To find the answer, change the question

What else can you ask?

What should I do with my life?

This is a question I asked myself for a decade. My problem was that I was interested in a lot of things, and I could imagine an entirely different life play out depending on which one I pursued.

In one vision, I was a professor of Peace Studies at a friendly liberal arts college, living in Vermont (a place I’d never visited) with a small sheep farm off campus (really leaning into some peace imagery).

In another, I’d open a restaurant in northern California and invent French-meets-West-Coast cuisine using only local ingredients and seasonal recipes. Then I realized….Oh yeah someone already did this.

In another, I’d go into public radio, cut my hair short and develop an authoritative speaking voice. I’d report the news from afar, or start a radio show suspiciously similar to Fresh Air, and get to meet interesting people like Seth Godin and Snoop Dogg.

These lives were completely distinct, and contrasted each other. How was I supposed to pick one, forever??

To help me find my calling, people around me would ask me questions like “What lights you up?” Or send me the Mary Oliver prompt, Tell me, what is it you plan to do with your one wild and precious life?

No pressure!! That just gave me more anxiety about 'getting it right.' What if I found myself in Vermont on the sheep farm and realized in 20 years that my true calling was hiding somewhere in the California woods all along?

Meanwhile, as I was spending my days and night trying to figure out WHAT THE HELL LIGHTS ME UP!!???, a lot of my friends were already racking up resume points by simply choosing something. They were working fancy office jobs, even getting promoted, while I was furiously journaling about my woes and doodling the outfits I’d wear as a professor.

Portrait of a daydreaming and confused administrative assistant

I was stuck. So I changed the question. I stopped asking “What should I do with my life?” And I started asking:

What matters to me right now?

Well, what mattered was that I had to wake up at 4:30am to get to my barista job, but I still gave myself a quiet moment in the morning before scurrying to the train. I painted silly pictures, I read about food and God and Brooklyn and wonder, and I made myself a nourishing little meal with dinosaur kale and eggs from the farmers market—a weekly indulgence paid for with cash from the tip jar.

The entirety of my counter space

What mattered was that I loved many of my customers: a Buddhist priest, a symphony cellist, an Irish construction worker. They all had important things to say about life that I will always remember. I also hated some customers, and I vowed to avoid becoming like them at all costs.

My art outside the cafe

What mattered was that I got off work around 2pm, and on the rare day when I wasn’t rushing to my next job, I’d take an hour walk home. There was a long row of hydrangea bushes mid-commute that guided me through the months and seasons: blooming fully periwinkle in July and drooping dramatically in September. What mattered was that I learned how to notice these things.

About to do some noticing in my journal

What mattered is that I stayed up late, even though I had to get up early. In the summers I’d make blueberry compote after dinner, and I’d stroll over to the Lake Michigan after the blueberries had calmed down into thick sweet sauce and I could leave them to share their purple juices with one another in privacy.

Under the stars and skyscrapers, I’d walk along the shallow part of the water which was refreshingly crisp in contrast to the air heavy with heat. The sound of the waves was so slow and rhythmic that it seemed like the beach was sleeping; I should have recorded it and made some money selling it as a relaxing recording on iTunes. The water itself was black at 10pm and later I’d realize how clear everything becomes in the dark.

And it was there, in the darkness and blackness and waves, that I would hear words in my head, sometimes in full sentences, occasionally in full paragraphs. I felt excitement in my body every time it happened, and I still feel that same excitement to this day.

I started writing, and then drew what I wrote.

My kitchen table in 2009

And, years of writing and drawing later, I found the answer I’d been looking for. It took so much time, but all that time was spent observing and noticing and feeling and living the questions that would some day go in my books, my illustrations, and this newsletter.

Jump to 2022! I’m honestly still wondering what to do with my life.

I’ve been struggling the past couple years to make sense of how to keep making work that feels aligned with my values, in integrity with my opinions, and authentic to the purity of playful creativity….all of which used to come very easily to me. Online spaces have changed a lot since I started, and I’ve changed too. What to do with that?

The questions I’ve been asking have been frantic and chaotic: Should I delete social media and just focus on long-form writing? Should I ditch any internet writing and just work on a book? Should I get a different job and what should it be? Should I post once a week or once a day or once every six months? Should I hire someone to make these decisions for me? How do I do that? Is everybody doing Instagram Lives without me?

