Perfect Timing Is a Myth

On Building a Writing Career From Scratch

Special thank you to Microsoft Surface for sponsoring this week’s newsletter. In case you missed it, I’m hosting a free writing workshop at Cafe Nido in East Hollywood on June 30th in collaboration with Microsoft Surface, and the RSVP list is closed at this time. Seeing such an enthusiastic response to my first in-person event has been so gratifying. I’m so excited to meet some of you in person.

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It’s funny how some of the scariest things you can do in life read so small on paper. Moving across the country, then moving back. Quitting your job and starting from scratch. Dramatic, for sure, but hardly the craziest ideas a human mind has conjured up. These things are always the start of the movie, rarely the climax.

But as I was moving across the country and back, and most recently, quitting my job, it felt as though I was breaking new ground, the first woman on the moon. “No one knows I just quit my job,” I’d think to myself as I walked into every room. “No one knows I’m on the brink of a major life transformation.” But somehow it felt like everyone knew. That’s how it feels going from living in black-and-white to full color. Your own view of the world becomes so much more saturated; you assume everyone else sees more vividly now too.

I had been unhappy at work for quite some time, but also thoroughly intoxicated by the reliability of a full-time salary and paid time-off, stable and solid as a home’s well-laid foundation. I’m a long-term planner, an adverse risk-taker, a chronic rewatcher and rereader, and a lover of all things expected and unsurprising. Without a strong magnetic pull or a swift kick in the rear, I’m not one to ever leave my nest.

I knew months into working my first job that I would be leaving it eventually. Either a media layoff would bite me, a six-figure book deal would land in my lap, or gold bricks would start raining from the sky; it was just a matter of how and when. I patiently waited for years, nearly four to be exact, for the winds of fate to change, rendering me a passive participant in my own life. All the while, I stared blankly into my screen, remembering all the come-up stories of all the great artists of my time. Of them waiting tables, delivering UPS packages, and memorizing keyboard shortcuts. I tried to reap comfort, instead of despair, from the collective, modern human struggle, remembering that around the world, everyone was hustling away trying to make a life that felt worth living. Still, I ended every day more depleted than I started it, struggling to string words together on paper or in conversation.

It really did just dawn on me one day, in a way I thought it never would. With the amount of time I had available to devote to my writing, it would take many years for me to seamlessly leave my full-time job and trade one reliable income out for another. Nothing about this was going to be comfortable, whether it was drudging along, eyes glazed over, perpetually despondent and exhausted, or experiencing a little less financial security and a little more hustle. I was going to struggle no matter what; it was just a matter of which struggle I wanted.

So after four years, I traded out the cushy, numbed-out feeling I’d grown to hate myself for loving, and set forth on a less certain, more energized path. I left my full-time job and started cobbling together freelance writing gigs, my newsletter being among my only notable writing experiences. Part of what kept me hanging on to a job I didn’t like in a field I didn’t care about for so long was my lack of “traditional” writerly qualifications. A state school BA, no industry connections or academic understanding of how journalism or copywriting work. I’d been relying on my own self-discipline and editorial discernment for the past four years. I had no mentor to show me the way. Most of what I know about writing I’ve simply learned from reading and writing myself.

It’s, once again, a simpler lesson on paper, that you can be whoever you want to be, until you start meeting people who wear their agents, bylines, and degrees from prestigious institutions like hard-earned badges. It’s enough to make you want to recoil into your shell, jog back to the starting line, and do things by the book. But as it turns out, interesting people want to work with other interesting people, especially those who have found success in unusual ways. I know I certainly do.

I’m only a month or so into this freelance journey, so I’m not going to pretend I have years of sage advice to espouse. All that I’ll say is that there is never a perfect time to plunge into cold water. The timing didn’t feel right when I started writing my newsletter either. I felt awkward and embarrassed publishing essays to a readership of zero and sharing them with an indifferent social media following. But over time, the ice-cold shock of cringe becomes lukewarm, almost bath-like.

When I sat down to think through the itinerary for my upcoming writing workshop at Cafe Nido, busting this myth of perfect timing was the first thing that came to mind. I’ve been wanting to do an in-person event in LA for a while now, but I hadn’t gotten around to thinking through what it might actually look like. My mind was always on more immediate priorities, like getting an essay out every week. But I began chatting with Microsoft about a partnership right around when I was planning on leaving my full-time job, and the timing finally felt like kismet. When I told them about my idea of taking my online community offline and talking through this professional transition of mine, they were on board to partner with me, letting me hold the creative reins.

For four years, I wrote my newsletter in the early hours before my day job began, blinking the sleep out of my eyes, the orange morning sun just beginning to crest. I often felt inspired during this quiet time, writing before I had uttered more than two words to anyone, my brain at its most spongey. Other times, I felt exhausted, my brain a computer unable to boot up. The open tabs on my browser beckoning like blinking red lights, offering something far more stimulating than wrestling with my words.

But whether I was at my most inspired or most sleepy, I knew that if I didn’t reserve time to sit in front of a blank page, allowing the words to flow like water or coaxing them out like a snake charmer, I simply wouldn’t get any writing done. I made the best of my unfortunate timing, writing while energized and writing while depleted.

When writing while exhausted, I’ve always found it helpful to have a well of inspiration to draw from, which is why I write down any and every idea as it comes to me, no matter how big or small. This has been a longstanding habit of mine. In high school, I remember scribbling random thoughts that came to me throughout the day in a Personal Notes tab in OneNote on my school-issued laptop, my first computer, flipping back to my assignment whenever my teacher would glance over my shoulder.

Today, little has changed. I have a running list of essay ideas, some detailed and comprehensive, and others barely legible. Lately, I’ve been brain-dumping in the Concepts app on my Surface Pro, where no web-browsing tabs blink their flashing lights, pulling my focus. It’s nice to have one device where I can switch between typing essay drafts and drawing visual aids for less fleshed-out ideas. And it certainly doesn’t hurt that my Surface Pro is in Dune, this chic metallic rose gold shade that complements my desk set-up quite well. My writing workshop will involve a lot of handwritten brainstorming and color-coded calendar creation, so I’ve also been running through the exercises in Concepts to make sure they’re fully dialed in.

I <3 Concepts

I rarely plan my newsletter more than a week or so in advance. I’ll pull an idea from my running list at the start of each week and begin crafting it slowly, shaping a piece of clay into something readable. When Sunday, my publishing date, rolls around, I release it into the ether, done and dusted. The timing for publishing isn’t perfect either, but I’ve found that sticking to a tight schedule keeps a fire lit under me. Like my writing time, if I don’t hold myself to a publishing deadline, no work will be put out.

Life is, of course, uncertain. I could very well find myself in a full-time job again, or in a season of less writing. All that I have are the things that are in my control, so it makes sense to take advantage of those things. To implement living breathing structure, approach my newsletter-writing with creativity and care, use tools, like the Surface Pro, that support my structure and allow for flexibility, and surrender the rest.

The goal of my writing workshop is to impart some of this structure on aspiring and active writers. Dedicate time to think through what you might want to write about and when you might actually write it. Time to soundboard with like-minded individuals. Time that isn’t in the groggy hours of the early morning or the ten minutes between work calls.

There’s no such thing as perfect timing, but with a little intention, I think it’s possible to make decent use of the time we do have. Make it into something that’s not necessarily perfect, but at least serviceable. So we can inch, crawl, walk, and eventually even run towards the life we actually want.

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I hope to see some of you at my workshop next week! Click here to learn more about the Surface Pro :)