Ask HN: If you could start your career all over again, what would you change?
Regarding your professional career, what is the single decision you regret the most making?
46 comments
Not making more decisions. The things one regrets are the things not done. Should have changed companies/jobs more often. At the start it was great being part of a company/team for a long time, after that you realize that in the end it is a job (even it it's also a passion) and it's good to be exposed to different things.
Also wished I'd taken a bigger interest in somewhat core things sooner, e.g. static-typed functional languages and distributed systems. Basically seeking out challenges rather than performing well in my comfort zone. Still exploring less technical, soft areas with unknown outcome as yet.
Also wished I'd taken a bigger interest in somewhat core things sooner, e.g. static-typed functional languages and distributed systems. Basically seeking out challenges rather than performing well in my comfort zone. Still exploring less technical, soft areas with unknown outcome as yet.
I started a job and within the first 2 days saw a red flag with the CEO. I should have listened to my gut and walked right back out of that job. I spent years in a job I should never have started because the CEO had an odd mix of compassion and abusiveness that kept me on the fence for years, and I'm just recently realizing exactly how damaging that job was both personally and professionally.
If you have a bad feeling about a job shortly after you start, trust your gut and go.
If you have a bad feeling about a job shortly after you start, trust your gut and go.
I would love to hear some of those behaviors. I recently changed job and I am having such a bad experience, which could be easily summarized with my boss being “abusive and occasionally compassionate”.
It is so deeply confusing, to the point where I think this person might have a personality disorder, and I am wondering if I should quit.
He is very influential and established in the organization, so leaving would be my only recourse. I can see how staying in this situation a long time could semi-permanently damage my view of leadership and trust...
It is so deeply confusing, to the point where I think this person might have a personality disorder, and I am wondering if I should quit.
He is very influential and established in the organization, so leaving would be my only recourse. I can see how staying in this situation a long time could semi-permanently damage my view of leadership and trust...
The red flags I saw were are the exact red flags you'll see written up if you google "How to tell if someone is a sociopath". I'm not going to dissect the specifics of the person I worked with beyond that vague guidance because HN isn't the place where I'm comfortable having that discussion.
But I can tell you that yes, I would quit. I should have quit years before I did, and although it has worked out OK for me the last couple years, in many ways I deeply regret the years I spent living in that kind of scenario. The short-term hit you take by leaving a job is worth the trouble when you find a place to work that truly is a positive and healthy environment.
But I can tell you that yes, I would quit. I should have quit years before I did, and although it has worked out OK for me the last couple years, in many ways I deeply regret the years I spent living in that kind of scenario. The short-term hit you take by leaving a job is worth the trouble when you find a place to work that truly is a positive and healthy environment.
This sounds so obvious in hindsight but yeah, I really needed to google that, thanks for the suggestion. My boss exactly matches those behaviors, almost verbatim. Sucks to be me right now! I’ll have to repay signon bonus and relocation, but might be worth it at this point...
This was my experience fresh out of college and job seeking in the middle of a decent sized US recession. First boss was a functional alcoholic and psychopath who toyed with people for sport. Also exiting his 2nd marriage and on the way to burn through his 3rd. I stayed too long (6 years), realizing 1/2 way through it was him, not me. It took me another few years to find a "face saving" exit. Horrible time and time wasted. Get out asap whatever the costs.
I would love to be a professional chess player. I have been playing chess since I was 10. I have always been good at problem solving and maths. I didn't took chess seriously as I didn't see anyone playing it to earn a living, I didn't even know something like that exists.
Later in college, I won back to back chess tournament and with just a few days of practice. That's when I realized I might had a chance have I taken chess seriously since my early days in school.
Later in college, I won back to back chess tournament and with just a few days of practice. That's when I realized I might had a chance have I taken chess seriously since my early days in school.
I'm sorry you only asked for a single decision. I'd change multiple things.
1. Bet on myself sooner. Start a business SOONER.
2. Learn how to sell.
3. Study more material that'd help with improving programming skills, rather than business acumen.
4. Skip college.
5. Just START, rather than waiting for the perfect storm.
1. Bet on myself sooner. Start a business SOONER.
2. Learn how to sell.
3. Study more material that'd help with improving programming skills, rather than business acumen.
4. Skip college.
5. Just START, rather than waiting for the perfect storm.
This is pretty outlier advice especially no.3, can you elaborate more on your points?
Sorry for the rambling... I'm happy to elaborate more, if you like.
#4. I was a Business Management major. I learned far more about business by being in business for myself. College tuition for MANY majors is a complete waste of your money.
