13 Writing Exercises for Every Occasion

You’re reading an excerpt of Great Founders Write, by Ben Putano, writer, entrepreneur, and book publisher. He’s the founder of Damn Gravity Media, a publishing house that inspires and educates tomorrow’s great founders. Purchase now for lifetime access to the book and on-demand video course.

In this final chapter, I want to fill up your writing toolbox with some of my favorite exercises. There are tools for self-reflection, strategic planning, stress management, creativity, and more.

I’ve labeled each exercise with the following information:

✏️ Purpose: For example, personal growth, strategic planning, or writing craft

🕑 Time commitment: How long each session should take

⚠️ Difficulty: How mentally or emotionally challenging the task is (Scale of 1–5)

Try out each exercise. Some you’ll love, some you’ll never do again. My simple hope is that they inspire you to write more.

The Bug Book

✏️ Personal growth, self-reflection

🕑 Less than 2 minutes

⚠️ 1 (easy)

Think back to when you were a kid. If you were anything like me, you were fascinated with bugs—at least the type with fewer than eight legs.

You’d be in the backyard and see an anthill in the grass or a cricket on the fence. You lean down to get a closer look. You’d noticed the cricket’s legs, its eyes, and—are those wings? I didn’t know crickets had wings. You’d watch the ants march dutifully in and out of their home. Why are they doing that? Where are they going? What happens if I poke the anthill with a stick?

Did you have any emotional attachment to these bugs while watching them? Probably not. You were just observing, like a biologist observes a specimen.

Self-improvement is difficult because we’re emotionally attached to our own stories. It’s hard to separate our actions from our motivations—our true feelings from our insecurities.

You’ve probably struggled with this. I certainly have.

To help me observe myself more objectively, I use a writing exercise from legendary business writer Jim Collins, author of Good to Great.

He calls it “The Bug Book.”

As a teenager, Collins struggled to find what he wanted to do in life. A teacher encouraged him to “study himself like a bug” and record his observations. The illusion helped Collins see himself from someone else’s perspective—that of an indifferent researcher.

When I heard this story on The Tim Ferriss Show podcast, I immediately tried it out for myself. I used the bug book exercise to identify the type of work I enjoyed, activities that made me happy, and bad habits I needed to break.

I’ve created over one hundred observations in my bug book. Here are a few entries from over the years:

“The bug Ben was extremely hungover on Sunday and didn’t like it at all. He was also very embarrassed by being the most drunk person at the party. He’s going to try avoiding that in the future.”

“The bug Ben really enjoyed presenting [to the Social Media Club of Kansas City] on Friday. He felt in his element up on stage, teaching people and making them laugh. It was stressful and nerve-wracking at first, but he knew his info and did really well.”

“When the bug doesn’t get enough sleep, productivity becomes incredibly difficult. It’s like pulling teeth. Every step is a drag. When the bug gets enough sleep, everything just flows. Sleep it big for the bug.”

This exercise takes a little creativity. You must imagine yourself as both the scientist and the specimen. Here are a few tips for getting started with your own bug book:

1. Choose an on-the-go medium. You don’t have to use a physical journal for your bug book. I use the notes app on my phone and tag each entry with a label called “bug book.” I prefer using my phone because I can take observations wherever I go.

2. Be curious, but not judgmental. Ask yourself, “Why did I do that?” or “Why do I feel this way?” not “Why am I so stupid?” or “I should have known better.”

3. Write in third person. To stay judgment-free, refer to yourself in the third person. I go as far as to describe myself as “the bug Ben.” This helps keep up the illusion of studying something other than myself.

4. Be objective. Observe your actions, emotions, and the connection between them, but don’t try to assign a purpose or reason.

5. Make daily observations. Try to make at least one entry a day for one week. You’ll be amazed by how much you learn.

The bug book is one of the most valuable personal development tools I’ve ever come across, and I still make entries to this day.

Get curious about yourself, like a child who studies a bug.

