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Travel and Exploration

Travel in Jason's life functions less as tourism and more as a form of orientation — a way of testing assumptions, deepening relationships, and occasionally triggering the career pivots that wouldn't have happened at a desk. The through-line across documented trips to Southeast Asia, South America, East Asia, and the Mediterranean is the same: place produces a kind of attention that staying home doesn't. Brooklyn, meanwhile, is not a waypoint but a chosen home — rendered in the archive with the specificity of someone who has decided to belong there.

Brooklyn as Home Base

Jason and Amanda live in Brooklyn, and the neighborhood appears in the raw archive with enough texture to read as character rather than backdrop. The August rain vignette captures it best: Hurricane Debbie's remnants turning the first week of August into a soggy mess, the couple hauling wooden dowels wrapped in plastic across Brooklyn to Amanda's studio so they can dry in time for the Brooklyn Museum deadline, the TV in the studio corner running Olympic coverage from Paris while they work, the street lights out on Prospect Park's south side.

The "August Rain" essay moves between three simultaneous events — Amanda's tapestry being selected for the Brooklyn Museum anniversary exhibition, the Paris Olympics gymnastics competition (featuring Jason's former high school coach, Armen, and two Stanford gymnasts winning the U.S. men's bronze), and Simone Biles navigating what it means to be the greatest gymnast of all time at 27. Brooklyn is the location in which all three of these things happen at once, and the essay treats the neighborhood as a frame for reflection: "I think this might be your Simone Biles moment," Jason tells Amanda. Not the achievement alone, but everything that led up to it — the frustrations, the humidity, the persistence.

Evening walks are documented through Prospect Park and nearby streets: a private boys' school, a hill, a suburban pocket, muggy summer air with occasional breezes. Jason and Amanda walk Prospect Park at night when she returns from Thailand, forgoing the flashlight in the dark because Amanda, like her mother, doesn't want one. The apartment is small — a two-bedroom condo — and they know they will need to move if they have more than one child. The logistics of space, studio access, good schools, and public transit proximity are active considerations.

Brooklyn also appears as a backdrop for community: the Brooklyn run club, CitiBike rides to Amanda's Queens residency at MFTA, neighborhood walks with visiting family, and the constant background hum of the city.

Southeast Asia

Thailand

Thailand is the most documented international location in the archive, largely because of Amanda's Thai heritage and her ongoing artistic engagement with Thai communities and craft traditions.

Amanda travels to Thailand regularly for artistic research and cultural connection. One documented trip included visiting her father's hometown — a village about two hours outside of Bangkok — where she photographed salt fields (vast rows of salt piles formed by evaporating ocean water) and the people who work them. The photographs are described as beautiful; the experience was clearly moving for her. "She wishes I was there," Jason writes, "in part to snuggle with her and comfort her, but in part to be a part of these experiences that she's having."

The time-zone problem is its own minor grief. When Amanda is in Thailand and Jason is in Brooklyn, one of them is winding down while the other is ramping up, and conversations become parallel broadcasts rather than actual exchanges. Jason doesn't do well as a bachelor: "I eat microwave meals from a frozen meal delivery service. Life is just working out, creating content, getting on calls, and looking at social media."

Amanda's artistic work in Thailand goes well beyond tourism. She has traveled to the Ban Na Meun Si community in Isan (northeastern Thailand) to collaborate with the women there, learning and integrating traditional weaving into her own practice. The tapestry selected by the Brooklyn Museum — a crimson red banner with a Thai poem in golden thread — emerged directly from this collaboration. Her themes (reclaiming textile legacies, matrilineal revival of cultural loss, the transmission of wisdom through women's hands) are inseparable from the specific geography and communities she visits. See family-and-personal-history for more on Amanda's artistic practice.

Jason's mother, Shixin, also travels to Thailand — evidenced by the detail that she brought back tomato seeds from a meal during a family trip to Greece (implying multiple international trips are a normal family activity). The seeds, technically not legal to import, are now growing in planters in her Newton garden. "I love that she did it," Jason writes.

Malaysia and the Startup Ecosystem

The raw archive notes a trip during which Jason wrote "Two Days with Malaysia's Emerging Startup Community" — observations on the local startup scene, the early-stage founders he met, and the texture of entrepreneurship outside Silicon Valley and New York. The Malaysia visit sits within a broader category of travel-as-professional-expansion: going somewhere to understand a context you couldn't understand from home.

Singapore appears separately in the archive through a "drinks dinner" note that captures a late-night conversation about crypto protocols, Taylor Swift as a creative and business model, the high standards of artists who are difficult to work with, and Singapore's extraordinary success in digitizing government services — they planned to have all consumer-facing government services digitized by 2024 and finished two years early. The comparison to U.S. government tech efforts is implied and unflattering.

