. And to try and look at your current role through the lens of a mentor, start helping when you see an opportunity for mentorship.


What do you like doing? I went management a few years ago, and while sometimes in the back of my mind I think about doing it again, I'm extremely happy as an IC, especially in the challenges of my current role. For better or for worse, I love observability and automation, much more than 'management'. In objective terms maybe my career has gone backwards, but personally it has not.

On Mentoring People: You don't have to be a manager to mentor people. In fact, an interesting part of being a manager that I discovered is that you often don't have nearly as much time to mentor people as you do if you are a senior/lead IC. Probably (rough numbers) 20% of your time is spent managing up, 40% managing sideways and 40% managing down. And there's a lot of work to do in that 40% that is not "mentoring".

But it's never too late. Every new job I start it seems within a year someone is asking me if I want to be a manager. Good managers are hard to find so if that's really the path for you it is not closed off at all.

Given that this is HackerNews, I assume your 25 years of experience are in software engineering/tech, but is it in something else? Also, you say "I have 25 years of industry experience and I feel I should mentor people...". What does 'should' mean in this case? What is the source of that pressure?


It sounds like something straight from a motivational calendar, but it is actually true: Don't look back at your decisions, and more importantly, don't compare your career against others.

Long version: As other said, there is no way to know that you would be a director now. Even if you were, there is no way to tell you would like being a director. There is no way to know your colleague is actually happy as director. And there is no way to know how your life, and not your career, would have turned out had you taken the manager role.

I think there was a reason you didn't take the manager job, it's a fair assumption that those reasons have been valid back then. Think about those reasons, if they are still valid today your move to another filed was no mistake. If they are different now, your move wasn't a mistake neither, but it might be a reason to consider a move "back" to management.

If you enjoy your job, but not the hours or being an IC, think about moving to a different role in that field. If you want to become a true expert, being an IC is actually not that bad. If you want to be a manager, chances are you won't be as good in your field as an IC would be ultimately.

But don't feel the urge to become a manager because you are somewhat jealous of your former colleague-turned-director.


I think you can actually flip this situation around a little bit. You've now learned about a couple of things that are really important to you:

- You're ready to move on from being an IC - You want to help or mentor others

There's no way to know how any given decision is going to turn out. There are some that are obvious but usually you won't know until to make a choice and live it for a bit.

You seem to have the ability to pivot - you've done it twice in 2 years. So now that you know the direction you want to go, you can either work with your management towards that path or you can seek out another opportunity that aligns with your current goals / desires.

You're not incredibly stupid nor are you necessarily a bad decision maker. You took a shot and it didn't work out. A lot of folks get stuck and never make a decision because they're worried it won't turn out. You had the guts to pick a path and, while it didn't work out, you've remained employed, broadened your experience base and learned more about what you want to do now. I applaud you for taking the shot!

In terms of professional help, possibly a mentor or career coach.

(FWIW - I did something similar about 18 months ago and am now pivoting back into a leadership role because I've discovered I miss it as well)


It sounds like you're agonizing over past decisions. Been there, done that!

We're all human and have to make choices with imperfect information. Sometimes we pick the right choice, sometimes we don't. All you can do is learn from it, and this helps you inform your future choices, e.g. we get a bit wiser in the process.

Figure out what your goals are - if you really want a management role, then figure out how you can get there from now and start taking steps towards it. It might be studying an MBA part time for example. Or getting involved in leadership activities, like being on your local HOA board, school board, or similar. Ask your manager what steps you can take to move into a management role. Follow the philosophy of "act like the role you want" and you may get noticed as having leadership / mgmt potential.

Beyond that, if you are agonizing over the past like it sounds like, there may be underlying emotional issues you need to sort out with a professional. Like for me, I have struggled life long with intense self criticism and over analysis of everything I've done. Like agonizing for weeks/months over a decision, something I said, etc. and beating myself up over it. That kind of thinking process _is_ pathological and a professional can help.


People make mistakes. Sometimes you can learn from them. A few questions to consider:

- Did you talk to people who were product managers or program managers, and learn more about the role, prior to taking that leap? If not, this might have helped you realize that you wouldn't have enjoyed the role

- Did you do research on the future career paths for managers? This might have helped you realize what opportunities you were passing up on

- Did you do research on the average compensation for managers/directors/PMs? If compensation is important to you, this is definitely something to plan ahead

If you did all of the above, and things still didn't work out, just accept that you made the best decision you could have with the information you had at the time. That's all any of us can hope for. And mistakes are bound to happen despite that.

Regardless of whether or not the mistake was preventable, it's done and it's in the past. Learn what you can from the past, and then focus on the present. If being a manager or director means that much to you, pivot your career back towards the management track. Yes, you will feel frustrated that you "wasted" the last few years in other unrelated roles. But don't let sunk cost fallacy rob you of the best decision you can make today.


I think in a management role, you have to think on your feet, even on long term things.

It might be better to transform your role into something that fits what you want while still serving the position/s that you are in.

