Heyo! I’m back with this month’s issue of Tam’s Jam: my curated collection of resources and lessons around living a meaningful life.

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I just got back from Mexico City after a 10-week trip and I loved my experience. I'm back in LA with family and will be in the Bay Area next week.

In this issue: Accelerating personal breakthroughs, creating your guiding questions, making friends in business, climbing mountains that don’t exist and more. Vamos!

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How to accelerate personal breakthroughs

I embarked on my first solo international trip nearly five years ago.

Cape Town. Mexico. Atlanta. Austin. Chiang Mai. Vietnam. Toronto.

As I stepped into the airport with a one-way ticket, I thought I’d achieved my dream.

See five years before that, I had dropped out of college to work directly for startups.

To get a “real-world education.”

As a young and ambitious kid with a chip on his shoulder, I was a dream employee.

• I took on responsibilities that everyone avoided.
• I said yes to opportunities, even if I didn’t know how to do them yet.
• I took pride in being the first one in the office and the last one to leave. (Thanks Kobe) 💜💛

Since my whole life centered around my career, I quickly climbed the ladder.

I went from doing free work for years to earning a real full-time living.

I met authors and podcasters who were my biggest inspirations in entrepreneurship. Some later became my clients.

I finally had enough income and confidence to try this famous digital nomad life.

As the plane took off, I didn’t realize how little I knew about myself and the world.

The thing was that since I was so focused on work, I didn’t live any of the normal experiences that most kids had in their early 20s.

• I didn’t go on dates or go to parties.
• I’ve never traveled except for business conferences or networking purposes.
• All my friends and colleagues were at least 5 years older than me, but usually 10 or 15 years.

I even refused to listen to music because it would be more productive to listen to podcasts at 2x speed.

Yes, I know. I was a freak. 🙈

This trip was the first adventure where I could rewind and do “kid” stuff. And I’m so glad I went!!

• I tried new activities for the first time like surfing, acro-yoga and Thai massage.
• I downloaded dating apps for the first time and faced my fears to go on dates.
• I adventured with new friends to visit farmer markets, temples, pyramids, waterfalls, clubs.

Most importantly, I met amazing humans who were living vastly different lives than me.

They didn’t care what I did for work.

In fact, they didn’t care about work half as much as my little tech bubble did.

For the first time in my life, I realized that there may be more to life than my career.

When I wasn’t out and about, I had so much time to be by myself and think.

• What would life look like if work didn’t come first?
• What are some of the things I’ve always wanted to do but haven’t yet?
• Why am I working so hard in the first place? What are my true motivations?

Silly and useless philosophical questions like these. 😜

After I came back from my travels, I made the bold decision to sunset all my consulting clients.

I had worked so hard to climb up to the top of my ladder once to realize this wasn’t the path I wanted to continue on.

What path did I want to take? I didn’t know.

But that’s ok.

What was more important was saying no to the things I knew I didn’t want.  Then I could figure out the rest on the way.

I would have never guessed what unfolded next:

• I took a sabbatical where I studied and competed competitively in chess for 7 months. One of the top 5 experiences of my life. ♜
• I nervously took my first Bachata class (like a more sensual dance style of Salsa) as a 2019 new years resolution and stuck with it. I’ve met some of my closest friends through Latin dance. 🕺
• I stumbled upon a dream job opportunity in Toronto to dive deeper into community building and live in a brand new country. It was the perfect “next chapter” for me that has definitively shaped my 20s. 🍁

I’ve definitely chilled out over the years and have been happier ever since.

But I wouldn’t have made any of these changes without going on my first solo trip.

How to know if you’re on the right track

As humans, we tend to assume we are always on the right track.

But when we have an ample amount of time to ourselves, it gives us an opportunity to reflect and think.

Am I actually on the right track?

Whether it’s a day to yourself in nature, a solo adventure, or the pandemic forcing us to be indoors, many people slowly started to realize the path they’re on is not where they want to be.

Hence major life changes for millions of people in the last two years: the great resignation, romantic breakups, or moving out of their cities to a completely new place.

Here’s an equation I made up to make sense of the world:

Solo Time + New Perspectives = Personal Breakthroughs

Unless you completely hit "rock bottom," we don't often have aha moments when we are so busy in the grind. While traveling to Thailand and hiking a mountain to discover your life purpose can be a cliche, there is some truth behind why people actually have personal breakthroughs.

I'm not a huge fan of Tony Robbins' full-day personal growth workshop. But I can't deny his Date with Destiny events are effective for certain people (His Netflix documentary is a great watch).

I believe it has less to do with Tony Robbins himself but more around the fact that people have put aside an entire weekend for solo time plus being in a room with attendees from all backgrounds gives them new perspectives.

