#24: The Art of Reflection
unfolding and rewinding in Sea Ranch
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Ah, late December. Like clockwork, a big clock perhaps, this time re-emerges every year and with it comes Christmas lights, visible breath, and accessories for warmth that I’m too stubborn to buy, like earmuffs and scarves. Whether we acknowledge it or not, this season is deeply ritualistic. We conduct rituals like cross-country flights to visit relatives, gift-wrapping for family even though we all share the same Amazon account and reflect on the year that’s coming to a close.
Last week, when I was sprinting through my last few days in New York City, I already knew that I wanted to write my next piece on reflection. After all, this year I jumped from one adventure to the next; sometimes with so little time in between trips that I didn’t even bother to unpack my bags. In parallel, I adopted new habits of journaling, meditation, and device-free walks that enabled me to digest the constant change. The circumstances created the perfect storm and showed me how useful reflection is. Yet ironically, it wasn’t until I actually reflected this weekend along the California coastline of Sea Ranch that I realized the last few weeks in NYC left me hastily disoriented.
On the first night back home in the ‘burbs, the pitch black silent room was too dark and too quiet for me to fall back asleep. I must’ve gotten used to the street noises and bright LEDs that streamed through my curtain-less studio in Chinatown, Manhattan. I had unknowingly acclimated to the constant hum and chatter from being engulfed by hordes and skyscrapers. Internally, my mind mirrored the external. I scan my body, but I can’t find the OFF button on me. A master puppeteer has me on strings jolting in directions I didn’t even know were humanly possible. It feels like I’m back at youth tennis camp in an agility drill with the reaction ball.
Returning to Sea Ranch
Kudos to the past Me for having the foresight to plan another end-of-year retreat in Sea Ranch, California. I tend to not celebrate many holidays or even my own birthday; to me I think they’re mostly arbitrary dates. There’s something about the end of the year though. The demarcation that divides the present from the future. A permissible way to format the chapters in the book of life. It might just be a different number, but I’ve found that the advent of a new year helps me to reset and calibrate.
After living nomadically for almost three years, I want to travel live more intentionally. From now on, every trip should have a purpose or a theme. That doesn’t mean having a printed out hour-by-hour schedule or setting OKRs (god forbid). It simply means being thoughtful about why I am doing this. With this year cascading from one trip to another without much room to breathe, I knew I had to return to Sea Ranch again to reflect.
Located north of San Francisco along Highway 1, Sea Ranch emerges from the marine layer. Developed in the 1960s, the ten-mile town was conceptualized by a group of architects who sought to live lightly on the land. All Sea Ranch homes were created with similar slanted timber-frames to “establish a ‘territorial partnership’ with any structure placed within it, not upon it.”
Adherence to their original architectural and design concepts resulted in the evolution of an ‘intentional community’, one that is unique on the California coast, if not the world. - The Sea Ranch Association
The integration of architecture with nature and moody fog curling through the tree line evokes the ideal environment to reflect. So in between home-cooked meals and exploring communal spaces with four friends, that’s exactly what I did.
What even is reflection??
To me, reflection is the process of setting aside time to examine experiences, thoughts, and actions. Without the proper structure, I would run off in whatever direction I was first oriented in. I would think I’m doing the right thing, but instead, any innocent bystander would see a blindfolded fool aggressively swinging at the air instead of the piñata filled with delicious candy. By taking a step back to get your bearings, you can arrive at better outcomes (and actually hit the target) which is counterintuitive given reflection can only occur in a state of non-doing.
In races of all kinds, speed is singlehandedly the most important measurement. But life isn’t a defined path with arrow signs, pacesetters, or water stations. Often, we aren’t even given a map to follow. Instead we must rely on a compass to set us in the right heading. The crucial directional component is what distinguishes velocity from speed. Reflection is the process to first pause, and then capture inputs to set a new direction. Go slow to go fast.
Ultimately, reflection is to learn about yourself. Day after day, we stand in front of the mirror and the only thing that we notice changing is our clothes. With more time apart between seeing each other, it can be easier to see how our friends are evolving more than ourselves. Without carving out intentional time to observe oneself, it’s easy to lose sight of the gradual, but compounding changes.
Time spent in self-reflection is never wasted – it is an intimate date with yourself. - Dr Paul TP Wong
Why reflect?
