When I started writing online in 2020, I had no plan, no format, and no idea what I was doing—just a blank page and a desire to express myself. It was liberating to write whatever came to mind, without worrying about rules or conventions. But as I ventured deeper into the world of blogging, I began to notice something: most blogs followed a rigid structure, neatly packaged like essays they taught us to write in school. It made me wonder—did I need to write that way to succeed, or was there a different path worth exploring?
The Pressure to Follow a Formula #
I noticed that content creators, in an effort to distill what makes writing good, tended towards creating clear-cut frameworks or templates that “successful” posts needed to follow. These creators also often claim that if you follow these formulas, it will guarantee success, generating a lot of views and engagement. These frameworks suggest, for example, that maybe you write a listicle, or follow a problem-solution structure in your blog. Or, maybe you talk about lessons learned, or bust a myth. Although these templates can be helpful in specific use cases, they can also be limiting. It’s easy to start thinking that all you need for a good blog is to check off these boxes.
For me, this approach to writing was further solidified when I participated in Nicholas Cole and Dickie Bush’s Ship30for30, a challenge where you commit to writing and publishing an atomic essay (consisting of 250 words or less) for a month. I noticed that, with such a short format, the pressure to “have a point” or follow a certain structure was stronger. You don’t have as much room for “fluff”, so you have to be clear about where you want to go, even before you start writing. I loved my experience during this challenge, but what worked for me then didn’t work for me next.
The Fear of Uncertainty #
As I transitioned to long form memoir writing, I realized I couldn’t take the same approach that I did with the atomic essays. When a memoir was 4-5 pages, I could plan a story arc that closed out satisfactorily by the end. However, when I thought about writing a book-length memoir, I didn’t know what the “point” would be by the end of the book. How could I possibly know the point, I thought to myself, when I could make it any point in my life? And the “real ending” hasn’t happened yet? In other words, because I wasn’t dead yet, it didn’t feel like my story had a resolution. And if I didn’t have a resolution, how could I possibly start, not knowing where I was going to end up?
I was aware these doubts had the potential to hold me back, so I made a simple commitment to write at least 500 words a day. I showed up dutifully at my keyboard, day after day for several months. During this time, ILYS was the perfect tool—it allowed me to express freely instead of letting my perfectionism keep the words from spilling out.
With this approach, I made plenty of word count progress over the next few months. But I couldn’t shake the fear that I didn’t know where I was going. It was unnerving! The longer I wrote, the more I felt like I could be completely wasting my time. What if, at the end of all this, I realized I would need to scrap 90% of what I’ve written?
I longed to be like my classmate in memoir class who had outlined her memoir from start to finish. She could purely focus on filling in the words, having total control and clarity. I longed to have that confidence, a map to follow. But since I didn’t know where I would land, an outline wasn’t possible. Doubts began to fill my mind—was I a fool for thinking I could write a book? Could I even do this?
Finding Clarity Through Chaos #
One day, I was in an online writing session with London Writer’s Salon. At the start of each session, they share daily inspirational quotes to encourage us in our craft. On this particular day, they read a quote that caught my attention.
“In the earliest days of drafting, I’m often working in fragments of language and disconnected images, partial scans and half conversations and unordered events. Why indulge in such chaos? Because what I’m trying to do in the first draft is to discover the book I’m writing by writing the book.”
—Matt Bell, Refuse to Be Done: How to Write and Rewrite a Novel in Three Drafts
I felt a pang of validation as I considered that, maybe, I was actually on the right track. I immediately bought Matt Bell’s book and pored through its pages. In it, Bell, professor and author of 12 books, assuaged my doubt, assuring me that “oscillation between perseverance and a profound doubt” are a “pretty common sentiment among novelists”. Importantly, he normalizes the feeling of lostness as an author, of not always knowing where you’re going before setting out. He uses his novel, Scrapper, as an example. When he started writing it, he wrote for nearly a month about his protagonist before even knowing his name.
