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What are your biggest career regrets?
68 points by pskittle on Feb 17, 2015 | hide | past | web | favorite | 77 comments



Not starting a side project earlier. And listening to everybody saying that hard work will get you places.

Maybe I've just grown cynical. But your employer doesn't care about you or what you do. All he cares about is how much money he can make with your energy. Know what hard work gets you? A pat on the back and more hard work.

Gone are the days where you could build a career based on mutual respect and trust. Nowadays it's just a list of previous employments. Nobody cares how good you are or what problems you can solve. All they care about is overqualified warm bodies. Hire skilled developers and throw them on meaningless tasks controlled by business politics. At least this seems to be the general experience among my peers.

If you want to be successful, become a good politician. It's the only thing that will make your life better. Anything else is just a lie designed to squeeze more value out of you.


> And listening to everybody saying that hard work will get you places.

> Maybe I've just grown cynical. But your employer doesn't care about you or what you do.

Hard work will get you places. But nobody said anything about hard work for your employer. You have to work hard, but you have to work hard on your personal goals.

If that means climbing the ranks at an organisation. Do that. Climb them as hard as you can. Identify what gets them climbed. Do that above all else.

If that means starting a business. Launch a side project. Or two. Or twenty. Or even fifty. However many it takes until you have enough of a side-income to drop your job and live off of yourself.

If that means starting a VC-backed business. Well, work hard on knowing what ticks the checkboxes for VCs. Work hard on meeting a lot of VCs. Work hard on whatever it takes to get VCs to dump money into your idea.

The world is literally your oyster.


Look at Silicon Valley. Look at all the big players in tech. Which is more important, hard work or politics?

We live in a world where who you know is more important than what you do. You can have the shittiest product on the market. If you know the right people, you can push everyone else into bankruptcy.

Hard work doesn't get you anywhere. Being able to sell things does. And when you sell yourself instead of your work, you may as well start calling yourself a politician.


Why do you think being good at politics isn't hard work?


Being able to sell things is very hard work indeed.


I'm sorry for your situation. I assume you're in the USA.

I care about our team and their wellbeing more than I do profit - although the two can go hand in hand if you reinvest in your people.

We send folks to conferences, as they learn and network, which is good for them and us. We generally give annual raises around the 15% mark. Above all we don't allow or accept the master-slave relationship anywhere in the company, and we're careful not to hire people who we feel will want to dominate other people.

I'm sure, in fact I know, many employers are assholes who treat their team like slaves - but it's not a universal law.


I'm a little intrigued by a 15% raise year of year ? How long can you sustain that rate ?

I'm supposed to be happy if I get 5% or really happy when I get 8% after extraordinary accomplishments. And if you performed extraordinary this year, that same level of performance doesn't get you 5% next year.


We reward merit - if you muddle along and half-ass, we worry about how to better motivate you, and typically grant a small (5%) raise inline with cpi inflation.

If someone is working their socks off, then we're not shy rewarding it.

In terms of sustainability - if we hire a fresh grad at £24k, by year four they're on 45 or so, assuming all is well. Most we pay anyone currently is about 60k, which is a very respectable income in a small city 100 miles from London.

Essentially, as long as someone produces more and more value for the business, we reward them more and more.

It also helps to have a decent war-chest, as this gives you confidence to pay people properly, knowing you've a year or more of salaries in the bank.


> I assume you're in the USA.

Europe. This kind of thinking probably originated in the USA. But all the tech CEOs I met so far idolize Silicon Valley. It was only a matter of time until they adopted the american way of thinking.

> I care about our team and their wellbeing more than I do profit - although the two can go hand in hand if you reinvest in your people.

Are you hiring?


Yes, for php and frontend devs.


I noticed this after we got bought by an American corp. They suck you dry and toss you.


This is the general feel of business in America. Aggressive, combative, winners and losers.

British capitalism tends to be based far more on mutual respect, trust, and benefit.

We don't work with US clients any more.


