Ask HN: What would you do if you could start over?

75 points by mathiscool11 ↗ HN
Does anyone here feel like they took steps that ended up unexpectedly slowing their career/progress? If you could go back 10 years with the knowledge you have now, with the sole goal of having an idea that could be a successful startup, what would you do different?

I'm looking for things such as: -College major -Career field -Bad life decisions -Relocation -Finances -General personal development (Not work/startup related, such as working out) -Career development

Please feel free to add anything you think is fit, even if it isn't on that list

142 comments

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I would get a job in SV in 2012-2013 instead of 2021 and made a decade of "big" money, expanded my network etc... instead of working a decade in average companies which don't care too much about software development
i know plenty of folks who wish the opposite ;)
I too know of such folks (including myself) but I think we say that only after making the bank!!!
I wish I'd fixed my sleep earlier, it became ten times easier to accomplish everything after I addressed my chronic insomnia.

I also wish I'd left the tech industry sooner. Now that I'm in a field that's a better fit for me, I just wish I could have the same length of career as some of my coworkers in it.

Which field are you in now?
How did you fix your sleep?

I have horrible sleep hygiene and it worries my sometimes. I’ve had bad sleep habits starting as a teen so it’s been hard to break out of them.

Personally for me, my sleep started getting a lot easier and better after I started lifting weights.

I lift heavy weights for 1-2 hours every other day. My body forces me to sleep 8-9 hours/day to recover.

I don't know what he did, but for me was very basic sleep hygiene added with Cognitive Behavioral Therapy for Insomnia (CBT-I), there are several people on YouTube sharing how to do it. With their guidance, I fixed myself after years of suffering from it.

The tipping point was going to bed only when sleepy and forcing myself up at the same time every day as much as possible. Problem is, some weeks will be super rough, but I kept trying and even with an imperfect execution that made me sleepy again at bedtime, which I thought was something I had lost forever. To lay down and sleep.

If it is okay to ask:

What helped you the most with the chronic insomnia? Do you have any advice?

Thanks

I can chime in here:

For me, it was a combination of things, here's the order I've tried: 1. Lift weights 2-3 times a week. 2. Avoid caffeine after 10:00am. 3. Stop eating like an idiot. 4. Go to the doctor and get blood work done. Turns out my hormones were all screwy. I had to get three different opinions before I found a doctor who gave me more info than "go to sleep sooner" and actually gave me some vitamins and hormone pills that helped a lot. 5. Therapy (CBT). It took me going to 3-4 therapists before I found one that jived with me.

For some people you just need to do step 1 or 2. For me it took all five. My biggest lesson is that doctors are just people to who are trying their best. Don't be afraid to see more than one or push them if you're not getting results. They can only help you as much as the feedback you give them.

It was totally worth doing all this though.

> Avoid caffeine after 10:00am

Also: Avoid caffeine for the first 90 minutes of your day.

The lifting did it with me. And going to bed at 10 every night for two years in my early 30s, because there was someone next to me I wanted go be like.

I wish I'd been diagnosed with this incurable sleep disorder and gotten treatment earlier. That and I wish I'd sold my house in 2019.
When I went to that conference in like 2011 where the guy who created Dogecoin made fun of it and said it was an indication of how idiotic crypto was, instead of thinking to myself, "Yeah, that makes sense," I should have bought as much of it as possible.

Jokes aside, I feel like the last 10 years have largely been like that. The more you took massive nonsensical risks, the more likely you were to be handsomely rewarded. So, basically, everything I did that I considered "prudent" 10 years ago, I'd do the opposite.

I bought a machine to mine dogecoin in (2013?) and just never hooked it up... no ragrets =(

I was into the silly subreddit at the time, when they sponsored the racecar. Seemed like a fun time. Turns out they actually hit the moon after all...

I would've focused on game engine development and gone into the game industry instead of chasing the money in web/web-adjacent tech. It's almost impossible to make that kind of change now without taking a massive pay cut and it genuinely makes me sad almost daily
Becoming an indie game developer on spare time could make you happy
I've made several half-attempts at this over the years, but it always ends up falling to the wayside when life gets hectic. Maybe one of these days I'll finally push through though!
Could you work on an open-source game engine in your spare time, then use that to pivot across? And/or get a web-dev job in a games company and then try to get an internal transfer?
My wife has suggested the latter a few times and it definitely seems like the most realistic approach. I have a small game engine I've worked on off and on again over the last few years, but it never feels like I have enough time to make real progress
If you're into game engine development and C++, Godot is very accessible for new contributors. It's a great place to explore that stuff while also making (small or large) contributions which will actually get used and appreciated by a growing number of serious game developers.
I think you have to take a pay cut regardless

I worked in games ~20 years ago at my first job, and then got a huge increase when I moved outside the games industry

Games just don't pay well. I respect people who do it for the love and art of it. As far as I can see, low pay is part of the deal.

