A Beginner’s Guide To Journaling & Writing Daily Diary Entries

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

In this week’s Deep Dive, we want to talk about journaling.

Otherwise known as “keeping a diary.”

Journaling, or writing in a diary, is a powerful way to understand yourself better, set and track your goals, and remember all the interesting things you’ve done over time. There is no better way to hear yourself, become conscious of your thoughts, and take actionable steps forward.

Even if it's just a paragraph, three sentences, or jeez, one sentence, doing a quick check-in and writing down what's happening in your life will document your growth as a human. Over time, you can literally see your life progress right in front of you.

Long term, writing in a diary will keep you grounded and sane.

Let’s dive in.

What’s The Difference Between A Diary And A Journal?

A journal and a diary are both great for personal writing, but they serve different purposes.

A diary is for documenting your daily life.

  • Record your diet and what you eat
  • Keep track of your workouts and results
  • Note everything that happens during the day

A journal is for reflecting on your thoughts and feelings.

  • What are you grateful for?
  • What are you trying to achieve?
  • Why did you yell when cut off in traffic?

Whatever you call it, we recommend making a habit of capturing and inspecting your life, whether it be through journaling, diary keeping, logbook entries, or “secret notes.” The point is to write this stuff down.

Why Learning How To Start Writing A Diary Is Among The Best Decisions You Can Make

Writing is thinking, and writing in a diary is how you sharpen your thoughts.

If you commit to the process of diary keeping every single day, or even once a week, over a long enough time horizon you will notice dramatic changes in the way you think, write, reflect, “talk to yourself,” and maybe most importantly, your ability to build and maintain simple (but powerful) habits over long periods of time.

Consistent writing in a diary allows you to create all these things in your life—and more.

How Do You Start Writing A Diary? 5 Tips for Starting Your Diary Writing Habit On The Right Foot

Ready to spill your heart out and create your own personal time capsule?

Here are 5 tips that will help you get started on the right foot.

Handwritten Diaries Vs Digital Diaries: Which Is Right For You?

There are 2 ways to keep a diary:

  • Short form
  • Long form

For short form, use a physical diary.

Handwriting is labor intensive and forces you to choose your words more carefully. Only write down what is necessary: a list of questions, your daily agenda, a one sentence rant on what’s irritating you. Do this enough, and your brain will automatically start prioritizing what to write.

For long form, use a digital word doc.

Your goal is to write down anything and everything. Get it ALL out. Capture as many data points as possible: what’s new in your life, what big decisions have you made, what’s getting in your way. Then, at the end of the year when you re-read everything you’ve written, you can spot Macro Trends in your life.

Experiment with both forms.

The most important thing is that you are writing. Choose whatever form aids your writing and causes the least amount of resistance.

Diary apps, journaling journals, meh.

If they work for you, use them.

But truthfully, there is no more honest mirror than a blank piece of paper.

Decide What to Write In A Diary

Don’t overcomplicate it.

Decide to write whatever you want when you sit down.

  • Wins & milestones
  • Realizations & decisions
  • Things going well & things to improve

Then open a blank page and spend 15 minutes writing whatever comes to mind.

  • Don't edit for grammar
  • Don't censor yourself
  • Don’t pause to reread
  • Let your hair down
  • No erasing

Vocalize what’s happening in your life. Just say it. Don’t edit it. Don’t think about it. Just say what’s happening & how you feel about it.

Uninhibited writing will help you clean out the pipes so fresh water can flow.

You aren’t writing “for anyone.” You are writing for yourself, with yourself, so you can continue to learn about yourself. Your goal shouldn’t be to write well. Your goal should be to write clearly and honestly so you can see where you are, how you’re feeling, and what you’re thinking—and then make decisions in your life that allow you to move forward effectively.

The more you put in, the more you get back.

Set Aside Time Every Day

Your goal should be to write for 10-30 minutes per day.

10 minutes is the minimum, but 30 minutes is the goal. 60 minutes is what you get when you are clearly processing through something and need to talk things out with yourself. If you don’t have 30 minutes to write one day, then at least get down 5 to 10 minutes of quick thoughts.

It will seem insignificant from day-to-day, but at the end of the year you’ll be surprised.

Jot Down Thoughts Throughout The Day As They Come to You

If you want to level up your diary routine, you need to capture ideas.


Ideas come and go quickly. And when something catches your attention, there is usually a reason.

Set up a system so that you can immediately capture what captures you when it happens.

  • Quick capture on your phone
  • Whiteboards in the shower
  • Notebooks all over the place

You will never remember everything. And you don’t want to lose the golden nuggets that pop up during your day—no matter where you are or what you are doing.

Then once you have captured an idea or thought, bring it into your daily writing routine to level up how you process your thoughts. Review what you captured and start asking yourself reflective questions like:

  • What do I think about that?
  • Why am I stuck here? How can I get unstuck?
  • What am I missing here? What am I wrong about here? Why?
  • Why do I think that way? If I keep thinking that, what might happen?
  • If that’s true, what else is true? If that’s true, is the opposite false? Where’s the proof?

Most people go their “entire” life without reflecting—and before they know it, years have gone by and it's too late to change.

Don’t let this happen, leverage your pen to level up.

Go Back And Read Old Entries Over Time

You’ve built your daily diary writing habit.

You’ve created a system for capturing thoughts and reflecting on them.

Now it’s time to step back and take a Macro Level view of all your hard work.

It's easy to get caught up in the day to day & lose sight of the bigger picture. Which is why we recommend you do a monthly review of your diary.  Block 60 minutes off at the end of the month and slowly walk through each page of your diary.  As you review each entry, look back, look at the present, and look ahead.

Looking back:

  • At the end of the year, what will you look back on with pride and fond memories?
  • What lessons did you learn about your health, relationships, and business?
  • This creates a wonderful ledger of wins and progress.

Looking at the present:

  • In what areas are you most satisfied? Least satisfied? What’s working? Not working?
  • Based on these areas, what will you do more of? Less of?
  • Double down on the things that bring you positive results. Eliminate the negative.

Looking ahead:

  • What are you thinking about for the month ahead?
  • What are you excited about? Thinking about? Uncertain about?
  • Write a letter to your future self that you can read at the end of the next month.

Now, at the end of the year, you can collect each monthly review and distill your entire year!

Additional Resources To Go Down The Rabbit Hole (For When You Struggle To Find Things To Write)

  • ​4 Journaling Prompts that will change your life: What did I do yesterday? What am I working on? What’s coming up? What am I grateful for? These 4 simple prompts can be a very easy way to get your reflective juices flowing—and words pouring out onto the page.
  • 500 Morning Pages in 500 Days to reclaim your art and make time for creative thinking. The term “Morning Pages” comes from the best-selling book, The Artist’s Way. In this short Twitter Thread, Dickie explains how writing Morning Pages for 500 days in a row impacted his life, and also shares a series of reflective questions you can use to prompt your own Morning Pages.
  • ​22 Questions to reflect on and make your next year your best year. These are questions anyone can use, at any point throughout the year, to check-in and see how things are going, what needs to be improved, where you want to steer your ship next in your life, etc.
  • The Analog Diary to make your notebook useful. These aren’t writing tips, but the structure outlined in this article will help you get control of your notebook.  A little organization can be enough to free your creativity.

That’s a wrap for today!

And as always, the only way to get better is to practice.

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