I am a pretty lame guy and always have been. I'm fairly okay with that. Mostly keep to myself and do my own thing. But, I know myself and I know I'll regret not having lived some crazy life when I was younger as my knees start to ache more, I have commitments/responsibilities, and I can't push as hard as I can now.
I can't tell if I've lived an exciting enough life to be content, but I'm fairly sure the answer is I haven't. I've been to raves and parties, experienced heartbreak, and done some dumb things in my time. But I've barely traveled, only dated/kissed/slept with one woman, have never had a particularly strong friend group, spend most of my days in the corporate grind, and have kept fairly clean aside from excessive alcohol and caffeine use.
In a couple of years I'll likely have golden handcuffs with my job, I have a startup with some employees I'm responsible for, and in a couple of years I'll likely own land. I feel like I'm focusing so much of my time on locking down stability so I can do the wild things I want to do (party in Ibiza, find love in Morocco, drive recklessly through Monaco, blow something up on my land, have a romantic getaway with a stranger in Cancún, build a home with my own two hands, etc.) that I'll be in my mid 30s by the time I'm able to do them. Nothing wrong with mid 30s, but at the rate I burn myself I'll be lucky to still be moving moderately nimbly.
All of my grandparents were exceptionally poor. My parents worked extremely hard to make us middle class. The vast majority of our ancestors were average or poor. I am dead set on establishing something future generations can benefit from. Use trusts and investment vehicles to ensure my sister's children (I think I've given up on wanting children) will have resources to blaze their own trail. I don't need to be a billionaire, but it is going to take some money. The kind of money you only make through hard work when you're young if you're not well connected.
So, that's the situation. I am committed to working hard to create a pool of resources for future generations. But, I'm also keenly aware that I will look back on these years and regret not having lived to the fullest. Simultaneously, there is a bit of a Catch 22 where some level of money/savings is needed to fund that reckless lifestyle. All the while I am rapidly approaching an age where I'm not sure all of those experiences will be achievable for me anymore.