Seeking discomfort was totally worth it. Leaving my stable SF tech job to take a travel sabbatical in my late 20’s felt scary. But if I didn’t pull the trigger, I also wouldn’t have met my wife, moved to Singapore, and enriched my life with many priceless experiences. Leaning into my fears was the right move in retrospect.

Discovering what you really value is hard work. In my 20’s, hard work looked like grinding at the office until 9pm on a Monday night. In my 30’s, I now realize it’s even harder in some respects to do the inner work needed to clarify your guiding values. This has been a common theme with readers I spoke with recently.

Sometimes you need to discard old scripts to grow. One of the more painful parts about transitions is realizing that to move in the direction you want, it means giving up past narratives you told yourself. For example, scripts like “I’ll be happy when I get the next job offer / promotion.”

I’ve never regretted pursuing my curiosity. It reliably results in amazing memories, and I realized that what I ultimately care about is living an interesting life.

Life is a series of 5-10 year seasons. Earlier in my career, I put pressure on myself to map out my career like a strategic chess game. Now I’ve learned to let go of this expectation and just commit to the current season. This feels freeing.

0-to-1 is much harder than scaling IMO, but also more fun. What I’m doing now feels harder and higher stakes than anything I’ve done previously. But, I also feel very alive doing it. Like I’m leveraging every ounce of talent, skill, and network I possess—instead of using only 50% of my potential.

You’re probably not running enough small experiments. Looking back, most of the times when I waffled on whether or not to launch something new due to perfectionism, I could have saved myself the anxiety and just ran a small experiment.

Branding has more impact than I anticipated. By rebranding from Money Abroad to Portfolio Path, the energy in my conversations with readers feels noticeably different.

Build leverage for sustainability. Too often portfolio careers get treated as self-employment. But I think a better mentality is business ownership. I have seen too many friends burn out by doing everything themselves without leveraging team or technology.

I’m excited about community-led growth. Back in 2014, I was having growth team meetings with our VC partners (ex-growth execs at Facebook). Everything was about data. Today, many channels are getting saturated, so building community is what’s working (even Maven’s CEO just doubled down). I’d love to build more of this muscle at Portfolio Path.

Stay focused on durable growth. I’ve been tempted to tap into trendy topics for growth, but I know I shouldn’t get distracted. I’ve always admired how Japan has 33,000 businesses that are at least a century old. On the other hand, I also appreciate Silicon Valley’s culture of accepting failure to innovate and grow. My gut instinct tells to shoot for a mix of this experimentation and long-term thinking.

I see AI giving rise to more 10x non-technical workers. Every week, I’m challenging myself to implement a net new AI-based workflow. Content agents with Claude, AI-first automations with Lindy, and app development with Vercel V0 + Cursor + Supabase.

My dream for AI is to unlock more creative potential. Productivity aside, what I’m really psyched about AI’s generative potential from content to product design.

It’s not only early retirement/FIRE or bust - there are many options in between. After Business Insider published a feature on my Coast FIRE journey, a dozen friends reached out to talk about Coast FIRE. One friend mentioned how he was saving 50%+ of his income to achieve early retirement in the next 6-8 years. But then what? He wasn’t quite sure yet. After we chatted, he realized this is what he needed to figure out first.

Financial stability provides flexibility to make bigger career bets. On the flip side of the coin, I have seen just how powerful financial stability has been on my psyche. Immigrant mentality, perhaps. But knowing my household has a clear financial plan in place allows me to sleep much easier at night. And frees me up to take just a few more risks in career and business in my 30’s than I did in my 20’s.

My investing strategy has remained unchanged. My strategy since my 20’s has essentially been to earn more, live below your means, and invest the difference. While there’s a lot of fear in the markets right now, my strategy and asset allocation has stayed mostly the same. I continue to hold 65% equities — US (VTSAX, VOO + VXF) and non-US (VTIAX, VXUS) — 15% real estate, 15% cash, 5% high-risk/fun money.