Reflection and Vision Letters

✏️ Self-reflection, self-compassion, strategic planning

🕑 30–60 minutes

⚠️ 3 (Moderate)

Like the bug book, writing letters to yourself—past or present—is another way to look more objectively at your life.

For several years I’ve written a vision story to myself around New Year’s. This is a letter I write to my present self from the perspective of myself one year into the future. This letter focuses on the year ahead (or the year past from the writer’s perspective), what went well, what didn’t go well, and important things I’ll have learned. The vision letter can help you anticipate pitfalls and challenges before they happen.

But this year I added another letter to my year-end review. CommitAction, the productivity coaching service I’ve used since 2021, introduced me to the concept of a reflection letter. In this letter, your present self writes to your past self from one year ago. This letter is naturally more concrete than the vision letter because you’re reflecting on the past, not imagining the future.

Writing this letter had a surprising impact on me. I was full of compassion for my past self—someone who had huge dreams but also massive insecurities. I got emotional when I told myself, “That goal you set of building a publishing business? You fucking did it. You did it, dude.”

In my opinion, there’s no better way to build gratitude than writing to your past self. Because no matter how bad the past year was, there is one undeniable piece of good news: You’re still here. And if you survived the past year, you have a chance to thrive this year.

Give the reflection letter and vision letter a try. Write to your past self and have your future self write to your present self.

Worry Lists

✏️ Stress management

🕑 10–15 minutes

⚠️ 4 (challenging)

When I first started building Damn Gravity Media, I was drowning in worries.

There were big things like testing my business model, finding new authors, writing this book, and building my website. Then there were small things like registering my LLC, managing my existing content marketing clients, and building a budget. The tasks were never ending.

When anxiety took over, I found myself shutting down. My response to stress wasn’t to fight or flee—it was to freeze. This made things worse. With a seemingly endless to-do list, doing anything would have been better than doing nothing.

In one particularly desperate moment of anxiety, I decided to try something different: I wrote down everything on my mind on a piece of paper—my work tasks, life worries, chores, random thoughts, and personal doubts. What happened next surprised even me: my anxiety melted away. I had control over the situation again. I knew what to do next and I got back to work.

This was how I developed one of my most important writing exercises: the worry list.

The worry list is exactly what it sounds like. It’s a list of everything you’re worried about personally, professionally, and otherwise. It includes your physical tasks like “edit blog post” and “clean the kitchen,” but also your anxieties: “Am I being a good husband? Is my dog happy? Am I happy? Is my business going to fail?”

When your worries feel infinite, there’s something deeply reassuring about writing them all down and getting to the end of the list. You realize that your problems are finite. There is, in fact, an end in sight.

Start by writing all your to-dos and worries in list form. I mean everything—leave nothing in your head. Then go back through your worry list and immediately cross off the ones that make no sense. Am I being a good husband? Yes, we just had an amazing date night together. Some things aren’t actual problems, just projections of our self-doubt.

Then cross off the worries that are out of your control. You can’t affect the stock market or how a potential client is going to respond to your proposal. You can only make wise financial decisions and put your best foot forward.

What’s left on your list are tasks and problems that are in your control. Jot down an action item for each: What’s the first step to solving this issue? You’ll find that many of your worries are just a single step away from being solved. For everything else, block off the time on your calendar to complete it.

The worry list works because it takes your overwhelming problems and cuts them down to size: A single line on a piece of paper. If you find yourself frozen or spiraling from anxiety, write down everything on your mind. List out your worries so you can tackle them one-by-one.

Journaling

✏️ Personal growth, self-reflection, gratitude, self-love, stress management

🕑 5–10 minutes

⚠️ 2 (Easy)

Journaling is the simplest exercise to start building your writing routine. That’s because there are basically no rules. Research has found that journaling is a powerful tool for dealing with stress, reflecting on past events, finding gratitude, and improving your confidence.