If you say you want to mentor people, then it is something to develop. I think one key thing in any team is to always be solving problems, whether it be bugs or finding problems to improve. Take a few new or junior people and tackle the bug list together, figure out what can be done better and build on it.

My mistake was not moving to something new (new position, new company, etc.), but it helped to have a manager myself where we can brainstorm on my problem.

[EDIT: Also in my experience, dev teams need voices, whether it be control of the backlog, a way to advocate for the team, etc. I think those who can talk with their team and construct plans when dev teams struggle to find voices. By constantly solving problems with other team members, particularly seeking for them to solve the problems, you are helping them towards giving them a voice.]


Disclaimer: This is not medical advice and I’m not a medical professional.

This may sound snarky but it’s not. Focus on life and not career and do not give into impostor syndrome. I’ve been where you are and after a significant illness for my then 3 yr old (pre-covid, and she’s doing really well now) made me re-evaluate my choices.

Work smart in your career and make sure life is taken care of first. Working hard rarely nets results unless you’re working hard for yourself (i.e. your own business, startup, hobby, side hustle, etc.).

If your immediate friend circle is mostly people who are focused on career and advancement (if I’m being presumptuous is where the feelings of regret are coming from) I would work to slowly change it and find some other hobbies. At this point, with your paycheck you are doing a whole lot better than 95% of the worlds population.

If this is overwhelming you - please seek professional help fast.


> How do I deal with my feelings? Should I seek professional help?

Simply yes to question 2, as others have said. Feelings are real and need to be managed, just like anything else. Depressive feelings will slowly (or quickly) spill over into all areas of life and sap the light away from everything you love.

At 37, I have a job that pays the bills for my family, allows us to save adequately, and gives me time throughout the week to tend to the things that I want to (family, gardening, video games, p much in that order these days).

I've also been through 3 anti-depressants before finding one that worked. My goal is to get to a point in life where I can titrate off of it. The dose is low and my therapist says it shouldn't be hard, but not to be rushed.

Feelings do a lot of psychic work, good and bad. The body keeps the score. Find balance.


I think there is an element of the “grass is greener here”, of course you could have taken his path and enjoyed it, but if it helps I’m one data point that did take the management opportunity early and didn’t enjoy it. I pivoted to project management where I can be closer to the action without having the tedious line manager duties and I enjoy it much more.

Perhaps instead of looking back is there a way to look forward… in your current path what’s ahead and does it excite you. If not, what other careers would interest you (which aren’t this path that you wish you took). You may find yet another path that is even better if you expand your thinking.


You are making the mistake of getting 100% of your fulfillment from work and putting 100% of your career bet on your job. If you are highly talented and creative and good at making or creating things, you should never be trying to pin 100% of your aspirations on your job.

Likewise, if you have stopped learning, that is a big problem.

Instead you should be diversifying. Work less. No one will notice or care. Put in 40% effort at work, arrange your job so that you can get by and dedicate the other 60% of your energy to organizing something outside of work.

A community; a program; an event; etc. something non commercial (at first) where you can gain total freedom and control.

At work you will never get control. That was my experience. I also found that my excess need to create and ambition were largely a liability. You have a job. You get paid to sit in some box. If your ambition makes you want to outgrow the box, they won’t like it.

Grow your ambitions outside the company and keep learning and growing there.

Being management - my experience is it is a different set of skills and personality. Your skills atrophy and you become subject to politics. If you want to manage, hire someone off UpWork and go have fun.

If you want to mentor, found a mentorship network.

You are better off constructing your Plan B outside of work, learning all the skills you think you are missing there.

Your problem is boredom, underutilization, lack of growth, lack of learning. Becoming management at your current company won’t fix any of those problems it will make them worse.


Thanks for the responses. I guess I very much needed kick in the back. I am old enough to know that hindsight is easy and there is no point agonizing over the past. It’s too hard to put in the practice though. My real life friends have also told me that my identity revolves around my job. I realize it. E.g. Someone mentioned in this thread that they would hate to work with me. Even though it was a random internet comment talking to my throwaway handle, that comment hurt me. I do my best job irrespective of whether I like it or not. I take pride in doing good work. If I get paid top dollar, my employer gets his moneys worth. I guess I have to reframe my mindset and decouple my identity.

While getting a promotion is partly related to seeking validation through status/title, it’s not all that. I feel that at 45 I have limited time in the workforce to make an impact. I will probably work 10 more years before getting exhausted and calling it a day. Getting into management can put me in a place where I can help people grow in their career. I can make changes in management to make my teams life a bit easier. I never had a mentor or guide to bounce off my ideas about life or career. May be I could be that sounding board for my team.


Hey, I’m sorry you have to read comments like that. That was a dickish thing to say. You were open and honest about your feelings (in this case, that you were more diligent and intelligent than your coworker and yet made the wrong choice and ended up ‘falling behind’ them). It’s a shame that even in an anonymous forum people are so obsessed with self-filtering and coming across precisely correct, not too confident and not too self-effacing, that they end up punishing someone just for candidly articulating what’s going through their mind.