I've heard of (and been through) the same horror stories with british companies in the past, as well as Brazilian and German companies. I wouldn't say that's american-specific at all. It's just "business as usual" in most places.


>British capitalism tends to be based far more on mutual respect, trust, and benefit.

Anyone who's remotely familiar with the British East India Company should consider this the best joke they've ever heard.


> Nobody cares how good you are

> All they care about is overqualified warm bodies

Seems conflicting, no?


Only if you believe qualifications are a reflection of how good someone is.

Thought experiment: You meet two software developers who each have 10 years experience of C++. One has a CompSci degree. Does that in any way help you decide which is the better developer?


> Does that in any way help you decide which is the better developer?

No, but it has time and again proven that it tells you which is the better engineer. Not necessarily having a CompSci degree, but someone who's made it to senior year or even postgrad is, in my limited experience, an infinitely better engineer than someone who dropped out in freshman year or never attempted.

No, CompSci will not teach you how to code. But it sure does a hell of a lot in teaching you how to design systems and engineer solutions. Of course you also need experience on top of that, but it helps a lot.

Like, things that are completely obvious to somebody with a CompSci degree, might be wholly out of the range of somebody who is self-taught.

But as always, the question is: Is that something you need? Everyone can build you a CRUD app for sharing cat pics. Even a 15 year old high school student who codes on the side can do that. But who are you gonna call when your CRUD app needs to handle a million cat photos a day? Yup, someone with a CompSci degree.

source: being both that 15 year old high school kid and a CompSci person.


Yup, someone with a CompSci degree.

No. I'd call the person who's done something similar before regardless of their qualifications. Experience is far more valuable. That's the point I was making - two people with 10 years experience are at the the same level regardless of their respective qualifications, because they'll both have seen the problems and pitfalls firsthand (at least, you'd hope so).

Possibly the CompSci graduate will have dealt with them better the first few times they encountered problems (which is why a degree can be useful), but after that it's down to the relative merits of the individual and how interested they are.


I tend to disagree slightly. I have a math/cs degree, but work with a lot of physicists turned programmers. They are all smart and have plenty of experience at doing what they are doing, but have no idea what is out there CS wise. They reinvent the wheel quite often when building large systems. By not having the time taken out to read real cs text and instead focusing on just getting things done they missed a lot of sound computer science. They are all very bright, but just doing the relevant work only helps you on that type of work. Being exposed to a ton of different areas (as might happen in a cs degree, but there are other ways of course), lets you know what is out there in terms of different approaches.


They both have 10 years of development experience, but the one with the CS degree has 4 (give or take) years of additional experience in another setting (as an undergrad). It's not the same kind of experience, but it gives you a bit more more information about that person.

All other things equal (which they rarely are), I'd value 10 years dev experience + 4 years undergrad over 10 years dev experience + ?.


The game is not to pick the 'best' developer and employers don't have that ability. Employers pick the person likely to be most competent and then fire those that turn out not to be. A CS degree in this regard is light years ahead of some schmoe off the street who claims he/she is "the shit".


> And listening to everybody saying that hard work will get you places.

I try to work harder than average. If you don't, you get a lazy reputation, may not get a good reference, and might be one of the first to go in a round of lay-offs. However, I make sure I'm never the hardest worker. Some of the hardest working people I know are poor and too often taken for granted. I've never seen the hardest working person in a company get a fair deal. So, it's a balancing act, trying to work hard but not too hard.


How do I become a good politician?


Staying in a job for too long. I started fresh out of school at 18 and stayed there for over 10 years. During that time I got very few pay rises and always felt like I was being treated as a kid still despite my experience. When I finally left my pay jumped by over £15k. In the 4 years since I left my pay has nearly quadrupled and I'm in a much better position at a much more awesome company.


The easiest way to earn more money is always to quit - either they'll throw money at you to stay, or you take a new job with a higher salary.


Couldn't agree more. Its a pretty common case, with employers taking advantage of experienced freshies.


