Ask HN: What to do when you are successful, hate it, and can't seem to change?

Refuse. Do you have a problem saying no? Why are you not setting boundaries? If your home life is important to you then you need to speak your mind. Tell them 'No, I dont want your promotion, I will be going home at a reasonable time to my family'. Is that so hard? Here's another tip - accept remote positions, and remove any business education from your resume.

In my experience, doing this will ultimately end up in being let go as 'not a team player'. I was in the same position as the OP many times and got tired of always getting moved out of software into more business management. When I started saying no, I was always cut loose before long. Went to companies after this occurred and didn't say no, and got right back into the same situation.

Anecdotally. Mine is the opposite. I've noticed the more someone tends to delegate and / or say no, the more they end up becoming respected in the organizations I've worked in. It's not that they say "That's not my job". It's more that they say "I can not take that on with my current responsibilities and perform it at a level that it deserves."

You are talking about something else. Saying no or delegating is not an issue - that's just managing expectations.

What we are talking about is that it's not easy for companies to find people who are actually good at tech (not just faking it) and can also speak to a corporate room of C-level executives with ease. If you can do that, expect to get moved out of the engineering role within a year, unless you say no, in which case you'll be gone.

The problem is, it's never worth it. The equity will always be less than the higher ups, even when it's given, and even when it actually is worth something. Side note - I was once given 150,000 shares of a company, without asking for it, and I knew it wouldn't be worth a thing. I was also given 6,000 shares of a solid company, also without asking. No equity I've ever been given was worth what the company took to get it - which is, they need what you have - just pure brain power, stress and the ability to compete at an global technical level, and to translate that into shareholder value.

If I pour that much of myself into a company, it's going to be for a lot more than 50K of stock, or 100K. I've built systems that the company turned around and within a year it had netted $1.5 billion contract (yes, billion), which is what I was paid to do...but under no circumstances was I fooled into thinking I was paid what I was actually worth.

Well...we're actually talking about two different things (or that's what I'm inferring. One side of it is what you're expounding upon (the mgmt / engineering dichotomy)...which I agree with largely (although I think there's also room in some companies to be largely tech and advance up the ranks while saying no to those other responsibilities).

What I was getting at was the second aspect of it which was the "out of bounds time" alluded to when OP said "The problem is I don’t enjoy meeting with executives at 8pm over drinks to try to discuss the next big deal. I don’t like to make presentations late into the night to put in front of Venture Capital, Series A/B investors, or Executives." I was focusing on the "8pm" and "late into the night" parts of the phrase which is more lifestyle / time overreach than the other aspect.

OTOH, I've been lucky enough to get stock which came out to be worth quite a bit (granted it took quite a bit of effort to make that so). I've also had the stock which was worth very little in comparison to the effort. It's often a difficult thing to weigh as one is weighing effort, the market, and a lot of external things.

As a "doer", we are frequently not paid what I think we should be. To get paid that I think requires often taking on a lot more responsibilities that some of us don't often want to handle (sales, marketing, hr, legal, etc. ... ie running a company).

This is pretty much in line with what happens to me. Though I don't say no, I just leave. Another commenter asked why I am having to look for work so often, it is entirely by choice.

Frankly, I shouldn't be complaining as I have not been fired or laid off and a lot of others have it much harder in this job market. But getting into these situations and then looking up every 6 months and saying "Damn it, here I am again" gets old.

Honestly, I do have a hard time saying no. Rarely is the conversation "We'd like to increase your responsibility, here is some more pay and a new title". It's more like "Hey, your opinion in stand up this morning was awesome, can you sit in on this meeting." This seems to lead into "You can't make it to yet another meeting about strategy with the investor's? Do you know what will happen if you're not there! It's the end of the world!"

But, those are excuses that I constantly make. Your advise is solid, and much appreciated. I need to really strengthen up and just say no.

Better than saying no is using some negotiating tactics to take the pressure off you.

Use an external constraint and pre-disqualify yourself. So one day when you're not being asked out, ask to have a talk with the founders.

"Hey guys, had this talk with my significant other last night and they told me that while it was okay to put in some extra hours, I couldn't be burning both ends of the candle by doing both tech and business work. It makes me impossible to get along with, cranky and miserable."

