30-Day Journaling Challenge

30-Day Journaling Challenge

I’ve talked before about the benefits and art of journaling, and a great way to jump into this wonderful world of journaling is to have some guided practice with it.

Enter the 30-Day Journaling Challenge.

The premise is quite simple. Below are 30 writing prompts to use for each day of the challenge. It’s not necessary to wait for the first day of the month or when life isn’t so busy – now is the perfect time to explore your writing, develop a great habit that has amazing psychological benefits, and perhaps learn a little something about yourself in the process.

Here’s the thing: simply providing the answers to each prompt is one thing – but I challenge you to dig deeper into each of them, even if it’s difficult. Set a timer for 10 minutes and commit to writing for the entire time. If you’re not used to structured writing in this manner, it might be difficult at first to keep at it. You might think that what you’re writing is complete nonsense or just crap. Just keep writing. Try not to edit yourself as you write but instead let the words flow.

Here’s a checklist and a few writing pages to get you started. Ready? Let’s do this.

Journaling Challenge Checklist

  1. What would you like to accomplish with this challenge?

I’m a huge advocate for goal-setting as a way to guide your steps and help keep you on track. Maybe you’d like to develop a habit of writing. Maybe you are looking for a healthy way to express your thoughts.

  1. What are you grateful for?

Gratefulness is a telltale trait of a happy person. One of the reasons for this is that gratefulness forces us to focus on the good that’s in our lives, rather than the bad (which is oftentimes way more easy to see).

  1. Habit you’d like to make or break.

Habits reveal a lot about who we are as people and they are quite interesting to explore. We also have habits that are sometimes not the best for us – what is one that you can think and write about? When did you pick up this habit? How long have you had it? Maybe there’s a habit you’d like to adopt? Write about it today and express how having/not having this habit is effecting you.

  1. Letter to your younger self.

The saying “I wish I knew then what I know now” fits perfectly for today’s prompt. Think about where you are in your life right now – is this how you pictured life when you were younger? Most likely the answer is a resounding “NO!” Tell your younger self all about what to expect out of their life. BONUS: try to give advice without giving details of what you’ve experienced.

  1. Personal manifesto.

A manifesto is a “public declaration of one’s intentions, opinions, objectives, or motives” and today you will write your own. There is no “wrong way” to write a personal manifesto – this is your space to jot down some definitive thoughts. The types of manifestos in existence cover every single topic you could think of – from fitness to beginning-of-the-year goals to writing.

  1. Favorite quote and what it means to you.

Quotes are good in that they sum up a particular thought or feeling in a succinct way. What’s a quote that speaks to you?

  1. Write about a time where you felt true, deep regret about something.

The regret could be caused from something you did or didn’t complete, someone you wronged and didn’t take the time to make right, a fight you left unresolved.

  1. A secret you’ve told no one (or only a few people).

How is this secret affecting your day-to-day life? Is it affecting you at all? Why haven’t you told anyone the secret?

  1. Missed connection.

Write about meeting someone only once or about someone who was only in your life a short time and how their presence affected/impacted you.

  1. Letter to a loved one, living or dead

Letter-writing tends to open our minds up in a way that sometimes talking can’t. Think about a loved one (whether they are a friend or relative) and what you’d say to them if they were in front of you. Maybe you have easy access to them but can’t say what’s on your mind for whatever reason. Write it down. You don’t necessarily have to give the letter to them, but it’s your choice however you decide.

  1. A day in your life.

What’s it like to be you every day? You could easily say that your life is boring or that it doesn’t differ much from anyone else – I beg to differ. The way you view even the most mundane things in your life offer a unique perspective that no one else has. Honor that and tell us what makes your life your life.

  1. What’s your dream job?

Dream of working with animals all day? Or travelling 95% of the time to various places over the globe? What draws you to this particular type of work? And perhaps more importantly, what’s holding you back from it?

  1. Write about the thing you wish you had said.

We’ve all had those situations where you knew you should’ve said something but refrained for whatever reason. What was it that you should’ve said? If you could go back in time, would you say it? If you said it, would the situation (and any subsequent situations) have changed? How so?

  1. What would you do if you won the most recent Power Ball lottery?

Whether gambling is your thing or not, I don’t know many people who would turn one of the biggest cash prizes the U.S. has ever seen. If you won the Power Ball (or came into an absurd amount of money) what would you do?

