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?
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.
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.)
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.
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.
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?
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.
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.
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.
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.
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.
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.
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?
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.
- 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)
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.
- 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.
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.]
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.
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.
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.
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.
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.
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.
I'd suggest taking a break and working with someone who can help you process your feelings and move past them.
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.
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.
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.
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.
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...)
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.
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.
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.
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.
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.
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.
If you want to be a manager, then focus on those internal qualities first before you have reports whose lives you can make miserable.
You are the person in control of your mind, and your emotions.
Find some other way to feel. Measure yourself against yourself.
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
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'm 0/2 - I hate my job, and I don't make much at it. One out of two isn't bad.
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.
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
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.
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.
I don't have much advice but will be reading these replies with interest. You are not alone!
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.
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.
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.
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 :)
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 .
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.
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.
if so, what stops you from going into management now?
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.
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?
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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 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 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.