Well, I'll be an odd data point for you.
My life started with a crazy near-fatal illness, so that was risky enough, and its effects are still present in my life... it's not a risk I chose but it's here to stay. There's really no data on longevity or if I'll need more medical procedures in the future, so I get tested often. A few years back I had a massive blood clot and that was quite "exciting" as well. I think maybe in part because I do have this ever-present medical risk in my life, I'm kind of okay with everything else being a little quieter. I know really my luck has been extraordinary for me to be here and healthy and there's really no telling what the future could bring. So that's a very different feeling than quiet desperation. It's more like quiet gratitude.
As for my risks... I've always waited til the last minute to do anything but generally have excelled anyway. One gleeful time I didn't do an essay and they made me write it in class, and then it was chosen as the winning entry in a contest, so I got to lead a school ceremony. In middle school I made the cheerleading team even though I wasn't "popular", and I loved it. In high school I went on Adderall and that was conducive to a lot of adventures. I took the most academically rigorous program available, excelled, and then fucked off and ditched it because I got sick of spending every night writing multiple essays. I only applied to two colleges and only got into one. Against my parents' and doctor's wishes I took myself off my longterm maintenance medicine because I wanted to be able to thrive without it, and I did. I joined and eventually led an underground college group that secretly put on events for the joy of doing so, though we had to carefully skirt official procedure. I'm sure technically I could have been thrown out for that. I studied abroad in an usual location that included orienteering (getting dropped off in an unfamiliar forest in 20-below weather with only a compass and a map). I got lost at one point and had an incredible moment of lucidity, and I've never been afraid in a new location or being lost anywhere ever since. I blew a ton of money travelling. I experimented and found out you can take my little car up to 112 mph before it gets shaky. I told my boyfriend I loved him after only 3 months, poor kid. But I did. And we're still together. And I decided to go back to undergrad on my own dime recently.
I don't know how much you'd consider any of that "risky"... it's pretty tame... but no quiet desperation here. Poverty, frustration, impatience, fear, indecision, stress, and exhaustion. And probably far less daring than you were hoping to read about. But for me it's enough: meaning, and beauty, and joy, and life. I still want to travel more... I want to live in Asia for a while... I want to get married... I want to have a job helping people that I look forwards to... I want to get my SCUBA certification and yoga instructor certification... I want to own a really fast little sports car... I want to have kids and grandkids. I guess I'm not very good at seeing things in terms of risk and reward but I'm pretty good at seeing things in terms of letting my heart flow fully, and to me that's what matters.