Business is much like programming. There are many things you can learn from a smaller body of knowledge. The biggest gains are going to be made by DOING.
#3. There are a handful of books you can read for much cheaper than what it would cost you to pay for an undergraduage degree in Business Management. You can learn from those books what you'd pay tens of thousands of dollars for in tuition.
The BEST learning comes from practice, though.
For me, with programming... I'd ask all the typical questions. What's the best first language? what tools should I use? what frameworks should I learn? they are a distraction from what you really should be doing... practice. Don't wait to start. Don't wait for the perfect language/tool/framework/editor.
JUST START.
Pick something vanilla (no frameworks until later). Read about it. Write code badly. Write more code badly. Ask questions of other coders in $LANGUAGE. Put stuff up on GitHub for review. Get feedback. If you don't stop, you WILL get better.
DO. DO. DO. DO. DO. Reading is only the beginning.
#4. I was a Business Management major. I learned far more about business by being in business for myself. College tuition for MANY majors is a complete waste of your money.
Business is much like programming. There are many things you can learn from a smaller body of knowledge. The biggest gains are going to be made by DOING.
#3. There are a handful of books you can read for much cheaper than what it would cost you to pay for an undergraduage degree in Business Management. You can learn from those books what you'd pay tens of thousands of dollars for in tuition.
The BEST learning comes from practice, though.
For me, with programming... I'd ask all the typical questions. What's the best first language? what tools should I use? what frameworks should I learn? they are a distraction from what you really should be doing... practice. Don't wait to start. Don't wait for the perfect language/tool/framework/editor.
JUST START.
Pick something vanilla (no frameworks until later). Read about it. Write code badly. Write more code badly. Ask questions of other coders in $LANGUAGE. Put stuff up on GitHub for review. Get feedback. If you don't stop, you WILL get better.
DO. DO. DO. DO. DO. Reading is only the beginning.
Thanks for the elaboration. I think I came from the perspective of a programmer myself, and I consider myself quite a capable programmer. However business-wise, all from idea to execution (i.e., marketing, finance, law, customer support) etc is very lacking. I know I'm not alone in this, and there are a few of friends in my circle that go to get a Business degree (MBA) to learn more about business and make connections.
How do you yourself find what to sell, and educate yourself in that domain specific knowledge on that particular business?
How do you yourself find what to sell, and educate yourself in that domain specific knowledge on that particular business?
I took this one offline and sent an email to the one listed in your profile. it contains more personal data than I want to put out here in public.
Stayed in a toxic team long enough to injure my health. There are some things doctors can't fix. Definitely not worth it.
My experience with toxic teams is that they're always a career step backwards. They don't attract talent, builds enemies, burns you out, sometimes even costs you money. Burnout is probably the worst part. Lots of people quit tech not for the tech itself but because of the people.
I didn't take any more CS classes in college because during the first course I took my freshman year, there was a lecture and lab component. During the lab, you would code on a computer in an IDE and submit the projects/assignments. During the lecture you'd learn and then take written exams, which involved coding Java by hand. I had no issues with the labs and really enjoyed them, but I greatly struggled with syntax, etc, when writing the code by hand. I was 18, too stubborn, and butted heads with the Professor about it - I kept trying to argue why my lab performance should have demonstrated more of a competency in the subject than writing by hand, but the rubric was final and the exams were a large portion of the grade, and my grade suffered because of it.
After that experience, I declared my major to something non STEM and never took another CS course again, and ended up working for the first 4-5 years of my career in non engineering roles.
However I still ended up being pulled into coding as a passion all those years later, in which I self taught the CS coursework I needed online by taking Computer Science MOOCs and reading textbooks, etc, and now work as a software engineer.
I can't help feeling like if I was a little less brash when a freshman in college, I probably would have loved the CS major and my career could have been very different. I can't complain about where my life/career has ended up though, so perhaps it was all for the best.
After that experience, I declared my major to something non STEM and never took another CS course again, and ended up working for the first 4-5 years of my career in non engineering roles.
However I still ended up being pulled into coding as a passion all those years later, in which I self taught the CS coursework I needed online by taking Computer Science MOOCs and reading textbooks, etc, and now work as a software engineer.
I can't help feeling like if I was a little less brash when a freshman in college, I probably would have loved the CS major and my career could have been very different. I can't complain about where my life/career has ended up though, so perhaps it was all for the best.
I can't believe I am reading this because I feel like you just described the same exact situation I have experienced in college as well (except I still have one more year left). I switched from CS to a BUSINESS major after freshman year for similar reasons, absolutely despised the teaching environment for some of these massive pre-reqs/weed-out classes. The Java class in particular ruined it for me.
