Hey portfolio pathers,

In the past few weeks, I’ve been chatting with dozens of readers who are navigating career transitions in tech, consulting, and beyond.

As a 34-year-old who has worked with tech companies big and small across 3 continents, I penned down a few of my thoughts.

Let’s dive in.

SPONSORED

To get your brand in front of 7k+ professionals and entrepreneurs, fill this out and let's chat.

🌎️ 7 lessons from my global product career

Over the past 12 years, I’ve worked across Silicon Valley, Southeast Asia, and Latin America.

Each move forced me to “start over” in some respects.

Each region taught me profound lessons about building products and businesses, but also about navigating career and life.

Here are 7 career and life lessons I learned along this journey:

1/ Forget about being right; instead embrace being curious

In San Francisco, I was obsessed about making so-called “right” decisions in my tech career.

Every product decision needed to be informed by hard data. Every rollout required statistically significant results. Every career move had to be consulted with successful senior peers.

But after moving abroad, I realized just how much I didn’t know about the world, different markets, and how rapidly things change in these markets.

While the toolkit I learned in Silicon Valley was very useful, I had to let go of many assumptions to be effective in my new surroundings. And lean into being being curious about “why” things worked the way they did.

In the AI era, I’m applying a similar lens. I think of entering the AI market like moving to a new geography where you’re surrounded by new incentives/dynamics, cultural norms, etc. And since things change rapidly, it feels like moving countries every 3-6 months.

2/ Climb the right mountain (even if it means starting over)

In my product work, I often ran into debates of local vs global maximums. For example, do you milk the short-term profit of your existing cash cow vs investing in long-term bets to expand your addressable market?

The challenge with applying this idea to our personal growth is it feels cognitively easier to keep climbing the mountain you’re on right now (even if you know it’s the wrong one).

Instead, searching for the right mountain is a messy, intuitive discovery process. It often feels like starting over.

After 5 years of climbing the finance ladder, Shao Chen took a 60% pay cut to transition to tech. Yet he ended up thriving on this career path.

When I left SF to take a travel sabbatical, I didn’t know I wanted to build my tech career in Singapore. But by spending time in the region, I felt a gut instinct that this was where I wanted to be. This turned out to be the right move.

3/ It’s not about a bigger number, but about deeper alignment

In my 30’s, I now have several friends who chased the biggest salaries, but ended up miserable and giving it up. Why?

They admitted that pursuing the money wasn’t giving them the meaning and direction they wanted.

Yet the hard part of establishing meaning is this requires some degree of inner clarity. Otherwise you end up falling into a deferred life plan.

If you don’t know what you value, how do you bring more of it into your life?

This begs the question: how do you figure out what you value? Enter the next lesson…

4/ Make small bets regularly (aka always be experimenting)

Plenty has been written about experiments for market validation and growth. But this approach applies to how we do the inner work too IMO.

Before I decided to build a product team, I tested the hypothesis of whether or not I enjoyed managing people. Before I started this newsletter, I tried small writing experiments to see if I’d like it. (turns out I did and here we are over 120 editions later)

The reality is the chasm between thinking vs doing is a massive one.

While I appreciate clear thinking, it doesn’t cut it alone. I’m always asking myself: “How can I test this out with a small experiment?”

5/ New markets demand generalist skills

When I worked in Indonesia, I realized that new or emerging markets demand a completely different way of operating vs mature markets:

• I had to create playbooks from scratch, instead of following existing ones.

• I couldn’t “just be a PM.” I had to get comfortable wearing sales, partnerships, tax, ops, legal, compliance to get the job done. This felt like a big stretch at first.

• I had to connect the dots and get creative, especially when building products in categories where there weren’t clear models to follow.

Similar skills are demanded in the AI era. My friend Ines Lee recently wrote a great piece about how she’s complementing deep expertise with broader cross-functional skillsets to adapt to the reshuffling of tasks in jobs:

6/ Create leverage in your time and energy

This might be the most important lesson I’ve learned as I transitioned from full-time work to entrepreneur.

Time and energy have typically been my biggest bottlenecks to growth. Capital sometimes as well (e.g. to hire staff).

To solve this, I’ve been spinning up a host of AI agents, automations, and human systems. Of course, I’m trying not to overbuild (potentially a huge waste of time), but this is what’s most exciting to me about the age of AI as a business owner.

And if I were to extrapolate what I’m doing, I believe more people will need to become managers in the future—albeit as managers of AI agents.

7/ Choose opportunities that provide a margin of safety

Each time I think about the next play, I seek to establish a margin of safety.

I learned this idea from Warren Buffet.

Whenever he makes an investment decision, he looks for sufficient cushion in the event that things go wrong, he still comes out winning.

Since I don’t have a sizable risk appetite, I apply a similar approach to my projects.

Even if it’s not a significant financial payoff, what are the relationships, skills, experiences, emotional wins, or other benefits that I’ll gain from investing my time and energy in the project?

For example, when I joined a fintech startup in SEA, I thought about how even if it weren’t a financial success for me, I would gain experience in managing teams, building new products, and emerging markets—which would help me thrive in my next role.

In Summary

So there you have it.

Here’s a quick snapshot of what we covered:

1. Forget about being right; be curious instead

2. Climb the right mountain (even if it means starting over)

3. It’s not about a bigger number, but rather deeper alignment

4. Make small bets regularly

5. New markets demand generalist skills

6. Create leverage in your time and energy

7. Choose opportunities that provide a margin of safety

Thanks for reading. I hope you enjoyed these career and life lessons from my journey.

💎 Last Week’s Gems

• Klarna’s CEO announced an AI hiring freeze 12 months ago - now they are backtracking and hiring more human staff to support customer service. On the other hand, Shopify and Fiverr CEOs issued memos to their staff to adopt AI - or else.

• In the personal finance world, private equity is starting to go after retirement accounts. We can expect to see more pitches for alternative assets soon.

• Great practitioner’s piece on how they built a 7-figure AI consulting business. Hint: Cultural change and education are a huge part of adoption.

✨From Our Community

• Next Community Call: June 5, 2025 5pm PST / 8am SGT → Register Here

• Get Past Replays: You can access our vault of community call recordings here

• Spotlights: Taking a break from spotlights this week. What’d you think of the ones so far? DM me if you know of someone we should feature next!