After 1,000+ Days Of Journaling, These 10 Prompts Most Accelerated My Personal Progress

And in this edition, I walk you step-by-step through how to use them effectively

Aug 20, 2023

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Greetings from the Dutch Countryside!

I’ve spent the last 3 days off the grid, reflecting on the last few months and setting my intentions for the months ahead.

I try to schedule this time every quarter, tapping out from the day-to-day and zooming out to see things from a higher-level perspective.

As I prepared for the trip, I went about my normal routine of collecting questions to reflect on, books and podcasts to consume, and concepts I wanted to explore.

And today’s newsletter is part of that preparation process—gathering my most impactful journal prompts and putting them in a single note for me to work through with zero distraction from the outside world.

But rather than just keep those prompts to myself, I figured I would do a deep dive into each of them.

So today I’m going to walk you step by step through each prompt, when I use it, what it helps me with, and how you can gain value from it.

Quick heads up before we jump in—you can find a link to these prompts as a Google Doc and Notion Doc at the bottom of the newsletter.

Over the last 5 years, I’ve journaled over 1,000 times.

And during that time, I’ve:

Answered hundreds of different questions
Tested dozens of different apps, notebooks, and pens
And learned more about myself than I ever thought possible

After all of this experimentation, I’ve distilled all of the things I’ve learned and methods I’ve tried into 10 simple prompts that I rotate and revisit on a consistent basis.

The 10-Bullet Brain Dump
The Evening Shutdown
The Bottleneck Analysis
The 80/20 Life Audit
The Gratitude Reframe
The Billion-Dollar Reflection
The Compounding Projection
The Excitement Exploration
The Future-Me Mentorship
The Periodic Review

Let’s get to it:

Prompt 1: The 10-Bullet Brain Dump

Every morning when I crack open my laptop, this blank note stares back at me.

And I’ve been starting every day like this for the last 5 years.

Sometimes I give the bullets a “theme” like startup ideas, concepts I want to write about, or people I should reach out to catch up with. But most of the time, it’s just a list of 10 bullets that started swimming around in my brain the moment my eyes popped open. So I’ll spend about 10 to 15 minutes hashing out these ideas as my double espresso works its magic through my veins.

I start my morning this way for 3 main reasons:

It allows me to start my morning with intention. If the first thing I see on my computer in the morning is a browser with 100 tabs, my day is pretty much over. The open loops will grab my attention and immediately cloud my brain. But if the first thing I see is a blank Apple Note, I will spend time processing whatever is top-of-mind, rather than reacting to things that feel urgent but aren’t important.
It’s something I know I want to do every day for the rest of my life. No matter where I am, who I’m with, how old I am, or what I’m working on, I know I will wake up with ideas to process. So since this is an infinite game I’ll continue to do for a long time, I want to build my day around it as the foundation.
It leads to better decisions, clearer thinking, and better habits. I use this writing time as a “coliseum for thought.” It’s during this time when I work through decisions, expand on ideas, or just close the loops that are eating up my mental bandwidth. When I go a few days without this time, I feel noticeably less “sharp” and in control of my actions & decisions.

In doing some reflection on this habit, I can point *every* good thing in my life that has happened over the last 5 years back to it.

That’s why I recommend it as the easiest way to build both a journaling habit and a writing habit. And there’s no need to overcomplicate it either. Just follow these 2 steps:

Before bed, leave your computer screen with all windows minimized except a blank note. (You can also do this with a physical journal which I often do on the weekend.)
In the morning, open your laptop, set a 20-minute timer, and brain-dump 10 bullets on whatever ideas come to mind

Run this experiment every day for a month—and I promise the results will amaze you.

Prompt 2: The Evening Shutdown

My morning journaling is free-flow, unstructured, and built to explore ideas.

My evening journaling is quick, structured, and built to consolidate ideas.

Every night before I shut my phone down, I pop open a Jotform survey and answer the following questions:

Rate the day on a scale of 1-10
What are 3 wins or moments of progression today?
What are 3 potential wins or moments of progression for tomorrow?
What is 1 lesson or realization you want to distill from today?
What is one area you could improve tomorrow?
Upload a photo of the day

This takes me no more than 5 minutes and I can do it anywhere, in any city, at any time, as long as I have my phone.

In the past, I’ve experimented with other ways of journaling at the end of the day. Handwritten, on my computer, via voice note, etc. But I’ve settled on this format for a few reasons:

Low friction. I find my willpower dwindles throughout the day, which means I need the absolute lowest-friction routine possible in the evening if I’m going to keep up with it sustainably.
Ends the day focused on the positive. By taking a moment to reflect on what I did well that day and what I can do well tomorrow, I’m constantly reinforcing the actions that lead to progress.
Creates a “ledger” I can look back on over time. I pipe my answers to these questions to a Google Sheet, each day representing its own row. Then, at the end of the week, month, quarter, or year, I can scan back through every single day to look for patterns.
Forces me to capture more photos. Since I know I have to upload a photo of the day, I’m constantly on the lookout for highlights and moments to capture.

