where the wind blows

on focus, optionality, and optimization

I’m biking up Yonge St. and the wind is ferocious. It pushes me back; if I’m not careful my bike begins wobbling, and I face much resistance as I slowly pedal through the wind in efforts to reach my destination. I have to push past it, I think. I must, or I risk falling. All I can hope for is that the wind will stop sometime soon. 

But on the way back, I find it’s easy. I’m not using the same amount of force I used before. Things feels calm, they feel natural, and I feel free. The winds guide me to where I am trying to go. They propel me to think about the winds in my own life that I either find myself resisting against, or surrendering mercilessly to.

✻

I’ve been thinking a lot about focus recently. What matters to me, why they matter, what to focus on and optimize for, whether to go fast or slow, etc. It appears there are an infinite number of options. I find myself torn between different hobbies, career paths, even micro-decisions like whether to stay in on a Saturday night or go out. I first wrote about this in insatiable, where it feels like there are a million menu options at the all-you-can-eat buffet, and they’re comprised of all your favourite foods.

It’s a good problem to have, but one that begs the questions: How do you choose? Where should I be spending my finite time and energy? What am I optimizing for?¹

“Almost everyone I’ve ever met would be well-served by spending more time thinking about what to focus on.” ~ Sam Altman

I’ve particularly been reflecting on this Sam Altman quote, once from reading the excerpt directly from his article How to be Successful, and another time when referenced in Escaping Flatland. In Karlsson’s piece, he refers to life as this “multi-armed bandit”, a name derived from a probability theory problem.

A gambler faces a slot machine (“a one-armed bandit”), except this machine doesn’t have one arm—following some twisted dream logic, it has k arms, arms sticking out in every direction. Some of these arms have a high probability of paying out the jackpot, others are worse. But the gambler does not know which is which. The problem is pulling the arms in an order that maximizes the expected total gains.

…

The gambler needs to learn new knowledge about the machines and simultaneously use what they have already learned to optimize their decisions. In the literature, these two activities are referred to as exploring and exploiting. You can’t do both things at the same time. When you explore, you are pulling new arms on the bandit trying to figure out their expected payout. When you exploit, you pull the best arm you’ve found. You need to find the right balance. If you spend too little time exploring, you get stuck playing a machine with a low expected payoff. But if you spend too much time exploring, you will earn less than you would if you played the best arm. This is the explore/exploit trade-off.

— Henrik Karlsson, from Think more about what to focus on

I’m currently trying to figure out what these arms look like for me. Doubling down on my independent design practice vs. pursuing other full-time design roles, what community events to both run/host and attend, and whether I decide to run, gym, climb, or play volleyball consistently.² Each arm yields a different set of results when pulled, and often requires optimizing for opposing things. For example, I know that investing in crafting my design portfolio would yield positive results in either scenario revolving around my career path. However, the freelance portfolio often optimizes for breadth of work whereas the product portfolio optimizes for depth. I can’t pull both arms at once.

Creatively, I would like to dedicate myself to writing for this Substack, but every additional minute spent on it means less time allocated towards other design projects in my backlog. I technically could still work on those projects on top of writing, but this would also eat into my time spent working to make a living among other higher priorities such as good health, which feels infeasible to shift focus away from.

While I know that I could do all of these in theory, I also know that means only maybe 1-2 of them can be done well at a time. When my focus is split, it feels like my heart is only half-in everything and I don’t feel like I’m putting my best foot forward into the various arms. It’s also simply unrealistic for me to believe I will always have the energy to put my 100% into all the things I care about. I yearn to be all-in. I wish to commit myself to something, but not just anything. I want to love something AND be able to dedicate myself to it fully.

That’s where focus comes in.

Focus isn’t just about saying no to things. It’s about saying no to the right things, to the things that require a sacrifice and have a relevant opportunity cost for saying no to it. Paraphrased from Steve Jobs, true focus is saying no to things that with every fibre of your being you want to say yes to and can’t stop thinking about, but you say no to it because you’ve committed to focusing on something else. For instance, it’s not enough for me to think I’m focused through saying no to watching k-dramas since I’m prioritizing work, because the sacrifice isn’t equal. It doesn’t carry the same weight of importance. Rather, it’s having the courage to choose between similar opportunities indexing on somewhat opposing benefits. Maybe you turn down an attractive full-time opportunity because you just committed to starting a business, or decide to move abroad for a new job when all your friends are going to New York. In either situation, you’re in pursuit of something you think you’ll love, while deliberately choosing to step away from something that you also love. It’s the decisions that break your heart a little (or a lot) to say no to, but you know it’s the right call to make for whatever your current goals are in life within the duration you’ve set. That’s focus.

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So, what am I choosing to focus on now?

I’m not done exploring in the slightest, but I think I could really benefit from starting to pull a little on the arms I know has been working for me. These days, I often preach how I like to optimize for things like serendipity, silliness, laughter, fun, giggles. A large part of this has been achieved through community, and doing so has brought me more fulfillment than I’ve had in years (as evident in the love letter I poured my heart into over my communities in Toronto). With that being said, as of a few days ago I started going on a social media (mainly twitter/IG) break to get away from the world for a while and really think about what I want to focus on (cue: this post), as well as actually make meaningful progress in those directions. I’m currently on this break until May at the very least. If I’m slow to respond to any DMs, this is why :’)

This also means I’m on a semi-break from my community engagements, since most of it is fostered on Twitter (X). I have deliberately chosen to step away from something I love so much for a little while, because I actively want to dedicate more of myself to my craft. In order to hit the ground running in May with various community events I’m hosting, I’m going to need some time to A) really reflect on how I want to show up in the communities I want to see flourish as well as meaningfully engage with all the people I love, and B) focus on practicing within the level of craft I want to achieve, or in other words making progress in closing the gap between my taste and my abilities.