But many people let perfectionism hijack their journaling habit. They feel the need to journal every day, in the perfect notebook, with perfect thoughts. They have an all-or-nothing mentality when it comes to writing.

My wife Mary struggled with this for years. She didn’t want to “mess up” her journals with writing she deemed not good enough. She didn’t want to commit to a journaling routine because she didn’t want the pressure of having to write every day. This led her to not writing at all.

But she eventually found a journaling routine that worked for her. First, she found a format that made it easy to get started. She always struggled with writing on a blank page, so she started using The Five-Minute Journal, which gives you the same writing prompts each day. Most importantly, Mary lowered her expectations. She doesn’t write every day, and that’s ok. She writes when she needs to.

It’s one of life’s most persistent and peculiar paradoxes: by letting go of expectations, you tend to exceed the ones you originally had in place.

There are countless ways to approach journaling. Personally, I enjoy just writing about my day and how I’m feeling. But sometimes it’s useful to start with a few prompts. Here are 12 twelve my favorite:

1. Gratitude: What are three things I’m grateful for?

2. Self-Love: What are three things I love/appreciate about myself?

3. Daily affirmation: I am … [e.g., a writer, a badass founder]

4. Values: Today I want to be known as [list three to five values you care about; e.g., trustworthy]

5. Goals: What do I really want? Why?

6. Productivity: What is one thing I can do to make today feel like a success?

7. Challenges: What am I struggling with right now?

8. Problem-Solving: What would [person you admire] do in this situation?

9. Reflection: What are three amazing things that happened today/yesterday?

10. Self-Improvement: What would have made today/yesterday better?

11. Wisdom: What is in my control? What is not in my control?

12. Self-Confidence: What’s something I did today that makes me really proud of myself?

To get started, choose a writing medium that’s simple and accessible: either a notebook or even the notes app in your phone. Then set a goal to journal for five to ten minutes a day for one week.

Ecological Goal-Setting

✏️ Strategic planning

🕑 90–120 minutes

⚠️ 5 (Difficult)

If you’re an ambitious person (and if you’re reading this book, my guess is you are), your goal-planning process probably looks like this:

1. Look at what your largest competitors are accomplishing

2. Set a large, number-based goal with an aggressive timeline (e.g., $10M in revenue in six months)

3. Write it down in a notebook or on a white board

4. Forget about it

When setting goals for our businesses or personal lives, we tend to pull big numbers out of thin air. I know I’ve done this dozens of times. These goals are exciting, but have little or no grounding in reality. The only thing these types of goals do is set you up for disappointment.

Don’t get me wrong: big, aggressive goals are great. But if you don’t have a plan to achieve them, they aren’t goals at all—they’re dreams (or worse, delusions).

To set the right goals for your business, use a technique called ecological goal-setting. This is an exercise I learned from Peter Shallard, a business psychologist and founder of CommitAction, a coaching service for entrepreneurs.

Start by setting a BHAG: a big, hairy, audacious goal. Then ask yourself these twelve questions to get clear on why you want to achieve that goal and how you’ll get it done:

1. What, specifically, do you want? Consider what your ideal future looks like: What you’re doing, with whom, and the impact you’re making.

2. Where are you now in terms of achieving this goal?

3. What will you see, hear, and feel when you succeed? Try to imagine this moment as vividly as possible.

4. How will you know when you achieved it? What evidence do you need?

5. What will this outcome get for you or allow you to do?

6. Is it 100% self-initiated and self-maintained? Is any part of this goal out of your control? (Or in the words of Naval Ravikant, is it permissionless?)

7. When, where, and with whom do you want to achieve this goal?

8. What resources are needed?

9. Why do you want this? Ask yourself this question three to five times to get to your core motivation.

10. What will you gain or lose if you achieve it?

11. What will happen if you achieve this goal? What won’t happen if you get it?

12. What will happen if I don’t achieve this goal? What won’t happen if I don’t get it?

Take your time answering these twelve questions. They will save you months of wasted effort by ensuring your goals actually make sense in the grand scheme of things.

