Taking risks in your 20s

[WonderSeeker]

A risk is decisive action toward a personal desire in the face of incomplete understanding. —Yours Truly

I'm 28. After having spent the last 4 years taking tons of risks far beyond my comfort zone, I can say the following.

You're damned if you do, damned if you don't. BUT...

It's much easier to take risks in your 20s than in your 30s. And it's easier to do so in your 30s than in your 40s. And 40s than 50s. And so on.

I know this from having chatted with dozens of men and women in their late 30s and beyond, when I was into pickup and when I was an Uber driver. Having children, settling in one location, aging parents, and other responsibilities all potentially make it challenging to take risks.

Also, as you age you gain experience, regardless of whether you attempt to consciously accelerate your results at a young age so you can make room for self-actualization and spiritual realization.

Therefore, the same risk for a 20-year old isn't as "risky" for a 30-year old in theory. The 30-year old should choose something he/she is more worthy of. 

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For me personally, I've moved cities 5 times and moved countries twice in the past 4 years. I've tried 8 different jobs, including commission based sales and my own online business. I've also approached over 400 women in a 2-year span, and spoken to 7,000+ people in general in a 4-year span.

The businesses failed and I lost thousands of dollars (while already 60k in college debt). The first couple cities I moved to I absolutely hated. The women I dated were terrible matches that I should have known weren't right. But from that expansion and exploration I learned invaluable things about myself and the world.

I was damned because I DID. And yet I would not dare go back and change any of it. 

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But... Here's the thing I don't get:

How do you tell a wise risk from a fool's risk? I am done taking fool's risks because I am older and wise enough to see there's a difference. Yet, I don't know what that line actually is. I presume it's outcome-based, or probability based. Or maybe even gut-feeling based. (To be honest I'm speculating).

Right now in my life I'm making steady progress. My income is solid and allowing me to pay off debts faster than ever. I'm creating increasingly honest relationships and friendships. And finally after moving around ever 6-12 months, I am living somewhere I could see myself for the next 3-5 years. All with more ease than the grinding risks I took before.

Relative to the short-but-explosive progress I had in years past, this is more slow and stable. It feels more right and honest. But it is slow, and a part of me wants to take more risks — albeit intelligent ones — as I'm still very young and determined.

How do you know the difference and is it best to build slow and steady safely rather than quick bursts? Relative to what I had before it's better. But slow too.

Edited 15 minutes ago by WonderSeeker