#40: Chainsmoking Good Days ∞

progress without plans, growth without goals

At the start of the year, I gave up my job title, a mask that didn’t fit my multidimensional identity, and my paycheck, a financial Tylenol which temporarily soothed the dissonance between my values and actions. The day after I quit shattered mental models of how I thought the world works. I found myself doing the exact same thing as I did the day before: painting continuous curved strokes against the jagged alpine canvas of Jackson Hole, Wyoming. I expected to experience some physical grief or tangible loss in my day-to-day after losing my job, but not much changed. If anything, I felt lighter. Here I was, skiing on a weekday with a bunch of rich old white men. They fit the traditional model of success and in contrast, I had just ejected myself off the conventional path. But in that moment, we were doing the exact same thing: skiing deep pow with no end goal in mind besides having fun. Did this mean that I was also somehow successful? At the time, I didn’t think so.

Every day, I wake up without an alarm and immediately go for a walk. I don’t even know the actual time of when I wake up anymore not only because it varies, but also because I don’t check my phone until a couple hours into the day. On my morning walk, without any distractions or upcoming scheduled activities, I’m free to observe how I feel and what’s going on around me. When I’m at the gym and can both see and feel my progress, when an idea flows through me to written word, when I’m coaching someone and hear their mind click when they let out an audible “mhmm”, I feel great. What is that though, if it’s not success?

Although I’ve only recently had the space to explore what success means to me, it’s been on my mind for years. I used the spray-and-pray strategy for job applications and forced myself through the multistage interview gauntlet. Whenever I was asked “What accomplishment are you most proud of?”, I’d always get a bit queasy because I’d have to BS my way with some random project I worked on as a cog among many in the corporate machine. In reality, I’m most proud of the multidimensional life that I’ve built which strives to find harmony and balance the many sides of me. Through intentionality and tradeoffs, I’ve been able to quench my thirst for knowledge and nourish my soul. I’m constantly tightroping the fine line between intellectual, ambitious city dweller and adventurous nature lover. I can’t say that in the interview though. What they really want to hear is how many dollars of “impact” did I create and how did I manage to create “alignment” with my “cross-functional stakeholders”.

Sublimate: from State to Process

As much as I like what I’m doing right now, I’m hesitant to feel successful because it’s such a loaded term. What I’m doing deviates from the popular definition of success and it feels wrong to claim that I’m successful. So what is success then? A state to strive for? But then what happens when you reach the finish line?

For a while now, I’ve waded through fluctuating amounts of discomfort after having realized I’m not as proud of my resume achievements as I am proud of my eulogy virtues. In a way, the 4.0s from high school AP classes, the EECS degree from UC Berkeley, and the product manager job title are all the same. Prestigious, shiny objects. Through some soul-searching and inner work, but also observing that no one gives a shit about where I went to school or where I used to work, I’ve realized I care more about my values, processes, and beliefs.

To forgo traditional, legible markers of success leaves a gaping hole to fill in. I independently discovered that success is a relentless process that demands careful attention and continuous refining. An infinite game whose primary objective is to keep on playing. For months, I’ve teeter-tottered between Einstein in his eureka moment of discovering E=mc² and thinking I’m batshit crazy. To acknowledge this new definition of success would not only mean abandoning a well-mapped trajectory, but also an entire reorientation of my current life to stay in the game. I found solace in the words of others. In August 2016, a month prior to launching Invest Like the Best, Patrick O’Shaughnessy wrote Growth Without Goals. In it, he references the Indian philosopher Jiddu Krishnamurt says:

Man lives by time. Inventing the future has been his favorite game of escape. … there is no tomorrow for us to be peaceful in. We have to be orderly on the instant. It is only then [when the mind is completely still] that the mind is free because it is no longer desiring anything; it is no longer seeking; it is no longer pursuing a goal, an ideal—which are all the projections of a conditioned mind.

To which Patrick expands on:

Inventing the future is another way of saying “setting goals.” Success, especially in the West, then becomes about achieving those goals. We accumulate accomplishments and call it success. Success means something very different to me, and I think being a great father will be about effectively communicating this different definition of success to my kids. Success is about building a set of daily practices, it is about growth without goals. Continuous, habitual practice(s) trumps achievement-based success.