After Action Review

✏️ Strategic planning, self-improvement, team-improvement

🕑 30–45 minutes

⚠️ 3 (moderate)

When building a business, lessons will be repeated until they are learned. The best organizations don’t just reflect on the past—they use a deliberate system to capture those learnings and implement them.

The After Action Review (AAR) is a tool developed by the US military to debrief and learn from past missions, successful or failed. After a mission, the team recaps by asking four questions:

• What was supposed to happen? (mission and intent)

• What did happen? (results)

• What went well?

• Where can we improve?

In my opinion, a project isn’t over until you conduct an AAR. Otherwise you risk letting valuable lessons go to waste. Spend time with your team to review every project, event, launch, and campaign. Make sure to capture improvements in a place where you’ll see and implement them for the next project.

You can also do AARs for yourself. For example, I’ll conduct an AAR at the end of a difficult week. Not only does this help me capture important lessons, but it reminds me of what I did well that week. AARs give you an objective, balanced perspective on your past performance, and most importantly, insights on what you can do better next time.

Pre-Mortem Planning

✏️ Strategic planning

🕑 30 minutes

⚠️ 3 (moderate)

Some people resist the urge to think about the worst-case scenario. But if you’re really committed to achieving big things, you need to think about what could go wrong.

The pre-mortem is an exercise developed by psychologist Gary Klein. Unlike an After Action Review, a pre-mortem is conducted before embarking on a new project or path. Your goal is to visualize the failure of your endeavor and figure out how to avoid it.

It starts like this:

Imagine it’s the day after the big launch and it was an unmitigated FAILURE. How did things go so wrong?

Answer this question in as much detail as possible. By projecting yourself into the future, you’ll see pitfalls you didn’t consider before. For example, you may envision that no news outlets picked up the story, or your brand partners weren’t as committed as you expected. Maybe your team didn’t know their roles on the day of the launch.

Andy Ellwood, an entrepreneur and executive coach, takes the pre-mortem one step further. At a recent offsite with his startup team, he asked these four questions during the exercise:

• Final moments: What happened moments before it was over?

• Time of death: When would you know it wasn’t working?

• Cause of death: What was the fatal blow?

• Final wishes: What will you have wished you had done?

These questions make the pre-mortem even more real and concrete. “I have never seen more clarity and urgency,” Ellwood said. “The team is ready to run through walls together.”

The more detailed you can be in your pre-mortem, the better prepared you’ll be for the unexpected. Add details big and small to put yourself in the shoes of your future self. Feel the emotion of the situation. Then work backwards to determine how to win and avoid disaster.

Decision Review

✏️ Decision-making

🕑 5–10 minutes

⚠️ 2 (Easy)

There are several variations of the After Action Review. One of my favorites is something I call a decision review. Instead of focusing on outcomes, as the AAR does, a decision review focuses squarely on your decision-making, regardless of the outcome.

In her book Thinking in Bets, psychology professor and professional poker player Annie Duke argues that your decisions should be evaluated separately from your results. In poker, as in the real world, there is a lot we can’t control that affects the outcome. The best we can do is try to make better decisions.

At the end of the week, month, or quarter, ask yourself three simple questions:

• What good decisions did I make? Why were they good?

• What poor decisions did I make? Why were they bad?

• Where can I improve my decision-making tomorrow?

If you find these questions useful, take it a step further with decision journaling.

Decision Journaling

✏️ Decision-making

🕑 10–15 minutes

⚠️ 3 (moderate)

Decision reviews are useful, but it’s hard to be objective when evaluating a decision after the fact. Hindsight bias can creep into your analysis and alter your view. The best way to improve your decisions is by evaluating them before and after you get the result.

Decision journaling is simple: whenever you make a major decision, write it down in a journal or note. Explain why you made the decision and a hypothesis about the result. Be as specific as possible. Then add a reminder in your calendar to review your decision after the result.

