it's a lovely world out there beyond work
a retro on blowing up my life and reimagining what I want work to be
summary: With no scheduled work engagements for the first time in her life, a Chinese-Canadian millennial reflects on what led her to taking a time-blocked career break then an indefinite career break. She ends up taking a vacation (travel) from her vacation (unemployment/sabbatical) and hopes that by preoccupying herself with travel rather than job applications, she will have a clearer picture about what she is looking from work, how it will fit into her future life, and how she will achieve that by working for herself.
I. I do not dream of labour as a transaction
Since mid-2022, I have been building my vocabulary to say, in a professional sense, “I do not dream of labour.” Labour at its ideal is an exchange, and at its worst is a transaction. When it’s an exchange, it feels fruitful, equal footing, reciprocal care, transparent values, a pendulum of favours and returns. When it’s a transaction, it feels flat, bounded by limits, and boring — for something that’s supposed to take 40 hours a week.
Instead of exchanging my labour with an employer primarily for money, what if I exchanged my labour with society primarily for fulfillment?
“Why did it feel so taboo, I asked, to approach work the way most people did, as a trade of my time and labor for money? Why did we have to pretend it was all so fun?” — Uncanny Valley, Anna Wiener
In the tech workplaces Anna describes, work feels designed to be fun, complete with everything you would find in an all-access pass to an arcade. In a corporate workplace, the work and at first, onboarding and figuring out the work does feel fun (even without the arcade-like furnishings), particularly for people who have thrived all their life on their ability to figure things out.
In January 2020, I started a consulting internship, my gateway to full-time employment, in Berlin of all places!. It was the path I had manifested years ago during undergrad after realizing 2 things: 1. that no, I was never going to be a software engineer or a primarily technical worker. & 2. that I wanted to work in Europe after graduation.
The shimmer of a city with artful roots and underground mayhem and hilarious moving-to-europe-as-a-foreigner moments kept me in an eager, roll-with-the-punches kinda state. On weekends, I flew to new capital cities on my checklist. On weekdays, I searched for pho & asian food that tasted like the ones at home (not too sweet of a broth). I look back at those 2.5 months so fondly.
Then bam! pandemic. move home. bam! start full-time.
“As early employees, we were dangerous. We had experienced an early, more autonomous, unsustainable iteration of the company. We had known it before there were rules. We knew too much about how things worked, and harbored nostalgia and affection for the way things were. We didn’t want to outgrow the company but the company was outgrowing us.” — Uncanny Valley, Anna Wiener
Two years in, that’s when my relationship with work started to change. I was comfortable with the work, work was patting me on the back and offered me opportunities. I grew closer to my work friends and we became friends independent of the work. The workplace kept growing in revenue and size, the spotlight of DEI came and went, the culture started to shift. Understandably so! Growing pains! But with work’s growing pains and the days starting to feel like a routine of Zoom calls, I started shifting my energy out of the work day.
Growing up in the suburbs of Toronto, I always had a pessimistic view of the city — what was so good about being in a grid of skyscrapers? But after lining up a promotion and acknowledging the convenience of being close to family and home, I decided to give downtown Toronto living a try — a limit of 1 year. It was one of those decisions that I made purely to have stronger conviction afterwards. I still didn’t like the city and I didn’t see myself moving back permanently, but I warmed up to its perks: the concentrated neighbourhoods of culture, the rotating food scene, the frequency of events. All significantly stronger and higher than Vancouver, but to me, having a little bit of all of this is enough.
“I had reached the promised land for millennial knowledge work. I was making eighty, ninety, then a hundred thousand dollars a year doing a job that only existed for, and on, the internet. Mostly, I wrote emails for a living. Mostly, I worked from home. The job asked so little of me, I might have forgotten I had it — except for the fact that it required me to be online.” — Uncanny Valley, Anna Wiener
The millennial knowledge work itself was great! I loved the different projects and my wonderful colleagues but I didn’t feel the need to dedicate all my energy into work anymore. I actively sought non-work things and consequently started to challenge the time and space that work filled in my life.
When I moved downtown, I had plans to maximize my 1-year stint. I went to drop-in pottery classes at the Gardiner, biked to flight school at Billy Bishop twice a week, hopped between laptop-friendly coffee shops in the afternoons of the workday — things I could only do when living in the downtown core.
I also had other dreams. Dreams I forgot I had already mentioned at work in the early days of my career. Hilariously in character of me to consciously be dropping hints about my multifaceted self from the beginning. One such dream was to teach snowboarding in Japan but I wanted to hold onto my consulting career a little longer — I had hopes that I would feel inspired to return, to pursue another promotion, to see the open, caring, conversational culture return.
Should you choose to leave before you feel compelled to stay?
Or should you choose to stay until you feel compelled to leave?
”None of us had anticipated that success would be to the detriment of what made the place feel special — what made it feel like ours. The new employees treated it like any other job. The new employees had no idea.”
— Uncanny Valley, Anna Wiener
We often know what’s coming before we acknowledge it. We collect and forget about weak signals until the answer is undeniable. Once you’ve mentally crossed the threshold of believing you hold a fake job, change becomes necessary and imminent. When your intrinsic motivation starts to waver, your reputation starts to separate from your capabilities. When you start gathering less energy from social interaction as an extrovert, maybe it’s not an existential crisis but rather the scenario itself? Trust your hunches when it’s time for a change. I’ve realized that I’ve always been more thankful for swift changes than the time I’ve spent dwelling on them.
Once you reach 6 figures, quit (or at least consider it).