Of course, this equation is only useful if you take action and experiment with your personal breakthroughs.

What are your guiding questions?

I assumed smart people had this life thing figured out. So I’d simply copy how they lived their lives and be happy.

For example, some people make their life decisions based on inspiring questions like these:

1. How can I impact the most amount of people in this world? (Inspired by Effective Altruism)
2. What choices can you make today that minimize the regret you'll feel as an 80-year-old looking back on your life? (Inspired by Jeff Bezos)
3. What legacy do I want to leave behind? (Inspired by the entire Self-Help genre)

In my early 20s, I wanted to live my life by these questions to feel smarter, cooler, or more altruistic.

But every time I did, I felt like I was doing things to sell an image of myself that wasn’t actually me.

If you’re like me, you might have done something like this too.

So I had to ask myself the hard question:

How would I want to live my life if I was being truly honest with myself?

I’ve had a long think before coming up with my own set of guiding questions:

1. Am I learning?
2. Am I having fun?
3. Do I feel connected to the people around me?

That’s basically it! 😁

Of course, I want to help others, make money, and have power.

But if I was being brutally honest with myself, those are not my main motivations (at least for now).

For you, it could be about money. Or family. Or building things. Or social justice. Or always being creative.

Whatever it is, be honest with yourself and own it.

Don’t judge yourself because it’s different than mine or Jeff Bezos or Mother Theresa.

Be wholeheartedly you.

Sure, things could change and you’ll need to update your set of guiding questions.

That’s life!!

Life would be atrociously boring if everyone knew their paths at birth and we just checked off the boxes like robots.

Seek new experiences. Put yourself outside of your comfort zone. Be open to changing your mind. Spend time solo. Ask yourself the hard questions.

Steve Jobs has a famous saying,

“You can’t connect the dots looking forward. You can only connect the dots looking back.”

You don’t know how your decisions will play out in the grand scheme of your life. It’ll only make sense once you do the things and reflect back.

I wouldn’t have the clarity I have now without going through all of my life experiences. I’m sure you wouldn’t either.

But what do I know?

Be the judge for yourself.

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What I’m reading/watching

💸 The First Million podcast episode #123 (Audio - Spotify) — My old boss, Sam Parr who founded and sold The Hustle, shared a funny story about me being super cringe and dorky when I first started my career at 19. People send me this clip every once in a while and it’s always entertaining to listen to. Start at the 57:45 mark.

📈 Inflation and the cost of every day items (/r/dataisbeautiful) — A beautiful visualization of the rising costs of goods in just the last two years. What should we do about it? My most recent essay explores potential solutions along with what I’m personally doing.

⛰ That Mountain You’ve Been Climbing Doesn’t Exist (Article - Steven Schlafman) — “The real work is not in the climb someone else or society set you up for, but in becoming who you truly are in every moment. If you understand yourself only in relation to a series of false summits, you don’t understand yourself. The sooner you realize this the sooner you can begin to live your life on your own terms and enjoy the freefall. When you recognize this you’ll know you are perfect just where you are—in mid air, with the rest of us.”

🚸 Whose Child Will You Choose To Be? (Article - The Daily Stoic) — While we cannot choose our parents, “we can choose whose children we would like to be.” As someone who had to grow up without the unconditional support of my parents, this piece really resonated with me.

🇲🇽 MEXICO: Dangerous, or Magical? (YouTube - Van Neistat) — A superb video essay on what makes Mexico amazing. My favorite quote from the video, “There’s a saying in Mexico where ‘In the United States, everything works but nothing works out. But in Mexico, nothing works and everything works out.” I would also add something along the lines of, “In the U.S., we have more than enough and no one is satisfied. In Mexico, we have just enough, oftentimes less than enough, and we are content.”

💜 SURPRISING FRIENDS and FAMILY after 3 YEARS (YouTube - Ahrièn Azodi) — A compilation of the most heartfelt and authentic reactions to his surprise return back home. I legit teared up watching this. If I had to choose between a million bucks or having the relationships he has with his friends and family, I’d choose the latter any day of the week.

👭 Make friends, not contacts (Article - Hustle Fund VC) — I got a new writing job helping 13,000+ first-time founders grow their businesses! This topic is near and dear to my heart (and I also wrote a book about it): making friends in business!

👶Parents of Twitter: What are the best centralized resources with checklists of what any prospective parent should start thinking about from trying -> pregnancy -> early child-rearing? (Twitter) — This thread is a gold mine for soon-to-be parents!

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Tweets of the month

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🙂 Before you go

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Thanks for reading! See you again next month.

With gratitude,

Tam