Monday Musings - Monday Musings (How I Improve)

Hi friends,

Based on the number of email responses, last week’s Musings was the most popular one I’ve ever written. This week, I’m revisiting the list format.

A few years ago, I had dinner with Tyler Cowen. Over Indonesian food, we talked about how knowledge workers should train as deliberately as athletes. As Tyler has written: “What is it you do to train that is comparable to a pianist practicing scales?

My answer is a little peek behind-the-scenes of my writing process. It's about the lifestyle I've designed to improve my craft, generate ideas, and build a company. Here it is:

1. Write every day: I dedicate my mornings to writing. Since most of my writing falls into the “important, but not urgent” category, I block off time in my calendar to make sure it happens. To preserve this creative space, I rarely schedule meetings before noon. Writing in public refines the clarity of my thinking. My routine is driven by three deadlines: two weekly newsletters, a weekly call with my writing coach, and two Write of Passage cohorts each year.
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2. Live in Austin: The Texas capitol is a home-base for Internet writers, podcasters, and education entrepreneurs. Most of my away-from-the-computer time with is with these kinds of people. After all, no matter how plugged into your scene you are digitally, certain conversations only happen in-person. Besides the interesting people, it’s hard to get distracted in Austin. This lack of FOMO keeps me focused on my work, while the warm weather inspires walking and reflection.
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3. Travel with intent: While my life in Austin is designed for focus, my life on the road fuels my cultural and intellectual stimulation. I travel with the same intensity I bring to my work. I read extensively, interview locals, and hire tour guides whenever possible. I capture notes on my experiences in cities so I can write about my impressions afterwards (here are my reflections on Austin, Detroit, Montreal, and San Francisco).
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4. Time with older people: I spend significantly more time with people much older than me, compared to others my age. I place an emphasis on extended in-person time with them, either by traveling together or visiting their homes. Though I treat them more like friends than mentors, I regularly ask for their advice.
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5. Curating my social group: I rarely party, drink, or watch sports on television. I’m much more interested in deep conversations instead. Socialization doesn’t need to be 'productive,' but it should be fun and interesting. I host a formal dinner salon series in Austin and organize a few small-group dinners each week. I rarely attend conferences though. Socializing with a bunch of strangers tires me out and makes it hard to get work done.
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6. Mistakes Page: I reflect on all my mistakes by asking three questions: (1) What went wrong? (2) What was I thinking at the time? (3) How can I prevent this from happening again? The process takes less than five minutes and has helped me identify consistent patterns in my behavior.
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7. Blunt and Honest Feedback: After every Write of Passage live session, my team does a 60-75 minute debrief. Critiques of my performance as a speaker have made me a better storyteller and discussions about the student experience have made me a better learning designer. At the end of each cohort, I read every piece of qualitative feedback from students, much of which focuses directly on my performance as a teacher. Inside the company, I receive feedback from every single employee when we do performance reviews. Outside of work, I try not to get offended by what friends say, so they're comfortable being direct and honest with me (which also makes oxygen for provocative ideas).
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   8. Systematic Reflection: Though the majority of my day-to-day improvement comes from the seven bullet points above, I have built-in time for reflection too. I go for a walk alone on most days for 60-90 minutes, which keeps me centered throughout the week. At the end of every year, I also publish an extensive Annual Review. I begin by reflecting on the goals I set for the previous year and end by setting new goals for the upcoming year. This method of consistent reflection keeps me honest with myself and aligned towards my goals.

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