I always know I’m losing the plot when my questions start getting way too specific. Creativity is one wild and fantastical gift, which was never meant to be smushed into a world of “How often should I post?”

So last week I asked myself a different question:

What do I want to say?

And my entire outlook softened. It didn’t become clear, but it softened. I stopped wondering when I should post, and instead I wondered what I would express, if I could express it freely.

Tools waiting to be put to use

Whenever I attend author events, I always hear a similar series of highly specific frantic questions from the audience: questions focused on numbers, facts, technology.

How do you format your book? Do you use Google Docs to organize your writing or something else? How many hours a day do you write?

It almost feels like we pretend that creative work is locked in a room and we can’t figure out if we need a key, a password, or a number combination to get in…so we just keep asking questions until the door flies open and you’re greeted by Sophocles or something.

I get that, and I used to have all the same cart-before-the-horse questions because I thought I had to get my setup all correct before embarking on any creative project. Much later I realized that, if you really want to be a writer, you just have to…start writing.

And when the writing labor pains throb so much that you’ll do anything to get your beloved work out the world, you’ll figure out whether you want to use Google Docs or Word. And you’ll figure out how to say it, whether you print off copies of your book and hand them out in front of Whole Foods, or sing them from a rooftop, or find a publisher.

“How do you format your book?” is the wrong question.

“What do I desperately want to tell people?” is a better one. This is apparently something I need to re-learn all the time.

When the question changes, you can start living into the answer rather than trying to figure it all out in your sweet little head. The head is not meant to solve the puzzle; the body is much wiser. If the body isn’t feeling the answer, then it’s not the right question.

There’s a memorable Sex and the City moment that demonstrates this superbly:

Carrie is fretting over what to do with her current flame, who is perfect on paper but their conflicts are growing worse and worse.

Great Sage Samantha Jones replies, “As far as I'm concerned, the test of a good relationship is Are you like this [frowns] or like this [smiles]?"

You feel the answer in your body! The question to ask is usually an astonishingly simple one.

For example:

A few years ago, New York and I weren’t getting along very well. I thought the people didn’t like me and I wasn’t cut out for the ambitious environment, and so I started asking myself a bunch of pressing questions to help me find a solution: Do I move? Where do I move? What would I do somewhere else? How long should I give New York? Can I break my lease? Would things really be better in, I don’t know, Tucson?

Then, on one of my crankiest afternoons, I went into my corner bodega for some boring purchases: paper towels, dish soap, fizzy water. The store owner rung me up and, then, no-nonsense, handed me a sunflower.

“Want this?” He asked without a smile.

I’m guessing it was going to get tossed out and I was not particularly special for being in the right time and place to receive some expired flora, but it transformed my quandary.

It symbolized a type of grace that I’ve only found in big cities, particularly New York. I’ve traveled a lot and I’ve never had so many of these kind, no-frills moments anywhere else. My pent-up anxious questioning slipped away, and I realized this is my city too—even if I’m not as ambitious as others. I committed to New York a few days later by adopting a cat and naming her Sunflower to remind me of that constant undercurrent of grace.

A soothing sunflower

A soothing Sunflower

From then on, my question was, What’s keeping me here?

I vowed to keep my Magical Things I’ve Seen in New York list growing, and to look out for moments that made New York a sweet home for me to live. This later turned into the first chapter I'd write of a book that told the story of making NYC my home.

Zora Neale Hurston famously wrote, “There are years that ask questions and years that answer.” While this is taken elaborately out of context from Their Eyes Were Watching God, it stays in my mind as an orienting prompt: Which questions am I asking or answering right now?

And when the questions get too chaotic and the answers aren’t yet inhabiting my body, I switch up the prompt.

What else could I ask?

How could I simplify the question?

What matters right now?

The answer is probably already there; the question just needs to find itself.

P.S. I'm leading a creativity retreat this October 7-9 in the Blue Ridge Mountains of North Carolina where we'll dive into some of these juicy questions together. I can't wait to meet you and ask what's going on in your brilliant mind. Learn more HERE!

The retreat center!

Welcome to Out of the Blue, a weekly reflection on something that's caught my attention, and an attempt to learn deep lessons from the shallow and light wisdom from the dark. If you haven't subscribed yet, sign up for free here!