profile

Story Rebel

[Story Rebel Digest] Pirouetting


Hey rebels!

I spent the weekend sewing a light trenchcoat (a bit more on that in today's deep dive article), and I'm so ready to trade my heavy wool coat for this cheery red cotton twill! Our neighborhood's daffodils and hyacinth are fully in bloom, so spring must be just around the corner... right?

Speaking of just around the corner, don't miss the Story Rebel Mixer! It's a casual hour-long zoom call where you'll get a chance to ask me questions and chat with fellow rebels. We had a really wonderful conversation last time, and many delightful connections were made.

Join us this Friday (March 20) at 12pm Pacific.

I'm looking forward to chatting with you all! Register here.

—JK

IN THIS ISSUE:

  • Building authority
  • When to pirouette (and how)
  • A cornucopia of rainbow business delights!

💰 This article from Kit's blog feels very timely given conversations I've been having lately with aspiring authors. I routinely tell folks that while it's absolutely possible to earn good money from the sales of your nonfiction book, most authors who are making a good living are using their book to leverage other opportunities. Get some inspiration with 5 systems that turn your expertise (and book) into sustainable income.

👀 I've been toying with the idea of restarting my lapsed Substack after listening to this podcast from Sam Vander Wielen. I initially started my Substack newsletter, From Chaos with Love, as a way to process what happened to me after my eye injury, and talk about my creative life. I moved to my personal blog/Kit when I shifted to focus more on writing about storytelling, entrepreneurship, and nonfiction book writing—but that left a bit of a void when it came to writing my more personal essays.

If I decide to fire it back up, you'll be the first to know.

Pirouetting Between Draft and Outline

After last week's deep dive on outlining, somebody emailed back with a question. They wanted to know what to do when it felt like the book was tugging them off course from the outline that they had set.

They asked: “Is it okay to go back to the outlining phase? Or should you just keep writing and make it work?”

The way a lot of coaches talk about outlining can make it feel like it’s a discrete stage in the writing process—a box to tick off in your project management tool so you can move on to the drafting stage.

Once you have a solid outline, you're golden.

I find this attitude trips authors up for two reasons.

Cue the performance anxiety!

First, if you go into the outlining phase believing that you have one chance to come up with an amazing outline, it puts a lot of pressure on the process that doesn't need to be there.

Last week, a book coaching client told me she was nervous about committing her thoughts into an outline because she worried about getting it wrong.

And that's fair. There are a lot of artistic pursuits where taking a big step feels irreversible.

For example, I love to sew. Right now, I’m working on a red trench coat inspired by the one Emma Stone wears in the movie Bugonia.

I spent hours testing the pattern, ordering sample fabrics, buying the perfect organic cotton twill (hers is wool, but I wanted something lighter), prepping the fabric, and laying out the pattern pieces.

Then I stared at my cutting table a long, long time before I finally grabbed my scissors.

I needed to be absolutely certain of my planning process. If I'd made a mistake, I could end up ruining several yards of this expensive fabric.

The great thing about writing a book is that nothing is ever set in stone.

Until it’s sent to the printers and bound up between covers, everything can be moved and changed and reordered and fixed and improved. From the first few lines of the outline to the polish of the final draft, you can’t screw up your manuscript.

So, go ahead! Write down all your amazing ideas! Play! Get creative! Outlining should be fun, not constricting.

Stuck on the wrong trajectory

The second way writers get tripped up by this thinking is in the drafting process of the book.

In my experience, most books buck the outline at some point.

That’s absolutely okay! You learn more, you refine your argument, and you end up needing to make changes.

If you find yourself doggedly sticking to the outline when your book wants to veer right, you’ll run into trouble.

You might start losing the joy of the writing process. The book might start feeling stale and lackluster. You might start experiencing writer's block.

Whenever those signals pop up for me, I know that’s my subconscious' way of telling me that I've gone off track somewhere and need to re-evaluate.

Knowing when (and how) to pirouette

Personally, I tend to vacillate between the drafting and outlining process. This is especially true with fiction, but even with nonfiction projects, the act of actually writing the book teaches you so much about what the structure should be.

I’ve sent nearly every one of my ghostwriting clients an email (generally about halfway through the book) saying, "Hey, I took another look at the outline, and I think I’ve figured out a better direction. See attached."

So what do you do when you have an outline but you feel your book tugging you off course as you're drafting?

—> Read the rest on the Story Rebel blog.

🧠 I'm really looking forward to this live panel next Wednesday: Closing the authority gap: Transform your brand from unseen expert to leading voice. Kristen VanderHoek, who I know through the MixerMind, will be leading a discussion that promises authority-building strategies for knowledge experts and smarty-pants service providers. It's free to attend. Register for free here.

✒️ Will you be attending Kit's Craft + Commerce conference? It's June 10–13, 2026 in Boise, Idaho—and I plan to be there! They just announced that James Clear (author of Atomic Habits) will be one of the keynote speakers, joining a lineup that was already rather exciting. Let me know if you'll be there, I'd love to meet up!

🌈 Today is the last day to grab the resources in the Online Biz Owners Pot of Gold.

If you missed my earlier emails, my friend Linda Sidhu curated a roundup of 90+ resources from handpicked experts to help you get the support you need to clarify your business strategy, sell more of your services, and become more visible this year. All for free!

Whether you want help with:

  • Growing your email list with aligned subscribers
  • Writing conversion copy confidently
  • Attracting ideal clients effortlessly
  • Getting on more virtual stages
  • Managing your mindset to overcome anything
  • All of the above

I personally contributed the 60-Second Story Kit, which includes:

  • Signature Story Workbook
  • Tell Your Signature Story in 6 Prompts masterclass
  • 6 Signature Story Oracle Cards

Talk soon,

JK

P.S. Don't forget to join us for the Story Rebel Mixer this Friday! Register here.

Written by Jessie Kwak

Story Rebel

Learn how your story can help you grow your business, spread your message, and make an impact in the world.

Share this page