However, now once again I find myself really wanting to give it another go and feel ready to take on the advanced coursework, but tuition is expensive. Do you have any advice to a rising college senior who is about to wrap up a seemingly textbook business major but feels impassioned by coding?
However, now once again I find myself really wanting to give it another go and feel ready to take on the advanced coursework, but tuition is expensive. Do you have any advice to a rising college senior who is about to wrap up a seemingly textbook business major but feels impassioned by coding?
I'm not sure I regret the job choices I've made, but if I knew how healthcare laws would have changed over the last decade or so I would not had the same priority for finding a job and probably would have spent more time trying to make it as a writer. I have a pre-existing condition so in 2008 it was very valuable for me to obtain employer-based health coverage before I aged out of being covered under my parent's plan.
If I knew that the age until which you are covered by your parent's health plan was going to be extended to 26, I would not have focused on getting a stable, nice benefits job. I would probably have tried making it as a writer, and unless I had some big break I would have probably considered grad school (which I was planning on for my first couple years after college until I found I preferred working on real world projects to research more or less).
Not 100% sure how that would have worked out. I probably would not have gotten married until I had a stable position somewhere, so I'd be starting my family much later (if at all, if my writing career took off I might be more focused on that), almost certainly wouldn't have ended up with my wife, since the circumstances that brought us together would be very different, odd to think about...
Probably would be more ambitious but with less happiness than I am now, but it's very hard to say. So I don't regret the path I went down, but it's strange to think that so much of my life was based on an assumption (that I needed to secure employer-based heathcare ASAP) that ended up being wrong.
If I knew that the age until which you are covered by your parent's health plan was going to be extended to 26, I would not have focused on getting a stable, nice benefits job. I would probably have tried making it as a writer, and unless I had some big break I would have probably considered grad school (which I was planning on for my first couple years after college until I found I preferred working on real world projects to research more or less).
Not 100% sure how that would have worked out. I probably would not have gotten married until I had a stable position somewhere, so I'd be starting my family much later (if at all, if my writing career took off I might be more focused on that), almost certainly wouldn't have ended up with my wife, since the circumstances that brought us together would be very different, odd to think about...
Probably would be more ambitious but with less happiness than I am now, but it's very hard to say. So I don't regret the path I went down, but it's strange to think that so much of my life was based on an assumption (that I needed to secure employer-based heathcare ASAP) that ended up being wrong.
Working for a company and thinking of work in terms of "career". If i could start all over again, i would be trying to do something on my own.
Ship more often, launch more often, learn to validate ideas sooner, have fun along the way.
I wish I knew how to recognize a bad manager, and what to do when you find yourself working for one. I was eager to prove myself in my first job out of college, typical overachiever. Naively believed that if someone was a manager it meant they were good at what they did and wanted the best for you too.
Didn't realize until I burned out what a loss of time and energy it was putting so much effort into trying to do a 'good job' for someone who lacked empathy and was just not suited for management. It took me years to unravel the damage from that experience. I went into new jobs with what I would describe as PTSD learned from that first job. It was a professional trauma, and I didn't realize how disordered that startup and management team was until I worked at other places. I learned a lot from it. But it set me back a few years.
That brings me to my next point. The exciting, glamorous startups with high profile executives and investors are often just a huge mess under all the flashy PR and social media personalities. I don't regret learning that the hard way, just wish I wasn't so naive and allured by brand names at the start of my career.
Didn't realize until I burned out what a loss of time and energy it was putting so much effort into trying to do a 'good job' for someone who lacked empathy and was just not suited for management. It took me years to unravel the damage from that experience. I went into new jobs with what I would describe as PTSD learned from that first job. It was a professional trauma, and I didn't realize how disordered that startup and management team was until I worked at other places. I learned a lot from it. But it set me back a few years.
That brings me to my next point. The exciting, glamorous startups with high profile executives and investors are often just a huge mess under all the flashy PR and social media personalities. I don't regret learning that the hard way, just wish I wasn't so naive and allured by brand names at the start of my career.
Getting into the habit of ‘always be interviewing’, stayed 4 years at my first job where there were limited pathways.
The decision I most regret was moving to a city without many tech jobs (Philadelphia). The difference in number of available jobs, salaries, working conditions, and even the intelligence of coworkers is kind of mind-blowing, now that I've moved back to a city with a lot of tech jobs (Seattle). The cost of living is higher here, but it's worth it.