Don’t let it get you down. Think about all the opinions you’ve had about internet strangers, how little information they were based on, how unlikely it was that they were correct, much less represented the totality of who that person is. Imagine someone actually adjusting their self-image by the opinion of someone whose only knowledge of them is two paragraphs of text. That’s mad. I know we’re inclined to believe criticism more than praise, but I really hope you can focus on the positives and the helpful comments from this thread, and find a happier way of living. I wish you way more than luck.


Just wanted to offer: you're not alone. Your story is pretty much exactly the same[1] as mine, down to the titles/roles and your general age. I've concluded that switching back to Eng is not the way: You'll be starting from zero again. Not sure the answer on how to get into management and start growing again, it's been a bunch of doors closed in my face so far, too. It's a chicken-or-egg problem: You won't be hired or promoted as a manager unless you've managed before. Frustrating to say the least.

https://news.ycombinator.com/item?id=31208950


Everyone you meet is a knot where two strings intersect. Sometimes these strings twist around each other for a while and it's very natural to judge your path with another. In the very short term this might even be accurate, but then strings diverge and go on towards infinite more collisions. Any comparison of more than the briefest timeframe is meaningless. You don't steer your path as much as influence the variables that determine direction. You do this through both action and inaction.

1. If you want to impact your path, choose intent over accident

2. The direction of your current vector is more important than your life's total displacement

3. Life is lived when strings intersect, with each knot influencing future direction

4. There are no cartesian coordiantes for your final goal. You define an ideal as your target and make progress towards it; both change over time.

More pragmatic: spend some time with your former colleague, reconnect, enjoy their company. Find out what they've been doing with their entire life, not just their job title. Realize that maybe you're focusing on a single dimension in a forest of many, and perhaps your head-to-head comparison isn't as relevant (or important) as you initially thought.


As others have said, I agree that you should seek professional help and find a way to re-evaluate your thinking about your career. From this post, it seems like you've gotten stuck in a feedback cycle of resentment. To make that more clear, note that many things you've said here would seem to imply you look down on your coworkers and/or on the work they do. There's the obvious example of "I was hard working and intelligent than him", but more telling are phrases like "I am extremely unhappy being an IC", "I have 25 years of industry experience and I feel I should mentor people instead of moving JIRA tickets around" and "Yet here I am being ‘advanced beginner’ in a different role every couple of years doing grunt IC work" suggest that you look down on the people who actually get things done at a company. How many IC's want a manager who views them as beneath them? What company would be exercising good judgment putting you into a role in which your resentment might trickle down to your reports?

I'd suggest taking a break and working with someone who can help you process your feelings and move past them.


One of my bosses quit Microsoft in the late 80s, right before the company exploded. Your mistake isn't as big as that.

I tried to make my own startup for years in my 20s, making nothing for years. My salary is so far behind (hopefully not for long) and I could've FIREd by now if I'd just worked at regular tech companies. I just get angry at myself every few weeks but try not to think about it the rest of the time.


There is no shortage of opportunities to go into management. Good managers are hard to come by. So any time you can demonstrate that you have the skills and willingness to be a manager, most employers would welcome that. You can try to find management roles in other smaller companies who might be more open to your lack of management experience. Please don't mind but it seems to me that you are being jealous of your former colleague. It seems you were OK being an IC for 25 years and now that you have seen a peer succeed in management role you hate being an IC. Do not base your happiness on what others have. Know what makes you happy and try to get that regardless of what other people are getting / have gotten. If it helps, I have been an IC for 18 years and plan to be until I retire because I don't like management and I am quite happy with that. I know I'll never make executive salaries but I am ok with that. I optimize for happiness and less stress instead of money.


First things first: ask your new leadership if there's a path to another such opportunity, now that you've changed your mind on if you should've taken it. Let them know what you want. Don't assume your boss can read your mind or knows what you want.

If you don't want to do program management or product management, but thought you might in the past, at least you have learned those things now!

It would surprise me if there are, at the very least, no opportunities to mentor people and shift some of your time away from direct pgm work into mentoring or other such managing-without-direct-people-responsibilities roles. If you want to manage, are you open to doing it in PGM?

But (a) don't assume it will solve all your problems and erase feelings of regret, and (b) don't assume you'll naturally be good at it without possibly having to rethink a lot of how you work, and (c) then focus on emotional issues and work style issues directly in a forward-looking way instead of just looking at the past.


I've done my fair share of "woulda, shoulda, coulda" in life, it was a total waste of time.

At this stage in your career, I'd stop waiting for others to allow you to do what you want. Eliminate your expenses, save those paychecks for several more months, then quit and start a consulting business or similar. Put yourself in the drivers seat in any case.


I recently saw that two people who joined a former employer of mine after I did have stayed with that company all this time and both now run the company (one is CEO, the other is CTO). I thought hmm that could have been me, if I hadn't jumped ship.

But I don't lose sleep over it. Everything is easy in hindsight and I've had other experiences, some wonderful and some not, since that I wouldn't have had if I had stayed.

