Hey friends,

Last week, I asked you a simple question:

What’s a problem (or struggle) you’re experiencing that I can help resolve?

Well, let’s just say that I was pleasantly surprised to see the mountain of answers that arrived in my inbox. I’ve tried to reply to as many as I can, but just know that I’ve read every single one. Thank you for being so open with me, and if you still want to contribute your own answer to that question, feel free to hit reply and let me know.

All right. Now onto today’s reflection.

Over the past few months, I’ve been working on a number of stories about all kinds of topics: ambition, success, listening, and more. I’m still in the process of crafting and refining them, and am excited to share them with you when they’re ready.

With that said, I was recently chatting with Thinking In Stories alumni about the creative process, and how to make it more enjoyable over time. And one thing I realized was that enjoyment isn’t about ease, but more so about accepting the texture of challenge that’s right for you.

I wanted to expand upon this point further, which is what today’s reflection is all about. So when you’re ready, let’s dive right in.

​The Thin Line Between Delight and Doubt​

I’ve been writing online for over 5 years now, and one would assume that it’s gotten easier over time. That the longer you do something, the more you’ve figured out the mechanics, allowing a sense of effortlessness to accompany your pursuit.

Well, let’s just say that effortlessness isn’t the right descriptor here.

As any writer will tell you, there isn’t a point where things transition from “difficult” to “easy” in perpetuity. Of course, there are some pieces that come easier than others, but you can’t import that sentiment into the next piece through sheer will. Creativity can yield patterns, but those patterns don’t emerge simply because you want them to. They are a force of their own, often arising and falling without your conscious awareness.

This is precisely why creative endeavors don’t get easier over time. Since there’s no governable trend that you can identify, there are no set mechanics that you can exploit and reuse. As a result, every piece is a somewhat novel experience, containing surprises and tangents that you didn’t expect going into it. And because you can’t predict what you will create, that makes the process itself quite challenging.

The nice thing about challenge, however, is that it’s a source of great meaning.

Writing is challenging because it exposes your blind spots in real-time. You’ll write out a resonant thought, only to see that it may not connect well with the overarching theme of your story. Then you might get stuck, question what exactly you’re writing about in the first place, and doubt everything you’ve written thus far.

But at the same time, writing is so rewarding because of the clarity that emerges from the process.

There’s an interesting parallel between cleaning your room and clearing your mind. When you clean your room, you’ll have to first make your room messy as a means to organize it. You’ll move chairs out, shift tables around, and stack piles of clothes in a corner before moving everything back into neat configurations. And it’s only at the end where your room looks much cleaner than it previously was.

The same dynamic applies to writing and what it does for your mind.

When you decide to write, you’ll wrestle with a bunch of half-baked thoughts as a means to make sense of them. You’ll scramble together an anecdote, test an idea in a sentence, or sort through some quotes before assembling it all into a cohesive piece that indicates a sense of order. And it’s only at the end where your thinking feels much clearer than it previously was.

What this means is that any route to clarity must make use of chaos. The path to a given destination must contain a seed of its opposing force, or else there isn’t enough friction for you to deem it worthwhile.

This is why meaning resides in the thin line between delight and doubt. The delight comes from the hits of clarity you gain from being engaged in a pursuit, whereas the doubt comes from the friction that must be embedded within it. And the more you oscillate between delight and doubt, the more that endeavor shines with purpose.

When people ask me how writing can be more enjoyable, I like to respond by asking them why they want to write in the first place. Some say that it’s the right medium to express themselves. Others say that they want to find their people by sharing their ideas through the written word. Some even say that they’re not sure, but they do it because they understand how beautiful the art form is, and they just want to be a part of that.

Regardless of the reason, what’s clear is that there’s an element of delight that has drawn them into writing. The disconnect, however, is that they’ve forgotten that doubt is just as important. Doubt is what makes you reconsider what you know through a different lens, and to update your thinking as a result of taking a renewed perspective of your thoughts. It’s to consider alternative approaches to evergreen ideas, and to experiment with them so they could be made novel.

And through this process, you’ll arrive at an insight that was once obscured from view, which allows delight to re-enter the scene and balance the equation yet again.

That’s it for today’s reflection. Was there anything that resonated? Anything that didn’t? Hit reply to let me know.

Thanks for reading, and feel free to share this email with anyone who might enjoy it. Have a great rest of your week!

-Lawrence Yeo

P.S. Since today’s reflection was all about writing, it’s fitting that I share The Examined Writer with you here. It’s 3 hours of self-paced material, all designed to elevate your writing practice.

I’ve actually created a free 3-day email course on the topic as well, which you can access by clicking here. Hope you enjoy it.

P.S. Thanks to Kelsey Weaver for adding your support on Patreon! It means so much. If you’d like to support More To That and get access to book recommendations, exclusive AMAs, offline posts, and other reflections, join as a patron today.