excellent question. it's the 21st century reincarnation of "what is happiness?"

here's my recommendation, based on what worked out quite nicely for me. first, get paid. then, do what you like.

on getting paid

Naval recently said something like "trying to be happy without physical comforts is playing on hard mode." it's possible, but it's not any fun.

for example, friends are awesome, but once they're your roommate it sucks. and you need roommates if you make $50k /year in NYC. i know, because i once made $43k /year in NYC and lived with 4 girls in Brooklyn. then i moved in with 2 girls in Harlem. so i had to work nights and weekends just to pay my bills, which were > 60% of my monthly income. and that's not even the kicker: i had no skills and i was fat!

after teaching myself a bunch of stuff people are willing to pay for, i started getting paid. and every aspect of my life improved, except my sleep. but even that became a superpower, when i realized sleeping 8 hours a night is #fakenews.

on doing what you like

i wrote in another FAQ what it's like to have money. to save you a click, it's like the whole world becomes a buffet. but just like at the real buffet, if you consume too much you get sick. and you regret going up for that 7th plate.

everyone -- whether you're rich or poor or 37 or 12 -- has probably heard about the idea that "having X won't make you happy." and this is totally true. but what we also believe, each of us deep inside, is that "I am different." oh yes. unlike Robin Williams, i will be happy when i make it. i will love my life and tip waiters $1,000 just because. and maybe you will. but you probably won't.

so i think we all have to experience this for ourselves. we have to see the mountaintop before we can comfortably shrug off the anti-climactic view. you can't just hear about it by some washed up hollywood burnout.

on mutually exclusivity

i'd like to remain in the spirit of the question, which essentially assumes that when you work for someone else there is a trade-off of less personal fulfillment, more material fulfillment, and vice versa when you work alone.

this is often true, but not for the reasons you might think. it's not because "all bosses suck" and "all your ideas are so much better." it's because when we eat what we kill, the inherent risk itself is exhilerating. (for the right people). in fact your day job making $100k (theoretical) may be objectively more interesting, fulfilling, and contributory to world peace than anything you hack on in your basement.

BUT.

it's the ideas you make with your bare hands that you value the most. just like how your kid is the smartest, cutest, and going places. not those other kids. (whose parents feel the same)

mind the order

all this to say: you can't skip to the Enlighment Phase without first experiencing pain. you need the pain of "not enough," and you need the pain of "plenty but still not happy," before you can fully appreciate independence.

some other, more tactical benefits:

• when you're getting paid you learn about yourself, and you compound skills for later


• when you're on your own, you need every skill you can muster (see: suspension of reality) to compete


• when you're getting paid you can suppress the lack of freedom with your own apartment, booze, and nice things


• when you're on your own, safety nets feel good; "get your reps in" and be welcomed back anytime

fortunately, life is not about settling for the lesser of two evils. you can have resources and purpose at the same time.