What's the point of regretting?

For example, I could regret I didn't leave my previous employer earlier because they just didn't pay me more money eventhough my skills and impact had gone way up since starting there. But not leaving that job taught me my own value.

And knowing my value has now materialized in the form of lots of appreciation shown by later employers as well as better money and more challenging jobs. In the previous job it did suck to realize I won't be rewarded for my hard work but, in comparison to what followed, that suckage was a bargain price and I'd never waste my time regretting it.


Being shit at building lasting relationships with former colleagues and people I worked with. In the end that's what it all seems to come down to, a network of people.


Regretting things in your life is awful. I learned a LOT from not finishing deadlines, messing up complete branches of code and working on projects I don't like at all! In the moment I could have a regretted it, but looking back on things, it was always a valuable life-lesson.


It's very true, you often learn most when things break or you have to work with old and bad code which makes you realize why certain design patterns exist


Going to college.

Made me waste 5 years of my productive life, to leave me in debt that made me waste 4 years working just to pay that debt, this year will be my first real year working to actually earn money.


My biggest "regret" was deciding to stay in the ERP space. When I originally jumped in via an internship, I did so because I wanted to get a better understanding of the monolithic systems that ran most the world. I got pulled into an interesting project, became an expert of sorts, and before I knew it I found myself with what felt like golden handcuffs.

I'm hard pressed to say I actually regret it because I've gotten myself to a very comfortable point in life with plenty of options and I've met a bunch of great people along the way. I really only dislike my ERP choice because I've become an expert in technologies that aren't easily leveraged outside of the enterprise space and my interest there is waning.


Mistake #1 - leaving a secure job at a pre-IPO company before I vested in order to join a company where I had greater authority.

Mistake #2 - using my authority to hire several friends from school who hadn't previously held responsible full-time positions.

Mistake #3 - trusting them to manage themselves.

My friends were all smart but none of them really cared about the business or each other. They just preferred getting paid to not getting paid and slowly left after the novelty wore off. One of them even wrote a draft of a crappy novel when we thought he was coding, which we found when cleaning out his desk.

We've all since moved on. Some of them are now quite successful. But I was burned pretty badly by that experience and am no longer friends with any of them.


Not meeting more interesting people outside my discipline in college. My network is mostly limited to people in my field because I spent too much time with people similar to me because that was easy and comfortable.


This. Have you found a way to fix it?


If you are a software guy, especially a web guy? Making it known that you are willing to help all kinds of people with whatever they might want to do leads to all kinds of connections. I'm friends with music video directors, musicians, designers, artists, doctors, scientists, many of whom I met through doing a project for a friend of a friend.


My first regret: having not the balls to do what I really wanted when I was a teenager.

I went to the university mostly to please my parents and to reassure them. I think that was my biggest mistake and I never really learned anything there.

My second regret: quitting. I'm getting bored very easily.

I'm thinking about 2 projects I started with friends where I left the ship eventually because I felt less motivated than them. Now they are both making tons of money and expansing there companies (while I'm still trying to figure out what to do with my life).

I also started a lot of projects which I will probably never release, but that's a pretty common thing.

The last one: working for someone else.

Studying led me on the logical path of getting a job. I first said to myself that it will be temporary and I listened to people who were telling me that I had to have a little experience before launching my own thing (and my advice is: don't listen to their bullshits and do what the fuck you really want to do). The truth is that when you get a job it consumes you and you can forget what your dreams are pretty quickly.

The counterbalancing point of this last regret is that I met extraordinary people while I was an employee, who are still very good friends nowadays. Actually the guy with whom I'm trying to build a startup right now is a former coworker of mine ;)


Big mistake: Joining a start-up with non-technical[1] "idea people" founders as a young father during the last year of my studies. Put a lot of effort into it, got little recognition, burned out all resources (money, friends, family). Have been doing the work of an entire dev team, 12h days, weekend work, and still got like "Oh, you go home already? What about all the work? I've been sleeping in the office and doing super important stuff!" There were days I didn't see my kid for days. Before, my colleagues promised me a super relaxed time, "you can go home early and play with your kid!"