It’s easy to take what we have for granted, but if you look back far enough, there is a time when the Past You wanted the life of Present You. Through reflection, we’re able to recall those moments. I can relive the first time I skied out west at Northstar. It blew my mind to ski on anything other than icy east coast hills. The twenty-or-so frustrating surf sessions I threw myself at before finally being able to stand up (not an exaggeration). The nervous excitement I had when I started this blog back in April this year. On most days, we wake up and think What’s Next? Rarely do we intentionally take time out of the day to think about the past. Reflecting removes the burden of the future temporarily and allows us to trace our progression with gratitude.
Life is a mirror and will reflect back to the thinker what he thinks into it. - Ernest Holmes
Without the built-in breathing space to contemplate, inertia keeps us in a constant state of assuming what we’re doing is optimal. Over the years, whenever I stumbled upon a new newsletter, I would subscribe if it seemed decent. I followed random “thought leaders” and threadbois on Twitter thinking that would make me smarter. It didn’t occur to me that I don’t have time to consume all this until I sat down in our Sea Ranch cabin and realized I’m drowning in the endless firehouse of content.
No one’s perfect. Across our habits, activities, and relationships, some are positive (like flossing), while others not so much (like smoking cigs). The challenge is in discerning which is which and then acting accordingly. Knowing which parts of your life to double-down on and which to remove is crucial. Imagine the worst case allocation for relationships. This would be like cutting off all of your besties and then spending all that extra time with people you don’t even vibe with. In reality, we should be doing the inverse. Spending more time with those that give us energy and intentionally avoiding those that drain our energy. Reflection is the process of sorting all of this stuff out because you simply can’t make these decisions in between your 10am standup and lunch run to Sweetgreen.
Loops of Reflection
I’ve mainly been referring to reflection as this singular term, but it actually comes in different shapes and sizes.
On shapes:
Writing isn’t the only form of reflection. One night in Sea Ranch, we plopped down on the couch with glasses of wine and shared how this year went and our goals for next year. One wanted to be more authentic to herself. Another wanted to be more in tune with her emotions. And one simply wanted to be less bloated - which by the way, is a valid goal. I find myself only able to reflect when I’m not being bombarded with messages, notifications, and myself telling me to get shit done. The shower and steam room are my reflection safe havens. I’ve had so many insights pop into my head while sitting in the gym’s steam room that I will often speed walk past the showers to my locker just to pull out my phone and note down the thought before coming back to shower. Sometimes they’re epiphanies, sometimes they’re simply reminders. Either way, I value the discovery so much that I have to record it.
On sizes:
I came to Sea Ranch to conduct my annual review, but throughout this year I’ve also adopted other forms of reflection: the daily journal and the monthly reflection. These three practices form concentric loops that help me continuously evaluate how I feel and if I’m on track with my goals.
With a different cadence and format, they each have their own purpose.
Daily Journal
After I wake up and move around a bit, I fire up Notion and I answer a few short prompts followed by a summary of what I did before. It’s nice to reflect on the previous day. Because it’s so recent and the memories are fresh, it almost feels like I get to relive the half-life version of the day. The frequent cadence allows me to traverse through decisions, planning, and scheduling with agility. However, it’s too lightweight and rapid to make any key decisions or big realizations.
Monthly Reflection
On the last day of every month, I run through a template of questions that forces me to reflect on the last 30 or so days. I run through the tactical highs and lows of the month which is straightforward, but I also recap key decisions and why I made them, as well as note down what I wish I did better. Starting next year, this is also when I’m going to check in on how consistent I’ve been with new habits I’m trying to form and plan major milestones for the next month.
Annual Review
For the past four years, I’ve conducted an annual review. Recently, I’ve been seeing tons of productivity gurus shilling their annual review templates, with some even charging money. I’ve always used the Ultimate Annual Review template by Steve Schlafman, an executive coach who I like because he reminds me to be kinder to myself when the stereotypical advice from coaches is all about optimizing performance and embracing the #grind. Not only is it free, it’s also more comprehensive than any other template I’ve seen.
The first part of the annual review is lighthearted and fun. I scroll through all my photos from this year and mark down the major moments month by month. This is the second year in a row where I realize “oh shit, I did a lot this year” only after completing this section.
