[JonFish85]

As others have said, it all depends on what you define "success" as. Clearly the OP has done things that fulfill him.

Although the OP makes no mention of it, when I've talked with friends & family about "success" and all that, following dreams is great. One big thing to keep in mind is that the future is also uncertain. Retirement is the biggest thing that comes to mind. I have many friends who have foregone saving for retirement in order to follow their dreams, no matter how "irrational" that may be (I use quotes because that might not be the right term).

20, 30, 40 years down the road, who is going to be paying for retirement? It's great that "you" have memories of doing great things! But the bills have to be paid. Is it going to be your friends, who worked those boring, monotonous jobs? Will their 401k accounts be taxed so that they have to pay for your retirement? Will mine?

What about kids? I have family members who did follow their dreams to do whatever it is they want to do, and then start having kids. Without a solid job, boring or not, someone has to pay for the kids. Either it's charity from family, or it's the government via taxes.

Anyways, that's some things that I think about when these topics come up.

[jonnathanson]

A critical issue in "following dreams" is the way in which people do it. Case in point: I have two close friends who decided to become poets. Not "poets" in the colloquial sense, i.e., liberal arts majors with no quant skills. Poets, as in people who hope to earn a living writing poetry.

One of those friends has been writing poetry her whole life, has become phenomenal at it, got into the Iowa Writers Workshop, has been published in the New Yorker on multiple occasions, and earns a respectable living in academia. The other abruptly quit his day job at the age of 33, declared himself a poet, and enrolled in some beginner's classes. I support his dreams, but I do not support the order in which he took those actions.

People often forget that chasing "dreams" is hard work, and it follows the same principles as chasing success by more conventional means. In fact, the less conventional of a career you chose, the more conventionally hard you'll have to work to make that career remunerative. Following your passion is a wonderful thing, but you need to do it sensibly, strategically, and skillfully.

[gutnor]

That's what's keep people in those "boring" jobs rather than taking risk when they are around 30-ish.

That's a great misconception about the social net. It is considered a socialist idea, but really it has its place in capitalism too. Knowing that you do not risk being in the street with health cover for you, your wife, your kids and dependents is a great relief that stimulate people starting new businesses.

Obviously the downside is that other more (money-)conservative people will have to pay in taxes. However, that's a political scapegoat. The real reason why people complain they are being taxed to pay the lifestyle of others is mainly because middle class is slowly disappearing. They are getting poorer, an other people lifestyle is hastening that process, however not causing it.