How Do You Want To Live?

Being on the inside, and then the outside, and figuring out what’s next.
Published Date
Sep 3, 2023
A little disclaimer—this reads best on desktop screens, given the abundance of video and the weird layouts crafted in Notion. Sorry for evoking the ghost of late-2000s web design.
Also, part of my desire with this blog is to get real, with all the emotions and warts that typically do not find much space in other’s writing in this industry. Life is about more than being just one thing, forever; I choose to make this space for everything that captures my heart and attention, and is a full reflection of me.

I just came back from a long summer trip—the longest I’ve ever been away from home at one time. We went to the Philippines, where I was born until my parents came to the U.S. as young doctors in residency back in the early 90s. My grandfather, who is 85 now, lives somewhere closer to the south of the country, there among his siblings and a network of my father’s family that nestles him in support.
I have a relationship with my family that is complicated, as many families and the ties between them are in that part of the world. I’m queer, and trans, from a deeply conservative country that sees but does not legally recognize (or wholly accept) people like me, or my partner.
I wanted to spend time with my grandfather, and my parents, and the extended family that I’ve kept at a distance over a sense of fear of what my presence would incite, with it’s abundance of Lolos (filipino for grandfathers) and traditional viewpoints about life, gender, and who their family is supposed to be. The question of “Would I be accepted?” weighed on me constantly.
It felt like after peering in from the outside, from an ocean away since I came out in 2018, I was going to be back inside the ring of my big, grand family. I was going to be there with them for a whole month—I knew I would have to deal with whatever may come from being on the inside again.
And admittedly—things were much better than I had hoped. My family made mistakes, dropped faux pas (plural) and introduced us to creatively awkward situations. Yet, despite that, I felt a pervasive openness and warmth for me and Josue, if not a full understanding of us. After some time there I felt a relief that things from the inside were more kind than we had expected and been prepared for. For me, that was enough.
Our time there was hot, rainy, and filled with long days packed with moments of family, with a fews days tucked away from the monsoon, hiding in the comfort of the apartment my parents had rented or the home they built for my grandfather.
My grandfather’s place was small and single level—built not too long ago in anticipation of the needs of a life aging upward. It’s continuously open windows and lack of air conditioning in it’s main living area gave it a tenuous boundary between inside and outside. Life, like the geckos that would show up on the ceiling of the room we stayed in to my chagrin, came in and out with ease. Ants could be annoying, but they would be tolerated. It was worth it to occasionally catch the warm breeze of the outside from time to time and to hear the songs of the cicadas and birds chime in undistorted.
I spent a lot of time there with my grandfather, helping him with crosswords and seeing him connect with Josue in a way that made my tender heart beat.
Josue and I found time to explore by ourselves too. We got to spend a week in the resort town of Boracay alone. We partook in the instagram bonanza of an aesthetic fake dutch town in the hills above Cebu. We sat at ease in clear water, white sand, and a lack of immediate responsibility, if only for a moment.

The last decade has been a weird time in my life. I spent about a quarter of my 30 years in the world at one company that, through it’s ups and downs, became successful. Alongside it, I came out as trans, learned how to lead, and made the most of the lucky intersection of my life and the company I would retroactively thank my 22 year old self for joining. For the longest time, I made a home inside spaces that, even with bumps in the road, welcomed me as someone who they trusted and valued.
Through my own upbringing and developed insecurities, I craved that critical feeling of acceptance—and in that decade I cashed in my career success regularly for that validation. So much so that I grew a fear of losing it that played into my imposter syndrome and burnt me out in search of proving it wrong, again and again.
Now, through my own volition, and years of building up the strength (and means) to do it, I chose to eject—to live without that support structure for the first time in a long time. Going outside of tech, and a career, and all that it provides, even for just a moment.

After the Philippines, Josue and I went to Japan — to see friends that had moved there, and to spend time with others that were joining us a week after we landed.
The feeling of difference, from both the lush, crowded, and haphazardly-grown aesthetic of my home country and the rags-or-riches feeling I find living in San Francisco, was pervasive.
There was a beauty to the unexpected moments. There too was a distance to the culture given our foreignness and our limited (but extant due to months of Duolingo!) understanding of the language. I relished but did not fully envelope myself in this travel, for better or worse. I had other things on my mind.

notion imagenotion image
While I was in Tokyo, we decided to watch Hayao Miyazaki’s final film, titled “How Do You Live?” for Japanese audiences but coming here to the U.S. as “The Boy and the Heron”. We watched, un-subtitled and with limited Japanese, and filled in the gaps later. Reading reviews and discussing with our Japanese speaking friends could fill out the nuance of the dialogue we lost in translation. We mostly let the animation cells flickering in front of us speak for themselves.
I won’t spoil you, but one of the underlying threads of the movie is a kid, having gone through a difficult time, figuring out how he wants to move forward in life. Wrapped in the magical, ethereal trappings of Miyazaki’s work is a grounded reflection on the agency we have to define the life we live and lives that we affect along the way. It was a timely watch, given what was on my mind.

I spent a lot of time during my trip, inside of momentary pauses sitting on rainy buses and on walks searching for air-conditioning to relieve the hottest August in Japan’s recorded history, thinking about where I am as a person and as a designer/engineer/leader. It was melancholia and introspection in a foreign country—a cliche I was grateful to have the time to partake in.
I thought about the kind of life that I left behind when I quit DoorDash. I knew it was still out there somewhere—aka being a design systems focused people leader that pulls together impact through 3 parts will, 2 parts wit, 2 parts being able to bridge gaps, and 1 part being able to out-EQ more problems than the average bear.
But, I also thought about other lives—ones that are scarier in their unknowns but more riveting for reasons other than stability. I considered if I had the grit and the north star capable of generating that conviction to start something of my own—startup, studio, or some combination in-between. I wondered if I could again be the one that coded and designed the thing rather than the one that supported the person who made the thing. I wondered if there was a slightly askew multiverse of the life I had lived, one where I took myself less seriously, and saved myself some of the grief I created with my own anxieties.
Part of why I quit that old life is that I wanted to find one that better aligned with the parts of my personal garden I had left parched with less attention than they deserved and needed—my health, my relationships, and the parts of myself that gave me energy and purpose, and not just validation and the feeling of acceptance. This year I’ve notched a few steps closer to tending to a more vibrant garden of life. I’m not quite there yet; more dirt left to dig and seeds left to plant.
I still don’t have answers, per se, on what my future ultimately looks like. I do now have some ideas of how I can explore, figure out what’s next, and take the time I need to navigate the discovery of both what I want and what I need out of whatever my life turns out to be.
One of the things that I learned (un-ironically) from the corporate values of the company I helped build was the idea that there is only so much that you can learn from looking outside to compare and benchmark yourself—that ultimately, the most consistent and practical way to be the best version of yourself is to ask: “am I better than I was yesterday?”
The thing that I’ll add now, after taking this time to travel and reflect on how to apply this to me as a person is—”How do I want to live? And am I living up to that standard more today than yesterday?”
Life is a series of lives and figuring out what you need from each of them. I’m working on discovering and building my next one—today, and tomorrow, and every day after.

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