Basically, my point is that these things happen. You can't predict the future, you do what you feel is best at the time with the information you have. Sure, sometimes you make choices that in hindsight turned out to be the wrong ones, but that's part of life. I don't have any advice on how to deal with it, though. I guess you need to learn to let go of things that are ultimately out of your control. Learn from the past, but don't antagonize over it. Perhaps seeking some therapy might help you come to terms with it.


It sounds like you need a career counseling therapist, yes. Basically a psychologist or psychiatrist that has a specialty in career counseling/transitions/issues. I think it's great that you're focusing on dealing with your feelings rather than trying to troubleshoot the career aspect.

I don't think you're stupid at all. Many of us (most of us?) make career mistakes and do things we regret. We cannot turn back the clock, but we can always start to build the future we want. Believe in yourself! You can do it!

I couldn't find much online in the way of search for therapists, maybe someone has a better way to search. Psychology Today shows some results (https://www.psychologytoday.com/us/therapists/ny/new-york?ca...)


If you have the feeling "I wonder if I should talk to a professional?" the answer is probably "yes." A good therapist can do wonders. (A bad therapist can do damage, though - so it's imperative to find a good one and that may take a while.)

But don't beat yourself up - these decisions are hard, and many people second-guess their decisions. Maybe you were wrong, maybe you made the best decision but neither decision would have been optimal.

If the management path isn't open to you at the new job, or you don't like the company, then it's time to start looking elsewhere.

Don't focus on how you perform vs. somebody else given the same opportunity. Maybe you're smarter or would've done better, but you can't know that. Just focus forward and try to make the right decisions with the hand of cards you have now - not the hand of cards you had a few rounds ago.


> You claim to be more hard working and intelligent than him

Dude, intelligence is not nearly as useful in this world as we are made to believe.

And, you say you are smarter than him? That automatically makes it so that I would never want to work under you. People that tend to waste cycles on comparing their intelligence to others tend to be insufferable, egotistical, and boring. (To say nothing of the fact that intelligence is largely incomparable.)

Management need people that make good, obedient little minions for upper management. Who can make their bosses look good while simultaneously shielding the team from them. You don't have to be 'intelligent' to do that, in fact it might make the job harder.

> I feel incredibly stupid. I am losing confidence in making good decisions.

Why you gotta be so extra about it? You lost out. Big deal. Pick yourself up and move on to the next opportunity.


>People that tend to waste cycles on comparing their intelligence to others tend to be insufferable, egotistical, and boring.

You don't have to compare intelligence to notice that you're edit: r/smarter/more intelligent (or that others are r/smarter/more intelligent than you). Especially when you're working together with someone for a long time.

After a while it's like knowing you're shorter/taller than someone - you won't notice and you might be wrong if the difference is small - but when it's a large difference it's just something you know even if you never consciously thought about it.


I have never found a circumstance where those comparisons are actually useful in the sense that they can make me a better person. All they have ever done is make someone (usually me) feel better about themselves.

Every time it has come up, the situation has been a trap of some kind

And what is smarter anyway? Book smarts? Street smarts? Your coworker may not have intelligence in the same areas as you, but I bet there are areas in life where they will kick your ass

What a lot of people are really asking is, 'how experienced is this person in the same areas that I am?'


I shouldn't have used the word smarter - I meant to say intelligent.

I think intelligence is just "processing power", there are people that catch on faster, can evaluate more angles simultaneously, are able to wrestle with complex ideas - once you start working with people on new/hard problems you notice who struggles to keep up and who outpaces you.


Agreed, but I think many of the ways that manifests can be acquired with experience if you're looking at one thing. I think the idea we are both getting at is capacity for learning, or quick thinking, and for that you need to see that person perform in a suitable environment, which the workplace is probably not providing.

And again, these are all components of intelligence but missing large parts of the bigger picture. What about the ability to make a point or debate well? Or charisma? Those are social skills, you might say -- social intelligence? So then is intelligence simply the sum of ones skills and ability to pick up new ones? Maybe, but then how does that apply to your specific situation?

My point is that intelligence is probably undefinable. "I am better/more experienced/more capable than this person at X and Y" is probably what you should be saying to yourself instead.


2 video´s and one short story:

1:'The Fringe Benefits of Failure, and the Importance of Imagination' -JK Rowling (https://youtu.be/wHGqp8lz36c?t=1166 --> 19:26)

2: Matthew McConaughey winning Best Actor | 86th Oscars (2014) (https://youtu.be/wD2cVhC-63I?t=116 --> 1:56)

3: Story You are not your work, your work is not who you are, it is what you can become. The real question is who do you want to become and how do you want to live while becoming that?

I think the happiest people don´t see there work as work, they made there passion there work, become really good at is and then feel that they receive the inner duty to also change some things of the proces.


The key is likely that your experience and possibilities for unique contributions are being ignored and you're being used like someone just out of college. The "other path" others are so focused on is a red herring.

This is a problem I see at tech companies generally. Your title and rank on some formalised ladder that some exec thought up are been used to determine what your contributions to the company can be. Contrast this with seeing what unique perspectives and contributions your experience can bring to a team. The company is leaving some amazing possibilities on the floor, because the system they've created has no place for individuals, only "headcount."