If you would be interested in a deep dive into this survey, how I use it, and how to set it up for yourself, hit reply or leave a comment to let me know.

Just like the morning journal, there’s no need to overcomplicate it or try to figure out the perfect system from the beginning. This is something I’ve been working and iterating on for a few years and still don’t have 100% right.

To get started, just start a new note in your phone called “End of day survey” and start to jot down your answers to a few of the questions I’ve listed (or whatever other questions you want).

Prompt 3: The Bottleneck Analysis

Mathematician Richard Hamming was known to sit down with experts from other fields, cut the small talk, and ask two questions:

What’s the most important problem in your field?
Why aren’t you working on them?

This was off-putting to many colleagues—and it’s worth digging into why.

Everyone has an answer to the first question. The biggest, most important problems are obvious to anyone working in that field. But the second question is a pain point.

Why?

Because it forces the person to confront the brutal facts of their situation.

Answers to "Why aren't you working on them?" will be some combination of denying, blaming, complaining, or defending. Which is exactly why Hamming asks them. The confrontation of the brutal facts comes only after all of these excuses are out of the way.

That's when the real work begins.

Now, I’ve adapted this idea to go far beyond just thinking about my career. Whenever I’m focused on improving a certain area, I start with this “bottleneck analysis” question to identify the most important thing to work on.

For example, in the past, I’ve asked:

What’s the biggest thing keeping you from improving your health? And why aren’t you working on it?
What’s the number one thing preventing your business from growing? And why aren’t you fixing it?
What’s the most important thing you could do to improve your relationship? And why aren’t you working on it?
What’s the number one distraction keeping you from knocking out your focused work? And why aren’t you removing it?
What’s the biggest limiting belief keeping you from starting that creative project? And why aren’t you breaking it down?

This simple question pattern helps identify 1) the most important thing to work on and 2) the biggest thing preventing me from working on it.

The more I focus my time, energy, and attention on these “most important” bottlenecks, the faster I can progress.

This has been an important realization of the people I look up to who seem to move faster than everyone else. They don’t have more time, more energy, or more intelligence. Instead, their efforts are always put toward the “highest leverage” work.

And it’s the relentless daily focus on that high-leverage work, compounded every day for years, that leads to their outsized success.

So to use this one, pick an area of your life you’re looking to improve. Set a timer for 30 minutes and ask the following two questions:

What’s the most important thing holding me back from achieving X?
Why aren’t I working on that?

Prompt 4: The 80/20 Life Audit

If you’re not familiar with the 80/20 rule (also known as the Pareto Principle), it goes as follows:

In any system, 80% of the outputs come from 20% of the inputs.

Once you learn about the 80/20 rule, you see it everywhere.

80% of your profits come from 20% of your customers
80% of your bad moods come from 20% of your actions
80% of your work output comes from 20% of your time

So this question takes this idea and applies it to your life, in 2 parts:

The first 2 questions identify the areas of your life that you feel are going well and the areas of your life you feel could be improved
The second 2 questions help you look closely to find the 20% of people, places, habits, and beliefs that are leading to 80% of your good results and 80% of your negative results

From there, you can double down on everything leading to your good results and ruthlessly remove everything leading to your negative results.

For example, my answers to these questions helped me:

Go 500 days without alcohol to underwrite the role of it in my life
Realize the importance of writing every morning for 90 minutes
Recognize the job I was in was not one I wanted to do forever
Identify the relationships that were no longer serving me
Change my weekly routine to better align my activities

As I write this, I’m headed off to an Airbnb in the Dutch countryside for a few days of reflection heading into the end of the year. And this is the prompt I’m going to answer to kickstart the weekend. Reflecting on this one always leads to the asking of quite a few more questions afterward, which is why I want to have plenty of time and space to answer them.

The next time you’re looking to do a full “audit” of the different areas of your life, block out some time (ideally 1-2 days if you can) and answer these questions:

What areas am I feeling satisfied with?
What areas am I feeling dissatisfied with?
What are the 20% of activities that are leading to the areas I’m dissatisfied—and how can I remove those?
What are the 20% activities that are leading to the areas I’m dissatisfied with—and how can I double down on those?
What steps am I going to take today based on this analysis?

Chances are, you’ll easily find a pattern of people, places, habits, routines, and beliefs that seems to contribute to all of your positive and negative results.

The hard part comes after—when you have to figure out what to do about it.

