On this day five years ago, I was preparing to return to Seattle from a two-month residency in Italy. It was a time of many firsts: the first time I had taken an extended leave from work since I was sixteen and the first time I had lived outside of the United States and spoken a language other than English in day-to-day life. It was the first time I had found the inspiration to write a book-length work and the first time that I had actually written anything long enough to be called a book.

At 36, it was also the first time that I felt I had created something with artistic integrity.

That last note is what made the day’s transition more bitter than sweet. As I packed my belongings, I was surprised to realize how deeply I dreaded returning home. In two sun-drenched months of finding my creative way, doing what I wanted to do in the time I wanted to do it –telling the stories that I felt I was born to tell– the idea of my once-beloved Seattle had become the opposite of home. It was no longer a nest but a cage full of soul-quashing rules. At that moment, I knew I couldn’t go back to living the way I had, and yet, my old life awaited for me to resume it — empty apartment, workplace duties and all.

Amidst this, I could feel the strains of a new self being birthed; here it was, the beginnings of the creative life I had always wanted crowning in Italy, and there was nothing I could do to stop it. Excited as I was for its arrival, I wondered how this newborn outlook would survive back in the chilly, gray daylight back home. As I rolled my clothes like crepes and tucked them inside my tattered-but-trusty purple suitcase, I fought the call of the clattering din and lively chatter from Campo dei Fiori below. The sounds drifted up through the large open windows, promising fun and delight if only I’d stray from my task for a moment. That, I realized, is what I had become afraid of in my grown-up life back home: letting go and having fun.

I don’t use the word fun trivially. Growing up, fun did not merely represent enjoyment; to my parents, fun was equivalent to goofing off, meaning that having fun or playing was a waste of time. Fun came with a heavy hint of disapproval. Who knows whether it was America’s Puritanical roots, the pressures of the modern workplace, my mother’s immigrant family’s dream of New World success, my father’s Germanic blood (work makes worth), or even my membership in gloomy Gen-X, but the idea that fun was actually valuable and necessary to life and art, had been bred out of me. That ideology is what I didn’t want to return to.

For someone who has always wanted to be a writer, you’d think doing what I love would be easy, but early in my childhood, my parents categorized writing as fun. This label and its shadow definition affected both the way I saw writing but also how I viewed work. I intuited that fun and writing were not as valuable as work and, consequently, that work was serious and, in order to be taken seriously, one’s work could not include fun.

Last night at dinner, a friend told a story about her artistic sibling who, at a very young age, regularly called the family into his room to view his newest paintings. After allowing them a moment to absorb the work, he would fold his arms and urge them to, “Praise me!” We all laughed at the retelling of his bald demand, but it got me thinking about the agency he was creating for himself by demanding recognition, deserved or not. Somewhere, somehow, between the ages of birth and eight, he had exerted his will as a creator and leveraged the tacit and implicit support of his family to help further his craft. What he did was fun but it was also work. It is no surprise that this man has grown up to be a professional artist.

This is why I sometimes wonder if I’ve joined the creative path too late. What happens when a person only begins to discover the power of fun in her work (and her life), or the capacity and freedom she has to create art, in her fourth decade? Is there enough time to assimilate the education I’ve missed out on as a youngster? How do I maintain fortitude against constant acknowledgement at my workplace for being organized and “linear” rather than creative? The phrase “If only I had started earlier…” is a spiderweb I brush away at every day.

Today, when I talk with MFA grads, I kick myself for not knowing in my twenties how grad school might have opened up a more fulfilling career path and writing practice for me. Similarly, when I read Joan Didion or Richard Hugo and realize that the kind of writing I do has historic precedents (hello, Civita di Bagnoregio, you Triggering Town), I wonder what else I’m unaware of. Am I simply an unwitting product of their work, which I can and do absorb by merely living in the current day? Would it make a difference in my work if I was formally educated in established movements that I could draw energy from, or collectives that might help me understand what kind of writer I am and want to be? Is it better to stumble onto all of this by myself, however slowly, however messily, without someone pointing the way? I go through cycles of discovery, delight and frustration as I happen upon theories and writers who are new to me, whose work lends insight into my practice, which I didn’t know how to ask for or seek out. I am thrilled to find clues that resonate, then afraid of what else I am missing or will never discover, and then thrilled again that the world is full of so many things to know and never know.

In spite of the self-initiated art projects and the work I’ve written since returning from Italy, I don’t yet know how to make the leap between what I do for a few hours a week (also known as fun) and the bulk of my life experience. Creativity is not a race –I know this– but it doesn’t mean that I don’t feel a sense of loss for the time I’ve spent dutifully carrying out someone else’s notion of success. Perhaps more critical is that I’m not sure how to stop doing it, day and again, try as though I might. It’s what I’m programmed to do and I do it well. This rubs me raw.

When I returned home in October 2010, I discovered that the path I had bushwhacked to find my creativity had simultaneously jeopardized my job. My employer at the time hadn’t taken kindly to me leaving for two months but, more to the point, the new outlook that I returned with shattered my previously-held definition of what was really important. Success was no longer about job titles or rank, things that others could grant to me, but about freedom, agency and voice — things I could only achieve on my own. And I knew, with a sense of profound joy and sadness, that once I had eaten this apple I could never return to the land of not-knowing. That is why I say, with deep affection and gratitude, that living in Civita for two months ultimately ruined my life.

This morning when I sat down to write, it occurred to me that I am in another time of creative transition, only I can’t point to a residency or singular experience as the catalyst. There are several, I think. The Tin House Summer Workshop in Portland. BinderCon in Los Angeles. The AROHO retreat in New Mexico and our class’s pilgrimage in search of red. A writing workshop on shame by Alyssa Nutting at Hugo House. Elizabeth Gilbert’s lecture on creativity. Writing a novel last November in Seattle Central Library. Writing and recording poems on ugliness and self-worth at Jack Straw. A long-distance friendship and correspondence with my writerly friend, Jen.

There are books, too —All the Light We Cannot See, The Triggering Town, Fun Home, Excavation, The Faraway Nearby— and two volumes on how to celebrate Jewish holidays. By happenstance, I’ve recently paired The Beauty, a book of poems by Jane Hirshfield (thanks, Jen!) with Can’t and Won’t by Lydia Davis as my nightly reading these days. When read together, the length and cadence of the short works play off of each other in surprising ways, yielding some of those aforementioned juicy clues about writing. Davis’s dream accounts and seemingly simple two-line stories play off of Hirshfield’s finely wrought poems in a companionable dialogue that enriches both works — and, together, teach me things that I wouldn’t have arrived at on my own.

There is no lesson plan or structured output for any of this except the writing itself — no clear objective ahead but also, and for the first time, no obvious barriers, either. The work is the work and it is as big and fun as I can let it be. This is why I apply for residencies, grants and fellowships, so that I can make more room for art in my life. When people ask me how I carve out time and energy to write and to apply for all of these things, I struggle to explain. It is, in fact, not work for me but fun, and I lose time while doing it, like falling through the wardrobe into a new and fascinating world. I forget that what sounds like fun to me sounds like work to them.

This weekend, a friend commented that, during a recent vacation to Tuscany, she took time off of writing because her days were so busy with sightseeing, resting and eating. Someone commented that the break must have been welcome, perhaps even a time of creative recharge, especially given the beautiful setting.

In response, my friend wrinkled her nose, shrugged and said, “Any day that I don’t write I feel kind of angry and bunched up inside.” I know exactly how she feels.