I'll let you know what the solution to this is a soon as I find it. I'm already stagnant and wishing I could use my skills instead of checking boxes.


"Suck it up Butter Cup", EVERYBODY makes career mistakes. It's how you recover from them that set you apart.

Promotions and jobs aren't always based on merit and hard work. A lot of times it's being at the right place at the right time, proximity and how you are perceived by your superiors.


IDK if this makes you feel better, but I hope it does: after 4-5 years of being a dev, I decided to go to law school and now hate the practice of law (law school itself was alright and I did some cool stuff), and now I want to go back to being a dev. It's possible, but I obviously gave myself a huge and unnecessary career and financial obstacle.

In any event, you sound like you would benefit from a gratitude practice and looking into other spiritual and emotional type of advice. If you have 25 years of industry experience, you are old enough where you should have the maturity to have a more positive and understanding experience about this, and if you don't, then that's ok--now you have something to focus and improve on that will benefit all aspects of your life.


A good engineering manager doesn't need to be "smart" or even really "hard working". They don't even really need to be technical, just have good relationships with their lead. Good managers need to have some sense of responsibility to their reports, they need to take and invite criticism, and have the drive to change according to that. Most managers in tech do not have these qualities, for whatever reason we hire a notoriously self-centered, egotistical bunch, focused on their own success. All that to say, it sounds like had you gone the manager route you'd likely have been that manager.

If you want to be a manager, then focus on those internal qualities first before you have reports whose lives you can make miserable.


https://en.wikipedia.org/wiki/Just-world_hypothesis

You are the person in control of your mind, and your emotions.

Find some other way to feel. Measure yourself against yourself.


You don't even know if the other guy is happy or miserable in his director position...


Okay, a fair few things to comment on. Firstly, you can't turn back time. You have to design your new brand and reputation if you want to change your career trajectory. I suggest you look at your real value, strengths and weaknesses and be honest about how people see you. It does not seem that other people see you or your value as you see yourself. It sounds like you are angry, but if you use that emotion to push yourself to create a new brand and build the skills to demonstrate your value, you won't need any professional to deal with your emotions. I hope this helps.


You are not alone, I think many of us have made similar mistakes. I have also recently made a bad career mistake, I was being promoted to management but without salary increase so I turned it down. Also I lacked confidence in my management abilities. But now I wish I had taken the job, gained confidence, and looked for salary increase by switching the company.

A few suggestions, at least, I am doing these for myself:

* Volunteer to mentor and lead without official title * Read books on management * Improve public speaking skills * Seek mentors and be mentor to others * Focus more on building my network instead learning new of technical skills


Do you have any suggestions on management books?


Not yet, but I have bookmarked this post and will likely buy a few books from here: Ask HN: Books to read when you transform from SWE into SWE Management?[https://news.ycombinator.com/item?id=30497703]


You sound like you're caught up up on what you should have done in the past, rather than what you could be doing now.

It seems like you enjoyed your former employer, just not the role you ended up in. Is the bridge burned there, or could you pivot back to your original role, then try to work your way into that manager role, down the road? Perhaps even jump into that manager role right away? Don't think about the director role right now.

As a pop song said: "if you want to be somebody else, change your mind". Attitude is everything, approach your situation differently.


I wonder if you are applying some selective bias, with that one decision and with that former peer. Did many of your former classmates and peers go off and land dazzling career positions? I doubt it. You probably made a ton of good decisions that you are discounting. A professional would probably apply some CBT techniques to get you thinking about the problem from a different perspective. I am a long time IC and have similar negative thoughts about, should be higher up the food chain, etc., and I find that those CBT techniques help.


Hey, I’m not the OP and I’m not in that particular position, but I wanted to say I really appreciated reading your comment. It’s rare in this thread to see a comment from someone who’s admittedly unhappy with their current position, but still optimistic and empathetic, as well as self-aware about their thought patterns.


If you're making a huge paycheck, just endure it. Maybe find something outside of work to enjoy.

I'm 0/2 - I hate my job, and I don't make much at it. One out of two isn't bad.


I’ve done the product management and people management roles. Product management, when done well, is hugely impactful to the company. Product management when done poorly rarely turns out a bad product, as there’s too much of a safety net to fail. People management when done well, becomes a well oiled machine that accomplished miracles. People management when it goes poorly - is an absolute nightmare. I’ve been in all those scenarios, and hesitate to recommend people management.


Your role in any institution hinges so much on perception and past behavior that a larger change may require a change of workplace. Once perceptions of colleagues are fixed, it is almost impossible to change them and get another "reputation." You'd have to apply somewhere else for a position that better suits your expectations, and if you can't get one, change your expectations or work further on your CV.


First of all don't beat yourself up over past choices, especially ones like this where you have no idea how things would have turned out if you'd acted differently (I know it's easy to say and hard to do).

Should you seek professional help? maybe, having someone to talk to openly about these sort of feelings can be very beneficial and a professional's distance can make them more objective.


Was in a similar position. The way I coped was not to think of the past, life’s too short to do that. Be in the present and build your future.

