personal / family-and-personal-history · article
personal/ · 2,151 w · 10 min · ✎ dialogue

Family and Personal History

Jason Shen is a first-generation Chinese American — son of two immigrants who arrived via scholarship, husband to a Thai American multidisciplinary artist, and, as of 2025, a new father navigating the same terrain of presence and transformation his own father walked before him. The family story is one of deliberate intergenerational repair: a grandfather who was emotionally unavailable, a father who tried harder and mostly succeeded, and a son who writes and coaches and talks about all of it openly, on purpose.

The Immigration Pattern

Jason's father arrives in the U.S. first on scholarship, mother follows, child joins at age 3. This wasn't coordination; it was the shape that late-20th-century academic immigration took for Chinese and Southeast Asian families navigating U.S. visa pathways. The pattern recurs often enough to feel almost structural, a family biography written by immigration policy as much as by personal choice.

Anping Shen — Jason's Father

Early Life and the Weight of the Past

Anping grew up with a father who worked constantly and mostly ignored him — except to scold. Two memories stand out. In one, young Anping bought plastic flowers to brighten a red glass vase someone had given the family; his father yelled at him for wasting money. In another, he wanted to subscribe to an intellectual magazine a professor recommended; his father yelled at him again. The emotional texture of their relationship was one of near-total withholding, interrupted occasionally by functional support: when Anping needed post-graduation opportunities, his grandfather leveraged his position to secure him a teaching fellowship — after Anping finished third in his final exam, which was good enough.

The grandfather died of cancer in 1983. In the grief that followed, Anping married a woman he had been seeing for four years but was uncertain about. He had tried to break it off; she spoke to his father, who told him: "You can't do that to a woman. You've been dating her for so long. You have to follow through." They married without photographs and with no family present — his mother was two train days away and couldn't make it. The marriage couldn't be consummated. She left, came back briefly, left again. They divorced in 1984. Anping began dating Jason's mother later that year, married her in 1985, and Jason was born in 1986.

The detail Anping returns to in the Walk with Dad essay is not the humiliation of the failed marriage but something more philosophical: he didn't feel "fully human" even as an adult until he came to the United States. China, he implies, constrained his emotional and personal development — not only politically (through the Cultural Revolution) but interpersonally, through the norms around feeling and expression that shaped his father's generation and then his own.

The Confucian Milestones

In January 2017, when Jason turned 30, Anping wrote him a letter mapping his own life against a well-known Confucian framework:

"I was determined to learn when I was 15. I became fully established when I was 30. I knew what I was doing when I was 40. I figured out my fate when I was 50. I was able to resist any distractions when I was 60. I was able to follow my heart without worrying about making mistakes when I was 70."

Anping's personal mapping:

  • 15: The Cultural Revolution began; he started teaching himself.
  • 30: Graduated college; became a full-time teacher.
  • 40: Certain that education would be his career field.
  • 50: Knew he'd have a good family life and a solid U.S. career.
  • 60: No longer distracted by competing ideas; knew what he was doing.
  • 70+: Finally able to follow his heart.

He closes the letter with quiet pride — in Jason's emerging independence, in Amy's readiness for Cornell, in Shixin's growing ease. "I count my blessings," he writes. The letter is a transmission: here is the map I used; here is where you are on it; here is what to expect.

Running for Newton School Committee

In 2017, Anping ran for Newton, MA School Committee in Ward 3 — and won. He raised $12,000, knocked on more doors than any opponent, and mobilized the local Asian American community in ways that challenged the assumption that "Asian Americans don't vote." The campaign produced one moment that has become part of family legend: when a constituent claimed Newton's schools were antisemitic, Anping responded directly: "I lived through the Cultural Revolution. You have no idea what you're talking about." His credibility wasn't partisan; it was experiential, earned across decades of actually living under ideological coercion.

The civic dimension of his father's life is not incidental to Jason's understanding of it. Anping worked two jobs for years. He listened and engaged even when Jason had opinions he didn't approve of. He modeled a form of presence — imperfect, incrementally improving — that Jason explicitly tries to carry forward. See also: civic-engagement-and-government.

Shixin Mao — Jason's Mother

Shixin is a gymnastics coach at Massachusetts Gymnastics Center in Waltham, MA. Her most notable athlete: Houry Gebeshian, who competed at the 2016 Rio Olympics. Where Anping is reflective and philosophical, Shixin is theatrical, emotionally direct, and highly relational — she tends her garden, smuggles tomato seeds home from Greece in a napkin, coaches with intensity, and pushes hard for the things she wants.

The clearest example: when Anping initially didn't want Jason to come to the United States, Shixin refused to go without him. She is, by Jason's account, the source of his theatrical energy, his comfort with close relationships, and his ability to push through pain in short bursts — characteristics that showed up in gymnastics and show up now in his coaching style.

Her response to Amy coming out as gay took time — more time than Anping's, who expressed warm support. This difference, noted without judgment in the family archive, is one of many places where the family's emotional work is still in progress.

Amy — Jason's Sister

Amy is roughly 13 years younger than Jason — young enough that Jason grew up effectively as an only child, with Amy entering the picture as he was heading into eighth grade. She attended Cornell and is in a relationship with a woman named Emma.

