Took me about 2-4 years of job hopping to get up to a salary respectable for my level of experience.
All this said, it was definitely a tough period in my life, and I'm kind of happy, that it's over. My son is going to school this fall and does not require as much attention as when he was a toddler. My projects are kinda "finished", meaning that I'm not actively working on them anymore. If I'm reading something nowadays, it's mostly history, philosophy and natural sciences. Having time for myself, playing an occasional video game, going out to skate or just hang around in the city is important to keep sane and not lose the desire to work anymore.
So yeah, I've learnt first hand, what "hard work" really means, and learnt to value free time, leisure and hobbies.
I lived a semi-bohemian lifestyle until I was 30. I worked maybe 25 hours per week and spent a shitload of time working on hobbies and doing hours of yoga every day. I took a lot of drugs, drank, slept around voraciously, and travelled across the US and to countries all over the world.
When I turned thirty I decided it was a good time to do adult stuff, so I did. I never accumulated debt and had always put away a small amount of retirement money through my 20s, so I wasn't terribly far behind. It took about two years to go from making $30k to making $100k.
There are trade-offs, but I'm at peace with my choices. I own a house, still work on my hobbies, got married, and I don't think I'll have many regrets around stuff-I-didn't-get-to-do.
And no, I never had a trust fund.
When I reached my mid 20s, the business folded and I was forced to find work elsewhere.
I worked hard from 25-30.
At 30, I lived in Asia for a year (my dream that I couldn't actually realize in my 20s) and worked remotely (low pay and hard work, but was very good pay for where I lived).
Now that I'm almost 40, I have a house and make more money that any of my previous jobs. My job is actually the easiest it's been in decades, mostly because I overworked in my earlier years and working a regular job is rather boring and slow compared to my usual pace.
I think working hard in your 20s is required if you want to have a good life in your 30s+.
As I was approaching 30 I made a career change to tech. I did work too hard during this period because I was working full time and also spending all of my free time teaching myself new skills. Honestly it was a dark period because I wasn't sure if there was a light at the end of the tunnel in terms of breaking into tech and I was very unhappy with my job at the time. I studied on the bus. I studied after work. I studied on the weekends. It was like working two full time jobs.
I got lucky and was able to get a job as a software engineer. I spent the first year working too hard. I reported for my regular hours and then worked every night babysitting upgrades because I felt like I had to prove something or pay something back for the opportunity.
Overall, I think I took myself too seriously in my 20s. I'm glad I put the effort in because it was worth it in a way. But my perspective changed when people close to me started get old, sick, or both and passed away.
My perspective changed and I don't take myself as seriously anymore. However, I still struggle with feeling like my time is going to waste. Sometimes I have hard time relaxing and doing something for fun like video games because it isn't contributing to my personal development. I guess I'm still figuring that out.
First few years out of University I was working 2x as many hours for 1/2 the pay I make now at a startup. But honestly, I had just moved to LA anyway at the time and lived with the people I worked with (we lived/worked from an apartment) so it wasn't a big deal.
Financially I'm in an excellent place (2ish years worth of expenses saved up, more if I left Los Angeles for a low cost of living area). No debt.
Nowadays I don't work as "stressed" anymore, but I get a lot more done and work MAYBE 50 hours on a bad week, usually closer to 40. Probably because I quit drinking during the week and prioritized exercising and learning Chinese in the mornings.
I highly recommend anyone having a tough time prioritizing exercising to just bite the bullet and pay for a personal trainer. Especially if you're making over $80k a year, it's easily the best money I spend. It'll make you less stressed, more confident, and generally happier. People like to work with happy, stress free, confident people so career-wise it's the best money you can spend too.
I worked broad though. I held 18 jobs through my 20s -- selling Kirbys (vacuum cleaners) and life insurance, working in China as a 3rd party inspector, bus driver, working on a solar commune, developing custom manufactured parts (think bearings), IT guy (Level I and II) and importing solar panels, among others.
This was not intentional. I just never felt settled and wanted to try a little bit of everything.
I look at my peers (like my wife and my brother), who stuck to one thing are doing far better financially than I am. However, I still don't know if I'd trade places. Some of those experiences were fantastic.
In my 20s, my work week was roughly 40-50 hours at software startups. I very, very, very worked late or on weekends. I had few obligations outside of work, so I had plenty of time to pursue interests, get outdoors, hang out with friends, etc.