He says, on the other hand, that planning your book out and creating outlines isn’t necessarily bad. Unless, he adds, you let the outline become a straitjacket. The danger of outlines is that they sometimes stifle what a novel wants to become:
“One of the surest dangers a novel faces in its early life is a writer too eager to be sure of what it is. Pay attention to your own desires, but listen to the pages you’re accumulating: as you play on, writing your story, sooner or later the pages begin to play back. That’s the moment a draft comes to life, if you’ll give it room to breathe.”
I began to realize that, when I didn’t know where a story was going, my core fear was wasting time. In knowing the end destination, I convinced myself I would be able to map the most efficient route and avoid obstacles. I could convince myself I was in control of the process; I could quiet the anxieties that came from not knowing what would happen.
Architect vs. Archaeologist: Two Paths to Creativity #
So, then, how do you know if you should write in an exploratory fashion, or create an outline?
It all depends on what approach you want to take and how you want to feel in the process.
- Do you want to have the approach of an architect, designing an end product to be followed to the exact specification?
- Or are you more of an archaeologist, not knowing what you might discover?
An architect has faith in their vision and their knowledge of physics knowledge to create a safe and viable structure from scratch. An archaeologist would be delusional if they claimed the same, as they rarely know what they will find or how new information will inform what they will do next.
There’s a time and place for efficient maps and plans. Perhaps, for example, you only have two weeks off from work, and you would absolutely die if you didn’t catch the major bucket list items when traveling to a new place. Maybe you even planned the trip with a particular purpose, like scuba diving with the sharks in the Maldives or journeying to see the Aurora Borealis in Iceland during the fall equinox.
The trip may be incredible—exactly what you expect. Or, you might find that, when you get there, there are other exciting things you would rather be doing. Since you planned this trip months, it would be either impossible or cumbersome to reschedule your reservations. But, say, you were able to change your plans—you would be thrown into an abyss of chaos and uncertainty as you scrambled to fill your time with vacation-worthy experiences. Or, maybe, you have an openness to wander outside into the street, curious about what you might find.
Better Than I Could Have Planned #
This is where I found myself a few years ago when I ended up in Paris for a day. I didn’t have time to stand in lines to see the Eiffel Tower or to wander the Louvre. Instead, I booked three different walking tours at the last minute in three different areas of Paris, figuring out transit and taxis as I went. On the walking tours, I got to see several main attractions that didn’t require waiting in line, like the Arc de Triomphe and Notre Dame before the fires.
I took note of anything that piqued my curiosity, planning to circle back later. That’s how I ended up strolling along The Bouquinistes of Paris, over 900 book carts by the Seine, watching a cheesy comedy show for foreigners in downtown Paris, and topping off the evening at a live cast showing of the Rocky Horror Picture Show in French. I remember sitting in that tiny theater in the student district at the start of the night, thinking I would be in for a quiet evening. However, as the movie began to roll, I realized, with a V on my forehead, popcorn flying through the air, and cross-dressing cast yelling inappropriate comments in a language I didn’t understand, that I was very wrong.
It was crazy and chaotic, but it’s one of the best memories of the trip. And that’s the joy of not planning, and not knowing what to expect. If you don’t plan, things could end up disappointing or even disastrous. However, if you don’t plan, it can also end up being better than you could have ever planned. And when it happens, it’s pure magic.
Connecting the Dots Backward #
Writing a book can feel just like that—surprising and delightful, a conversation with the story itself. Like hiking a mountain, you might only pay attention to the ground beneath you, your feet crunching into the gravel beneath you. After some time, you’ll wonder how much progress you’ve made, turning around to look. When you do, you’re shocked by how tiny the people have become and how clear the winding path is from where you stand. It’s like the famous commencement speech by Steve Jobs, where he declares “You can’t connect the dots looking forward; you can only connect them looking backwards.” We can’t always predict how things will end up. We can do our best to avoid obstacles or make plans to achieve our goals. But if we could see into the future, knowing everything that was going to happen—what would be the fun in that?
Take ILYS for a ride #
If you’re ready to experience the benefits of writing without a plan, ILYS can help.
Create an Account