Now I'm freelancing with friends, making good money, flexible hours, feeling much better already! Finally paying off the debts I made during the startup time. Also working at a real company can be quite nice!

Startups are like cults, you only realise what it was after you left. Got myself dragged into this sick mindset of overworking. And as it turned out, we've been working 90% of the time for nothing! Not exaggerating here. Hope it will pay out at least, but not sure about that even... I had better worked half as much time as a freelancer and just bought the shares for money.

Fresh fathers and mothers out there, beware! Startups have to be really family friendly, then it could work. Considering we've only been doing 10% valuable work that eventually contributed to a good product, I believe it's possible to work, say, half as much, have a good work life balance and still get a better product shipped in the end.

[1] With "non-technical" I mean economics people, the "We have a super great idea and are looking for somebody to just do the little boring work of just executing it" bunch. I enjoyed working with non-technical people in general very much, but I've had bad experience with business people, those that only care about money, not about the product or employees.


I took an easy job (UK financial software) when I was downsized from a job that I loved (Embedded systems). I told myself I'd quit within one year and either move to somewhere else in the commonwealth (NZ, SA, Canada) or do a year of university in Sweden on a course I found really interesting, with a view to getting back to Embedded work. I did neither, and I'm still there.

I'm moderately well paid, I have a plan to save money + quit, I moved to a new country and now have a lovely girlfriend, so I'm still in a happy situation - but I wish I could have had these things and pursued my career a little better.


Taking too long to perfect something when I could've iterated with imperfection


Sticking with my first start-up for too long after it became obvious to me that it wasn't going to work out with the team I had. We were almost dead, then received a flurry of interest from accelerators, accepted an offer and spent another year going solidly nowhere.

I learned a lot from the experience, but there was a point at which I should have called it quits. Then again, I guess I learned that as well.

I don't regret having done it, and I accept the time lost as a necessary price, but looking back I think I could have saved myself a lot of time by calling it quits a year sooner.


Assuming that the place I worked at would always have work for me. I'm older, so I didn't have the newer philosophy of job hopping for experience, and believed I could make a career at this one place. I was there over 20 years and had 2 positions. It was union so I was making good money just from the seniority. I was on my 3rd supervisor (previous ones retired) and we didn't get along so well. I got laid off and trying to find a new job I was like a baby getting born -- didn't know a thing about the outside world. It's been tough.


Staying in college at a school that didn't let you change majors (Cal Poly). I picked up what I can in night school in the years following and have cobbled together the job a 25 year old should have now that I'm 32. Worst mistake of my life, not just career.

If you're in a major you don't like and can't switch, drop out. University is largely a scam that exists to impoverish students and adjuncts for the benefit of a bloated administration.

Junior college, however, is an amazing thing and I encourage it for anyone.


(From your comment to this:) "It took me an entire extra year just to get one class I needed to graduate"

Yeah, from what I've read, a lot of state schools are much less of a bargain than they appear because they simply don't care if you can really graduate in 4 years. The private school I went to would move heaven and earth to make this possible, deal with unexpected overflows in majors (you could pick any and change to any as you wished), etc., which is one of the things you pay the big bucks for.

I have something akin: gross parental betrayal I didn't cotton onto soon enough, resulting in my fruitlessly mostly wasting a decade trying to get the necessary undergraduate science degree, which includes useful recommendations for graduate school, i.e. lower tier schools aren't good for this, for the career I'd prepared for starting in 1st grade. Programming and system administration were just things I was good at, but I didn't truly dedicate myself to programming until all that drama was over, with a huge opportunity cost. Never tried to learn a lot of more pure CS when that would have been a possibility, then again I started seriously studying software engineering in high school.