Moving away from Seattle after college before I had another job lined up. I quit the job I had in college (it was software dev but in the university) and went on a long road trip across the country. It was the single worst decision I’ve made in my entire life. (Probably)
That said, I couldn’t have known that entry level jobs were going to be so incredibly difficult to get after college. Almost everyone and their mother thought I’d have no trouble cause he’s so smart, has job experience, went to good school, etc. But most of them were extremely privileged and never had issues finding jobs /or/ had completely irrelevant experience.
I’d highly suggest talking to peers who are just a year or two ahead of you. They might shine light. Sadly, I had none to go by. I was entirely alone and had no relatable peers.
That said, I couldn’t have known that entry level jobs were going to be so incredibly difficult to get after college. Almost everyone and their mother thought I’d have no trouble cause he’s so smart, has job experience, went to good school, etc. But most of them were extremely privileged and never had issues finding jobs /or/ had completely irrelevant experience.
I’d highly suggest talking to peers who are just a year or two ahead of you. They might shine light. Sadly, I had none to go by. I was entirely alone and had no relatable peers.
I would swap the 4 fruitless years in postgraduate academia for 4 years of team experience in a large IT corporation. My startup was very successful, but could have grown faster/easier (than 60-odd people in 14 years) with more such experience (as solo founder).
Did you jump out of a PhD?
I'm going into my fourth year now and just feel like I'm stagnating and not being challenged in my lab anymore. I've been thinking about the quote "If you're the smartest guy in the room then you're in the wrong room" lately. At this point both of my PIs and my lab manager have openly told me that I'm the strongest member of the lab. I know it's not just me anymore and I feel like I want to get out and move on to someplace where I can grow, but also don't want to waste the four years that I have invested towards a PhD.
What was your experience?
I'm going into my fourth year now and just feel like I'm stagnating and not being challenged in my lab anymore. I've been thinking about the quote "If you're the smartest guy in the room then you're in the wrong room" lately. At this point both of my PIs and my lab manager have openly told me that I'm the strongest member of the lab. I know it's not just me anymore and I feel like I want to get out and move on to someplace where I can grow, but also don't want to waste the four years that I have invested towards a PhD.
What was your experience?
> Did you jump out of a PhD?
Yes, sort of ... I was planning an academic career and had a 4 year contract teaching and researching at uni while doing my PhD, but failed to get the PhD in that time (because of lack of motivation / other interests and projects). Never really got the hang of focusing on churning out papers, enjoyed teaching and short-lived research more. Didn't get along too well with the (much older) colleagues at the dept. either.
After that, I freelanced for a year, during that time I got a great job offer at an EA company for game development but decided not to move to the US for it. A few months later I got talked into accepting VC for one of my hobby projects, so the company was founded. The 4 years I "wasted" were at least somewhat formative and I would have regretted not getting a taste of academia. In the end, entrepreneurship was a good fit for my personality, the joy of doing exactly what I wanted and getting very positive feedback, validation and compensation just from making my work available to the public was the best reward.
At hindsight, trying more things and getting more industry experience as an employee would have been useful, but I can't complain.
Yes, sort of ... I was planning an academic career and had a 4 year contract teaching and researching at uni while doing my PhD, but failed to get the PhD in that time (because of lack of motivation / other interests and projects). Never really got the hang of focusing on churning out papers, enjoyed teaching and short-lived research more. Didn't get along too well with the (much older) colleagues at the dept. either.
After that, I freelanced for a year, during that time I got a great job offer at an EA company for game development but decided not to move to the US for it. A few months later I got talked into accepting VC for one of my hobby projects, so the company was founded. The 4 years I "wasted" were at least somewhat formative and I would have regretted not getting a taste of academia. In the end, entrepreneurship was a good fit for my personality, the joy of doing exactly what I wanted and getting very positive feedback, validation and compensation just from making my work available to the public was the best reward.
At hindsight, trying more things and getting more industry experience as an employee would have been useful, but I can't complain.
choosing ME over CS simply because the college was way more prestigious. College rankings don't matter beyond your first job.
Bingo. I majored in math because I was interested in it. Had I known the difficulties I’d have getting a job because of it, I would have doubled in CS.
I had people literally just tell me at career fairs, “you’re not qualified,” because my degree didn’t have the word “computer” in it. It took most of my self control not to educate them on who built the first electronic computers.
I had people literally just tell me at career fairs, “you’re not qualified,” because my degree didn’t have the word “computer” in it. It took most of my self control not to educate them on who built the first electronic computers.
Taking a job knowing that the boss was incompetent, but he thinks he is t a top notch.
