Routine: Power and Peril

Wake up eight hours after going to sleep. Meditate. Light exercise. High protein and fat breakfast. Take the train, or run, to the office. Triage. Respond to urgent issues while attempting to make a dent in my coding backlog. Lunch. Most demands have petered out and now I can focus on a bigger software development or strategy research task. Reach flow state, if lucky. Pretty unremarkable, as work routines go.


This was my routine, with enhancements over the years, since moving to Chicago and embarking on the Kapital Trading adventure in 2009. Upon reflection, I realized my regimen had evolved to meet the challenges I faced. As a cofounder, the buck stops with you and anything important or urgent is ultimately your responsibility. My schedule allowed me to respond to problems as quickly as possible while making progress where it was needed — typically enhancing our technological infrastructure or developing new trading logic.

Of course, nothing comes without trade-offs. A workflow that allowed me to be responsive had the consequence of limiting my opportunities for clearheaded focus. Under the right circumstances, glimmers would appear of capabilities I normally lacked. On the occasional holiday, when I worked with no one else around. During an early morning flight when I could disconnect and think without the usual distractions. These opportunities allowed me to develop high level plans, and more effectively evaluate complex projects with many moving parts. I could see the lay of the land in a way that was obscured by the day to day turmoil of my normal routine. Upon realizing this, I would try to deliberately replicate these low distraction environments. Once a week I tried to block off an hour immediately after meditating, and focus on whatever seemed most important at the time. I had great results, but as is often the case I couldn’t sustain the habit.

Chicago winters are brutal. After years of doing battle, it was time to throw in the flag. In December my good friend and colleague Derek joined me in escaping to warmer clime: renting a three bedroom house in Ocean Beach, San Diego.

This was exciting. A new living and working location — our third bedroom — brought a change to both physical and social surroundings. Predictably, such a large shift came with a disruption to existing daily patterns. Rather than taking the train to work, I was skittering out of bed and instantly arriving at the office. I could eat breakfast first thing in the morning, or maybe later? When would I exercise? In some ways, it felt like I was facing a blank slate. I knew that after some time my workflow would settle back into a predictable schedule. But what would it look like?

I took the opportunity to change things up. In Sex Sleep Eat Drink Dream: A Day in the Life of Your Body, Jennifer Ackerman writes:

Studies show that alertness and memory, the ability to think clearly and to learn, can vary by between 15 and 30 percent over the course of a day. Most of us are sharpest some two and a half to four hours after waking. For early risers then, concentration tends to peak between 10 A.M. and noontime, along with logical reasoning, and the ability to solve complex problems.

Knowing this, I tried flipping some things around. At the end of every day I now take time to reflect on my situation, and plan a single Most Important Task for the next day: What is the one thing that I can accomplish which pushes the ball forward more than anything else? This becomes my highest priority. I start first thing after meditation. If all goes well, I don’t come up for air until task completion, or at least significant progress, is celebrated. During this period I ignore miscellaneous work issues that arise, as well as any attention splitting side tasks.

Upon establishing my MIT habit I realized that much of my typical work — writing code, responding to “emergencies” — could now be done by others, or sometimes not done at all. Conversely, some of the most valuable work that I could do — planning and prioritizing — was not receiving sufficient attention. Planning an MIT separates the tasks where I uniquely can add value from those that I am better off delegating to others, or just dropping entirely.

The habits of effective people vary significantly and there is probably no “one true way”. Scott Adams follows a relatively strict daily regimen which he finds optimizes for available energy and maximizes creative output. Meanwhile, Marc Andreessen prefers to eliminate scheduling from his life entirely. This allows him to maximize chances for serendipity, and free up resources which can then be deployed when a truly great opportunity reveals itself. Routines can be great for executing a plan or honing a skill, but are rigid. They make it difficult to respond to a rapidly changing landscape.

Imagine yourself as a kind of riverbed through which the liquid of life flows. Your goal is to allow as much of this nourishing elixir to flow through you as possible, thereby harnessing and directing its energy. But unlike how water flowing over dirt carves its own path, you need to adjust your shape to match the flow. Most of the time, the flow of life is stable and you can settle into a comfortable capturing arrangement. Once in a while, the waters shift. How will you adjust to these shifts? How will you become aware of them?

Moving to a different city and transitioning to working from home was a powerful catalyst for re-evaluating my routines. I realized that the way I was working was no longer a good match for the kind of work I needed to do. I also realized that it was not necessary for me to move across the country to figure this out. Back in Chicago, for example, I could have more formally tried working from home for the first half of some days. I could have worked one day a week at a coffee shop. I could have tried working without internet for a few hours a day. And maybe you can try these things, too.

To do your best work, you need to adapt to the changing demands and capabilities of your craft. How do you know when the time has come? Maybe you cannot, but if you experiment you may stumble upon improvements. Regularly force yourself into unfamiliar situations. Try new things and be open to change. Periodically evaluate how you spend your time. Occasionally one of these experiments will bear fruit and you can make a more permanent adjustment; once again letting the waters flow.