Reframe: Habits to Rituals

I’ve always had an aversion to write about habits because it includes trivial things that everyone does like brushing teeth, but also because I associate the term with productivity gurus who make $10-a-pop selling Notion guides and explaining how to solve all of your life’s problems with a nifty to-do list. But in the literal sense, yes - I concede that this “set of daily practices” that Patrick refers to is synonymous to habits and they are the core of “growth without goals” or in my own words: progress without plans.

Recently, I declined some exciting plans that a friend proposed because in that moment, I would rather read and write than go on a spontaneous adventure. I offered a half-assed explanation of “I guess I’m just a creature of habit now.” to which the friend scoffed at. That wasn’t fully accurate of me because the thing is, they’re not just habits. It might just be semantics, but the words we use shape our thoughts. Our thoughts shape our perception. And our perception shapes reality. Perhaps ritual is a better term to describe what I am not willing to give up. My set of daily practices is as vital to my wellbeing as Christians going to church on Sunday or my Muslim friends praying five times a day. In fact, the very essence of me, by way of simply counting time spent or self-attributed meaningfulness is this set of rituals that I devote to.

Reconsider: Making Plans and Setting Goals

There’s nothing inherently wrong with making plans or setting goals. It’s certainly possible to sit down, think really hard, form a plan, and then execute on said plan flawlessly. Where I take issue is when people view this formulaic way of thinking as the optimal strategy to live. We spend so much time researching vacation itineraries and career paths thinking that it will bring us happy memories and fulfilling work. The truth is, more information can actually make us even worse at predicting the future (which no one can actually do to begin with).

Perhaps the encoding of these rigid frames comes from corporate culture infiltrating our personal lives. Job requirements, career ladders, and OKRs impose a sense of linearity for how the world works when life is a constant stream of unpredictable unfolding. To answer “I don’t know” or “we’ll see how it goes” when an interviewer asks you “So where do you see yourself in five years?” gets you an instant rejection. In doing so, we associate uncertainty with incompetency and inversely overweight the ability to think about the future.

Making plans is at best an approximation of reality. They represent just one potential state among an infinite set of possibilities. To anchor to them assumes that the current version of you is sure of what the future you wants which fails to factor in the fact that people change. I’ve seen how much my goals have shifted over the years to no longer blindly fixate on them.

Setting goals creates artificial boundaries that separate what you judge as progress from everything else. Fixating on growth in a constricted tunnel ignores the magic that happens in the periphery. If you set a goal of walking 10k steps per day, but then find yourself aggressively swimming laps one day, are you really gonna beat yourself up for missing your goal even though you got a solid workout in?

To put it bluntly, goals are for losers. That’s literally true most of the time. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal—if you reach it at all—feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. That feeling wears on you. In time, it becomes heavy and uncomfortable. It might even drive you out of the game… If you achieve your goal, you celebrate and feel terrific, but only until you realize you just lost the thing that gave you purpose and direction. Your options are to feel empty and useless, perhaps enjoying the spoils of your success until they bore you, or set new goals and reenter the cycle of permanent presuccess failure.
- Scott Adams

In this situation, the complex is easy while the simple is hard. Rather than thinking about what goals you want to achieve and what plans can help you achieve them, just start with where you are right now. It’s simpler to work forwards than to work backwards.

Beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living within that way of life.
- Hunter S Thompson

Discover: Your Good Day

It wasn’t until two months ago when I was on the rural island of Lombok, Indonesia when I stumbled upon this simple, yet profound idea of living one good day at a time. The time zone difference and low cost of literally everything created the perfect self-discovery storm. Armed with a blank canvas of time and powerful US dollars, I was free to do whatever I wanted. But instead of seizing the day, I felt tension in forcing myself to do what I thought I should do, like surfing multiple times a day or going on all-day adventures. Eventually I surrendered control over meticulously planning out each day and instead woke up every morning and asked myself “What would make today great?”

Just like everyone’s body has its own internal clock called the circadian rhythm which dictates when we feel hungry and sleepy, I think we each have an optimal rhythm in how we wish to live based on our personality, our desires, and working style. While in Lombok, I naturally eased into starting every day with a phone-free walk followed by yoga. I know myself well enough now to know that although I’m not energized enough in the morning for an intense workout, I feel the best when I can loosen up and get the blood flowing.