Also thinking I had plenty of time to work things out; turns out I have a genetic disability that permanently took me out of the work force in my early-mid '40s (picking a date is hard because it started when I was 37 and I turned 41 when the dot-com crash made finding employment very hard).

I.e. make the most of the here and now without foreclosing on the future (as I've seen others now regret).


Cal Poly Pomona? Or Cal Poly SLO?


SLO. My degree in physics came after constant failures as I spent most of my time outside class struggling (and failing, horribly) to complete classes I couldn't manage, and trying to learn to program in what little extra time there was. I tried to switch to CS and ME to no avail. However, by the time I realized it wasn't for me (after all the first couple years were general ed requirements) I had sunk so much time in to it I thought it was better to stick it out.

It wasn't. It took me an entire extra year just to get one class I needed to graduate (mind you they have plenty of money for a fancy gym and new buildings, but not for professors to teach classes). I only got out when I was 25 and a sad, bitter, angry shell of a person.

There's a happy ending, though. I left San Luis Obispo, started going to night classes at Ohlone College in the bay and later Santa Monica College, and finally built up enough of a skill set to work in ad operations, then support, then support engineering. I had thought I was too stupid to do anything, but I did well in my classes after Poly and professionally.

Since then I've tried to adopt a motto to enact change before life has the opportunity to do it for me. You are never secure, so don't pretend you are. I thought I was in a decent position in SM when I left for Ireland on a working holiday (it had always been a dream of mine to live abroad). I was terrified to leave a good job for a country with a crappy economy. Lo and behold my whole department was shut down a month after I left, and after a bit of networking in Ireland I ended up with a position better than I had at home. How long this will last I don't know, but I know that it won't be forever (nothing is) and I am always looking out for what's next, and trying to improve my skills (lately I've been in to brewing automation and getting better with Arduino).

That was long-winded, but I guess I also felt like I should point out the positive learning that came from it.

I still should have dropped out, though.


Taking a job for the money. It was my first job after university and I was poor, so it seemed like the extra £2k was worth it, but it wasn't.


This may turn out to be a theme of this thread - you, me[0] and another person [1] so far have roughly similar "I took a job for money" regrets.

[0] - https://news.ycombinator.com/item?id=9061451 [1] - https://news.ycombinator.com/item?id=9061437


I don't regret anything, but perhaps I should have been more patient and level-headed regarding my career choices. My choices have been quick and swift, perhaps too quick and swift. It would have been interesting to have seen what would have happened if I had chosen otherwise - but I'll never know.

Life is all about finding your own way, and enjoying the experience.


Underestimating own skill and especially judgement of a situation as a young employee. Fear of larger organisations, complex processes that leads to avoidance of these type of projects. I've gained confidence over the years, now its easy. But it has led to regrets about missed opportunities. Also, not starting earlier with a side-business.


My biggest career regret is to look for a better career rather than "building" one on my own.


Entering a wrong branch of work only because it paid good, now I am stuck with knowledge that is not really interesting and am doing double effort to learn new skills and start a new job career. Hopefully I will be able to use some of the experience I have acquired up to now.


Becoming a software developer


Can you elaborate?


Don't want to be a downer, but after many years (15+) a software developer, I'm pretty sure I should have gone to business/economic school.

A few things that spring to mind:

a) badly paid compared to the value produced (still better paid than teachers)

b) ageism in the industry

c) the developer ego's (in general) for some reason are over the top, making it impossible for people to have normal discussing about various topics (you can see it here in HN) almost as bad as discussing politics

d) the next best biggest greatest thing being discovered every 2 months by 20 year olds that just discovered something from the 70's and you still have to pretend to be enthusiastic about it for networking/job interviews

e) sexism in the industry

f) in general, a sense of immaturity both on the development/architectural side, but also on a personal level in most places/conferences

g) networking has more to do with success than actual skills, at least in business school you learn that from the get go

Maybe I'm just getting old and want to scream at kids to get off my lawn.