The concept of decision journaling comes from the world of stock trading. Traders often use a tool called an investment journal to record their trades, their reasoning behind it, and a hypothesis for the outcome. After the trade is complete, traders have an objective record of whether their strategy was right or wrong.

Decision journaling gives you the most objective view of your decision-making process. It allows you to separate good decisions from bad outcomes, and most deceptively, bad luck.

For example, say you decide to partner with another business in your industry on a joint marketing campaign. They have a larger audience than you, and you have a skill set they need to take full advantage of it. Your hypothesis: $100K in revenue in six months.

But after six months, you’ve only made $25K together. What happened?

It turns out their audience was large but mostly unengaged. You made the right decision to partner with a larger company, but you chose the wrong partner. In the future, you’ll evaluate a partner’s engagement metrics before agreeing to a joint campaign.

Try decision journaling for yourself. Next time you make a big decision, write it down. Record your reasoning and a hypothesis for the outcome, then set a reminder in your calendar to review. Did the decision turn out how you expected? If not, what happened? And what can you improve for next time?

PR/FAQ

✏️ Strategic planning, new product launch

🕑 5–10 hours

⚠️ 5 (Difficult)

Amazon is one of the most innovative companies in history. They’ve revolutionized dozens of industries, including retail, cloud computing, logistics, publishing, smart speakers, and more.

One of Amazon’s secret weapons is the way they communicate within the company. Most organizations rely on PowerPoints and spreadsheets to present new ideas. But at Amazon, PowerPoint slides are banned and replaced by six-page written narratives. The first twenty minutes of every meeting are eerily quiet as everyone reads the narrative from the product lead.

The PR/FAQ is a style of narrative developed specifically for new product development. Two long-time Amazon executives, Colin Bryar and Bill Carr, cover the process in detail in their excellent book, Working Backwards: Insights, Stories and Secrets from Inside Amazon.

“Written narratives will convey your ideas in a deeper, stronger, more capable fashion while adding a key additional benefit: they will act as a forcing function that shapes sharper, more complete analysis,” said the authors.

The PR/FAQ is a tool every founder should use when considering a new product or service to deliver. It shifts the conversation from, “What’s good for the company?” to “What’s good for our customers?” It’s fundamentally an exercise in empathy.

The PR/FAQ is split into two sections: the press release (PR) and the frequently asked questions (FAQ).

A press release is something typically released at the end of product development and right before launch. Instead, Amazon flips the conventional model on its head. Product owners write the press release at the very beginning of the development process. This is how they introduce the project to the rest of the team. It forces the product owner to think through the most important question: “Why should the customer care?”

A standard press release has seven sections and is no more than a page long:

• Title: Announcement of new product or service

• Sub-title: One sentence “pitch” for customers

• Summary paragraph: Sharing details such as what the product does, why it was developed, and how much it will cost.

• Problem paragraph: Explain the challenges customers face that led to the development of the product. The “old” status quo.

• Solution paragraph: Highlight the most valuable features of the product or service that solves the customer’s problems.

• Testimonial: Share quotes from customers (in this case, fake customers) explaining why they chose the new product/service

• Next steps: When, where, and how customers can purchase the new product or service.

Following the press release is the FAQ section. Here is where the product owner must consider and answer the hardest questions they can think of. The FAQ section is typically split into an external FAQ (questions from customers) and internal FAQ (questions from team and company leaders). Amazonians try to keep the FAQ section to five pages.

Creating a good PR/FAQ is much harder than putting together a slide deck, and that’s the point. It forces product owners to think deeply about the product or service from the customer’s point of view. It’s not uncommon for PR/FAQs to go through ten-plus revisions at Amazon.

In the earliest stages of product development, the only question that really matters is, “Why should the customer care?” If the product isn’t better in some way—either faster, more convenient, higher quality, or improves the experience—then all the other details don’t matter. The PR/FAQ will help you filter product and service ideas through this crucial question.