This sets your limits, puts the onus on some outside party, and presents the founders with a constraint at a time when the constrain is meaningless -- after all, they don't need you now. Then when an actual event comes up, gently remind them that you've already had this conversation. Offer to talk sometime during the day. Hell, have the biz folks come by the next standup. That way they can talk to the whole team.

The point is, you're not trying to hurt the founders, you're just placing some reasonable constraints on what's possible and what's not possible. It's not your idea (and in reality, it's not, it's just the way you are), and it's not the end of the world.

At the end of the day, you have to set limits. There are tricks to setting limits that reduce conflict. You should use them. But as long as you're needed for something you'd prefer not to do, you'll never completely eliminate that stress.

"Hey, your opinion in stand up this morning was awesome, can you sit in on this meeting."

There's your problem. Stop outing yourself. Don't give your opinion on things you don't want to be dragged into. Zip your lip. Then you probably don't have to say "no" to anything because they probably won't ask. Give opinions on those things that are related to the domain you desire to work in and then make polite noises about "not my area" or something if pressed on these other things that you don't really want to work on.

Have you considered whether an ownership stake in the company would change your point of view? If you really are valued for your insights on the business side, but you are supposed to give 100% to development as well, why not bump up the stakes? See whether they are just giving their monkeys to you (as in http://www.amazon.com/The-Minute-Manager-Meets-Monkey/dp/068...) ? You could always ask for a raise (if shares are too much to ask for). There's an equilibrium in front of you waiting to be discovered.

Are the ones dragging you to late meetings shareholders? Or maybe they work on commission? Or perhaps there's a big bonus waiting for them but not for you ? Find out whether money is the problem or not, it's easier to find the solution once you understand others' motivations.

I'm guessing you're more of a generalist than a specialist in one field and that's partially why you see things the way business would like "tech" to see. It's actually a good thing and helps you build better software. In the worst case just change job one more time, sometimes it takes longer than one or two switches to find the right place. Good luck!

Money might not make up for a depressing job, if he feels he's already making enough to support his desired life style.

I think he may feel a bit exploited, because he's not getting return on his extra investment. If he's apt in business then I believe that he can like doing it - just that the environment must appreciate it in the right way. We're wired for getting the right feedback, all very well described in the Flow book.

Any easy way to say "no" without offending is to describe the opportunity cost: I can do this, but this other Important Business Priority will suffer. Once they understand the trade-off, it ideally becomes a collaborative discussion to decide the best course of action instead of antagonism.

(If they suggest you need to suck it up and do both, just laugh it off as the wishful thinking that it is.)

If you think about it, this is a good answer to one of those bullshit interview questions "What is your biggest weakness?". I have a similar one which i've been working on a lot which is trying to have a better work/life balance. I used to have a lot of trouble saying no...and I worked a lot more than I do now. I _still_ work probably too much; however, my team now knows I will not be bothered from 6 to 8 pm as that's when my kid is home, lucid, and we're having some family time. Trying to find that balance is a constant battle.

Do you think you can _and_ should improve on this? Awesome. Introspection and room for improvement for the win!

Also, make yourself an invaluable engineer. If your strengths in business are so evident that you repeatedly get pulled in that direction you have 1. Actively hide those strengths and 2. Doggedly pursue engineering greatness.

Great engineers set their own rules. One of the best I know gets in at 9 and leaves at 4. His schedule is set and no-one questions it because he's obviously a better and more productive engineer than the rest of us!

You have a skill that is rare. Since supply is low, and demand is frequently high, price yourself accordingly.

What if he's not willing to sacrifice his work-life balance, even for a higher compensation?

Raise prices until the tradeoff is worth it or the demand reaches a tolerable level.

> Some say it is depression, but would I want a medication to fix what is obviously a lifestyle problem?

Medication is not the only solution to depression. The internet is a bad therapist. Consider a real one.

I honestly hadn't thought of it like that. Thinking this through with a number of other comments here and maybe I need to talk to a therapist about being less of a push over.

Yes, exactly. FWIW what you've described so far doesn't ring like depression to me; rather, you're unhappy because you keep finding yourself in a situation you don't want to be in. But this is something you should discuss with a professional if you have access to one you like.