Affordable childcare changes parents’ quality of life. Recently I’ve been thinking about how growing up, I saw my parents struggling to balance their careers and caring for a kid at home. They had no time to themselves. In contrast, when I lived in Singapore, I was shocked to see parent friends frequently going out with friends on weekends due to having an affordable live-in nanny watching over their infant.

Aside from childcare, health care and education present huge geoarbitrage opportunities. My wife and I started a 529/college fund, K-12 fund, and family fund to give our household greater optionality. But still I can’t shake off how much more affordable health care and education are in Australia vs the US. To give you a taste, my wife’s Aussie university tuition was $9k/year vs my $42k/year.

Tax optimization makes a big difference as an American. The US tax system is complex, but using strategies like 401ks, Roth IRAs, backdoors, and Foreign Earned Income Exclusion can help save you hundreds of thousands of dollars of taxes. On the other hand, when I filed taxes in Singapore, it took 10 minutes. Yet the tax optimizations pale in comparison to the ones in the US.

The right partner changes your life. Life as a whole goes from a single-player into a multi-player game. To being a team. When either of you win, it’s an opportunity to celebrate together. And when things go wrong, you get to commiserate or laugh about it with someone—instead of sulking alone.

Yet I don’t have any magical recipe for finding a partner. Meeting my wife at a hostel in Singapore was lucky. I don’t have much useful dating wisdom for single friends aside from fully expressing your values as much as possible because you never know when you run into someone that shares your values.

After 2 years, married life itself hasn’t felt vastly different. Caveat: We don’t have kids yet. The biggest change has been feeling a stronger sense of responsibility about planning for our household future.

Friendships ebb and flow, but treasure the ones that grow with you. Recently, I’ve reconnected with friends I lost touch with for a decade as we discovered we’re entrepreneurs on a similar path. It feels like we’re growing together which has been really enjoyable.

You can build a community anywhere. I have lots of friends who express fears of having to start over with making friends when moving to a new city. I used to agree, but I’ve changed my mind. It’s not been THAT hard to make new friends in a new city and keep old ones as long as both parties prioritize the friendship.

There’s something special about friends you make in your formative years. It’s been really cool to see how my closest friends from SF in my early 20’s and I have shared a strong bond despite having lived in totally disparate places since then.

Traveling together is my favorite way of staying in touch with old friends. Many of my close friends are scattered across the world. So taking an annual trip together has been a great way to make unique memories that we can look back on.

Happiness starts from within. I used to struggle with victim mindset and it took a lot of work to feel more accountable over own emotions. Pursuing uncertainty is a lot harder if you can’t find an intrinsic source of joy and fulfillment along the way.

Good sleep has been my biggest lever for quality of life. For most of my life, I struggled with quality sleep. This year, I made a much bigger effort, and it’s been working. I can’t express enough that 7 hours per night has made a huge difference on my daily mood, creative thinking, and ability to be present with loved ones.

I tried out functional health testing and liked it. I’ve done two biometrics tests through Function Health and the lab results have been insightful. I already made a few dietary changes in my daily life. A coaching component would make this even more powerful.

Adapt your schedule to your energy rhythm. In my 20’s, I clung to rigorous time blocks to try to tame my wild calendar. In my 30’s, I’ve learned how to double down when I’m feeling energized and cut my losses when I’m not. I like this approach to planning my day way better.

Lakes, mountains, and forests are my oasis. I’ve learned I’m just not much of a beach guy. Instead, I feel the most at peace and joyful at a lakeside cabin or resort framed by a mountain backdrop.

Learning languages is like cognitive traveling. By learning Spanish, it kind of feels like unfogging a new part of the game map. It completely changes my understanding of how to navigate a new territory of my brain.

The older I get, the more I learn from kids. Lately, I have been looking around for good role models for curiosity—and gravitate more towards kids than adults. Their innate wonder and appreciation feels like a huge unlock if you can retain this mindset into your 60’s.

Having fun is the best intrinsic motivation. I have been loving bouldering because it’s just about having good fun, not to achieve a fitness level. As a chronic overachiever, I realize that sometimes I can do a better job at applying this mindset to other parts of my life too.