Good list. If people still don't understand why experienced developers only want to work with other experienced (grownup?) developers: exhibits a-g


Hi

The worst of it all, I'm 32 (been working professionally since I was 16, and programming as a hobby since 11). I'm not supposed to be an old timer complaining about 'kids these days' but sure feels like it!

I'm actually working with a very nice team which until today at least, haven't exhibited any of the signs above, but all the other 14 years have been in situations like that.


and what career do you think "business/economics" would have led to, and what do you think it would have paid?


I can't edit my other reply so just going to do a new one.

One of the biggest eye openers I had as a developer and how I was being 'exploited' was when doing work for a consulting firm, the ceo of the company asked me to pick a open source app, change the logo and a few other things (2 days work), and the next day he presented the app as one of his 'business solutions' to some big shots (talking airports and big media companies) and was able with that to sell around 1.2 million euros in consulting services by demoing the open-source app and claiming a lot of the credit for that app. This is something as a developer I still cringe and would probably feel like I would need a bleach bath to clean myself but seems to be day-to-day from people that have MBA's or business/finance education.


I'm not complaining about my career by itself (I make good money), but it is still quite a few magnitudes lower than what I see my peers in business/finance making around here, and to top it off, seeing how their networks work is also something most developers never would think of using/tapping into. From easy entry to schools for their kids, to privileged access to clubs and activities (sorry, I don't know the correct translation for what I mean)


Getting a CompSci degree. Single biggest waste of time and money in my life.


I say the same as I never really turned up to University, however I knew I wanted to be a programmer afterwards and people wouldn't speak to me without that Degree...


Staying in aerospace/defense industry as long as I did (11 years). It is a dysfunctional soul-sucking environment that affected my health, both physical and mental.

I escaped a year ago and am so much happier now.


Not sure about defense, but what's wrong with the aerospace industry?


Putting things off in perpetuity. I should have finished my first big project at 19, 20, 21. I'm 26 now — still working on #1. The fear of not having enough time haunts me every day.


Not starting a business when I was single. Now I'm not and soon there will be kids.

I don't want to resent my unborn kids because they make starting a business impossible/more difficult.


Right there with you, I have a 1-year old and I'm finally working on building my own business. I built my first mobile app when I was pregnant while still working full time as a software developer.

I just never had the motivation to do something besides the 9-to-5 job before I got pregnant and I do sometimes regret that, but it's just the way it had to be for me. Working on your own business takes its toll on your social life so who knows, you might not have met your partner because of it... :)

Anyway, don't think too much about regrets, now is the best time to start your business! It will be hard to find time once you have children, but I don't resent my child for leaving me less time to work. You'll just have to be patient and accept that you can't work at the same pace as before. Find ways to work smarter, so you can get more done in less time.


I think you will be surprised how much it makes you focus and actually work better. Kids are the Great Motivator, they are also wonderful insight into product use at different ages. Involve them in your creations.


Honestly, everything is more difficult when you have kids - showering every day, for example - but the flip side is that it's a total procrastination killer. There are no more wasted days, or lost hours. I work harder and more efficiently than I ever have in my life, and while I certainly get frustrated that I don't have as much time as I'd like, I don't resent my daughter in the least. I doubt you will either.


Turn it around and use your situation as a motivator. It's hard, but it's worth it. I'm sure you want the best for your family and unborn child, so what better way than to start your own business. The longer you put it off the more you'll regret it later in life.


I agree. There will always be something limiting your "free" time, and you will always be prone to looking back and finding an excuse for why you didn't do X. Doing things as simple as rising an hour and a half earlier each day to put in one hour of quality work will eventually stack up until you are well on your way to starting a business. The only truly limiting factors are energy and motivation, and those can be mitigated somewhat by caffeine and stubbornness.


Not to learn from my mistakes, but regret them.


Not trying to build a business while in University, when you have nothing to lose.


stumbling across hacker news, my career hasn't been the same since


Getting a BA in history.


Nothing.


Not applying to YC




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