Dancing with the Chaos Monkey: Refining Goals, Building Work Cycles, and Decluttering


This article
came at the right time. After sixteen months of constant change — a job switch and four unexpected moves — and adversity — financial struggles, working overtime, and cancer surgery — I needed to be reminded of Nassim Taleb’s ideas. He’s the only writer, aside from Haruki Murakami, who has given me both perspective and comfort during times of uncertainty. When you read his work, it’s impossible to look at the world in the same way.
Up until now, I’ve been fixated on his philosophies of risk and causation (see: Fooled by Randomness and the Black Swan), but after the events of the past year and a half—and my determination to continue building the career I want despite them—I’ve become more interested in Antifragile. It’s an exploration of how certain things grow stronger through disorder. It’s not a question of resilience—bouncing back from negatives; it’s a matter of thriving on them. 

I’ve been chewing on this question for the past few weeks. During all of this craziness, I’ve maintained a strict workout, language study, and coding routine, which has produced some awesome results (and provided a constant source of joy and refuge from the rest of my life). About a month ago, this discipline started paying off. After months of tedious, uninspired coding sessions, I began building three apps and developing a Russian language course in a burst of creative energy. A few weeks later, I was offered my first professional opportunity as a developer at a Chinese language education startup. Then another offer came. Then another.
While my options were expanding, I started a Meetup group to connect teachers and developers who are interested in using technology to improve language education. Outside of my teaching job, I was networking, talking tech, and learning about new technologies. People were finally listening to what I had to say about mobile design and language education. I was in my element.
But all of the turmoil over the past year—and my refusal to deal with it emotionally— had taken its toll.
Two weeks ago, I found myself hit with a wall of absolute, utter exhaustion. At first, I simply decided to cut back on language learning and focus on getting up to speed with iOS development. I put off my Russian language challenge until December 1st and buckled down on my projects.
But then I started waking up late and binge-watching TV shows at night. I couldn’t focus or process any information. My muscles ached and my appetite was non-existent. I was burned out.
So, I was faced with a difficult choice: maintain the status quo and continue pushing myself into the ground, or give myself a break.
I chose the latter, and I’m glad I did. The workaholic in me needs to die, so I can perform better.

The Plan

Until November 28th, I’m not studying, practicing, or developing anything. Aside from finishing my application to Middlebury College’s Summer Language Program, I’m going to spend some time assessing my career and figuring out sustainable ways to achieve my goals.
This down time will be essential because I’ve decided to quit my teaching job, effective January 10th, so I can focus all of my energy on transitioning to software engineering. 

From Workaholic to Top Performer



I love working. Learning languages, building apps, reading and thinking are more pleasurable to me than a night out. Spending Saturday nights doing these things has never felt like a sacrifice.
The problem isn’t the work. It’s that the work occurs at the expense of everything else. My schedule is sustainable—energizing, actually— in a vacuum. But not in the context of day-to-day bullshit, which, unfortunately, is unavoidable.
There are three toxic habits I’d like to change:
  • When I have a goal, I sacrifice everything to achieve it: my health, sleep, relationships, bank account, and even my sacrosanct workout routine. Although I’ve convinced myself that I’m focusing, I’m actually creating tiny stressors that drain my energy and performance. This is a failure of time management.
  • Related to the first, I’m bad at walking away from work. Instead of doing power sessions, I spend hours on one task. This is a failure of efficiency.
  • Perfectionism. This is the driver behind my lack of efficiency: I won’t push myself to the next level, until I’m “ready”.
I’ve enrolled in Scott Young and Cal Newport’s Top Performer course to get out of these habits. As part of the class, I’ve started reaching out to developers I admire to get some career perspective. And I’m reading Creativity, Inc. and Manage Your Day-to-Day for additional strategies.
I’ve also committed to resuming my workout routine, healthy eating habits, and caffeine limit over the next two weeks.

Creating Work Cycles



To re-train my work brain, I’m developing work cycles—daily plans that can morph to accommodate unexpected crises or energy drops.
My to-do lists have always assumed that I’ll be at my best. This approach is flawed because, in the scheme of life, things are always subject to change. In short, it’s time to stop setting myself up for failure.
I’ll be posting goal-specific work cycles in the next week or so, but in general, I’m looking at creating two task lists: one for a normal day; one for a day when all hell breaks lose. By figuring out the minimal amount of work that will push me closer to my goals, I’ll avoid this trap in the future—and the self-loathing that goes with it.




Then there’s the clutter. Not necessarily in terms of stuff — I’ve been living out of one suitcase for close to three years — but in terms of how it’s organized. I recently read this wonderful post on how an organized environment, filled only with objects that evoke joy, enhances productivity and well-being. I’ve extended this idea to all spaces—including my technology.
And so, I’ve:
  • Deleted my Evernote account, which was riddled with unorganized notes and half-baked ideas, and started a new one.
  • Emptied Pocket, which had thousands of guilt-inducing unread articles.
  • Organized and cleaned out my computer.
  • Started developing a system of where to place things in my room.
Soon, I’ll be organizing my bookshelf, cleaning my bathroom (finally!), and giving away old clothes (before I replenish my wardrobe). It’s amazing how all of these little accomplishments have boosted my mood and cleared my mind.

Embracing Risk

Quitting my teaching job represents the end of an enlightening, but incredibly demeaning, work life. Knowing that I have three months to transition to a new career should be terrifying, but it’s actually quite invigorating. For the first time in my professional life, I have a clear sense of who I am, what I’m good at, and what my life’s work will be. There’s no better feeling.

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