Also some good advice: don’t kick yourself for your decision. It was YOU who decided it that way, if you were to rewind the clocks, the same person you were before would make the same decision. That was who you were before, so never beat yourself up over it


Most of your time in management isn't spent mentoring people. Most of your time is spent on pretty annoying stuff.


It sound like you make choices based on status and income instead of what you like and is good for you and your family.


Income can be good for your family... it's never just binary choices between good things and bad things, more like 6 of one and half a dozen of the other.


It sounds like it. Then again, doesn't a vast majority of people?


I don't think so, I think there's quite an evenly spread broad spectrum. And which people you come into contact with will be heavily influenced by your own choices in that regard. Work for a bank or a big corporate company and yes probably most people will be making choices for that reason. Work for a not-for-profit and most people won't have.


What has happened, you cannot influence. But you can certainly influence what's happening and what's going to happen.

The outcome of most actions in life is a coin toss. Hard work, dedication, and charisma can certainly affect the odds but at the end of the day it's a coin toss.

You will win some of them and you will lose some of them.


> How do I turn the wheel of time back and undo my career mistake.

Time, insofar as the smartest minds of all generations up to this point know, is irreversible. Worry therefore not of what has been, but only of what is and what is to become. Dwelling on the past will only beget more dwelling on the past, and dwelling on the past is, by definition, not constructive.

We accumulate memories so we could learn from the past. Figure out the lesson, integrate it into your self, and let go of the memory.

> I feel incredibly stupid. I am losing confidence in making good decisions.

In my experience, every moment of feeling clever is preceded by a moment of feeling stupid. That's the necessary step on the path of conscious evolution. The trick is keeping your faith in the process while you're riding out the lows. Feeling stupid is a necessary evil for you until you figure out how clever you are - or how clever you can be.

It can help to reiterate memories of success in times of failure. Surely your life is not a sequence of only stupid decisions; therefore you shouldn't feel only stupid. Just... partially stupid. And that feeling of partial stupidity reveals a weakness in you. Some aspect of being you haven't fully brought into the unity of being you. There's room for improvement. Figure out how to work around this weakness or turn it into strength.

> How do I deal with my feelings?

The first step in my non-professional opinion is to take control of your feelings. Stop them from flowing freely. Then allow thin streams of emotion to flow in turn, and inspect them. Let, say, your anger surface for 1 hour while ruminating on it. Then put it back into the bottle and figure out if feeling the way you did is a sustainable pattern.

Take note of where the feelings direct you. They can't speak, but they can point you towards the problem.

> Should I seek professional help?

Like every other decision in life this one has potential gains and an opportunity cost. Whenever the thought comes up, make a decision. Sometimes, reverse your decision and see how that makes you feel. At the end of the day though, theoreticals can only get you so far. You need experiential data to back up your assumptions.

Do it and regret it later, or do something else and forget about it until it comes up again. Adjust your preferences based on how the decision impacted your life.


Wow, did I write this in my sleep? Your path is exactly the same as mine: Bored IC -> Product Management -> Program Management -> Envious of Eng IC's who stuck it out and are now directors.

I don't have much advice but will be reading these replies with interest. You are not alone!


The nice thing about mistakes is that you can learn from them.

I find success sooths the ego but is often less of an education.

People switch between manager and IC over the course of their career all the time. This will probably become one of those stories you wheel out while mentoring an employee in a few years.


That kind of mistake is the sort of experience that makes grizzled veterans grizzled. So treat it that way; be honest with yourself and up-front in future interviews, in the sense that you took a chance, it didn't pay off, and now you're smarter for having lived it.


Yeah I've made mistakes too, not seized opportunities, slacked off when I shouldn't things like that. I'm more focused now and I feel like I've learned from those mistakes. You can keep those perceived mistakes in mind as you move forward in your career.


Managers do "grunt work" too, it's just that their grunt work consists of talking to people all the damn time.

Don't take a manager job (or regret not taking one) because you want the title or prestige. Take it because you like talking to people all the time.


> I was hard working and [more] intelligent than him.

Ultimately what matters is how well you work in a team and how much you're able to combine the best of everyone into delivering excellent products.

It doesn't matter how great an engine is if the gearbox is lousy.


Accept what has happened in the past because you can’t change it. Focus on what you can do today and tomorrow to make things better in the future. Energy spent looking back is a waste. Instead focus 100% of your energy on today and the future.


Question about this. The career path to high level decision maker seems to pass through JIRA manager. Why is that? Are there other parts to gain decision scope within a company that don’t require a stint in management first?


Sorry to hear about your situation. You can't turn the wheel back and you can't undo your mistake. The best you can do is to learn from it going forward and not to make the same mistake again.


"How do I turn the wheel of time back and undo my career mistake" - you don't. You evaluate and move forward: What is the next best thing for you in the current place and time?


by changing your attitude towards life. Ruminating on past which cannot be changed is meaningless, if there is any lesson to be learnt from past learn it and move on.

Similar thing applies to future as well, you can put efforts towards an outcome however it may or may not happen(who would have thought they will be locked down to their home for months in pandemic!)