Once my mind is primed, I enter a deep work phase which consists of reading and writing for a few hours fueled by black coffee. I’ve seen how much I can accomplish during these mornings, so now I purposefully protect my mornings from others and from myself signing up for distractions. My first meal of the day is usually around 1pm which marks a transition from caffeinated monk mode to slightly more normal human being. The rest of the day is reserved for working out, any calls, and hanging out. The sacred mornings have become a breeding ground to generate new ideas and hone my craft. The Jimmy Neutron brain blasts don’t happen every day, but I’ve learned to trust the unpredictable nature of ideas blooming and instead focus on what I can control: creating the optimal environment for creativity.

The object isn't to make art, it's to be in that wonderful state which makes art inevitable.
- Robert Henri

While my version of a good day was discovered in rural Indonesia, the beauty of this approach is that it can be applied independent of location and time of year. The morning walk, light stretching, deep work, afternoon workout, and spending time with people I care about in the evening can be replicated whether I’m in Lombok, New York City, or boolin’ in Chicago with my friend Joe (this week). The morning stretch can be accomplished at a lush yoga shala on a tropical island, in a NYC basement apartment gym, or on the turf field at a nearby elementary school (this morning before school started so I did not hear of any complaints about a strange but flexible man on campus). And all I need to do great work is my laptop, internet, and a melodic house playlist.

While this may look like a schedule, it’s far from something so predictable and rigid. It’s precisely the lack of defined start and end times that creates space for dynamically doing what I want, when I want. The vagueness behind “deep work” and “afternoon workout” is intentional. Some days comprise of reading hour-long essays on evolutionary psychology followed by surfing until the sun goes to sleep. Other days involve interviewing people for my climate newsletter and then pumping iron within the confines of a concrete jungle. It is the contrasting combination of an empty calendar with vital non-negotiables that allows me to fight the never-ending battle against productivity with the power of presence.

How we spend our days is, of course, how we spend our lives. What we do with this hour, and that one, is what we are doing. A schedule defends from chaos and whim. It is a net for catching days. It is a scaffolding on which a worker can stand and labor with both hands at sections of time. A schedule is a mock-up of reason and order—willed, faked, and so brought into being; it is a peace and a haven set into the wreck of time; it is a lifeboat on which you find yourself, decades later, still living. Each day is the same, so you remember the series afterward as a blurred and powerful pattern.
- Annie Dillard

Hierarchies, titles, and schedules are crucial for coordinating groups of people towards a common goal. But just because a coxswain keeps the crew team rowing the boat together in a race, doesn’t mean you need one yelling in your ear for your own individual leisure paddle across the pond. You don’t actually need a manager in your head telling you what to do and when to do it in order to get stuff done.

Patrick calls it growth without goals and I call it progress without plans. I use P-words. He uses G-words. The combination “PG”, aka Paul Graham, seems to agree:

But while you need boldness, you don't usually need much planning. In most cases the recipe for doing great work is simply: work hard on excitingly ambitious projects, and something good will come of it. Instead of making a plan and then executing it, you just try to preserve certain invariants. The trouble with planning is that it only works for achievements you can describe in advance. You can win a gold medal or get rich by deciding to as a child and then tenaciously pursuing that goal, but you can't discover natural selection that way. I think for most people who want to do great work, the right strategy is not to plan too much. At each stage do whatever seems most interesting and gives you the best options for the future. I call this approach "staying upwind." This is how most people who've done great work seem to have done it.
- PG in How To Do Great Work

Patrick’s “daily set of practices”, Paul’s “invariants”, and my “good day building blocks” are simple in theory, yet hard in practice. All I need to do every day is exercise my mind, move my body, and nourish my soul, but it’s easier said than done. Given I only internalized this mindset of continuous forward progress recently, the steps I took are still somewhat fresh in my head.

What you need to discover your ideal day:

1. Have the humility to acknowledge you may not be living your ideal day right now.

2. Free up time and mental capacity to play around and experiment.

3. Muster up the courage to try new things.

4. Do. Thinking is no substitution for doing.

5. Reflect. To know if you’re getting closer to what you’re looking for.

6. Refine. Over time, the definition of an ideal day will morph as you change.

7. Repeat. A great life is simply the summation of many great days.

To those who can consistently execute perfectly on plans and always hit your goals, kudos to you. You shouldn’t listen to me and just keep doing what works. As for me, I have learned to avoid making plans and setting goals and instead focus on one good day at a time. And now it’s that time of the day when I hit the gym and then make dinner with friends. ✌️