  1. Is there a cause or organization out there you contribute to or would like to contribute to? What draws you to this organization?
  2. Write about a time you failed at something.

Failures teach us things about ourselves. They can serve as roadmaps to our success if we let them. What do you think the lesson was in the failure? If given the opportunity to try again, what would you do differently?

  1. Your greatest desire.

I don’t mean the unrealistic, romanticized type of desire. I mean the burning passion in you that won’t go away and maybe even keeps you up at night. Could be something concrete like “own my own business.” Or you might not know exactly what it is but there’s this “thing” that won’t go away. Write about it.

  1. The perfect day.

This is different from your actual day-to-day. Write what your perfect day consists of from the time you wake up to the moment you fall into deep sleep. This is a day that may or may not have happened – so dream big and wild here.

  1. What grieves you?

This may be a tough subject to write about – the things, situations, or people that get to your spirit and effects you in noticeable ways. Maybe it causes your sleep patterns to be different. Perhaps you can’t eat (or overeat). Confront what grieves you.

  1. What excites you?

What is that thing that gets your heart racing and makes you excited to get out of bed every morning? Maybe you haven’t quite figured that out yet – and that’s OK. Think about the things you enjoy doing, write about them, and watch your excitement level rise.

  1. Place you’d love to travel to.

If there were no obstacles or financial boundaries, where would you go? How long would you stay there? Would you take anyone or go it alone?

  1. A goal or desire that scares you.

There’s a saying that your goals should be so big that they scare you a little. This means that the goals force you to move out of your comfort zone to accomplish them. Or maybe you have a desire that is so far out of your “norm” that pursuing it would bring about some change in your life.

  1. Top 5 things on your bucket list.

Why did these 5 things make your list? Have you already started making plans to make them happen?

  1. Overheard conversation.

Write about one you’ve heard (recently or otherwise) or make one up if you can’t call one up to memory right now. Where were you? Who did you overhear? What was the nature of the conversation?

  1. Forgiveness.

To not forgive someone is like allowing a poison to seep into your veins but expecting the other person to feel the effects of it. Think of someone who needs your forgiveness – and forgive them.

  1. Write about a lost valuable

What was the item that you lost? Why was it valuable to you? What do you think happened with the item or where do you think it is now? Does it still bring you pain to think about it?

  1. What makes your blood boil?

Righteous indignation. Peeved. Anger. It’s natural to experience situations, people, or behaviors that make us feel riled up. What is that trigger for you? Are you aware of yourself becoming angry or does it sneak up on you? Do you handle it well or is it something that you continuously work on? Write it out.

  1. Face your fear(s).

Everybody has fears in their life – whether they are rational or irrational, real or imagined, tangible or in our heads. What are yours? What gets your anxiety level up or causes you to panic? Do you know where your fears comes from? Do you handle your fears by ignoring them or confronting them?

  1. Real-life heroes.

While it would be cool to be able to fly around with capes saving the helpless and just being generally awesome, having a hero in your life doesn’t have to be so dramatic (or fictional) Who is someone you look up to? Why do you look up to him/her? Is your hero in your life or are you aware of them from afar?

  1. Retrospective.

Think of where you are in your life right now and see how differently things look in respect to where you were five years ago, one year ago, or one month ago. Has there been growth? Have the changes that have you’ve endured been for the better or have they made things more difficult for you? What have you learned from these changes?

How are you doing with the challenge? I’d love to hear about your progress!



  1. October 8, 2015 / 12:57 pm

    I love this post and am definitely going to accept this challenge! So many times we get wrapped up by completing tasks blindly and forget to think. We forget to explore truly what we want out of life, and participating in this challenge can be the perfect start at getting back to the core of what makes each of us desire and what components come together to make us great.

  2. October 29, 2015 / 2:07 pm

    I am up for this challenge and cannot wait! All of the things outlined are things I need to do on the daily to stay the course and make sure I am successful in meeting the goals I have set for myself. So glad to know I won’t be trying to do it alone!

  3. November 4, 2015 / 4:12 am

    You can certainly see your enthusiasm in the work you write. The sector hopes for even more passionate writers like you who aren’t afraid to mention how they believe. At all times go after your heart.

Leave a Reply

Your email address will not be published. Required fields are marked *