Amy is described as direct and perceptive. When Jason was approaching fatherhood and seemed insufficiently focused on preparation, she said to him, unprompted: "It's coming up pretty soon. You guys don't seem focused on it." She was right. Jason was indignant, then acknowledged the point.

She also wrote a poem — "Life is a Trail" — that Anping quotes with pride in his 2017 letter: "live life to its fullest." For Anping, it functions as something like a family motto.

Amanda Phingbodhipakkiya — Jason's Wife

How They Met

Jason and Amanda met as coworkers in the marketing department of a software company in Manhattan in fall 2014. Amanda's first impression of Jason: "dumb jock." The relationship shifted when they discovered their parallel histories — both had studied life sciences but left the field; both had serious knee injuries; both had creative side projects that mattered more to them than their day jobs.

After both left the company, they co-ran a boot camp for tech professionals called shipyoursideproject.com. The first kiss came in October 2015, outside The Boil in the Lower East Side.

The Proposal

In November 2017, Jason built a custom SMS chatbot that led Amanda on a scavenger hunt across New York City. The hunt ended in a section of Central Park that Amanda had originally introduced to him. Waiting there: a BB-8 robot holding a note that read "will you marry me."

The proposal is characteristic: technically inventive, personally specific, and structured so that Amanda's own taste and knowledge were embedded in the experience. He wasn't surprising her with his vision of romance; he was using technology to return her to something she had shown him first.

Who She Is

Amanda Phingbodhipakkiya is of Thai descent. She holds a BA in Neuroscience from Columbia and an MFA from Pratt, and she works as a multidisciplinary artist, STEM advocate, and TED speaker. Her work spans large-scale textile installations, public murals, and advocacy campaigns. Major milestones in the archive include: the "I Believe in Our City" subway campaign during the rise of anti-Asian violence in 2020 (the city's first-ever public campaign in support of Asian Pacific Islanders), pieces acquired by the Museum of Chinese in America, the Victoria and Albert Museum, and the Library of Congress, a cover story in TIME after the Atlanta shootings, and most recently, a crimson tapestry woven in collaboration with women in northeastern Thailand — with a Thai poem in golden thread — selected for an anniversary exhibition at the Brooklyn Museum. Jason calls this her "Simone Biles moment": not just the achievement, but everything that led up to it — the late nights, the humidity, the stupid dowels that wouldn't dry.

Married

April 26, 2019, at Fernbank Museum of Natural History in Atlanta. Officiated by friend Belinda Ju. The marriage is described throughout the archive in terms of texture and dailiness — working from home together, showering together, touching more often, co-listening to audiobooks. Physical closeness is named explicitly as something that deepens the relationship.

Becoming a Father

Jason and Amanda used a surrogate to have their daughter Ashton, born February 2025. The surrogate, Marshayla, was present at the birth with her mother. Jason recorded a pre-fatherhood video approximately one week before the birth to capture his state of mind before the event horizon.

His emotional accounting at that point: 60% excited, 30% warm and loving, 10% scared. A month earlier, the scared fraction was much larger. The shift came from preparation — reading, taking classes, talking to other parents — and from accepting that the uncertainty was structural, not resolvable.

Three things stand out from his pre-fatherhood reflections:

The parallel to other leaps. Jason identifies fatherhood as the third genuinely unknown transition of his life, alongside leaving home for Stanford and launching his first startup through Y Combinator. Getting married didn't feel this unknown; it was "such a smooth transition." The comparison to founding is precise: founders face the same uncertainty about the next month, the next product launch, the next round. Sitting with that uncertainty — rather than trying to resolve it prematurely — is what he coaches others to do.

What he wants to pass on. Four values: resilience (setbacks are not endings), curiosity (learning is how you adapt), excellence (use your gifts in contribution to others), and connection/intimacy (your inner world matters; so does everyone else's). He also expects his daughter to be neurodivergent — "I have ADHD; my wife definitely has a different way of looking at the world" — and wants to name and celebrate that from day one, not manage it quietly.

Redefined ambition. By 2025, Jason had moved away from the goal of building a $10 billion company. His stated ambition: a coaching practice that runs three days a week, July and December off each year, time to travel, three kids, and a life that supports his artist wife's demanding and often unpredictable schedule. "That is incredibly ambitious to do all of those things," he writes, "even if it doesn't look that way to my YC colleagues." The reframe is explicit: ambitious doesn't mean big; it means chosen.

The Intergenerational Pattern

Three generations:

  • Anping's father: worked constantly, mostly ignored his son except to scold, occasionally pulled strings, died of cancer in 1983.
  • Anping: tried harder. Worked two jobs for years. Listened even when he disagreed. Improved over time at emotional expression. Felt constrained in China; became "more fully human" in the U.S.
  • Jason: actively pursues emotional openness. Writes about it. Coaches others through it. Told his father directly that he wanted more acknowledgment for his book — and Anping received the feedback and agreed to re-read it.

The father-son thread is not a story of trauma overcome so much as a story of deliberate transmission: each generation looking at what it received, keeping what worked, and consciously adjusting what didn't. The adjustment is incomplete — it always will be. But the effort is named and ongoing.

Thread · 0 replies+ add reply
no replies yet — be the first to write back to this article.