Prompt 5: The Gratitude Reframe

For years I struggled to develop a gratitude practice.

Answering the question “What am I grateful for?” never worked for me. Sitting there with my journal and pen, I would scan the room and look for things in my immediate environment to list. My fresh coffee, the sunrise, my comfy work chair—it all just felt so surface-level.

Until one morning last summer, I woke up with *debilitating* lower-back pain out of nowhere.

For 24 hours, I couldn’t walk, bend, twist, lift, write, or take a deep breath without a surging pain radiating down my spine.

But when I woke up the next morning after damn-near 12 hours of sleep, it was gone.

Poof, like nothing happened. Completely back to normal—and it hasn’t returned since.

That morning when I answered my morning gratitude prompt, I had a simple answer: my back feeling better.

That’s when I realized—gratitude requires “relative” context.

For the previous ~200 times I had answered that question, not once had I been grateful for my healthy vertebrae. Years and years of taking it for granted. But the second it was taken away from me, I was overwhelmed with gratitude to have it back.

So now, I’ve extended this to reframe my gratitude questions.

My new questions ask me to think about what I’m grateful for relative to another time. Specifically, I ask these 3 questions:

What do I have today that I would have begged to have had years ago?
What do I have today that my 85-year-old self would beg to have back?
What do I have today that my current self if he was sick or injured would beg to have had?

When I frame the questions this way, I’m overwhelmed with answers and feel far more grateful as a result.

Prompt 6: The Billion-Dollar Reflection

There are two types of games in the world:

Finite games. These are games with set rules and set players with a defined way to play. The objective of the game is to win. Baseball, chess, and elections for example.
Infinite games. These are games without set rules or set players without a defined way to play. The objective of the game is to simply keep playing. Improving your health, writing poetry, or building a strong marriage for example.

I believe the key to a life of fulfillment is to find the infinite games you love to play and design your life around playing them forever.

To help find those games I want to play forever, I’ve used this simple question:

What could you not pay me 1 billion to stop doing forever?

The activities I would turn down $1 billion to keep playing are my infinite game activities.

For example, I looked back on a handful of my activities from the last month and ran them through this question.

For these 5 questions, the answer was no:

For $1 billion, would you never lift weights again? Absolutely not.
For $1 billion, would you never write for 90 minutes in the morning again? Absolutely not.
For $1 billion, would you never visit a new city again? Absolutely not.
For $1 billion, would you never talk for think about business again? Absolutely not.
For $1 billion dollars, would you never go to dinner with friends again? Absolutely not.

Exercising, writing, traveling, reflecting, thinking about business, and spending time fostering relationships—these are the games I want to play forever.

My answer to this question led me to develop 3 core values: progression, connection, and reflection. I’m working on a post right now that will dive deeper into these topics, so stay tuned for that one.

My answers to these questions helped me identify the activities I want to build my life around forever.

At the same time, it helped identify the activities I’m currently doing that I don’t actually want to do forever.

So from here, I asked a follow-up question:

If these are activities no amount of money could stop me from doing, how can I shape my life around doing them every day?

And that left me with a rough “daily structure” that I’m doubling down on during my time traveling:

Morning writing & idea processing for at least 2 hours (done first thing over a crisp espresso)
Spending a few hours in the middle of the day working on different businesses, collaborating with my team, and removing bottlenecks
Lifting weights or exercising in some way during the afternoon, tapped out from my phone with full presence on whatever I’m doing
Spending the evening with friends and loved ones, reflecting on the day, and exploring different ideas (that I can then write about the following morning)

The best part about this daily structure?

I can do it basically anywhere in the world
I can do it by myself, with my friends, or with my future family
I can treat each activity as a “container” for that type of work, which helps me work less by minimizing context switching

If you’re looking to find out what you truly enjoy doing (and what you’re doing that isn’t actually energizing you), give yourself an hour to reflect on this question.

Prompt 7: The Compounding Projection

Everything good in life comes from compounding.

And compounding comes from doing:

The absolute basics
With monotonous consistency
Every day for a long period of time

Said another way, it’s a combination of simplicity, consistency, and patience.

But, our human brains struggle to unlock the power of compounding for a few reasons:

Compounding is impossible to see in real-time
It’s hard to connect the small actions to the big result
Our society is built on instant gratification (which interrupts compounding)

Luckily, I’ve found a prompt that helps me connect my day-to-day activities with a long-term compounding result.

After a particularly good or bad day, I crack open a blank note and ask myself 2 questions:

If I repeated my actions from today/this week/this quarter for the next X period of time, where would I end up?
Is that where I want to be?

