I can remember how I felt from that tender age ‘til my 20s—like a heavy pencil pouch of responsibility, resilience, excitement, guilt, anticipation, angst, and pride. Combine this with an unusual eerie secret feeling that I would die young + a series of family financial traumas, and you’ve got some really potent fuel for living through beyond-traditional milestones, you-gotta-be-kidding-me-type dead ends, and a handful of unexpected gains.

I grew up in a business family. One that had incredible wind falls in each generation, and also losses so devastating that each following generation had to start from scratch financially, only inheriting trauma and painful unprocessed lessons. Because I was the youngest-born girl in my generation tapped to be the “responsible one,” I spent most of my free time with my parents and grandparents. I was in all the rooms they were in (business launches + closures, sales + partner meetings, routine IRS audits, will-writing, etc.) witnessing all the details, learning the hustle. It was like a daughter of immigrants-style MBA. I was both curious and resentful at the time, but it really prepared me to navigate life’s crazy ass curveballs and dead ends independently.

One of the most significant you-gotta-be-kidding-me-type dead ends was graduating in the 2009 recession. I had done “everything right,” paid my own way through college, and was ready to find my dream job, my freedom. Both my family in the Philippines and my parents were recovering from their own financial crises, and I desperately wanted to help. The economy had no jobs for me, but I knew how to hustle. I tried a number of different entrepreneurial things, including learning how to flip foreclosures. That was my first big girl business. That was my first moment of self-generated financial independence and my first experience with passive income. It afforded me time and money to contribute to family expenses, and start two businesses in areas I had actual interest in—jewelry design and experience production, while serving as the Executive Director of an award-winning, nonprofit dance company.

But just as fast as I built that first chapter of financial security, I also quickly fell out of it. I overcommitted what I could provide my family, I overspent on healing my burnout, and I was tired of the painful realities in how I was treated as a young Asian woman in the real estate industry. I wanted to GTFO. My jewelry and experience production businesses were not generating enough consistently to replace my real estate income, so I started to re-explore corporate opportunities. I only knew how to be entrepreneurial and at that age, Executive Assistant roles were a strong fit. I applied to all the ones I could find on Craigslist and landed my first corporate gig at Google. I found myself again in a whole new set of rooms, with some of the most powerful people in Silicon Valley. I like to describe my tech journey as my second MBA, a learning path parallel to the daughter of immigrants MBA.

I took myself on a colorful ride within tech, trying different roles each year and designing in my own 20% opportunities. My longest, favorite chapter was at GV (Google Ventures) as a Design Operations Partner and leadership coach where I worked with a world-class team to help leaders across a portfolio of 300+ high growth startups leverage the power of design thinking to operate more effectively. After GV, I joined Stripe as their first Head of Design Operations to establish systems to prepare for global scale. My time in tech has had its ups and downs. Systemically it was very individualistic and I encountered different flavors of frustrating treatment as an Asian woman. But it was also healing and liberating.

I rebuilt my financial stability surpassing my parents earnings before 30. I learned new mindsets + tools + investing techniques that equipped me to shapeshift my identity in ways that felt more connected and free. I formed life-changing relationships that encouraged me to explore what else power and purpose could look like if I weaved more of myself in. I had more funds + skills for entrepreneurial projects outside the walls of the corporate office, and I became very motivated to radically share resources, and integrate my learnings across the spaces I found myself in like the beauty of immigrant community care, creativity as a practice for resilience, asking for co-creation and not settling for permission or forgiveness, methods to work play smarter and not harder.

This second cycle of financial freedom led me to projects like funding a nutrition program for malnourished children, producing a private retreat for top women founders and investors in Silicon Valley, designing a Kickstarter-funded connection card game, co-founding a history-making Filipino food company The Sarap Shop, and building a business consulting practice.

In 2019, I decided to take a break from a full-time tech career to care for a major health scare with my Dad. During my Dad’s recovery, I retired my parents and began prototyping a semi-retired lifestyle of my own, maintaining 40% of my time on pure leisure activities and my other 60% on business design consulting and leadership coaching projects. Within this current cycle of experiments, I operate two 6-figure community-focused businesses and maintain a lifestyle that feels in alignment with my values and my chosen family.

Covid definitely threw me more curveballs, and at a volume that has been challenging to process at human pace. But because I’ve been through cycles of building > creative destruction > rebuilding, I’ve moved through the pandemic with more peace of mind and confidence. I trust I am capable and know how to design a life that is more stable AND meaningful than I, or generations before me, could have imagined.

I’m excited to further deepen my practice of peace and healing as I go, exploring how to have my wealth and impact last beyond my generation. And I’m excited to be on this third exploratory chapter within New Dimes, with a community of folx similarly designing their own paths.