As great patron saint master oogway says: yesterday is history, tomorrow is mystery but today is a gift. That's why it is called the present :)


Hey, I sold $1m (today) worth of DOGE for 900€ a few years ago. Don’t worry about decisions in the past. Just try to learn and get better. Don’t beat yourself up.


Will you still consider it a career mistake if something very positive happens tomorrow that you could have never gotten to without the path you have taken?


sounds like you've built your whole identity around your job. curious, Do you have any hobbies or interests outside work?

Lots of people ( including me) are in the same boat as you. I don't think you've made a mistake. Getting promoted to Director has nothing to do with 'hard working and intelligent', I actually think being 'intelligent' is a negative in getting promoted to director .


It sounds like you're going from success to success, big career mistakes usually end in the unemployment office or at least a demotion. Your old coworker the director is probably making himself miserable because his cousin is a CTO and maybe that cousin went to high school with Elon Musk.

You already recognize the big problem is how you're processing these feelings. The place that I would start is forgiving yourself for having them. It's part of the human condition to feel jealousy, regret, inadequacy, etc. Definitely work on processing them, letting go of them, figuring out where they come from, but try not to beat yourself up for having them in the first place.


To be honest I'm in a similar boat but not as bad as you. I have friends, peers who's college/education wasn't as good, people who I mentored, friends who aren't as intelligent go up the career path, get fancier titles, whatever.

First I'd have to say I'm happy with what I'm doing. I am making an impact to my very large company, to my team. I took a management route, because those opportunities don't come around. I am trying to promote someone and I told her the same. Take the opportunities as they come.

However unlike my peers, I'm not job hopping, or going to smaller companies for titles. If that's your boat, then that's fine. Sounds like it is, or it isn't for you.

In your more serious case - one analogy I can give is like...getting married. You may have a few girlfriends/boyfriends. Some are good, some or bad. Maybe one gets away. But the only way to find out who you want to marry is having those experiences. You can't look at someone else, see them marry their first boyfriend/girlfriend and come away with envy.

You've learned what you like, or don't like. I'm sure there's something out there that would make you happier - and you've been able to narrow it down.


A lot of the people have significantly less experience than you so heed with caution.


sorry IC = independent contractor? and you're upset that you didn't get into a management/mentorship role and instead remained a developer?

if so, what stops you from going into management now?


IC = Individual Contributor. It's a bit of a nebulous term, tbh.


why is stuff like this pushed to the surface here? i don't want to see whiny content like this on HN.


There is no intrinsic value to being in a management, leadership, or even a founder role. It's really a shame that we have embraced this nonsense of uplifting and celebrating roles and titles over contributions and outcomes.

Nobody gives a shit if you are a director of engineering but they may well care very much if you solve their problem.

It's all vanity and ego run wild. The reality of business is that the only two things that actually matter are building shit and selling shit. This is how to easily differentiate between cost and profit centers and who is essential vs expendable in an organization.

You should only be driven to be a manager or director if your fundamental skillset is dealing with bullshit to enable other people to do value creating work by getting it out of their face.

If you think you are moving a bunch of JIRA tickets around you should take a hard look at what a legit engineering manager deals with. And then add in trying to resolve bullshit conflicts between grown ass men acting like children, talking people into getting involved with your high risk/low reward squad, forcing people to make a decision and start moving instead of arguing endlessly, having really uncomfortable conversations on the regular, firing people who have a mortgage and kids but have undeniably become a risk to the business even if you like hanging out with them, identifying, defining, and enforcing the processes and changes to keep everything from falling apart...

Your 25 years of experience don't necessarily have any impact on dealing with all that bullshit. You have to be fundamentally organized and passionate about driving others to succeed and absorbing damage so they don't have to in order to be a really legit manager. Unfortunately titles and position in the hierarchy has become irrationally coveted and rewarded in many organizations and people who are "senior" slide into these roles and fundamentally suck at it and create misery for their direct reports and commit unforced errors that put the entire business at risk because they don't know or really care what they are doing.

Do not envy and covet joining that squad.

The only thing that really matters is creating dope shit that people want to use and making money while you are doing it. What role you are playing in the organization isn't meaningful compared to whether or not it is winning or losing.

There are plenty of lone-wolf IC's out there pulling down ungodly amounts of money because they are just destroying it and the best way for them to create value is for everybody just to get the fuck out of the way.

Only become a manager if you can be an excellent one and crush it and don't think for a second that just because your former colleague slid into a lane when you didn't that he is succeeding and you are failing. He has a whole new problem now to make a bunch of other people successful and absord all their bullshit for himself to be successful. That's the job. You can only admire and envy him if and when he has crushed it and you are certain that you could have crushed it even harder and should have taken that shot.

And if that is where you are at start interviewing for management roles, grab one, and put the ball through the basket to prove it.

You haven't made a career mistake you are just ruminating on an insecure head trip. And fuck that, you don't need, want, or deserve to live that way.


1. Professional help is always good - whether you're in a good or sad place. Therapist fit is important so if the first time it doesn't work out, consider "shopping around" until you find somebody that a) You feel understands you b) You feel you can trust c) Is helping you in a way that you feel is helpful and productive. May take some time but most good things in life do.