I think that's a great idea.

Most "medication"(ie: antidepressants) is not a solution to depression either. But yes. talking helps.

You must be making baller money. Just live frugally, bank it away and invest it. And in a few years you will NEVER HAVE TO WORK AGAIN.(or just work on your own projects)

Your advice of living frugally and investing is good, but since you need, let's say $5M, to retire in your 30-40s with the expectation of living the same lifestyle, "a few years" is much longer than you might think.

If you're living frugally, your annual expenses will go down. Supposing you continue living frugally after retiring (which is easier, since you have more time to "DIY" expensive things you formerly hired someone for or paid extra not to have to do), you don't need 5 million. Wow no.

Let's assume the common 4% withdrawal rate. $5 million will provide you with $200,000 a year for all eternity. This assumes you never do anything for extra money. It further assumes you never put any money back into the investment (because, you know, you're not saving for retirement anymore).

Going even more conservative with a 3% withdrawal rate you'll be pulling $150,000 a year.

Interest is beautiful, living frugally combined with interest is even more so. Supposing you wanted to pull $30,000 yearly you'd only need $750k.

More on this at mrmoneymustache.com

But.. interest rates are currently running below inflation (here in the UK). With that happening, you're going to need to top up the fund to something higher, to ensure withdrawings can increase in line with inflation for the rest of your life.

5M? Are you crazy? Thats insane. At 6% interest that's 300,000 a year alone in interest.

I was talking about a simple lifestyle to get lattes and travel and work on your own projects, you're talking about bugattis and the rivieria.

In my opinion you have a seriously distorted view of whats important.

Well, I'm just some guy on the internet. You really have no idea what I think is important in life, so withhold your judgement.

You're probably right that I overestimated the amount. Since frugal investing isn't my goal in life, $5M was a made up figure. What I'm saying is that the number is higher than it might seem.

It depends on how aggressive you are with your financial planning. Remember, this is the rest of your life you're planning for. Are you just going to get lattes and travel until you're dead, or do you want to raise a family? Do you want your children to go to good schools? Do your projects require capital investment to be successful? Do you want to be an angel investor? Are you interested in philanthropy?

Counting on 6% interest in perpetuity is reasonable, but is probably more aggressive than I'd be willing to go. What happens if the stock market takes a dive? It's not out of the realm of possibility that your net worth could be cut by 30-40%. That means that your interest income would be cut by the same amount.

Also, once you're out of the industry, it's hard to just come back and get another job. The software industry is pretty strong right now, but will it be in 10 or 20 years? Will you still have the skills you need to compete, after years of working on whatever you want to work on?

Let's say your planning figure is 4% instead of 6%. Although $1M is a lot of money, if you're talking about living off the interest, each $1M yields $40K gross a year at 4%. After 20% in capital gains taxes, it's $32K. If you have to pay AMT (which you will, if you're an American making money off of investments), expect an effective tax rate closer to 30%. This means that you can expect a net yield of $28K in interest per $1M of capital.

Also, remember, if you're spending every cent of interest that your investments earn, they will never compound, and you will be at the mercy of inflation (about 2%) and your risk exposure will be dramatically higher. You should try to plan to have net income that you can reinvest.

$5M gives you $200K gross or $140K net. That's a very handsome income, but if you want money to reinvest and you want to keep a conservative risk profile, it's not Bugatti-Riviera money. If you're willing to burn down your initial capital, it's a lot easier, but then you have to consider your risk -- and whether you're interested in leaving an inheritance.

Regardless of the actual amount you're talking about saving, my point is that it's probably more money than it seems like, and it takes a tremendous amount of time to save it working 9-5.

Does it really cost $5M to retire in your 30s?

A general rule is that you can live indefinitely if you withdraw 3-4% of your investments annually to pay living expenses. There are calculators out there (Google 'FIRECalc') that work out the odds of success (i.e, not going bankrupt) with various starting points and spending rates. At 3% there's about a 95% chance of success over a few decades, based on the past performance of the financial markets.

Let's say you spend $5k/month normally, as a round number. That works out to between $1.5M ($5000x12/3%) and $2M ($5000x12/4%) to sustain your living expenses indefinitely with no further income.