Vietnam and Cambodia

Referenced in travel itinerary notes as part of a Southeast Asia multi-country trip alongside Thailand. The archive doesn't develop these in detail, but they appear as part of a documented pattern of regional exploration.

Peru

The Peru trip carries more weight than most in the archive because of what happened while Jason was there: he read a book by Etsy's VP of Design. That reading led to a blog post about design. The blog post, apparently, made its way to people at Etsy, leading eventually to his role as a product manager there. The causal chain is speculative from this distance, but Jason cites it as an example of travel creating conditions for unexpected connection — the mind is differently available when it isn't at a desk.

Machu Picchu is noted in the raw files. Peru reflections are also documented. The trip functions in the narrative as an example of the broader principle: travel as information-gathering that isn't in the trip's stated purpose.

China and Family Geography

Jason was born in Suzhou, China — his family's origin point. Shanghai is documented separately (things to do in Shanghai), suggesting at least one visit. The Chinese-immigrant family story means that "going to China" is not quite tourism; it is also a form of returning, visiting a past that is simultaneously close and estranged.

Anping's early life in China — the Cultural Revolution, the cramped housing, the public bathrooms outside the bedroom, the heat and cold — gives China in the archive a specific texture: the place his father felt not quite fully human, the place they left, the place that shaped everything that came after.

Greece

A trip to Greece is documented through Shixin's tomato seed story — the seeds she took from a last meal and carried home, which are now growing in her Newton garden. The image is small but telling: a woman who coaches gymnasts and grows flowers, who traveled internationally and couldn't bear to leave behind something that might bloom. The Greece trip was planned with friend Bilal (who later married Cynthia Wu in San Francisco's Conservatory of Flowers).

India

A personal trip to India is noted in the archive. Jason's coach as of late 2025 is Shruthi, an Indian woman with "a round face, thin gold wired glasses, and a septum piercing" who lives in India — the coaching relationship itself bridges the geography.

Japan

Ashton's first-year birthday video notes include footage from a trip to Japan that was accidentally included in the upload. This trip was taken a few months before Ashton's arrival, Dec 2024 through Jan 2025.

Washington, D.C. — Government as Geography

Washington D.C. appears in the archive as a distinct kind of travel destination: the city where Jason spent time as a Presidential Innovation Fellow under the Obama administration, after Ridejoy shut down. A decade later, he returns with Amanda for PCAH (President's Committee on the Arts and the Humanities) events she attends, and finds that "the street grid, fall air, and grand monuments reminded me of my time in this city a decade prior in a government tech fellowship where I understood very little about how organizations worked."

The D.C. walk essay is about risk and the absence of guarantees — prompted by the surroundings but not about the place itself. "I had taken a leap after my startup Ridejoy had run aground, not knowing what would happen after the 6 month program ended. Unlike traditional government jobs, this one carried no guarantees. I moved to New York and spent 9 weeks sleeping on different friends' couches until I landed a job and then an apartment." D.C. functions in the narrative as a site of past risk-taking, revisited from a place of greater stability. See civic-engagement-and-government for the full PIF story.

Travel as Inflection Point

The clearest pattern across documented trips is that travel creates conditions for unexpected career or relationship pivots:

  • Peru: Reading design content while traveling → blogging about it → Etsy connection → PM role.
  • Malaysia: Observing a non-U.S. startup ecosystem → broadened understanding of global entrepreneurship.
  • Thailand (Amanda): Repeated trips deepening her artistic practice → Brooklyn Museum tapestry → MoMA and gallery placements.
  • D.C.: Failed startup → fellowship application as escape hatch → network that eventually produced both co-founders' Nava, and Jason's path toward Etsy and then coaching.
  • Newton visits: Returning to the childhood home puts Jason in contact with a version of himself that the present usually obscures — the family photos, the gymnastics trophies, the wedding pictures, the garden.

The common thread is not that travel produces epiphanies. It's that travel changes the conditions under which attention operates. You read differently on a train in Peru than at a desk in Brooklyn. You see your wife differently when she's navigating her father's hometown than when she's working in her studio two blocks away.

Fatherhood and the Future of Travel

With Ashton's arrival in early 2025, the travel calculus has changed. Logistics for weddings and in-person events are harder; international trips require more planning. Jason notes in the Amanda-in-Thailand essay: "I know these trips will only get harder as we start to grow our family, so I'm glad she's able to have this kind of cultural moment and this inflection point in her artistic practice."

The vision Jason articulates for his future life — three kids, work three days a week, take July and December off each year, travel — suggests that travel is not expected to diminish but to restructure. The ambition is a life that travels, not a life that occasionally escapes.

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