As an aside, let’s remind ourselves that we can reinvent ourselves. The world gatekeeps social sciences and gatekeeps STEM, but anyone can learn anything — so why are we holding each other back?
II. Reclaiming life as time well spent
Teaching snowboarding is one of the simplest and best jobs I’ve ever had. I will say that to even become a snowboard instructor, let alone teaching abroad, is a feat of economic stability. It takes time and money to invest in this sport, learn, be certified, and live like I’m vacationing on this working holiday. I feel grateful that this is where I have been able to spend some of my career savings on and that I’ve chosen to do this now rather than earlier. But back to the job’s simplicity, this was the first time I had a full-time physical job. It is exhausting! Waking up at 7:00am, then on the mountain from 8:30am to 3:30pm. An extremely fulfilling job if you love this work and being outside and one that exhausted me physically more than mentally — a welcome change. By being physically exhausted, I felt satisfaction for having exercised and moved my body to different places each day, something I often only got when I ran errands during my work day or travelled. That in itself makes it a job I love, without even getting into the morning runs, and the snowsport instructor vibe that is hard to replicate in other workplaces, and the powder snow dumps. Beyond it being a job though, I felt another sense of satisfaction where I felt that it was an incredible way to spend my time. The monetary return wasn’t high but the emotional return has set my expectations for ‘time well spent’ on a higher level.
When we aspire for work-life balance, what if we considered it as an energy flywheel where we have both stimulation and rest in both? What if a sustainable relationship with work is one that encourages commitment?
“We tend to associate freedom with freedom from work, or leisure time, in the simple sense. Precisely because so much of the actual work we have to do is not meaningful, and we can’t see the purpose and the point of it. The emancipatory point, however, is not to be free from work, but to be able to be engaged in, and committed to, activities and work that are meaningful in themselves.”
— Martin Hägglund, Wolfgang Tillmans on Photography and Spirituality
While I retreated away from the internet, the AI race stepped up. It was like I ventured into a forest of flowers within earshot of the roaring highway. I care about these developments on the internet. After all, this is the industry that I’ve chosen to work in. But intentionally separating myself from it for the time being allowed me to see knowledge work particularly for the tech industry as just one industry in the world, rather than the dominating one, particularly in North America. It’s been grounding to remember that the internet and the digital world is nevertheless an augment, one path for innovation rather than the end-all.
III. Spotting the Sheikah Towers
While teaching snowboarding, I quietly panicked about my future. And in that moment of panic, I latched onto an opportunity that I thought I’d miss out on without considering its effect on my original intentions for this career break. I overlapped two work commitments and forgot about the impact on my energy reserve. Doing good work isn’t hard but to invest yourself emotionally and show how much you care takes time and intention. Working part-time while travelling wasn’t the plan. But if it was, then I would’ve taken March a lot slower and set aside days to rest and work in coffee shops. If I did it over again, I would’ve done one thing at a time. Give yourself the luxury of time when you can.
Living in Japan was the first part of my big adventure era, spanning between my time in Toronto and the next place I move to. In an unexpected turn of events, I quit my part-time job for a complete reset. By doing so, I made space for unstructured time and agency, for a hunch-based approach to my days. In the first week, I mostly slept. In the second week, I mostly read Uncanny Valley. In the third week, I started to edit videos. I do feel like I blew up my life, in a ticking time bomb fashion where my decisions since my working holiday each marked a ticker on the countdown, and ended with my indefinite career break.
But like Link waking up from his slumber, I feel clueless but guided. In Breath of the Wild (which I’m finally playing after owning this game for years), there are Sheikah Towers that rise above the land and when activated, unveil parts of the map. But there isn’t a particular order to this part of the game, you can explore the open world then activate the ones that feel within reach. I feel similarly about the rest of my life — there’s lots to pursue and little limitations, and who knows what’ll open up next.
It also feels like I’m starting on my Pathless Path as I explore what work could be! If I sketched a digital garden of my interests, third spaces and spontaneous joy would be in the middle, with branches into the snow industry, the outdoor industry, better social media, and innovation in general. I’m convinced that my interests are all related and that I can link them all through work rather than leaving some behind. I’m increasingly excited about building something from idea to reality. But before that, I’m taking the next month to brainstorm a big list while on-the-go to avoid falling into the trap of ten thousand false starts. Maybe I’ll open up a third space in Vancouver? A hostel in Niseko? A coffee shop / event space? A nature x STEM ed program?
By the time you’re seeing this, I had all the intentions to publish my first travel video on my time in Niseko! I’m so proud of this edit — but it’s not quite ready. I spent my midnight hour reading the last parts of BASIE!BOP!JAMAICA! and feeling again, that there is more to life if only we listened better.
As I’m figuring out my future, I’m reminding myself of two things:
Everything you put online is a resume builder
When you consume, remind yourself about the delight it is to create
A few weeks ago, I saw Hamilton (!!!) with my best friend! It reminded me to think about my legacy, what I would be proud to be known for. It reminded me that the game is exciting but there’s more to life than the its relentless pursuit. And reminded me how lovely and silly it is to have friend groups and how lucky I am to have such wonderful friends.
We often underestimate other people’s memories of us. After all, our memories are better at reminding us of what others have done for us rather than the things we’ve done for others. I love how willing and excited people are to catch up and reconnect even when our last memories together are so far behind.
That’s all! I just love it here. I’m heading on my vacation (travel) from my vacation (unemployment/sabbatical) tomorrow. Have a wonderful summer (not to be confused with the bland wishes of hags)!