“I Physically Put My iPhone in a Different Room, Sometimes Under Lock & Key”

Portrait of Jeff Wilser

I forget how I got to know Jeff Wilser, but when we met for coffee, he mentioned that he had an idea for a book about Alexander Hamilton — something fun, and also very informative. I told him that I thought his idea sounded terrific; this was even before I saw the Broadway show Hamilton, and now that I’ve seen the show — and loved it as much as everybody else — I think Jeff’s idea was even more terrific.

Well, he did write that book, and it just hit the shelves: Alexander’s Hamilton’s Guide to Life. It’s a book that manages to convey lots of information and big ideas with a light touch.

I was very interested in what Jeff had to say about Hamilton; I also wanted to hear what he had to say about habits and happiness.

Gretchen: Which habits are most important to you?

Jeff: Sticking to a reading schedule.  Everyone enjoys “reading,” but I’ve found that without a strict schedule, and without iron discipline, my reading habits quickly fade into oblivion. So I have a very concrete and nerdy plan: I aim to read a book a week. Sometimes two books in a week, sometimes three, sometimes 0, but at the end of the year, I need to have read at least 52 books. (I envy those super speedy readers who can devour books in one sitting; my speed is average at best.) The game of 52 books in 52 weeks becomes something of a puzzle, where to squeeze in, say, a 900-page biography, I’ll read maybe two short Graham Greene novels.  I’ve found that this habit—of obsessing over the schedule, even tracking it in a spreadsheet—keeps me focused on books and makes me a better reader.

What about writing habits?

I need to write first thing in the morning. I need to do this before I fuss around with anything else.  Before email, before housekeeping, before research, before tweaking my fantasy football lineup.  That’s how I wrote Alexander Hamilton’s Guide to Life.  First thing in the morning, every morning, I wrote for several hours and only then, later in the day, would I pivot to reading and research.

What gets in the way of your healthy habits?

I’m easily distracted. True, everyone says that they’re easily distracted, but in my case it’s so extreme it’s cartoonish.  Sometimes I can’t even read a single news article without re-checking twitter or my email 5 different times—not an exaggeration.  The siren song of the internet always gets in the way…especially when writing.  At times it’s crippling.

So what’s your hack for this?

I remove the internet from the equation. I use Freedom, a program on my Mac, to disable any connection to the internet. But that’s not enough—I also physically put my iPhone in a different room, sometimes under lock and key.

What’s a simple habit that consistently makes you happier?

The morning cup of coffee. It’s essential.  When I traveled to India for two weeks, at the risk of being an Ugly American, I lugged pouches of instant coffee.  If I were ever sent to prison, this is the thing I would miss the most. (Besides not getting shivved.)

What about habits do you wish your 18-year-old self knew?

Ladies are not always super thrilled with the habit of playing video games.

What habits do you wish you had?

I wish I was in the habit of speaking on the phone. I broke the habit many, many years ago, and now when the phone rings, I panic.  It doesn’t matter who it is—my family, my best friends in the world—the phone trips me out.   I thought about creating a new habit where, every day, I had to place one outgoing phone call. But that seemed too daunting so I tweaked it to once a week…and that still seemed too daunting.  Someday soon I will try and instill this new habit. Maybe tomorrow. Or next week.

Have you ever been hit by a lightning bolt, where you changed a major habit very suddenly?

 This might count as cheating, but I’ve adopted some habits very quickly for writing assignments. And I LOVE IT. One time I ate only junk food for 30 days (and lost 11 pounds…the secret was calorie counting.) One time I went on a juice cleanse. Or went vegan.  Even if the habits don’t stick long-term, a sudden immersion into a new habit gives perspective, challenges your old norms, and gets you to recalibrate your life a little. I’m a big fan of Habit Hopping.

Do you embrace habits or resist them?

 Habits are what make me tick.  When I get on a good habit groove then I’m firing on all cylinders, and when my habits lapse everything else seems to crumble.  Inertia is a powerful thing.

 Has another person ever had a big influence on your habits?

I’ll have to go with the obvious one here: Alexander Hamilton.  It’s a cliche to hear that you need to work really hard, but that’s exactly what he did, from a very young age, and it’s my belief that these habits of his, more than genetics, are what made him great.  He made it a point to read every day. He constantly scribbled notes in a journal. He collected facts and quotes and useful arguments. It looks like genius from the outside, but really it was the result of hard work and, well, excellent habits.  That’s one of the entries in the book: “Turn Grit into Genius.”

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