Ask HN: Dealing with Career Mistakes

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?

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.

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.

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.)

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.

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.

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

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

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.

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.

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.

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’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.

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.]

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.

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?

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.

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 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.