#30: Living and Working in Seasons 🌍

exiting winter hermit mode

As a function of abandoning the 9-5 Monday-to-Friday work cadence and deepening my relationship with nature through outdoor sports like skiing, surfing, and backpacking, I’ve become aware of how much I change with the seasons. When I first started working, my daily rhythm was dictated by the digital blocks of meetings on my work calendar. Now, my entire state of being (emotions, actions, orientation towards newness) ebbs and flows with the environment I am in. Since quitting my job, I’ve replaced my artificial alarm with natural sunlight and while it’s still ski season, I select which days I’m going to work based on the snow forecast. I’ve swapped out the guiding constraint in my life from Google Calendar to Mother Nature. Left to my own devices, I’ve had to figure out how I want to work which may be just as important as what I work on.

Back when I was working a corporate job, the rest of my life was oriented around the workweek. With the privilege of a remote job and a manager who trusted me, I had the luxury of being able to slot in chores and workouts throughout the day. With that said, work came first and I would plan my days around meetings like a kayaker navigates whitewater rapids. When I first started to “sneak out” from my remote office (aka wherever my laptop was), I felt equal parts nervous and badass. Here I was, going to the gym at 11am on a Tuesday. I felt like I was getting away with getting paid to work out and extracting money from Big Tech without realizing that the opposite was happening during all those late nights I stayed up working.

Initially, I wasn’t totally comfortable with “sneaking out” so in between sets at the gym, I kept my eyes glued to my phone, swapping between Slack and email, thinking that I would get caught if my little green bubble turned off. That tiny status indicator was like the heartbeat monitor in every dramatic hospital movie scene. It represented the lifeline of me as a worker. Green meant I was alive and active, but grey indicated inactivity, the equivalent of flatlining as an employee.

the same thing

Working late in NYC in 2021

I first realized the mismatch of when I wanted to work and when I was supposed to work in the summer of 2021. I was living in NYC, but still had to attend meetings during west coast evenings. During the morning, I was ready and eager to work, but my colleagues living in California, Australia, and China were still asleep. I would try to get as I could done, but would inevitably need to wait until later in the day to get a response.

In the evening, the buzz of work would peak around the same time as invites to grab dinner. On multiple occasions, I would meet up with friends, but then have to rush to the nearest WeWork to take my last couple of meetings. I even took some late night meetings from my friends’ apartments if they lived close enough to the restaurant. I definitely noticed that I was always the only one who brought a backpack to dinner. In order to figure out how much time we still had left to eat, I would mentally count backwards from when my next meeting was and factor in time to ask for the tip, pay for the meal, and walk to my impromptu remote work refuge.

Shifting to a natural rhythm during ski season

Operating within the constraints of my late west coast schedule led to some overwhelming evenings in New York City, but turned out to be in my favor during the winter. For the last three years, I’ve lived in mountain towns across Colorado, Utah, and California and without any morning meetings, I could ski for a few hours before my first meeting. With my calendar empty for the first few hours every day, if I wanted to ski, I could. Without consciously thinking about it, my days began to mimic nature. If there was an incoming storm delivering fresh snow, free of any obligations until noon, I would ski. It was this newfound affordance to start thinking about making plans that previously weren’t even a possibility that felt so invigorating. I experienced the magic of the mid-week powder day, the pinnacle of skiing conditions combined with zero lift lines. Looking back, it was probably that first ski season living in Frisco, Colorado and Park City, Utah that set me down this entire path of questioning why I should remain a full-time employee when I value the freedom and control over my own time so much.

Working in seasons

Most white-collar jobs follow artificially-generated seasons. Accountants are slammed in March as tax season is imminent. Tech employees follow bi-annual planning cycles arbitrarily coordinated by mid-level management. However, most blue-collar jobs follow naturally-generated seasons. HVAC technicians are busiest during the summer when everyone wants to upgrade their A/C. Farmers must grind during the planting and harvesting seasons so they have enough sustenance to get through the desolate winter. The majority of the world actually works in harmony with nature; those of us who live life centered around digitally recurring stand-ups, all-hands, and one-on-ones just haven’t fully realized it yet.

The first step to consider work as a cyclical pattern of seasons is to first decouple the belief that work must follow a static repetition of 8 hours a day, 5 days a week, 50 weeks a year (factoring in vacation). We should not blindly assume that the current way of working is the optimal way. Much of the standard 9-5 workday are still the remnants of the Industrial Revolution, when productivity and economic output were tightly correlated to the sheer number of hours worked.