There is the outside chance of a massive hit, but most game devs aren't owners, and risk is proportional to reward

I’d put even more emphasis on getting into the right companies, spend more time at companies that worked for me, and spend less time at companies that weren’t working out.
I’d probably go into finance. Seeing the TC my friends brother in law is clearing in his early 30s is nutty. I’m taking $1m BONUSES
I’m 40. What I’m doing today, I wish I would have done at 30. Jiu jitsu, striving to be the absolute best version of myself, working with my hands, building other skills besides coding.

At 30, I wish I was doing this stuff at 20. Health and fitness were a priority, focusing time on things that bring ROI into life including more career oriented, less booze and idiotics.

I married and we had two kids in our 20’s, probably the best thing either of us ever did. Wish I could shift this earlier a few years as well so we’ll have more years together as they grow old and have their own families.

Sorry if confusing, on mobile.

The older I get the more I too realize that “the best time to start anything is yesterday”
There’s that, and also “I’m capable of so much more than I realize.” Too much of life is consternation about bullshit that doesn’t matter. In moments of indecisiveness, sometimes I use the “look back” tactic where I imagine a future version of myself reflecting back to this moment. Will he care? Will this have actually mattered?

Helps me get through some bs.

“I’m capable of so much more than I realize.”

Turns out I'm capable of less than I realized.

"I’m 40. What I’m doing today, I wish I would have done at 30. Jiu jitsu,"

I was training yesterday and had the same conversation. I am a 48 1-strip blue belt and my body is starting to give on the wear and tear.

I'm a 2-stripe white belt. The secret to my success is that I keep showing up. Just don't ever quit.
Going back to ~18-20 years old: focus more narrowly when building things. Focus overwhelmingly on business services/productivity and never go anywhere near consumer oriented services. Focus more on the process of sales generation and less on unnecessary (unintended) complexity & features.

I learned the wrong lessons from the ~1994-2001 dotcom bubble era (as a teenager) and I wasted a bunch of years correcting various wrong ideas about business that I had picked up.

I’d worry way less about what other people thought of me and focused instead on quieting down the insecure voice in my own head. I might not be anymore successful financially or politically, but I certainly destroyed several professional relationships that could’ve grown into meaningful friendships or partnerships.
Take the internship at Google in 2012.
Take the internship at Google.
Having an idea that could be a successful startup is very close to unimportant. Lots of ideas can be successful startups, and having them is easy. The hard part is having a ton of drive, the right mixture of personality traits, and the privilege or luck to make it happen. I think these sorts of things are largely out of your control. Maybe instead of worrying about making a mistake and missing the boat, spend some time reflecting on why you want to found a successful startup and whether something else in life wouldn't be equally fulfilling.
I would have been a lot more aggressive about finding better roles in my early career. I had 2 good experiences for 4 years each, but I could have left both jobs after 1 year and had the same career progression.

I think my upbringing focused a lot on “stick it out” and “work hard and you will get recognized exactly like you deserve.” It was a passive laborer mentality from a blue collar area.

I took a sabbatical and after some soul searching realized it was more like “sharks that stop swimming drown.” Career and compensation took off after that.

Put everything I possibly could into a Roth IRA starting at 21.
At 21, I needed just about every dime I had to live on. If I had worked as hard as I could without affecting my grades, I could maybe have saved $2k.

In an index fund for 40 years with an average rate of return, after inflation, it would be worth about $35k.

Not enough money to make any difference at all, and to save any more would have probably had a negative rate of return because it would have negativity impacted my job prospects.

Now that I make more than enough money to save for an early retirement, I’m glad I had the experiences I did rather than save every penny I could through my 20s.

i.e., Convert your 401(k)'s to IRA, then convert the IRA to Roth via the "backdoor" that is not subject to the annual limits.
I would leave jobs that weren't working out sooner. When you have a good job, it's hard to leave. But there were times when I had a good position but didn't enjoy my job or wasn't very well thought of. It's easier to be a star when you are starting out, but when you get to middle or senior management you are much more likely to be controversial or get into difficult situations that your talent isn't going to save you from. Things aren't going well and you think, well I will just work hard or try to adjust to feedback. Sometimes it is best to just move on. My favorite jobs have been fun at the start and fun years later as well.
> Sometimes it is best to just move on. My favorite jobs have been fun at the start and fun years later as well.