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Not taking out a loan for a CS degree. It's gotten in my way so much, especially recently. The paper saying that you took some courses is way more important than a github profile with projects.
For what it's worth, you're better off not being saddled by student loan debt.
EDIT: To the downvoters: please explain how graduating with tens of thousands of dollars in debt is beneficial in the long run.
EDIT: To the downvoters: please explain how graduating with tens of thousands of dollars in debt is beneficial in the long run.
I didn't downvote you but if you are not from the US but want to work in SF Bay Area then not having a degree is a significant barrier to immigration.
You need 12 years of experience to be considered equal to a fresh grad of a 4 year degree in the eyes of immigration law.
I dropped out to start my first startup and while that was a great experience and catapulted me career-wise immigration is still a continual stumbling block.
You need 12 years of experience to be considered equal to a fresh grad of a 4 year degree in the eyes of immigration law.
I dropped out to start my first startup and while that was a great experience and catapulted me career-wise immigration is still a continual stumbling block.
it is beneficial in the long run because you dont face the issue that OP is facing....
Also the UK doesn't completely cripple you with student debt. CS degrees are also valuable, can pretty much get into any other field with this piece of paper.
Also the UK doesn't completely cripple you with student debt. CS degrees are also valuable, can pretty much get into any other field with this piece of paper.
It seems like OP is from the U.S., where, unlike the U.K., the education system knee-caps students financially. Hence, if one goes to school in the U.S. taking out loans isn't worth it.
I went to a respectable state school (to the point where people comment that they like the SDEs that my state school has produced when I speak to other devs) for my undergraduate degree, and I've recently become debt free. If I had gone for CS, I probably could have expected to be $35-40k in the red on graduation. While it seems abnormally high across the Atlantic, it wouldn't have been some catastrophic ivy league 6-figure loan pricetag that's become the debt figure people like to highlight so much.
Many people that I've kept in contact with who followed the CS track were more than able to pay off their student loans because most people I know went to state schools like I did. It would be unreasonable to say that there are no failure stories as there are plenty of those, but with the salaries in the industry even for juniors who find themselves working for slightly above average companies (envision $55-65k fresh out of college in the US and they still get to live at home), the loan would have absolutely been worth it.
Many people that I've kept in contact with who followed the CS track were more than able to pay off their student loans because most people I know went to state schools like I did. It would be unreasonable to say that there are no failure stories as there are plenty of those, but with the salaries in the industry even for juniors who find themselves working for slightly above average companies (envision $55-65k fresh out of college in the US and they still get to live at home), the loan would have absolutely been worth it.
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I started a business early and ran a few service businesses with some success. Cash flow was always a problem and working your ass off waiting for the big payout put a huge strain on my wife and kids.
It wasn't until both my wife and I were working full time that we started to accumulate wealth.
No commitments? Start a business early. Some commitments? A regular paycheck and saving as much as humanly possible makes it easier to take risks later.
It wasn't until both my wife and I were working full time that we started to accumulate wealth.
No commitments? Start a business early. Some commitments? A regular paycheck and saving as much as humanly possible makes it easier to take risks later.
Listening to people who say “sleep is for the weak” and “stop trying to understand things, just learn by doing.”, “stop trying to understand the universe”, and “just do the obvious thing.”
Different people are different. Personally, I find I am 5% as productive if I am working while utterly confused and running on 4 hours of sleep. It sucks to look back on my effort and see I made as much progress as Luigi Cadorna did on this 10th time trying to cross the Isonzo river.
Different people are different. Personally, I find I am 5% as productive if I am working while utterly confused and running on 4 hours of sleep. It sucks to look back on my effort and see I made as much progress as Luigi Cadorna did on this 10th time trying to cross the Isonzo river.
Pursuing advancement of technical proficiency over leadership. I would completely change that to focus more on administrative and managerial performance much earlier in my career. In my defense, though, leadership is really weak in software so that would require more initiative from less examples/guidance.
Not staying an extra semester to finish CS as a second major (my college required a senior thesis, like a mini–dissertation, for every degree). Having a minor in CS was about as useful in the technology field, career wise, as having a binary coded birthmark.
My biggest regret was ever taking a job in the first place. I should have worked for myself, my own business, from day one. Working for someone else robbed me of so much potential. Easily one of the biggest opportunity costs I’ve ever paid.
I wish I'd looked for more opportunities to work with and learn from more experienced developers instead of being so overwhelmed by imposter syndrome that I was terrified to take a job where anyone who knew more than me could judge me.
Choosing the wrong career. Finally moved from programming to writing fiction.
I should have learned awk and sed when they told me to.