Right away, these questions identify 2 things:

If time is working for me (and compounding to my benefit). For example, I know if I repeated the same healthy activities I did today every day for 5 years, I would end up in better shape than I am now. If I spent 90 minutes every morning writing like I did today, every day for 5 years, I would end up a much better writer than I am now. This makes it much easier to connect that boring rep or that boring writing session to a long-term result.
If time is working against me (and compounding to my detriment). For example, let’s say instead of ending my night with some foam rolling and reading, I doomscrolled Instagram for two hours. I might not feel the consequences of that tomorrow morning. But if I repeated that every single night for the next 5 years, chances are, I’d be less happy than I otherwise could have been. This makes it much easier to snap out of my bad habits because I can connect the seemingly harmless short-term action with the long-term negative result.

Prompt 8: The Excitement Brainstorm

This prompt is the world’s simplest dopamine hack.

Title a blank note “Excitement Brainstorm”
Brain dump 10 things coming up you’re excited about
Relish in the number of things you have to look forward to

Through my study of our dopamine systems, I’ve learned our brains derive more pleasure from the anticipation of an event far more than from the event itself.

Most of the fun of Christmas comes during the lead-up to Christmas morning
Most of the happiness from dessert comes from thinking about where you’ll go, what you’ll have, and who you’ll be with

So I’ve tapped into this realization (and the power of my dopamine system) by constantly reflecting on what’s ahead.

Before bed, I’ll brainstorm what I’m excited about the next day
Before a trip, I’ll brainstorm all of the places I’m excited to see
Before a wedding, I’ll brainstorm all of the people I’m excited to catch up with

This immediately elevates my state and keeps me motivated to find more exciting things to look forward to.

And there’s an added bonus of looking back at prior entries to see the things that excited me at a certain moment in time.

So give this one a try when you want a little boost.

Prompt 9: The Future-Me Mentorship

I recently picked this prompt up after hearing Alex Hormozi explain it in this video.

In the video, he breaks down the idea of the Solomon Paradox which says we give significantly better advice about personal scenarios to friends than we do to ourselves.

This reflection takes that paradox and turns it into something you can use to make better decisions.

The process starts with having a 30-minute “mentorship” conversation with your 85-year-old self.

Basically, you crack open a fresh note and simulate a conversation about whatever decisions you are working through,

This “future-me mentorship” back & forth works for a few reasons:

It helps you remember the things you know you should be doing. Future you is there to remind you of things you already know.
It works with someone with aligned incentives. Future you clearly wants what is best for current you.
Separates your rational self from your emotional self. Future you isn’t clouded by all of the emotions responsible for the poor decisions of current you.

I’ve started using this one primarily when I am faced with a big decision or when I’m giving something more mental bandwidth than I think I should.

When making a decision, I end up taking the one “Future me” would regret not taking
When I’m giving something too much mental bandwidth, I hear from “Future me” who looks back and laughs at how trivial that event ended up being

This is the newest prompt on this list for me and I’m excited to keep experimenting with it.

Prompt 10: The Periodic Review

Last but not least, we have the foundation of my reflection routine: The Periodic Review.

Spending time answering these questions forces me to document and cherish every moment of the journey. I know over the next 5, 10, 20, and 50 years, I’ll be grateful to have this “ledger” to look back on when reminiscing about a certain time period.

At the end of every week, month, quarter, and year, I crack open a fresh note and answer these questions:

What were my biggest highlights?
What were my biggest lowlights?
What areas did I move forward the most?
What areas could have gone better?
What are my biggest lessons and realizations?
What am I most excited about in the period ahead?

And each of these periodic reviews builds on one another:

At the end of the week, I look over my daily survey to answer these questions.
At the end of the month, I look over the answers to my weekly reviews.
At the end of the quarter, I look over the answers to my monthly reviews.
And at the end of the year, I look over the answers to my quarterly reviews.

And 10 years from now, I’ll skim back through the answers to my yearly reviews to create a decade review.

That will certainly be fun to write.

And if you want to build a journaling habit that lets you compound lessons like this over the next 1, 2, 5, 20, or even 50 years, you can click here to join Decision Journaling before it disappears in 48 hours.

To your clarity,

-Dickie

PS…If you want a sneak peek of one of the modules inside Decision Journaling, check out the first module here.

Boom, that’s it—thanks for reading. I hope you found these helpful whether you’re a seasoned vet or a complete journaling beginner.

Each of these plays a different role and purpose in my reflection process. I like to think of these as a “toolkit” where I start with the outcome I’m looking to achieve, then work backward from there to find the right question.

Also, I’ve put these prompts together in a list if you want to start answering them

And if you have any questions about these prompts, journaling, or anything else, be sure to hit reply or leave a comment to let me know. I answer every single one of them.

Dickie’s Digest

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