By my 30s, I was married and had a kid. I was still in startups, but in positions of higher responsibility. By the end of my thirties, no hour or day seemed sacred and 50-60 hour weeks were the norm. When my son was young, I dropped him off at school and kissed him goodnight in the evening. My wife, who also worked full time, shouldered more than her fair share of the child care load. We finally decided to sell the house in the burbs and move to the city. My commute shrank by an hour each way and being close to home meant I could do school drop off AND participate in after school activities since school, parks, athletic fields, etc. were all a 15 minute WALK from my office.
Now, I'm in my mid-forties. After the startup I was a VP at was acquired, I've lived the big company lifestyle. Most importantly, I'm back to 40-45 hour weeks and feeling far more balanced in my life. My job lets me take the time to spend with my family and doesn't interrupt my nights and weekends, despite still being in a position of higher responsibility.
If I could do any era over, it'd be my 30s. I basically missed ages 1-4 for my son and was not a great husband/partner for my wife.
Did Paul Graham and Sam Altman both try to convince me to quit and join a yc startup or start my own. Yes at 2 different Startup schools they told me I was wasting my time. Shortly after I did join heed their advice and join 3 separate startups ... with mixed results.
Did I work too hard? Ultimately no, because it's like investing in the market. Yes you think you'd rather have more (booze, travel, video game, etc) at the time, but those things don't improve your life in the long run. And ultimately I wouldn't change where I am today for the world ... minus the pandemic / quarantine / civil unrest.
I graduated college shortly before the 2008 recession and wound up stuck in a very bad, dead end (for my IT career) job. But I was helping put my wife through college.
While it wasn't direct IT work, it was plenty of 'crunch' time with the sort of boss who though that a good 'punishment' was to restrict you to 60 hours for the week Or send you home for the day and have IT lock your account... in either case announcing it loudly so the whole team knows you're the reason they're going to fall further behind.
Sure, I got promoted around once a year and my salary jumped 10-15% per year without ever having to switch jobs. I learned a ton about enterprise software and architecture from real world experience. I went from zero to hero at my last job and became one of the most dependable people in my department in less than a year of working there.
But it took a heavy toll. I went through two wonderful relationships that turned sour from resentment. I worked 58-70hr weeks on average this year with no weekends for four months. The worst was a year ago when I worked 100hrs/wk for 5 weeks straight which led me to severe depression, a failed project, and a missed 10k bonus.
I never had energy to do side projects or anything else except play video games, which didn't counterbalance my work. I spent very little time on cultivating my relationship with my partner so being around them wasn't relaxing. I had ego issues even allowing myself to relax and give myself alone time because it wasn't time spent learning and growing. My life revolved around helping everyone but myself.
I turned down a 42k raise before I left my last job because I knew what the stakes were had I accepted it in exchange for staying. More money and accelerated experience won't give you a happy life. It will destroy it instead.
I finished my last consulting project a week ago and I'm just taking a few weeks to heal. No responsibility, no coding, no stress, no worry, no chip on my shoulder holding a club over my head. I meditate an hour a day now, which is very therapeutic, and I allow myself to play video games all day without judgement. It's time to celebrate me, and I'm loving it.
After I heal, it's time to start my own business. I'm tired of spending my valuable time and energy helping other people become rich while I clean up after every stupid political decision they make. People are way too aggressive on timelines and cost without understanding the consequences on the software and on the morale of their employees. I need to get out of the rat race and attain financial independence, which was my original goal before I worked so hard, I forgot where I was going.
But it did seem to go fast. Career wise I have progressed but I've always fantasied about doing the start-up thing. I've never even launched a proper (personal project) website
I don't know if I regret it though. I learned a lot and had cool experiences. Sometimes I think I needed to go through it to appreciate what I have now.
I will say though that I no longer have a huge desire to work at that "hot" startup. I've worked in one, and while it's cool to talk about at parties, it won't magically make you a happier person.
These days I'd much rather spend time after work with loved ones or tinkering on a silly hobby. I'm really glad I've been able to make peace with that. Like some of the people who posted here, I used to guilt trip myself for not spending every waking hour doing something "productive" - I now realize how toxic that mentality was.
TLDR: I worked a lot, learned a lot, and changed from it to hopefully live a more sustainable lifestyle in the future.