Hi, I’m Cissy.

I serve as the Regional Director of the Bay Area for 3i, a private investor community of 750+ exited founders & operators, GPs, fund managers, and family offices.

I write becoming | more myself, a newsletter where I explore what it means to be more human in the age of AI.

I coach founders and executives to accelerate their life's work by recruiting trusted executive assistants (EAs) who enable them to operate from their zone of genius.

I’m passionate about curating experiences that allow us to visit our edges. In my free time, you can find me meditating, reading, researching, writing, frolicking through national parks, urban hiking all of San Francisco, and hosting the occasional retreat.

Previously, I worked in product & community at Levels, advised consumer & enterprise startups at GV (Google Ventures), and worked in product & client services at Wellington Management.

a collection of my writing [full archive here]

introspection, ambition, and agency

essays on becoming more ourselves

• A lifetime of should-ing: the case for an existential crisis
• What fuels your ambition?: on the transition to clean fuel
• On giving up control: cultivating self-trust and de-optimizing our lives
• Thank you for triggering me: shining a light on the ways we're not free
• Life is a series of experiments: it ebbs and flows and comes and goes
• Dancing with our shadows: awakening the unconscious
• Role playing your way to a new identity: alter egos, experimentation, and learning curves
• The mourning of a new dawn: on dancing with joy and the whispers of grief
• Slowing down to speed up: making way for the consequential
• Trading goal setting for identity aligning: take a stand for your identity
• Atlas for the inward bound: a Christmas gift and reflections on an annual tradition
• Introspection through written word: a collection of essays for turning inward

flourishing in the 21st century

experiments in connecting with our intuition and coming home to ourselves

• Rest is for the dead and other misconceptions about worthiness: a prelude to the tech sabbath
• Renegotiating our relationship with technology: on returning back to ourselves
• Going news sober: on unplugging from the news cycle in pursuit of connection
• In pursuit of our inhibitions: the courage to live in our (sober) truth
• Nervous System Mastery: the art of interoception: a pre-requisite to being human
• A Call to Eudaimonia: experimenting our way towards flourishing in the 21st century
• Know Thyself: AI & the quest towards our truth
• Our modern (content) diet: food for thought

reflections on coming alive

essays on being moved by the life we have the privilege to live

• Speedrunning aliveness: lessons from the natural world
• I hate cold water and other reasons why I run into the sea: the case for starting the month with a hard thing
• The annual partnership retreat: a weekend that makes the heart grow fonder
• Year of doing the damn thing: on riding the new year energy
• 26.2 miles of solitude and aliveness: reflections on avoidance, meaning, and meeting myself
• Finding peace in 10 days of silence: surrendering to equanimity
• Hard things, good people: life on the edge
• Come alive in Banff National Park: a photo essay itinerary of sorts

modern work & self-expression

a collection of notes on our relationship with work, the state of modern work, and self-expression

• Introducing Work & Self-Expression: Cissy’s sabbatical field notes
• Who we are without work: an exploration on identity
• Some practical thoughts on diversifying our identity: the search for meaning beyond work
• The art of self-expression: surrendering to your game
• How to sabbatical: the inner workings of the in between
• 6 months of surrendering to the unknown: reflections on the four stages of sabbaticaling
• Knowledge work as an emotional act: an integrated approach to emotions, work, and productivity
• Emotions in motion: a tactical guide to embracing your emotions while working

cultural identities and family scripts

essays on reclaiming our cultural shadows, bridging our identity between two worlds, and co-creating new dynamics with our family

• Finding home between two worlds: growing up yellow in a black and white world
• The unraveling of old family scripts: on breaking generational cycles
• How to travel with your parents and not lose your shit: a guide to surviving (and thriving on) your next family trip

Elevating AAPI voices: a compilation of essays & a directory of writers

• The power of representation: you can't be what you can't see