> life advice
Can't help you with this; I'll just say life is a lot more than your job. So any "life advice" would be unrelated to being a software engineer or whatever.
> helping people by writing software
"Software" itself is just kind of like a building material; there's a very large number of ways you can apply it and things you can build with it. If you're more interested in "doing something meaningful/useful by writing software" than in "writing software to do something meaningful/useful", then you'll have to change the perspective a bit and actively look for it.
> happy
I wouldn't really know. Maybe the instances where I found something I wrote being used and liked by a user and being helpful to them, even if in a small way.
There have also been a couple of times where I built something which had some element of "fun" in the code itself. These do bring a certain happiness, but it's temporary, usually brief, and looking back it tends to sound silly and pointless. Some silliness and inconsequential fun is probably very good for your life, but it won't provide long term satisfaction on its own.
> regret
Yeah, some. But don't let regrets guide your life. They'll make you miserable.
I actually want to reflect the question back to you. I am a 27 y/o wanna-be software developer. Getting ready to start college for a CS degree. Is there any advice YOU have for ME?
You've worked for startups and found issues. I've worked for three startups and concur - you work yourself to death chasing "the dream" that you realize is just a lottery ticket. The ones with the winning ticket then yammer on about "meritocracy." It's utter bullshit, as you've undoubtedly discovered.
You've worked for the "big names" and found disaster. Been there, done that, too! The problem with large companies is your voice gets drowned out. There's very little you can do to effect change. You're just pushing paper. Not very fulfilling.
I've been happiest at midsize companies. There's no single definition of "midsize" but here's a useful definition: they're big enough to be a serious contender in their market, but they're not the dominant player in their market. Those companies tend to provide the financial security of the "big names", yet want to hear your voice and your ideas as to how they can become the dominant player in their market. Best of both worlds kind of deal.
As far as creating software goes, I've been happiest in product development. Your software is part of a solution being sold to a client. A lot of engineering-oriented companies provide those kinds of opportunities and tend to have an engineering culture.
As far as making your own product, remember, people don't buy software - they buy solutions. If you can't succinctly identify your customer's problem, then they won't believe you have the solution. Period.
For others reading this, here's something else you should know from someone who's had a loooong career in this field: when the MBAs take over management, it's time to go. I know, I know, I'm painting with a broad brush BUT my experience has been, time and again, when they show up to your company your company is likely doomed. I've seen way too many companies doing just fine until the MBAs showed up. Just look at what's going on over at Boeing now. They're just one example of thousands.
I'm not that much older (turned 40 recently), but my happiness in life comes from:
* Having an amazing partner who is kind, supportive, trustworthy and fun to be around. We don't have kids but raise a cat together.
* Having hobbies outside of work that intrinsically motivate me and bring joy. For me this is muay thai (kickboxing), bicycling, hiking, camping, kayaking, board games, singing, and trivia. Some of it I do alone, others I do with friends, but they bring relief through the week and give me something to look forward to after work.
* Working in small to medium-sized values-aligned organizations. For me this is the environmental & renewables field; for you it could be something entirely different. But it makes SO much difference to go to work in a place where people are passionate about the job because they believe in the cause, not just to pick up a paycheck.
* Working in an office environment and getting to know your coworkers. This isn't for everyone, obviously, especially if you're an introverted remote worker. But it's made a HUGE difference in quality of life for me and I wouldn't choose to work fully remote even if I could. (I actually have a remote job right now, but I don't like that part of it... wish I could meet the team in person).
* In general, treating people well, balancing their needs with yours respectfully but honestly. Little extra doses of kindness go a long way. As a result I have some close friends and many acquaintances whom I enjoy spending time with, whether it's coding together or playing a game or grabbing a beer.
* I've been programming for like more than 30 years (started as a kid) but that was never really my passion in and of itself, just a means to an end (a paycheck, yes, but also the ability to support causes I care about). It's just a thing that I do, not the thing that defines me, and so my happiness doesn't have to depend on it. I'm not even a very good programmer, just an average one who can communicate with clients & teams well.
* Trying new things every so often. That could be traveling to a new place, learning about a new culture (whether abroad or domestically, like one of the subcultures around you), learning new non-tech skills (makerspaces and meetups are great for this), taking classes at community colleges, watching documentaries, reading books, etc.
* Forget regrets. Learn from your mistakes and choose better paths, sure, but don't dwell on would've-could'ves. After a while, your life becomes full enough you won't even have the mental capacity to remember the regrets, much less the time to sulk about them.
In general, anything EXCEPT chasing riches. I think the traditional "American Dream" is kinda nightmarish and can lead to unbalanced lives and fragmented communities. It's better, IMO, to make just enough money to sustain your needs and spend the rest of your time and energy with the people, activities, and places that you love. If you don't have those in your life, find them! You have to cultivate hobbies/passions and relationships both; they don't just magically appear out of nowhere.
I'm not that older than you, but I decided to do stuff that I want instead of doing stuff that are good for me.
> what makes you happy the most looking back?
Saving money, "retiring" at the age of 30, traveling for 2 years, entering a monastery, leaving the monastery, and then starting to think about work again for real, not just as a way to escape the system.
BTW. After 3.5 years of retirement, I finally grow up to start something myself, which is an idea that was hunting me since teen years.