28 Writing Prompts To Make Writing For The Next 28 Days Effortless

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 1 of the 10 biggest problems all writers face:

  • Distractions
  • Over-editing
  • Perfectionism
  • Procrastination
  • Self-confidence
  • Generating ideas
  • Impostor syndrome
  • Writing consistently
  • Finding time to write
  • Loose feedback loops

(And, of course, if you want to crush all 10 of these 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 overcome the blank page by giving you 28 writing prompts to help you generate writing ideas for the next 28 days.

One of the biggest blocks to overcome as a Digital Writer is the fear of the blank page.

Even if you’ve been writing for years, on some days you just won’t know what to write about. You will lose confidence in your ideas. You will question whether writing is even worth it. This is the battle with the Resistance. And once you see that it’s a necessary part of the creative process, you can accept it and start to put systems (and prompts) in place to overcome it.

And if you want to dive deeper into the Resistance, then we recommend The War Of Art by Steven Pressfield:

But right now, we’re going to help you beat the Resistance by giving you 28 writing prompts to help you write for the next 28 days.

Before we share these, let’s break down how we categorize these prompts.

The 4A Framework: Every idea can be expressed in 4 different ways

This is a core idea we teach in Ship 30, and once you see it, you will spot it in all the content you consume.

Everything you write falls into 4 buckets:

  • Actionable (here’s how)
  • Analytical (here’s what)
  • Aspirational (yes, you can)
  • Anthropological (yes, you can)

And if you want an example, take a look at this post from Dickie:

Every one of the following 28 prompts falls into one of these buckets.

Let’s dive into each content bucket and the prompts you can use for your next 28 days of writing.

1. Actionable (here's how)

These are actionable, implementable pieces of content.

The reader should gain some new insight or instruction they didn't have beforehand.

  • Tips
  • Hacks
  • Resources
  • Ultimate guides

Take your core idea and help the reader put it into practice.

Here are 10 Actionable writing prompts to get your creative juices flowing:

  1. Share 1 underrated tip for solving a certain problem
  2. Share 1 framework that helps you get something done in less time or with less stress
  3. Share the 1 piece of advice to you would give to a beginner in your field
  4. Share 1 software tool that helps you the most (that most people know nothing about)
  5. Share 1 helpful website (that you think is rarely used)
  6. Share a step-by-step guide for accomplishing 1 specific task
  7. Share the 1 book that most helped you in learning about your topic
  8. Share the 1 podcast you listen to religiously—and what others will learn from it
  9. Share the 1 X thread/LinkedIn post/blog post you've bookmarked and reread multiple times—and what you learned from it
  10. Share the 1 blog post that once you read, permanently changed the way you see the world

Now, onto Analytical.

2. Analytical (here's what)

These are breakdowns involving numbers, frameworks, and processes.

Take your core idea and support it with numbers and analysis.

  • Industry trends
  • Surprising numbers
  • Why your idea works

This type of content helps the reader unlock a new way of thinking.

Here 7 Analytical writing prompts to help you explain your ideas:

  1. Share 1 stat from your niche or industry which people misunderstand and explain why
  2. Share an industry trend which most people think is the way the industry is going (and why they are wrong)
  3. Share the story of a big creator, founder, or expert and explain why they were able to achieve their success
  4. Share 1 personal habit which has changed your life and give the reasons why it’s been so impactful
  5. Share a major turning point in your life and look at it through the lens of wider studies and statistics
  6. Share a framework for how you make decisions and give examples of where you have used it
  7. Share 1 example of a growing trend in your niche/industry/hobby and why you think it matters

3. Aspirational (yes, you can)

These are stories of how you or others have put your core idea into practice to inspire your reader to do the same.

  • Lessons
  • Mistakes
  • Reflections
  • Underrated traits
  • How to get started

This bucket helps the reader understand the benefits they unlock when they see the world through this new lens.

Here are your 7 Aspirational writing prompts:

  1. Share 1 mistake you made as a beginner and what you learned from it
  2. Share the single most valuable thing you learned from a mentor
  3. Share your personal story—where you used to be, where you are now, and how you got here
  4. Share 1 piece of advice to your 5-years-ago self
  5. Share 1 common trait of the people you look up to
  6. Share 1 quote you live by—where you found it, and how it impacts you
  7. Share your personal playbook—how you achieved some result and the steps you took to get there

4. Anthropological (here's why)

These are things that speak to universal human nature.

  • Fears
  • Failures
  • Struggles
  • Why others are wrong
  • How you've been misled

Create a sense of urgency for the reader to fully embrace your core idea or be forever left behind.

You final 4 prompts—all from the Anthropological content bucket:

  1. Share 1 thing you believe that everyone else doesn’t—and why you’re correct
  2. Share 1 life-changing realization you made in your 20s/30s/40s/50s/60s/70s that accelerated your success
  3. Share 1 bad habit you broke in the last 12 months - and why it was holding you back
  4. Share 1 common trait people who fail in your industry have—and how the reader can avoid it

Boom, now that’s lot of topics to write about!

When you first use these prompts a nagging doubt will enter your mind.

This doubt is a faulty belief we have to eliminate.

And it comes in the form of the question:

“This is obvious—why am I sharing this?”

But luckily for us, that’s one of the big reasons to share your ideas, frameworks, stories, and experiences online. They might be obvious to you but not obvious to others. And once you start sharing these ideas, you will get feedback on them from your audience which will spark new ideas to write about, new questions to answer, and new information to share.

And on and on your Digital Writing flywheel spins.

That's it for today!

Chat next week!

–Dickie Bush & Nicolas Cole

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