It took a few years before I really decided to settle down, put down roots, and get married. When I decided to do it, though.. I went and did it immediately. I moved to a quieter, less expensive city, bought a house, a 20 year-old truck, and adopted a senior dog. My wife was the first person I dated in my new city, and she worked at the cafe closest to my office. She was probably one of the first people I met.
Fucking off in your 20s can be fun, but it can also be lonely and depressing and you're never immune from all the bullshit that makes life difficult... At some point in time, I decided that I would rather be scared than bored and based a lot of my choices around that particular value. And that's one of the trade-offs: A lot of things are not going to work out, a lot of plans are going to fall through. You have to be flexible. You're going to be on a financial tightrope sometimes. Things are easier being settled. But, having more to lose, I find myself more resistant to changes and more risk-averse.
The longer-term trade-offs are just financial and professional. I could have been investing more of my money, or bought a house earlier. Getting yourself to a higher level of income is fairly easy, but missing out on 5-10 years of professional experience is difficult to make up for and that has long-term financial side-effects.
The fact that things turned out okay for me probably has more to do with luck that I care to admit.
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.