3 Steps To Escape A Writing Rut (Even If You’ve Tried Everything)

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

Ahoy and happy Monday!

Welcome to another week of Start Writing Online—where every week we dive into the biggest problems all writers face stopping them from writing on the internet, building an audience, and monetizing their writing.

(And, of course, if you want to defeat these problems and master the fundamentals of Digital Writing in just 30 days, we'd love to have you in the next cohort of Ship 30 for 30!)

This week, we want to help you start writing again if you find yourself stuck in a writing “rut.”

Every writer dreads the inevitable moment when they sit down to write only to find themselves staring at a blinking cursor with no idea what to write next.

So you put off the writing for a day. You think you’ll feel inspired and ready to write tomorrow. Yet tomorrow rolls around and you face the same problem.

You start to enter a loop of:

  • Overthinking
  • Perfectionism
  • Procrastinating

Days turn into weeks. Weeks turn into months. And before you know it, you haven’t written or published anything in what feels like an age.

Luckily, we’ve been stuck in this kind of rut over the years and we’ve developed a quick and simple way to break out of it.

We use a 3-step framework we call the “One Take Timmy”—here’s how it works:

Step 1: Pull up a different “notepad” than you typically write with

We all have our favorite digital writing “place”:

So the first step is to switch up where you’re writing. But don’t just open another notetaking app. Choose the app you use to write to your friends or family or coworkers (you will see why in a moment).

Here are a few ideas:

  • Slack
  • iMessage
  • WhatsApp

The main goal here is to write in a different “environment” than the one that has you stuck.

Step 2: Pick one single person who might find value in the idea you’re thinking about

Now, no matter how much overthinking or procrastination you’ve succumbed to, we guarantee you have at least one writing idea tucked away up your sleeve.

So pick one.

(And if you don’t, then take a look at our Endless Idea Generator here.)

Often, our writing rut is caused by the fact we have a backlog of 50+ ideas. And that’s the problem. We have too many ideas. We spend too much time looking at all of them, trying to decide which one would be most valuable to the most number of people.

The result?

We end up writing none of them.

So to prevent this, we pick an idea and then find one person who would find it useful:

  • If it’s about writing, we find a beginner writer in our contacts
  • If it’s about business, we find someone who runs a similar business to us
  • If it’s about personal growth, we find someone younger who looks up to us

Your list will be different from ours.

All you need to do is think about the idea you’re writing about and who will get the most value out of it. And focus on them. The goal here is to make it so you’re writing something directly to one target reader.

With this person in mind, it’s on to the last step.

Step 3: Write “hey name,” then type out exactly what you want to say in one long brain dump

Nothing complicated here.

Writing the person’s name makes it feel like you’re sending them a direct message. Then, brain dump everything that’s on your mind about the idea. And don’t let your perfectionism or ego sensor what you’re writing.

  • No editing
  • No overthinking
  • No hitting backspace

Now, we typically write these out on our phone—and that means we can take one final important step.

We send it to the reader we had in mind.

(We’ll come to why this is important in a second).

Now we’re getting somewhere. You’ve brain dumped all our ideas onto the page. At the worst, you have an in-depth outline you can sharpen up in a few minutes to publish the next day. But oftentimes, we just remove the “hey name” and publish it directly.

And just like that, you’ve broken out of your writing rut.

Now, let’s take a look at the 3 reasons why the “One Take Timmy” method immediately gets you writing again.

Reason 1: It completely takes the pressure off of writing “for an audience.”

Most people suffer from writer’s block because they’re worried about what a massive group of people will have to say about their work.

So they overthink every word and spend weeks over-editing trying to make it “perfect.” But when you’re writing for one person, especially a close friend, that feeling melts away. You just explain whatever it is you’re thinking about as if they asked you a question.

And since you picked someone who you know would find it valuable, your level of conviction to write about it goes up.

Reason 2: It unlocks your natural writing voice.

The best content doesn’t look like content—it looks like a message in a group chat:

  • Simple words
  • Easy to read
  • No fluff

This is why we recommend using a simple messaging app to write that first draft. You come off more conversational, which makes it easy to read. Instead of fussing over adjectives or fiddling with adverbs, you just write out exactly how you would talk.

And this takes us to the final reason.

Reason 3: It immediately leads you to the next piece based on the person’s follow-up message.

And lastly, sending that messy brain dump to a target reader always leads to helpful responses:

  • “Could you say more on this part?”
  • “What about if I’m struggling with ABC?”
  • “Could you show me an example of XYZ?”

Now, you’ve got a handful of content ideas to work on, sourced directly from a target reader.

From there, you can either use the questions to improve your current piece or tuck them away to answer in the next one. Either way, you’ve got a pipeline of things to write about—which means you’ve rebuilt momentum. And just like that, your writing flywheel starts to spin again.

That's it for today!

Chat next week!

–Dickie Bush & Nicolas Cole

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