2. Acknowledge, if/when you can, that a) What you know now is not what you knew then and b) There's absolutely positively no guarantee that you would be happier had you chosen a different path. In fact, I'd go as far as to say that statistically, knowing what you knew then, you made the rational decision - number of technology experts who regret going into or being forced into management, is vast. So don't beat up yourself for having taken decisions that you have. In fact, I'm not even certain that you can confidently brand them as "wrong" decision, based on situation and facts you knew then.

3. Look forward. Hardest but most important part. You are where you are; you cannot change the past; perhaps you can learn from it; where do you go from here, and how?

---

My big suggestion is to spend as much time as you can, with your therapist and loved ones and yourself, to work on your emotional intelligence / mindfulness. That's my personal big lesson in life - I spent 25 years focusing on technical, so I personally am in catchup mode for emotional / personal knowledge and maturity (which still puts me ahead of 90% of my colleagues who most likely will never pay attention to it on a conscious level or put real effort into it).

Because here's the catch - there's ZERO guarantee that, if you had your former colleague's job RIGHT NOW, you'd be as happy in that role as they are (or, to be blunt, necessarily as successful; hard work and intelligence are useful but not sole factors especially in management track). There's the external environment and then there's internal processing and reaction to that environment. You have to acknowledge that your happiness is a combination of external environment and your reaction to it and the weighing could be any which way. I have smart, intelligent, successful friends and family members who change jobs every 6-18 months are are ultimately never happy in any of them; and I have friends who are in a job I would positively hate, but are happy. So my suggestion is to consider working on both internal and external aspects.

(and incidentally, emotional intelligence and soft skills are on average way, way, WAY more important if you are considering management path than subject matter expertise.)

If, worst case, all you are is 2 years behind your colleagues - that's nothing, in the grand scheme of things. If management and specifically people management path is what you want to do, 2 years lost is meaningless (from some perspective, I myself am "20 years behind" those who went into management the day they graduated, versus my two decades of technical and architecture work; and you know what? I'm doing OK :).

But do consider also what is important to you and how you can obtain it. If mentoring people is what you love doing... well, most directors do very very little of it. Best architects and senior engineers, who may be IC's on paper, do tons of it. So take the time to truly grok what you want, rather than focusing on that one Jones in the fast lane who seems happy :).

Best of luck!


I don't believe in making mistakes.

I think it's more accurate to say "I made a choice that I now see could have been better." Because, you know, most of the time, when we're faced with a decision, it feels like the best one we can make with the information available to us at the time.

The important thing is to keep that attitude in mind—to accept that there's no way to know what would have happened if you'd chosen differently, and that your choice was valid at the time. This will ensure you stay focused on the present and future decisions you need to make, so you can keep moving forward.


I think there's a good chance that you just hate work. Not that you're lazy, not that you hate working or doing work, because that's different. Corporate "work", the institutional nonsense that people have to do to prevent higher-status people from turning off their income, is an awful waste of time and involves very little actual work. It deserves to be hated.

I understand the unhappiness of being an IC, especially in midlife. You're not respected in that position; software is manage-or-be-managed, and if you're still in a "be managed" position at maturity, it's not a good look. Still, I think you'd also hate being a middle manager, to be honest. I know I did. You're not actually "mentoring" people as a middle manager (or as a PM; PMs exist to give executives a second management structure so "product" and traditional managers can be pitted against each other). Instead, you're a performance cop who works for even bigger assholes than you did as an IC. You'll have to be the face of awful decisions that hurt people's careers, and you'll have to make some really shitty ideas look like they were yours, so the execs (who asked you to push said shitty ideas) can distance themselves and be loved. You're in the position of transmitting orders, and you can't really protect your people.

I also don't think you can assume that you would have made Director just because a less-talented colleague did. Capitalist Party politics is its own game, and the people who are good at it are usually good at literally nothing else.

I don't think you should feel stupid for making a career mistake, though. The game is rigged and the Capitalist Party is hopelessly corrupt. If you weren't born into a hereditary upper class, you probably were never presented with any good options--just bad ones that looked good at the time. Your Director-level colleague might be working 70 hours per week and losing his marriage. He might die at his desk of a heart attack at 47. Anything can happen in the corporate world for all bad values of "anything".

As for what you should do, I'm in no position to give advice. I don't know you or your circumstances. You certainly aren't alone, though. Corporate capitalism has to pay people with constant expansion--not only do they expect their incomes to go up, but they expect the rate of increase to go up--to get them to overlook its awfulness, and the system can no longer support this. I won't tell you that it's going to get better (it's going to get worse first) but you're not a loser for making bad choices when you probably didn't have any good ones. You shouldn't feel bad about yourself. You're surviving. That's all most people can do right now. Some people, usually through no fault of their own, can't even do that.


> die at his desk of a heart attack at 47

I'm 47 - fun to see this as the age used to illustrate "too-young-to-go". I agree. If things go well, someday my age won't qualify for this use-case anymore.




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