Next, I review my goals that I set last year. It’s interesting to inspect the goals that I didn’t hit because sometimes the goal itself was badly set from the jump. For example, last year I set a goal to invest $20K into startups and crypto which was a silly mimesis-driven goal to have so I’m actually glad I didn’t come anywhere close to hitting it. There are other kinds of goals like achieving chiseled six pack abs. After failing to accomplish this goal for the last four years I can conclude three things: 1) I tend to set overly optimistic goals, 2) getting shredded is hard, and 3) I love food.
The annual review gets deeper into regrets, relationships, and lessons learned before transitioning into an audit of your current life across ten dimensions. I’m glossing over the details and zooming through what takes hours to do properly, but eventually I arrive at the planning section for next year. There’s space to think about things like purpose, goals, and habits. My favorite question is “If I knew I'd succeed what would I accomplish in 2022?” because it allows me to dream big while ignoring the fear of failure. I accept that so much will change throughout the new year, but I still find it immensely useful to jot down all my goals knowing that I won’t hit them all because “failure to plan is planning to fail”.
What I learned from this year’s annual review
To spare you the details and to retain my sense of privacy, I won’t go into my entire annual review, but I did have a few noteworthy realizations:
1) on phones:
The calmest, least anxious version of myself this year was when I went 40+ days without a phone. It’s no coincidence that the time I felt most zen was when my brain wasn’t getting pelted by pings, messages, and short-form videos all jostling and vying for my attention.
Everything we call civilization was invented in the last 500 generations—way too short a time for our bodies and brains to re-optimize. - Tim Urban
Think about how many designers and engineers Apple has on payroll whose sole job is to figure out how to get us to use our phones more. Now think about how every single tile on the screen is a separate company, each with their own squad of product designers aiming to improve KPIs like growth, engagement, and retention. The odds are heavily stacked against us individuals to have a healthy relationship with our devices.
Winning this David vs. Goliath battle to get my attention back requires a well thought out plan. During my annual review, I set the intention to avoid using my phone in the bathroom, the bedroom, when working, and even during meals. The last one is related to another goal to overeat less. It’s a lot easier to mindlessly shovel an excess of food into your mouth when you’re not actually looking at what you eat. Combatting the addicting aspects that result in doom-scrolling requires an equal, but opposing force of experience design. I’ve set up app limits, removed ‘bad’ apps from the home screen, and set up the double-tap-on-back gesture to switch my phone into black-and-white mode. I know I’m facing an uphill battle and won’t always adhere to this regiment, but you gotta start somewhere.
2) produce more, consume less:
If consuming is what enters your brain, then producing is what exits your brain. I’ve spent a lot of time consuming tweets, newsletters, podcasts, and books. This year I didn’t have a strong sense of direction so I allowed myself to wander and I was in Default Yes mode. In 2023, I’ll be producing a lot more (more to come 👀) and need to switch to Default No mode. It wasn’t until this annual review in Sea Ranch when it dawned on me that consuming and producing all compete for the same allocation of my time. I guess I thought that the time to create would somehow magically appear. Mid-reflection, I started to unsubscribe from no-longer-relevant newsletters, unfollowed folks on Twitter, and muted a bunch of people’s Instagram stories. This isn’t about me thinking I’m better than anyone else - it’s about protecting my most precious asset (time) from my monkey brain that craves quick hits of dopamine.
3) slow down:
It wasn’t all the time, but there were specific moments this year when I felt like I was trying to sprint a marathon. I was doing so much, but failing to stop and smell the roses. It was like eating a meal so fast that I could barely taste the food. Can you imagine spending $300 for omakase sushi and then proceeding to swallow every single piece of nigiri whole? That’s how I felt a couple times this year. Surrounded by trees and soothing sounds of ocean waves in Sea Ranch, I realized this and then adjusted. I delayed the launch date of one of my projects by two weeks and loosened my expectations for another. In 2023, instead of adhering to rigid schedules, I hope to find a sustainable pace by following flow.
Try it for yourself!
I do everything in Notion and created templates for the daily journal and monthly reflection.
And be sure to check out Schlaf’s Ultimate Annual Review Template - there’s still a few days left this year :)
Personal Updates
Over the past few years, winter has become my favorite season. Conventionally we associate winter with drinking hot chocolate, putting on a few extra pounds to help us stay warm, and staying indoors. For me, winter is when I spend the most time outdoors and when I feel most energized to get stuff done. If this December was an early indicator, my winter will be packed with launching new projects and of course, spending lots of time on mountain. I’m stoked! And excited to share a big update in the next one :)
