The Social Bet I Made in my 20s

This one was a game-changer.

Feb 07, 2021

This is part 2 of 5 of a series called “Why Relationships Matter.”
In case you missed it, here’s part 1.

There’s a saying that goes:

If you want to go fast, go alone.
If you want to go far, go together.

I didn’t always operate with this belief, but when I realized how important relationships were to me, it made me prioritize it in a way that forever changed my life trajectory.

It made me want to find my “tribe” -- people who “got” me, what I was about, supported me, encouraged me, and celebrated me. I didn’t want to “settle” when it came to something so important so I was willing to go to great lengths to meet the right people.

A few things that I did as a result:

Flew to NYC 5x, just for an evening event (arrived in the afternoon, took the last flight out)
Maintained a spreadsheet of 120 people I had meaningful conversations with in the span of 16 months
Attended the same conference 6x because I consistently met great people there
Bought a last minute ticket to D.C. for a dinner event (and flew back the next morning)
Went to a week-long retreat in Nevis to meet 20 other entrepreneurs, most of which I had only known via Facebook
Stayed up until 3am every Tuesday for 3-4 months to connect with people I met at One Salon
Hosted/co-hosted multiple Friendsgivings, BBQs, dinners for 30-80 people
I paid $50/month to be a part of a nerdy personal development community

And I did all of this as an introvert!

I often had to sleep 10 hours the day(s) after in order to recuperate.

I did all that… what for? What did I get out of it?

Here’s a non-exhaustive list of the ways that the people I’ve met during those years have made an impact on my life:

Skill sharing
- I lived with Ryan who was a prolific writer and also graphic designer. He helped me build and maintain my first website, my blog got 100k views/year, partly due to cross promotion and his technical support.
- My friend Kim Nicol introduced me to mindfulness/meditation about 6-7 years ago. She made it incredibly approachable and concrete. My experience of her flavor of mindfulness is a large reason why I continued to explore and investigate it.
- Kim/Teresa/Christina walked me back into the world of emotions -- I wrote about it extensively here
Co-learning/working
- Ryan/Dennis and I co-led a church community for 2 years, learned together and traveled together to teach/speak about Christianity
- Kim Han/Nick and I met weekly for 8 months to read 15 Commitments of Conscious Leadership and to support each other as peers in our growth in feeling our feelings, taking responsibility, and staying “above the line.”
- I’ve gone on multiple writing retreats with friends, just to write and hang out.
- I started co-writing every Tuesday with Candace 2 years ago -- still runs to this day
- I’ve done weekly peer coaching with various friends (up to 5 at one point) for the last 4 years
Content discovery
- Norman introduced me to Touchy Feely, which I attended two weekends of, both of which were instrumental in my journey with emotions. I also learned about Gottman’s research as a result.
- Madison introduced me to Esther Perel who is a marriage and family therapist that I’m a huge fan of that shapes my approach to relationships
- Norman, Chloe, and Candace were instrumental in helping me discover and label the idea of “co-life”
Projects
- Living with Ryan/Dennis helped me soundboard and bounce ideas around and that supercharged my YouTube channel, directly informing many of the 100+ videos I published (9 million views, to date)
- Orenda Academy was founded by Carl and I. Carl’s prior work and relationships helped bring on 3 part time coaches, our initial prototype cohort (which was promising enough for me to dive into it full time), and eventually our intern.
- Parent Project is a direct result of being in a weekly pod with Kim, Joe, and Tong-Tong.
- My Zone of Genius project is a result of Kim inviting me to do a book study club with her and others
Career:
- I learned about Fortune Builders because of a friend -- that was responsible for jump-starting my house-flipping career.
- I met the founders of Searchlight.ai (where I now work) because of an introduction because of our work at Orenda Academy
- Madison introduced me to Carl, my co-founder for Orenda
- I ended up being a part-time facilitator at MissionU (acquired by WeWork) because Norman was an employee there.
Romance:
- I met my first ex because she was hoping to interview me -- I happened to be in LA for a conference, so I offered to meet in person.
- I met my second ex because Norman brought her to a Friendsgiving event I was hosting

Nearly every friendship was developed because I was proactively leaning in to foster the relationship. Introductions were fantastic — it accelerated a lot of things, but it still took deliberate effort to foster depth.

Nearly every big career decision I made was shaped, informed by, or was made available because of those friendships.

Nearly every significant project I’ve worked on was informed by, supported by, or created with friends.

Nearly every major personal transformation was catalyzed or supported by friends.

It’s really hard to overstate how much of an impact friends have had on me.

I made this “bet” on the value of friendships in my life when I was 21 -- the fruits have been phenomenal.

Here’s some icing.

You may have heard of “The Happiness Study” that started in 1938 (that still runs to this day). There’s a TED talk of it’s core findings and a book written by one of its directors, but I’ll give you the 1-liner:

Close/warm relationships with family, friends, and community are the #1 predictor of good physical/mental health, financial wealth, and longevity.

I read the book when I was 27 and it just made me double down on my bet, and now I’m as bullish as ever.

Of course, if you’re looking for tactics (e.g. how do I find my own “tribe”?) you can find a tactical breakdown here.

Relationships have mattered in nearly every vertical in my life and it’s also been the source of a lot of meaning, gratification, and fulfillment. Don’t neglect it!

What resonated with you? What questions come up for you?

Musings, Reflections, and Life Lessons

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