🐧 17 life lessons I learned at 33

INSIDE: Living on 3 continents; career, health, relationships, and personal growth lessons

Today, you’ll learn in 10 minutes or less:

  • 🚀 How to discover your side hustle niche

  • ⚡️ Lessons on career, health, relationships, and personal growth from living 3 decades across 3 continents

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⚡️ 17 life lessons I learned at 33

I recently turned 33.

My reflection on this milestone is that life just keeps getting better in my 30’s. Whoever said your 30’s are “boring,” have it all wrong.

Although I typically write on money and business in this newsletter, I’ve received a lot of positive feedback about my writings on life in other venues. So I thought I’d give it a shot here.

Here’s 17 life lessons I’ve learned (one for every 2 years I’ve lived):

1/ The Universe doesn’t care at all about your accomplishments.

Like many high-achievers, ego is something that I’ve struggled with for most of my life.

I recall feeling pure bliss the day I got accepted into my Ivy League college. 1 week later, I was already hunting for the next achievement to unlock. This achievement-bliss-normalization cycle repeated itself throughout most of my 20’s—but achievement’s luster gradually faded.

Now in early 30’s, I feel more grounded in my pursuit of curiosity and autonomy. Even though I work more than ever as an entrepreneur, I’ve focused my energy and attention on the journey itself. This has helped me detach from ego and enjoy the process more.

2/ You can be just as grateful for pain as you can for joy.

I’ve learned the most about myself from moments of profound struggle. Competing in policy debate as an ill-resourced public school team against powerhouse private schools. Getting rejected after 70+ interviews. Managing early-stage products struggling against the brutal realities of the market.

In my 30’s, I have finally given more meaning to these moments of pain—irrespective of win or loss. I’ve learned resilience, heart, and tenacity. I’ve seen how I can go much longer and further than most people. And I owe this to the pain.

3/ Consistency is easy to talk about, but difficult to execute in practice.

In my 30’s, I’ve learned the secret to consistency. Here it is: To be consistent at 1 thing, it means you have to be inconsistent at 100 other things!

Being consistent at one thing is actually a trade-off of everything you decided not to be consistent at. By choosing to be consistent working on my business, writing this newsletter, and spending time with my wife, I’ve decided not to be consistent at climbing a career ladder, coding new AI products, meeting tons of new people, and 100’s of other things.

4/ You never know when it’s going to be the last conversation you have with someone.

In my 20’s, I didn’t give too much thought to the next time I’ll see my parents, grandparents or other close family members. Time seemed abundant.

Now that I’m in my 30’s, I’ve had several health scares from family members that got me feeling like time is scarce. For example, the window of time that I can spend with my parents is shrinking rapidly. One goal I have is to interview family member to one day share their life lessons and stories with the next generation.

5/ Choose your friends wisely. Watch out for those who don’t respect your time or needs.

Growing up as an only child, friends were like family. I’d spend a lot of time and effort to maintain friendships—even the far-flung ones or ones that weren’t always reciprocated.

In my 30’s, I’m much more focused on intent. If I can’t count on these friends in moments of need, then what role do these casual friendships play in my life? I’ve culled. This sounds stringent, but ironically, I feel like I’ve formed more genuine friendships in my 30’s than a decade ago.

6/ The best friendships are ones where you can grow together.

In my 20’s, friendships were about shared experiences and interests. Now in my 30’s, my favorite friendships are focused on helping each other other grow as husbands, friends, colleagues, leaders, athletes, and humans.

7/ Pick projects with asymmetric upside and margin of safety.

Potential upside and interest level were the main factors I used to use to decide on projects. In my 30’s, I’ve added margin of safety to the mix. The core idea: even if the project completely fails, you guarantee some form of outcome whether it’s money, skills, knowledge, and/or relationships.

8/ Identify the hidden rules of the game being played around you.

In my 20’s, I was still figuring out what game of life I was trying to play. As a result, I was more easily sucked into other peoples’ games and their criteria for winning. In my early 30’s, I’ve spent more time reflecting on what game of life I’m actually playing vs my peers. E.g. instead of climbing the career ladder to becoming a C-level exec, I’ve realized I’m pursuing my curiosity and independence instead. This has helped me feel more comfortable in my own skin. I’ve gained more courage to play by my own rules.

9/ Know when to play or fold your hand.

The flip side of being persistent is sometimes you’re barking up the wrong tree. When I was younger, I’d blindly work hard towards a goal long after others have given up. But sometimes there’s a good reason they’ve given up (rewards not that great). In my 30’s, I pause more to ask myself I should fold my hand, so I can play with better cards in the next round.

