7 questions I ask myself

When I don't know what to do next

Hey y’all,

Before I begin, I’d like to hear from you: What’s the most helpful question you’ve learned to ask yourself? Tell me in the comments:

I have 7 questions that I like to ask myself when I’m puzzled or uncertain about what to do next:

1. What was the best thing that happened yesterday?

This is a very simple question I ask myself every morning when I sit down with my four notebooks and I don’t know what to write about.

When Michael Bungay Stanier was working on his new Do Something That Matters Journal, he asked me if I would write an introduction about the power of journaling, and I sent him these weird pages that I actually wrote as an entry in my diary:

Michael didn’t end up using those diary pages in his journal, but he did include them as part of a PDF of “Best Questions” he solicited from 52 of his friends that he’s offering as a bonus goodie to go with his journal.

My best question — “What was the best thing that happened yesterday?” — comes from the character Paul Chowder’s advice in the novel The Anthologist, paraphrased by Nicholson Baker and quoted in Steal Like An Artist:

It always, somehow, seems to work for me and gets my pen moving.

2. Will this enlarge or diminish me?

This is a question for making big decisions. I first heard this advice in Oliver Burkeman’s last column for The Guardian, ”The Eight secrets to a (fairly) fulfilled life”:

When stumped by a life choice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist James Hollis for the insight that major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?” We’re terrible at predicting what will make us happy: the question swiftly gets bogged down in our narrow preferences for security and control. But the enlargement question elicits a deeper, intuitive response. You tend to just know whether, say, leaving or remaining in a relationship or a job, though it might bring short-term comfort, would mean cheating yourself of growth. (Relatedly, don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.)

It later became part of his marvelous book, Four Thousand Weeks.

A modification of this question is something I ask of art: Does this contribute to the variety of the world?

3. What would it look like to be done for the day?

A question for writing up today’s to-do list. This is a slight variation of another one of Oliver’s questions: “What would it mean to be done for the day?”

When you end the day feeling like there’s vastly more you ought to have done, you’re telling your nervous system it can’t take a break; and you’re reinforcing an idea of your work as an oppressive and insatiable force.

My work is never done, so I start the day in the studio thinking about what it would look like to be done for the day. What absolutely needs to get done today?

I try to start with low-ish expectations. And some days are automatically answered for me. (Mondays and Thursdays, for example, the answer to the question is always: pressing “schedule” on this newsletter.)

4. What did you really want to say?