This dovetails nicely with the conventional wisdom that over 30s is unemployable in tech fields.

So either retire penniless in your 30s and never work in tech again, or retire with $5M in the bank in your 30s and never work in tech again.

Also if your gross is say $120K and you keep about $90K of it and save most of it to retire, living off maybe $30K which is more than most Americans get, 5e6/30e3 = a mere 166 years of retirement, assuming your investments return about the real world inflation rate, which is a fairly realistic goal. Of course $5M in the bank and $60K/yr invested means you will have to start your savings program at age -60 or so if you want to retire in your 30s.

Its probably a lot simpler to just contract like my Dad did. Do your thing when you need the cash, and when you don't need the cash, don't work for awhile. Nobody wants the programming contractor to advise the board at the end of a 16 hour day, especially when they see your hourly overtime rate.

Do your thing when you need the cash, and when you don't need the cash, don't work for awhile.

How would you explain the gaps in employment? It seems to be a popular question.

I work at a startup with a development team of 9 people. Of those, one is in his 30s, two are in their 40s, and two are in their 50s. The rest, myself included, are late 20s.

Just because some parts of the tech industry fetishize young developers doesn't mean all of them do.

That depends entirely on what sort of lifestyle you're trying to sustain.

There shouldn't be much difference between the level of savings needed to retire at (say) 35 and (say) 45. In either case, you want enough that with low-end-of-plausible stock market growth, you're taking out less than growth is putting back.

There's some research around what level of growth it's safe to assume; how much you trust it depends on whether you think the past behaviour of the US stock market is a good predictor of the future behaviour of whatever you invest in. I suggest (but this is Not Financial Advice and I am Not a Financial Advisor) working on the basis that you can probably get ~2.5% of your investment out per year pretty safely. (Usually it'll grow more than that, even after inflation. That cushions you a bit against cases where bad things happen. I assume you are willing to trim your lifestyle back a bit in bad times.)

That means you need about 40 years' worth of spending in your savings. That would be $5M if you are spending $125k/year. In my opinion (about which you need not care), if you are spending $125k/year then either you are earning so much that saying $5M isn't going to be a big challenge for you, or else something is amiss with your priorities.

Since very very very few people make that much gross in their lifetime, I'd say hell no.

Maybe the OP is thinking 100K for 50 more years.

I can relate to this, though on a different direction and i know it easy it is to slip into another role, that you dislike. I haven't yet figured out how not to do it, even considering switching from these kind of jobs entirely just to avoid ending up in your situation.

If you're being asked to work outside of office hours alot, then no matter what your job or position is your company has an efficiency problem and that's something that should be addressed for the good of the company.

If you're changing jobs alot because you can't find one that suits your needs then you should be more aggressive and thorough in your search. Let those companies court you, not the other way around, and get everything you're hired to do written into your contract. If you're changing jobs that often just because you're supposed to in order to be considered successful then that's probably the biggest problem.

Freelancing is an option I guess, aswell as starting your own company without the intention to sell. That still makes for alot of work on the business side of things though.

Lastly, you seem like a guy who doesn't have too much trouble finding a job so risking your job by saying no seems like a small risk to take considering what you could gain. Also I'ld say that 9 out of 10 times you're just calling their bluff. You are an investment for any employer. If they lose you after 1-2 years they've basically thrown every penny they've ever given you out the window.

I think that telling yourself that you're "successful" can be a huge impediment to doing what you need to do in order to be happy.

If you are not happy with your job/life, then you are not successful. Take a pay cut and tell the business dept to fuck off, or go work somewhere else. Having money in the bank grants you that luxury.

This, this, and this again

It is tough to give you advice when we don't know your whole situation (do you need a job because of health care, for example).

Maybe you can just consult? That makes is easier to turn down work you don't want. And don't list your business experience on your resume/LinkedIn profile.