I don’t talk about it often, but going independent has been a journey filled with a lot of excitement and curiosity, but at the same time a lot of uncertainty and instability. I do think pursuing B) will take much more time than the short break I am allotting myself, but I’d still like to plant the seeds now and then spend the next quarter thinking more heavily on what I want for myself career-wise, while actually taking action to pursue those goals. I value all these arms a similar amount, so rather than removing them entirely I am merely shelving them away on rotation, placing a smaller focus on them until I have enough confidence to rotate my current focus out. By the end of May I foresee being able to have a better balance with my community involvement, and by June I’d like to shift craft into a top priority.

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These bidirectional winds can be anything from a career decision, to a lifestyle choice, to a community to invest in or a relationship to nurture. When I think about going where the wind blows, I see it as doing what naturally makes sense. Things that intuitively feel right, come easy, and are peaceful. See where it takes me, and see where I land despite the destination being uncertain or far away. In such situations, it’s easy to keep cruising regardless of an end destination because minimal effort is exerted to maintain my course, in the best way possible!

Alternatively, I could go against the wind. Actively fight to move towards something I’m not sure is worth all the resistance, but there’s intrinsic motivation and excitement for it that’s enough to tolerate the struggle. Whether that’s good or not is uncertain, but what’s known is that it’s a rocky path. It’s strenuous, it requires a lot of hard work, time, and effort. This path often requires much more conviction, as well as exploitation, to both survive and thrive.³

The different arms in my life are calling for different winds. Some of them will ride the more peaceful path, while others prove to be a bit more difficult. Perhaps the richest rewards lie in winds with a combination of both.

Until I know which is which, I shall keep riding. Slowly, the winds will take shape and begin to trace the outlines of my heart, carry currents that take the weight off my shoulders, and whistle harmonies that echo my heartbeat. Eventually, I’m sure I’ll hit jackpot. I patiently await those days.

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life roundup 𐙚₊˚⊹

• much of april has been a blur. within the first week or so I had travelled to attend three demo-based events, each in a different city: Waterloo (Socratica Symposium), Vancouver (Atelier Showcase), and Toronto (New Demos 2).

  • they were all wonderful, and it’s clear to me I value such activities, but it’s also equally important for me to recognize when I’m feeling a bit overwhelmed and I acknowledge that’s possible while still loving the communities I’m in (me, realizing i’m not, in fact, invincible :0). hence the short break !

• signed up for a 10k race because of some friends mentioned below when i haven’t ran one since high school! also climbed again for the first time in a loooong time

• visited home in Vancouver briefly to see family and friends (besides showcase) :)

• been playing a lot of Stardew Valley again (see footnote) whenever I have some downtime and loving it

• recently watched Exhuma at TIFF with one of my closest friends. super intense and impactful Korean supernatural horror-thriller, enjoyed and was terrified at the same time, ate gelato to recover. would recommend still if that’s up your alley

shoutouts ⋆⭒˚｡⋆

• somehow found myself in a lovely group of friends full of people who say good morning to each other and bestow hopeful wishes for the day (every day), people who push me to be a better version of myself and are slowly becoming my (sometimes literal) compass in life. shoutout jammy jams fr ♡

• T, who helped will this post into existence through another writing bet

• M and C, who gave super helpful feedback on this piece’s drafts <3

• M, N, C, and T who have all been hearing me out on some of this stuff, often resulting in me sending a slew of spammed messages that I am pleasantly surprised to receive meaningful responses to each time :’)

1. Funny enough, I’ve also been drawing parallels to these questions with my recent playthroughs of Stardew Valley, where I find myself in a constant battle between optimization and going with the flow.

In this world of endless optionality, you can grow crops, go fishing, hit the mines, raise animals, befriend all the villagers, etc., and you can end up dedicating tens of hours (some, hundreds or thousands) into trying to achieve the ‘perfect’ farm to your heart’s content. There’s a little voice in my head telling me to search up the optimal pathing for each day or detailed walkthroughs on how to do certain things, rather than trying to figure it out just by living each day and discovering new aspects of the game, akin to the real world. Why am I trying so hard to optimize everything? It’s definitely habits of a stubborn planner seeping through. Through this game though, I’ve been practicing patience and it’s reminding me that maybe I don’t have to go so fast all the time. I can take my time. If I don’t get something done right the first time I can try again the next day, next season, next year.

2. In a conversation with T, I say verbatim “ok no fr but like how do i commit myself to a [climbing] membership while also being a serious runner while also being a serious lifter and also becoming a volleyball god”

To that, he tells me “you can either water all the flowers and see slower growth in each bucket, or choose to hyperfocus on fewer options. [But] just because you say no to one [thing] now doesn't mean you can't come back to it in the future.” Perhaps some things operate on more of a timeline rather than a closed yes/no flow chart.

3. My struggle here though is with figuring out when this resistance might indicate alarm bells, vs. when it’s a sign of something worth pursuing. For example, if you’re trying really hard to make a relationship (with people, with projects, with companies) work against all costs, despite all the friction and tumultuous situations. How do you know when it’s worth it to work through something and make compromises, versus walking away? What if it doesn’t feel good now, but it will later if you just push a bit more to fix it? Where is the line?

The answers aren’t coming easily to me. But I’m figuring it out with you all (70+ now!) and I’m thankful to currently have the time and space to do so.