10/ Teaching is one of the best forms of learning.

One of my first managers taught me this lesson. But I really internalized this in the past few years, as I’ve grown into a manager, writer, and online course instructor. In these roles, I’ve had to learn how to teach knowledge and skills. Theory and frameworks are a start, but tangible examples and interactive exercises are crucial to put the knowledge into practice (but take the most time to prepare).

11/ Don't discount your emotion in favor of logic.

I learned this lesson in my mid-20’s, and it’s stuck with me since. Most of my internal struggle in my 20’s boiled down to the conflict between what’s logically “beneficial for me” vs emotionally “what I actually care about.”

For example, after Dropbox’s IPO’s, I started looking outward and received 2 dream job offers from top startups (both later had successful exits). But emotionally, I felt burned out and felt like now was the right time to pull the trigger on a life-long dream to travel across Asia, Europe and South America. After much internal debate, I chose the latter and haven’t looked back. Now that I’m in my 30’s, I feel like I’m viewing life through more of an intuitive lens.

12/ Dream big, start small.

In my early 20’s, I’d kick off new years by rattling off massive annual goals. But by the time December rolls around, I noticed I didn’t make any real progress towards these lofty targets.

Nowadays, I stick to writing down a handful of daily habits instead of listing several huge goals. Each habit must be actionable, so I can start doing it in week 1 of the year. This has helped me make heaps more progress in things like writing, staying active, climbing, and learning Spanish.

13/ Take advantage and get more out of your good days. Rest on bad days.

One thing that tripped me up about building good habits is feeling like I HAD to stick to a consistent daily routine. And feeling disappointed if I missed some days. Eventually, I realized this just wasn’t how my body worked—which operates on a cycle. Some days I feel incredibly creative and prolific. Other days I just want to chill, go for a walk, and watch Netflix.

Instead of fighting my body, I’ve learned to accept its rhythms and just try to get more out of the good days. This has made me feel a lot happier about my productivity in the long-run.

14/ Life is made up of multiple 5-7 year seasons. It’s a series of reinvention.

When I was younger, I saw my life more linearly. Like 1 long string of events that built on top of another. But by my 30’s, I’ve had exposure to people living all kinds of alternative lifestyles that are radical departures from their previous lives. And I admire them.

Now I view life as many seasons. Seasons give you permission to pursue something you’re deeply curious about—even if it’s very different from your prior life or career path. There’s still accumulation and growth from one season to the next, but it won’t look conventional. As Steve Jobs said, it’ll only make sense looking backwards.

15/ Let go of your anger, which distracts you from what truly matters.

In my teens, I was an angry kid. Even if I didn’t look it from the outside, I felt frustrated about a lot of things. Fortunately, I channeled a lot of this anger towards productive goals, like building websites on the internet, gaining admissions into a top college, and winning multiple scholarships.

With that said, anger sometimes led me to a victim mindset, instead of taking ownership of my life. That’s why I’ve worked on accepting and loving the angry parts of me. Through these efforts, I can now see my life more clearly from a 360 perspective. And hopefully make better decisions.

16/ Marrying the right person is an underrated life hack.

I got married in February 2023. What I didn’t realize when I was younger is how your life partner influences every dimension of your life. From supporting each other in our career goals to moving from Singapore to Mexico, having a life partner who is aligned with my life vision feels like my life expanding. As a a couple, new doors unlock. We can go places together, I couldn’t go alone.

17/ Sleep is the top priority, above all else.

When I was younger, I was an insomniac. Whether it was staying up all night playing Starcraft or finishing writing a paper, I developed bad sleep habits. This extended to college, where I continued pulling all-nighters in Baker-Berry Library, and my early 20’s, where I stayed out late socializing.

Now that I’m in my 30’s, I’ve been course correcting. Sleep is foundational to everything else in my life. The single biggest lever I can pull to feel more energized, positive, and motivated is by sleeping more.

🌐 Beyond your borders

🌏️ r/ExpatFIRE - What are your fire numbers outside of the US? (link)

🤑 Where you should put your money and when (link)

🇮🇹 Italy has finally launched a digital nomad visa – here’s how to apply (link)

🇪🇸 Spain to scupper 'golden visas' for foreign real estate investors (link)

👩‍🎨 27-year-old started a side hustle to get out of her ‘windowless office’—now her business brings in $25,000 a month (link)

🧰 Tool of the week

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📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

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