This is the position I was in starting in about 2001 at BEA Systems when I started helping out on tech due diligence for acquisitions. It sounds to me like you would make a good founder. Sadly, there are few strong engineers that can also work on the strategy of the company. I'm not sure why you are being asked to go out after work a lot, that doesn't seem necessary, but certainly having a voice at the top and a keyboard at the bottom has been very powerful for me. Maybe you just need to make it clear what kinds of things besides engineering interest you and things that you are not interested in doing. If you are truly not interested in directing the course of the company I can only assume that you need to stop telling them the right things to do...

Could it be that you are over worked? Let me flip it around - You are good at the business side of things so why not do that full time? Move to a completely managerial/business role and quit coding completely. Get your life back under control. Coding is something you can always do in your spare time. I work on side projects at 10 or 11 at night for a few hours and it's enough to satisfy me. Of course it depends on what you want but it seems to me that you are good enough to make more money by moving up the chain and you should think about not losing that. SLC is awesome btw.

> within short order I am snagged for business advising as well. This hasn’t been all bad.

Face it-- you're a unicorn. There's NO way you can just do Software Engineering. You're simply not wired that way. As for the stuff you hate to do, the challenge is mitigate and manage. Be upfront on your boundaries, set expectations. Moving forward-- meetings are on your terms and schedule. Applicable to your situation, here's a good read on setting the frame and prizing> http://pitchanything.com/book/

As another commenter said remove "anything business" from your resume if it is in there.

Also something that might help is trying to keep your thoughts for yourself(keep your mouth shut) in meetings for things not directly related to engineering or your team's work aspect. This might be a bit harder at first, been there and it takes a good exercise but at least for me it was in a company where we didn't have meetings at 8PM with execs.

Maybe this is easier than you think. It sounds like you have little trouble getting hired for SE jobs. Are you being hired for your business acumen? If not, take most or all that stuff off your resume. Then find another job as a software engineer. The other tack is to avoid startups. A large enterprise is much less likely to drag you into business discussions if you don't have a business related job discussion.

Maybe you'd be happier working for larger companies, where developers are rarely (if ever) involved with the business side of things. You don't need to go to a place as large as Google, just a place that's big enough that developers and business people are in distinct departments under different management.

Go on "sabbatical" - it's basically a holiday, but people will think you are being productive and not just relaxing.

You should argue that the sabbatical is a years off unpaid holiday. Take a break, but still have connections and commitments to the company.

It sounds as though you are quite skilled across two important areas. Would more money in your pocket make these extra duties more interesting? If not, speak up - they wouldn't want to lose you.

OR

Propose a compromise: you will consult on biz dev, but during day work hours.

Ask for less money (i'm willing to bet you're being well compensated for being in that hybrid role), and don't highlight those parts of your experience on your resume.

Are you willing to sacrifice the tailwind in your career that comes from leveraging your business skills?

> Over the last decade or so . . . .

Sounds like you're a bit long in the tooth. Has your development experience gone stale? What's your area of expertise?

I agree with nobodysfool who says to revise your resume. Gear it completely towards software engineering. Remove your law degree from your resume.

Then, look for new work.

Have you tried to not be a good business man, giving mediocre advice and make business mistakes to disaualify yourself from that part?

You live in Utah. Go take a hike, literally.

People equally skilled in programming and business are rare. Hell, even moderately tech-literate businesspeople are rare. So you are being recruited to positions where your combination of skills is going to profit the company the most.

What do you do? If quality of life is more important to you than money, you say no to the recruiting. Otherwise, you say yes. We can't make this decision for you. Everyone's value ordering is different.

Alternatively, your employer realizes they can get two employees' worth of work out of you, so they do.

I believe there's additional value being generated by having both skills at the same time, beyond the total productivity of two regular employees in their respective fields.

our latest hire is a very good senior engineer who was essentially working as a sales/marketing technical resource at his previous job, and was on a career track to become a vp of sales and marketing. he had "director of X" titles before that at large orgs as well. age early 40's.

when he quit and came to work for us, the first thing he said was "i want to make it crystal clear that i do not want to be an executive at your company. i want to be a senior engineer. i want to stay at home with my family and take care of your technical needs."

when you are clear with your requirements, and you get clear requirements from the employer, good situations can arise.

having said all that, he didn't need the extra money that comes with being an executive - he's doing just fine - some people do need the money, however. it's just a question of personal priorities.

Get a drug habit.