We can all learn from Amazon’s use of written narratives to drive innovation. It forces deep, clear, and concise thinking while giving your team the information they need to make good decisions quickly.

Copywork

✏️ Copywriting, writing style

🕑 10–20 minutes

⚠️ 3 (moderate)

You know good writing when you see it. But producing good writing is an entirely different skill set.

It’s like seeing a slick crossover move on the basketball court—you can’t just watch it and recreate the move yourself. You must practice. And practice. And practice until your arms fall off. You won’t be able to do the move until you develop the right technique and muscle memory.

As a kid in school, you were probably tasked to copy excerpts from a book. This wasn’t just busy work. It’s called copywork, and it’s one of the best ways to improve your writing.

Copywork is simply the act of rewriting a piece of writing you enjoy. The goal is to reproduce an exact copy of the original work: word for word, comma for comma. This process helps you develop the muscle memory to create great writing yourself. (I shouldn’t have to say this, but here’s your reminder to not plagiarize other people’s writing by passing it off as your own. This is just a writing exercise.)

You can use copywork to improve all forms of writing. If you’re working on your copywriting skills, copy the top-selling ads and sales emails. If better storytelling is your goal, rewrite your favorite short story or essay. If you want to learn how to write books, rewrite your favorite books.

Copywork is not a new idea. You might recognize it from the introduction of this book: Benjamin Franklin used a variation of copywork in his self-taught writing lessons.

If you want to become a better writer, start by copying the greats.

Freewriting

✏️ Creativity, stress management

🕑 5–15 minutes

⚠️ 3 (Moderate)

Freewriting is one of the best tools to unleashing your creativity.

I was first inspired to try freewriting by Natalie Goldberg, a writing teacher and author of several writing books, including Writing Down the Bones. She showed me the power of freewriting to knock down mental barriers and let your wildest thoughts flow like water through a broken dam.

This exercise is simple: Set a timer for fifteen minutes. Then start writing and don’t stop for anything. Don’t let your pen or fingers stop moving until the timer goes off. Write down whatever comes to mind, even if it’s gibberish. Let your brain go to places it’s never gone before. Let your fingers develop words they’ve never ventured to make.

Freewriting is more than just a tool for creativity. It will also help you defeat the perfectionist streak that holds you back. It teaches you to break through writer’s block—not with a scalpel, but a sledgehammer. If you find yourself staring at a blank page, set a timer and freewrite until you find the right words to start your work.

If you’re new to freewriting, fifteen minutes will feel like an eternity. If that’s the case, try to do it for ten minutes. Too long? Try five minutes. Still hard? Set a timer for just one minute.

Freewriting will set your mind on fire with ideas. It will break you free from the shackles of self-doubt, fuzzy thinking, and high expectations. For many people, freewriting feels like finding your voice for the first time.

40-Minute Fiction

✏️ Creativity

🕑 40 minutes

⚠️ 4 (Challenging)

What type of story would you tell if it didn’t have to be rooted in reality? Now is your chance to find out just how far your imagination can go. Even for non-fiction writers, writing fiction is a brilliant way to boost your creativity. It will make you feel alive with ideas and excitement.

If you’ve never written fiction, where should you start? I recommend an exercise I did frequently in middle school. The state of Ohio has a program called Power of the Pen, a state-wide creative writing competition. Each middle school has a team that competes at district, regional, and state-level tournaments.

The main event at these writing tournaments is the forty-minute fiction round.

Set a timer for forty minutes, then use a random writing prompt generator to give yourself a prompt (search online for “random writing prompt generator”). Use your forty minutes to write a short story based on that prompt.

If you’re struggling to get started, remember this: all fiction is rooted in reality. Even galactic sci-fi books reflect our human nature in some way. Don’t search too far outside yourself to find inspiration. Write what you know.

The benefit of the forty-minute timer is that it keeps you focused on writing and not thinking. This is the entire point. This exercise will unleash a typhoon of creative energy within you.