On some level, we already know how the seasons affect our personal lives. At the beginning of the year, we all collectively chant “new year, new me” with some haphazardly set new year’s resolutions. The short, cold winter days keep us inside and meeting up with people takes just a bit more effort. The summer is ideal for finally taking some time off for a well-deserved vacation; perhaps Europe or somewhere north. Around Thanksgiving and Christmas, we carve out time for family and some end-of-the-year reflection. If our personal priorities change through the seasons, how might we adjust our work periodization to better align with the natural flow of life?

My seasons

For the first 2.5 months of this year which also coincides with leaving my job in early January, I’ve been a complete hermit. Geographically, I’ve been hunkering down in the mountains of Lake Tahoe. There were multiple stretches of a few days at a time that I spent completely alone. This initial chapter in my career break served its purpose though. It took a lot of solo time reflecting and pacing back-and-forth to figure out what I needed for my personal projects. I spent the time creating climate newsletters and podcasts ahead of publishing schedule and reading books at a slower, but deeper pace. Going from full-time employee to full-time sabbatical brought some unforeseen conditions that I had to adjust to. I had to get used to having so much control over my own time, but also taking responsibility for how I would actually spend it.

Last week was a noticeable transition from winter solitude to spring awakening. I spent a day in San Francisco, visiting my old office and then attending a climate tech event at night. After writing about climate in isolation for a couple months, it was refreshing to meet founders and investors in the space.

The next day I flew out to Colorado to visit my friend Parker. I arrived late at night and we decided to leave for Crested Butte at 4:25am so I set my alarm for 4:17am. Yesterday, at 10am I was at 13,000 feet elevation on the top of Breckenridge. By noon, I was shuffling around barefoot on Parker’s front lawn (it was sunny and warm in Denver), organizing my skis back into the bag. We had enough time to grab lunch at my favorite Vietnamese restaurant and I was back home in the Bay in time for dinner. The pace is starting to pick up for sure.

Mount Crested Butte in Colorado, we boot-packed to the top and then skied down the left face

I think about how I relate to the seasons in terms of people and places. For people, how much time am I spending with myself? With existing friends? With new faces? For places, am I still? Or moving around a lot? Am I in the mountains, by the ocean, or surrounded by dense skyscrapers?

If this winter can be summarized as a hermit phase where I was more internally-oriented and stationary, then the next couple months of spring will be defined by an intense burst of travel. I’ll still be focused on existing people in my life, but the places will constantly change as I wrap up ski season, visit friends in Hawaii, and spend a couple months surfing in Southeast Asia. In the summer, I plan to slow down the pace of travel and make room for new connections. I know myself well enough to know that it’s impossible to focus on both people and places at the same time. It’s too early to say what fall will be like, but I suspect by then I’ll have a clearer picture for where my personal projects are headed and how I want them to evolve. Part of working in seasons is also accepting uncertainty and recognizing that what a season brings is often shaped by its priors.

The Seasons of a Man’s Life

I was reading this summary of The Seasons of a Man's Life which made me zoom out and recognize there’s different levels of seasons. On an annual level, there are the seasons that mimic the real natural world. But there’s also the “life cycle and its seasons”. Through interviewing and pattern-matching, the author finds recurring themes in a man’s life including the “Age 30 Transition” and the “Settling Down” period. Combined with listening to Bill Perkins, the author of Die with Zero, on the Peter Attia podcast, I’ve begun to internalize the notion that there is a finite, optimal time window for everything. Your current desires and objectives will not remain the same as you age, so don’t wait.

The first time I visited Bali, I happily stayed in a $4/night hostel. Today I still think I’d be okay with that kind of humble accommodation, but I’m also aware that the time window when I’m comfortable with this is closing. Maybe in two years I won’t want to stay in hostels anymore.

The reason why I travel so much right now is because I’m aware that this is the best time to do it and I may not want to do it later on in life. It might seem counterintuitive, but the more I want to focus on other things later in life like raising a family and building community, the more I want to travel now and experience unique adventures while I have maximum freedom and minimal responsibilities.

It’s in my opinion that my 20s should be for exploring as broadly as possible, geographically, intellectually, and spiritually. I would rather reach points of too much and feeling overwhelmed than play it too safe and look back with regret. I have a variety of competing ambitions and I’ve experienced firsthand at how impossible it is to do everything at once. So far, my approach has been to align myself with the natural changing of seasons and try to flow with it all. The winter brought me peace and solitude. Spring is emerging and will give me new ideas to think about. What will your seasons bring you?

a postcard from a small cafe on the way to Tahoe, perhaps a visual summary of this entire post