5 Writing Prompts For Your Next 5 Days Of Writing (And The Templates That Make It 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 give you 5 writing prompts (and 5 templates) that will make your next week of writing effortless.

When Cole was 24 years old, he had just graduated from Columbia College Chicago with a degree in fiction writing, and he was determined to make writing a full-time career. He asked himself where he should begin writing on the internet, and that’s when he discovered Quora.

  • Quora is a massive social platform for writers online (300M+ users)
  • Questions on Quora serve as endless writing prompts
  • Readers asking questions = "Write this and I'll read it"

It's a Holy Grail for writers.

Cole answered one question every single day, for a year straight.

  • Within 3 months, his first Quora answer went viral, accumulating over 100,000 views.
  • The next month, he landed on the front page of Reddit, accumulating over 1M views.
  • By the 6-month mark, over a dozen of his Quora answers had been republished in Inc Magazine, TIME, Forbes, Fortune, Business Insider, and many more.
  • By the 9-month mark, he had accumulated several million views and had become the fastest user ever to go from new account to Top Writer.
  • After 1 year of writing online every single day, he had effectively become one of the most-read writers on all of Quora.

The lesson?

Volume wins on the internet—especially when it comes to writing.

Which is why in Ship 30 for 30, we believe anyone who wants to write on the internet needs to build a daily writing habit and publish something every single day for 30 days straight. But, for a lot of people, the thought of putting out this much content is overwhelming. In fact, it feels downright impossible.

Volume isn’t impossible. It’s a habit.

Let’s dive in!

5 Writing Prompts To Kickstart (Or Restart) Your Daily Writing Habit

Any question that sparks an idea is a quality question.

  • They help you write quality ideas, faster.
  • They help you reach & engage more readers.
  • They help you build your timeless library of content.

Which ultimately means, you attract likeminded people and net-new opportunities.

Each of these questions might seem weird or random by themselves. But all together, they help you start creating a cohesive, well-rounded library of content that represents "who you are" and "what makes you, YOU" at scale.

Prompt 1: What was your first job, and what's 1 lesson you learned you'll remember forever?

Take a moment to reflect.

Think about your first job. What’s a lesson you keep coming back to, time and time again? In Cole’s first job, he watched his boss negotiate multimillion dollar deals. He listened to him give pitches that turned into national campaigns. The lesson? Money funds creativity, not the other way around. It’s forever etched in his brain.

What’s a lesson that’s stuck with you? And who taught it to you?

The Lesson Template

The Single Most Important Lesson I’ve Learned Working In {Industry}

Not all lessons are created equal.

Some lessons we learn are small. They are little reminders along the way of what truly matters. Other lessons are giant. They fundamentally change the course of our entire lives.

Over the past {X} years working in {Industry}, this is the single most important lesson I've learned about {Subject}:


And here's why:


Prompt 2: What's a mistake you notice beginners in your industry make all the time, and how would you recommend they avoid/fix it?

Writing about your “mistakes” is a never-ending category.

More than that—it’s ripe for terrific stories. But, It's not just about reliving embarrassing moments. It's about being helpful. Everyone loves a good “I made this mistake and here’s how I overcame it.”

  • Look at your accomplishments.
  • Share the mistakes you made achieving it.
  • Give your reader a roadmap to avoid it.

Help your readers learn from your missteps.

The Beginner Mistake Template

1 Big Mistake I Made When I Was First Getting Started In {Industry}

Like most beginners, I made a lot of mistakes when I first started working in {Industry}. But this was the biggest one, by far:

{Big Mistake}

Here's what happened:

{Explain Mistake}

But, it's also worth acknowledging that making this mistake taught me a ton.

{Explain Takeaway Lesson}

This is why I encourage everyone to see their mistakes (and "failures") as necessary steps along the path.

There is always a lesson to be learned.

Prompt 3: What's a book you've read that completely changed the way you thought about overcoming a specific obstacle in your life?

What are you reading?

More importantly, what should you be reading if you want to… and then fill in the blank.

For example:

  • Books that will make you more creative
  • Must-reads for maximum relaxation at work
  • Books that will change the way you think about life
  • Etc.

There’s a reason book lists are so popular, and it’s because readers see them as a starting place when searching for new material. The secret is to drill your book list down to a hyper-specific point or takeaway, and then curate the best of the best.

The Must-Read Book Template

4 Reasons Why I Think Everyone Should Read {Book Title}

{Book Title} by {Author} is the best book ever written on {Subject}.

If you've read it, then you know exactly what I'm talking about.

But if you haven't here's why:

Reason #1: {Reason1} {Explain why}

Reason #2: {Reason2} {Explain why}

Reason #3: {Reason3} {Explain why}

I can't recommend this book enough.

Prompt 4: How do you think about solving problems in your life? What's a framework you use? How did you learn this framework?

People love frameworks.

Everyone is looking for guidance, all the time. So if you can walk someone through the journey they’re currently on (or thinking about beginning), and help them avoid a problem step-by-step, they’ll see you as their guide—an “expert.” Frameworks can be applied to everything from workout routines to habit building, dating to video games.

Take anything you know and explain how you do it.

The Framework Template

I have been practicing {Skill} for {Time}.

Along the way, I have done all sorts of things to try to get better:

- {List a book you read}
- {List a podcast you listened to}
- {List a person you asked for help}
- Etc.

And all of these things helped me a ton.

But if I had to start all over again (as a beginner), this is the simple framework I wish I had for learning how to {Skill}

Step 1: {Step1}

{1 sentence why}

Step 2: {Step2}

{1 sentence why}

Step 3: {Step3}

{1 sentence why}

When you're first starting out, this is all that matters.

Prompt 5: What's a ritual in your life that you (try to) do every single day? What is it? When did you start doing it? What role does it play in your life? Why is it meaningful to you?

We’re always looking for new ways to approach our everyday lives.

What are your habits? What are good habits? What are bad ones? How do habits impact your daily life? How do they impact the way you make decisions?

Habits are a terrific category to write about, because as long as we’re human, we’re going to have (and want to improve) our habits.

The Habit Template

1 Habit All Successful People In {Industry} Have In Common

Most successful people share the same handful of things in common:

- They are {Outcome 1}
- They know how to {Outcome 2}
- They have {Outcome 3}
- They have {Outcome 4}
- Etc.

But in {Industry} in particular, I have noticed that the most successful people have this 1 habit in common:


And here's why:

{Explain why}

That's it for today!

Chat next week!

–Dickie Bush & Nicolas Cole

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