Habitual Advice

Supported by Greenhaven Road Capital, finding value off the beaten path.

In college, there was a professor who touted Automatic Bill Pay. Not only did he use it, but he also paid for it. The thing banks now offer for free, as a perk, used to cost money. How wild is that! But this still exists. I didn’t realize it either, but I was paying for ‘Automatic Bill Pay’. Only in the form of habits.

Many parts of life are automatic. Some use technology, checks to mortgage companies. Some use psychology, coffee each morning or smartphones in bed. Personal habits are like Automatic Bill Pay. They take time to set up, but once done require minimal updates and maintenance.

New habits work best in stable environments, installed habits work in any. I was reminded of this after seeing my brother and his one and three-year-olds this summer. Toddlers are unstable. They’re unpredictable and totally reliant. They’re great in many ways and my nephews filled my lap like they filled my heart, but they are terrible for routines.

This is obvious only with distance. My older kids are more predictable and reliant, but there’s always some kind of constraint on our habits. Habits need certain things to get started, especially in unstable environments.

Habits need motivation. Jocko Willink repeats that “discipline equals freedom”. I didn’t understand this until thinking more about habits. The regularity of important things (whatever that means to each person) makes other choices easier. Whether later in a day, a week, or a life.

Habits need investment. Tynan inspired the automation of all the grout-like tasks in my life. My bills are paid, emails are filtered, and food is delivered thanks to reading Tynan. He has an approach I’ve called Investments and Dividends and it’s the idea that some things are worth a lot of work upfront to reap the long term benefits.

Habits need commitment. Ramit Sethi navigated me to make regular investment decisions. It’s easier to look at the checking account after the money has been sent off to the wisest possible choices.

Habits need to be daily. Tyler Cowen and Stephen King both say that writing is a daily and regular task—like anything else we both enjoy and want to be better at. Daily is the only unit where people (like me) are incapable of lying.

Habits need locations. Guy Spier wrote of moving to Zurich, “I would also overhaul my basic habits and investment procedures to work around my irrationality…To my mind, this is infinitely more helpful than focusing on things like analysts’ quarterly earnings reports, Tobin’s Q ratio, or pundits’ useless market predictions—the sort of noise that preoccupies most investors.”

Habits need time. Naval said, “All the benefits in life come from compound interest; whether in money, relationships, love, health, activities or habits.”

Habits need the right tools. In the book, My Morning Routine, Shane Parrish said that he doesn’t use a smartphone. Why? “I’m not really a fan of trying to solve common life problems with apps and software programs.” Instead, he uses “some basic, old-school planning and discipline.”

Habits need kickstarting. Brian Koppelman was a blocked writer until he was thirty. He only blasted past when he found The Artist’s Way by Julie Cameron. “That was enormous for me. In doing morning pages, I freed myself from all this other stuff, from the curse of perfectionism.”

Habits need high switching costs. It’s easy at any moment to go and do something else. Unless we like the thing we’re doing, we’re good at it, and it’s beneficial in the short and long term. Businesses talk about raising the switching costs between products and the same approach can work for habits.

As students head back to school and routines change, best of luck starting your new habits. Thanks for reading.