10 bets I made in my 20s & how they turned out

I read the quote “the best time to plant a tree was 20 years ago, the next best time is now” in my early 20s.

I took it to heart when I read it and seriously thought about what things that my 30-something year old self would be grateful for.

1. Solve self-love

I understood that being insecure and getting my sense of self-worth from outside opinions was a shaky foundation.

I internally bet  that solving this would probably pay dividends in terms my mental health, confidence, and ability to relate to people.

I was right. Still on of the best decisions I made in my 20s.

2. Understand money

In the grand scheme of life, I had a sense that that if I solved money, everything else would be easier. Money just accelerates your ability to do things and gives you more options.

The moment I understood this, I knew I had to act. I jumped into real estate for 4 years after that and learned pretty much everything I sought to learn.

In hindsight, it’s made my 30s SO much easier.

After 2 years of my 9-5, I bought my first rental property, and after that, I’ve just been shoveling my money into various investments. Goal is to retire in the next 7 years.

3. Understand meta learning

I had the sense that knowing how to get really good at learning would carry dividends for the rest of my life in pretty much every domain.

It’s basically been the engine behind how I’ve been able to reinvent myself 5 times in 13 years, doing wildly different things, and why I’m considering a political career.

4. Build a support network / community

After reinventing myself a couple times, my social network reset each time. So I knew that the next community I’d surround myself with had to be people who’d be willing to embrace all the versions of me.

I didn’t want to keep rebuilding my inner circle from scratch.

9 months and 200 coffee meetings later, i finally found my tribe.

Most of my inner circle friends have known me through 3 reinventions.

5. Optimize for learning, not money

It made sense to me that money was just a byproduct of having skills.

Skills were a direct byproduct of time invested in learning said skills.

It seemed logical that money followed skill, and therefore, money followed learning.

My very first 9-5 at the age of 29 paid me $90k.

I was able to raise hundreds of thousands for company I’m working on now because the accumulation of all my abilities over the previous 12 years.

I was broke for most of my 20s, but I’ve spent all of my 30s so far earning a comfortable amount.

6. Stay curious

Despite growing up in a Christian household (my mom threw my pokemon cards away because it was apparently demonic), I had learned to be open and curious.

I ended up becoming close friends with people who were gay.

I ended up learning about super alternative lifestyles.

I ended up trying psychedelics.

I've dabbled in a lot of things.

And those things more often than not enriched me in really meaningful ways.

7. Keep teaching and mentoring

For most of my 20s, I did this out of passion and personal conviction.

Only in my late 20s did I learn that teaching was actually the most effect way to learn. This basically supercharged #5.

8. Live with integrity

Simply put, this was learning to match my actions to my words. Follow through on my commitments. Communicate if it slips.

Also, this was just doing right by people.

Doing the right thing when you can get away with not doing that.

The payout for me has been 1) being proud of the life and decisions I’ve made 2) no time spent ruminating on times I’ve violated my conscience 3) a reputation for having integrity.

This actually accelerated #4 in the long run since people would vouch for me.

9. Be generous

I liked giving already. But for a while, I had to just trust that giving was somehow going to serve me in the long run.

My model of the average rich person was that they were an asshole. I thought you had to screw other people over in order to be successful (that’s  what I perceived purely based off of media).

It wasn’t until I read Give and Take where I finally had evidence that being a giver could be an advantage.

10. “Build and encourage”

A mentor told me this.

I took it to heart.

For most people I meet, I try to do this. I try to help them follow their dreams, I try to help them reach their goals, I try to leave them in a better place than before they met me.

Turns out, people like you when you support them.

And I eventually met a lot of people who would want to help me back because I helped them.

Many of them are my friends today.

Building and encouraging helped me achieve #4.