An eleven year journal, on crossing thresholds in life
A non-linear journey in the making
Happy holidays from Livermore, California 🎄
I want to host a small end of year reflection journaling workshop (virtual), if you're free, please RSVP here, would love to meet or reconnect with you.
As I scramble to close the year at work, I want to make space to feel truly disconnected over the holidays, to look back on the year and sometimes, as in this post, the decade.
This post is written at a combination of my favorite New York coffee shops.
Butler @Williamsburg
Le Pain Quotidien @Bryant Park
Sammy L @East Village
St. Georges @West Village
∞
Eleven years ago, I started journaling in a special type of memory book known as One Line a Day. In this journal, each page represents a specific date repeated across 5 years. For example, today is December 20, 2024. On the same page, stacked above is December 20 from 2023 and 2022, and below the same day in 2025 and 2026. In between these lines, I gain insights into what I was thinking a year ago today, who I was spending time with, and what I cared to write down.
It can be a little scary sometimes.
One time, it was January 12, 2017, I wrote "I’m really over this job at this point." As I wrote those lines, I glanced at the page and here it is, the exact same sentiment exactly one year ago about the same job. Time flew by. I thought I was fulfilled and yet, this notebook spoke the harsh truth.
I told myself, I cannot live like this; I can’t let another year pass and feel the same. Ever since, this journal has become an essential part of my life.
The pages of this notebook are a reminder for ourselves, in the most honest form, of where life has been.
At the time, I had dreams of moving to Europe. Perhaps it was less about Europe, but about wanting to shake up life, creating discomfort, and taking the biggest risk I could think of. Looking fifty years into the future following the career path that I had, I didn’t like what I saw.
Finally, on June 4, 2018, in my greatest now-or-never moment, I flew to Finland on a one-way ticket.1
I “soul-searched” while sojourning around the world.2 Breaking free from the tech golden hand-cuffs, I realized there are endless possibilities in life: I could become an interior designer without formal education; I could travel indefinitely and it would still be more cost efficient than staying in New York City; I could build a company and find meaning in putting out my vision in this world.
These endless possibilities in the fifty year future are exciting.
∞
For some time, I was proud of my new experiences, proud of my ability to pack up the bags and fly.
My journal documents the many cities I’ve visited and yet, as I look at it again, a similar sense of stagnancy from before dawned on me. It has been six years since my flight to Finland. The greatest now-or-never moment is now in the past.
Flying to an unfamiliar city was an unfamiliar idea six years ago. The unexpected growth came from doing something unexpected. But today, traveling has become the new Comfort Zone.
Perhaps I’m the kind who constantly seeks progress and change; repetition felt uncomfortable. Once again, I asked myself: what is the most uncomfortable act I can perform right now to grow up a little more? Flying away, though still captivating, will never have the same impact it had the first time.
In true Alchemist fashion, I am looking for answer back at home, to stay in one place while confronting my urge to fly away. Instead of looking externally, I’m searching for answers from within.3
∞
I recently met a friend who said he’s always been in relationships; three long-term relationships and a divorce later, for the first time he’s learning to be alone and to enjoy the time of solitude.
I feel it’s as if our lives are reversed. I’ve traveled extensively on my own. Through years of “training” I finally found some peace in solitude (I say some because as an extrovert at heart, I’ll probably always prefer having company). For the first time, I’m seeking routine and consistency.
Often, the fear of being “behind” in life plagues me; at a certain age, I should have hit specific milestones. But maybe there isn’t a right order. There aren’t a set of templated milestones we are meant to hit. At this moment in time, I didn’t yet find the safety and security in a relationship, but I found traveling early. I didn’t yet build a great company that I feel proud of, yet I feel I’ve grown emotionally and felt fuller on the inside. Others, they started the act of raising kids early on and may never find traveling, and that’s okay because they are rich in spiritual experience and strongest on the inside.
Life is about the unexpected crossing of thresholds. These thresholds are sometimes external marked by career and environment changes. Other times, they require us to turn our awareness inward; they’re about relationships, spectrums of emotions, and faith.
Age is not a number. It's a process of evaluating how we are different today. As Steve Schlafman beautifully put, “it’s not about age, it’s about the ongoing journey of becoming.”
I continue to journal, continue to confront the past, embracing it as a lens to help measure my life.
I’m not sure what the next threshold I’ll cross in life will be, but I’m excited for the box of surprise. For now, this year feels different from last, and for that I'm grateful.
“Spent a day in a coffee shop trying to learn.” — March 6, 2016
Some things don’t change.
Special thanks to friends from Write of Passage and Essay Club for the edits and the ideas: Lily (
), Phil Chu (), Caleb Fallin, Charlie Becker (), Alan Wells (), Jamie Nicholson (), Stephen Olson (), Justin Mather (), Celeste Mitchell (), P Fitch (), Cam Houser (), Vidhika Bansal (), Vivaddhana Khaou (), Kat Koh (), and Aman Manik (), and for inspiring this post and your annual reflection templates.For those with the OCD brain wondering what happened between January 12, 2017 and June 4, 2018, I left the job in May of 2017 and started a new job at Google, then became the founding designer at a crypto startup in January of 2018. So it took another two tech handcuffs before committing to flying away.
I used to think that we must change our environment in order to change ourselves, while that definitely helps, I’ve learned that it’s also important to have more control of our mind – thanks to the dharma talks in NYC.
I like what you ended up doing with this essay Coco, and especially love how you ended it. Seeing what doesn't change feels almost as powerful as what does, if not more so. That 5-year journal idea is so cool, now I'm considering getting one! Thanks for sharing your reflections with us and here's to continuing to march to the beat of our own milestones.
I like how this turned out Coco! Especially how you brought more of yourself back into the milestones section.
Also fun to look at an image of your actual journal. The infinity sign detail for sections is a nice touch too, feels very in tune with the essay.