Why did you quit those?

i left two jobs that didn't work out. the problem is that the first one of those failed because i was working all alone, no team, and an overworked supervisor, and at the time i didn't know how to compensate for that (i didn't even know that it needed compensating).

it took me years to understand that i am driven by human interaction. what i am struggling now is how to translate that into advice. i mean yes, i should have looked for jobs that do pair programming. but every personality is different. how would a 25 year old know if that advice applies.

the best i can come up with is to try a few different jobs and pay attention what it is that that is fun.

but even there you can mislead yourself. i did a programming internship while studying and figured that i hated 9-5 office work. then i did foss development with roxen and pike and i absolutely loved it. but i thought it was the programming language, when in truth it probably was that i was working closely with the people that used the website i built. so i stumbled from one experience to the next without really understanding what made work fun.

i can work on side projects all alone for months at a time because i was solving problems for myself. or i can do the utmost boring work with a hands-on client. we worked together for 10 years. the most wonderful person i have ever worked with. working together made the dullest task enjoyable.

i suppose the common element is that there was a need that had to be filled. in one case it was my own, in another it was someone elses.

but how does that translate into actionable advice?

"but how does that translate into actionable advice?"

Perhaps, be aware of what you need in coworkers / end-users, and look for that?

Something that many in the tech industry completely neglect, thinking it's all about tech.

I think your comment is gold dust BTW, basically all of us need to figure out how to be HAPPY. And you've clearly stated what you need, which I think a lot of us need but don't always realise we do, which is to be important/helpful to other people. Much more important than making huge $$$$$$$$/ ££££££££££££ or being an expert in mega-cool-language-or-framework-X-which-will-inevitably-one-day-be-oboslete-however-much-we-pretend-it-wont

2014....let's see.... I'd finish the move that took years too long, and saved a ton of money in the process.

I'd have coded up a BitGrid and had chips done a decade ago, instead of just starting on it now

I want to go back to the 1980s, after high school, but before life wore me down. Marry the same girl, but 15 years sooner.

(comment deleted)
Done grad school immediately after undergrad, rather than waiting until my 2nd kid was on the way.

Missing that time with my kids was so... amazingly... stupid.

I would brake up with her earlier.
Should’ve talked to my doctor ages ago about my chronic nausea and stomach pain and pressed them until they discovered the cause was my Pentium 4 gallbladder.

Wasted a lot of time being sick for no good reason that I can’t get back.

Lawrence said it best in the movie Office Space.
Pursue more of the interesting opportunities when young, and don't let women get in the way - they're effectively unlimited in supply.

Opportunities to get in on something like the dot-com boom having ~all the relevant skills? Far fewer per lifetime.

Really some kind of oldschool advice from a granddad. So much wrong with this.

Let's start with the simple one, we don't know that the OP is a guy interested in women.

Would it change anything about the advice if OP was a woman interested in men, or any other permutation?
I am sorry, maybe we lived in a different time. I only have heard an advice "don't let women get in a way, they are unlimited in supply" from very disrespectful man back in the days. That is all.

Or is that a joke? Not very funny anymore. I have met a lot of smart women. My wife is definitely one of them. I wish I have met her in my 20.

We lived in the same time. Each person can talk about their own experience, a man has better advices for another man.

You're creating drama where should have none. His life advice to himself is to not focus too much/too early in women (or sex, love, ...), this is a great advice.

  > Really some kind of oldschool advice from a granddad. So much wrong with this.
  >
  > Let's start with the simple one, we don't know that the OP is a guy interested in women. 

Hey genius, it's advice to myself if I could hypothetically start over.

Are we reading the same thread? "What would you do if you could start over?"

Hey, sorry, was not tried to be disrespectful to you. See my other answer. Just feels like that way of saying is very old school and for me only related to disrespect to women.
I wouldn't build on others APIs. Figure out a way to own the content itself or not at all.

I would commit to things more fervently rather than trying to decide if it's good value to commit. There is a lot of value to be had in commiting that can outweigh flexibility

Buy a shitload of crypto.

Smoke less

Waste less time

Explore more of the world

Arrange certain finances earlier.

Whenever I think about what I could have done better 10 years ago (there's a lot!) I also remember that if I'd been more successful then, I probably wouldn't have found my way to where I am now, and I really like where I am now, and with whom. You've gotta sin to get saved, as they say.

But strictly in career terms, I wish that ten years ago I had taken full advantage of my legal right to work part-time, and gone to get a doctorate in a non-tech field. A couple years of living cheap would have given me career-mobility superpowers that I wish I had now that I'm older.

I feel the same way as your first paragraph. The path I took led me to where I am now, but I love where I am now, so perhaps that was the best path. I could say "I wish I started on my current path earlier", but who knows if the environment at the time would've manifested where I currently am if I did it differently from the start?