Should You Write Freely or Outline? The Best Approach for Your Book

Writing a book is an exciting yet daunting process. One of the biggest questions authors face is whether to write freely or create an outline first. The short answer? Both approaches have their place. The real danger isn’t in choosing the wrong one—it’s in getting so caught up in deciding that you never start at all.

Why Structure Matters

For me personally, I’ve always been a systems guy. I have a structured way of thinking, maybe because I grew up as more of a math brain. So, when I approach writing, I need some kind of framework—a skeleton to put the meat on. That’s not to say that you must do the same, but I’ve found that having an outline provides clarity and direction.

That said, writing is a creative process, and creativity requires freedom. You’re going to need both: structure and spontaneity. The key is knowing when to use each one.

How to Start Structuring Your Book

When I start a new project, it usually begins with a concept—something that fascinates me, something I can’t stop thinking about. Maybe it’s a question that nags at me or a theme I feel called to explore. From there, I often sketch out a rough book title. Even if it changes later, a working title gives me a sense of direction.

Then comes the structure. How should I arrange my thoughts? Is this a five-step process? A 30-day challenge? A seasonal journey—winter, spring, summer, fall? Structure helps me organize my thoughts so that, as inspiration strikes, I know exactly where to place each new idea.

The Creative Process: Free Writing vs. Outlining

This is crucial because writing a book isn’t like writing a song. A songwriter might crank out a hit in an hour, but a book is different. It takes time—weeks, months, sometimes years. And throughout that process, you’ll have moments of insight. Maybe you’re on a walk, in the shower, at the gym, and suddenly, the perfect sentence pops into your mind. If you have a structure, you know exactly where that idea fits. Without one, it might feel like you’re starting a brand-new project every time inspiration hits.

Think of it like planning a vacation. First, you decide: Do I want snow, or do I want the beach? Once you choose tropical, you narrow it down—Bahamas, Hawaii, somewhere else? Each decision brings clarity. But if you never commit, you might dream about vacations forever and never take one. Writing is similar. You need to give yourself some boundaries, some parameters, so that your creativity has room to flourish.

Balancing Structure and Creativity

But—and this is key—you can’t be so rigid that your writing feels lifeless. Books should move people, not read like a textbook. Imagine an artist painting a masterpiece. They have a canvas—three feet by three feet, framed and ready. Within those boundaries, they unleash their creativity. That’s how I see writing: structure provides the frame, but the artist in you fills the space.

The Best Way to Start Writing

So, should you start with free writing or an outline? My personal answer: start with structure. But the real answer is even simpler: just start. Whether you outline first or dive straight in, the world needs your book. You can refine, edit, and polish as you go. That’s why it’s called a rough draft—it isn’t meant to be perfect.

So get started. Make mistakes. Write messy. You can fix a rough draft, but you can’t edit a blank page.

If you have any questions about writing, publishing, or working with agents, drop them in the comments. I’d love to answer them in a future post.

When it comes to writing books, the fastest way to a bestseller is to have a bestselling plan.

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P.S. Are you working on your next book? Comment 'BOOK' below and I will send you a free 60-minute training on becoming a bestseller!