20 Journaling Prompts

To Jump Start an Inward Journey

Life’s been full the past few months. I can feel the frenetic pace coming to a settling. With the newfound spaciousness, I hope to rekindle my daily journaling practice. To facilitate that, I came up with these 20 thoughtful journaling prompts.

For me, sitting down and writing whatever comes to mind sometimes suffices. But sometimes I want access to a different wing of my mind. I need a key to the back door, to the secret portal, to the wisdom in the lockbox. I find these prompts jog and jigger something loose every time. Bookmark this and come back to it as you see fit.

1. The Wicked Witch

Villains from the stories that buttress our imaginations are often rendered as two dimensional characters. They appear as pure evil, their intentions paper-thin wicked. It entrains us to consider our own shadows with the same relative disregard.

Take any such ‘villain’ — from personal experience or from folklore — and tell the tale from their perspective. Make it believable, make it sing.

2. Shed to Tread Forth

We hold onto totems and inspirations of all kinds, consciously or not, to drive us forward in life. Sometimes they don’t serve that purpose and instead hold us back.

What is one thing — a memory, a gift, a framework, an expectation — that has served to bring you to where you are right now, but which must be given away now to help you proceed further?

(h/t David Whyte)

3. “The World Is a Beautiful Place”

In honor of the passing of landmark poet/activist Lawrence Ferlinghetti and this poem he wrote, journal using this phrase to start your lines: “the world is a beautiful place” — and just like the wicked witch prompt (#1), make even the shadows beautiful in your rendering.

4. A Friend Who Fell Off Your Train

People come in and out of closeness in our lives. Friends fall away for good reason or for no good reason. Write about someone who became a part of your life and then fell off your train. Who were they? What were some details about them? What did you love about that person? Why do you miss them, or why not?

5. Letter to a Lost Friend

Take the above prompt a step further. Write a letter (maybe send it, maybe don't) to a long-lost or somewhat lost friend with the top five things you've learned about life, love, and the pursuit of your happiness. And how they contributed.

6. I’m Four and I’m on an Adventure

Rekindling a sense of wonder can be a daily practice. Kickstart that wonder by pretending — no, inhabiting — your four-year-old self. Make up an adventure to go on. Make it one that your four-year-old self would write home about.

7. The Scar that Binds Us

Consider a scar you have, whether physical or emotional. Tell its story, its inception, its set of characters, the set and setting in which it was wrought. If it’s painful to explore, be gentle and curious. But unpacking the narrative around it is like melting the scar tissue.

8. The Other Life Still Being Led

Our journey forks off by will or by the whim of the gods. We are on a path, and then we’re not. We move, breakup, graduate.

What is the other life being led still at your former job, former relationship, former living situation. Who is that character and what are the failings. What did you avoid by choosing other than that path. What did you miss?

9. Recurring Nightmare

Get quiet and then let the following statement ripple through your blood and bones. Then write with the blood that comes from this.

I’ve had recurring nightmares that I was loved for who I am.

(Lyrics from a Muse song called “Hoodoo”)

10. Ancestor to Your Own Future Happiness

Imagine that you are an ancestor to your future happiness. What small action can you undertake today that your future self would be grateful for? What practice or conversation could you set in motion now that your future self would thank you for?

(Again h/t David Whyte)

11. The Things I Carry

Things we carry — objects, narratives, or memories — take on an outsized weight and meaning. When we focus on the things we carry, they become right-sized. We can then put them in their right place. Journal by starting each new line or paragraph considering something you carry, be it object or memory, scar or principle.

12. “I Am Both at the Same Time”

There’s a short Nayyirah Waheed poem that goes like this:

there is peaceful
there is wild
i am both at the same time.


Consider what two contradicting aspects you inhabit, both, at the same time. Follow the thread as long as you can go; there’s alchemy and redemption in this.

13. “Because It Was Once Broken”

This beautiful quote from writer/diarist Anaïs Nin is resonant and searching in all the right ways.

Consider the two tracks:

1) how has your connection with the world once been broken; how is it still broken?
2) how are your creative efforts contributing to a restored connection with the world?

14. Waiting, Richer than the Arrival

What are you waiting for? What are you hoping for in your life? What aspect of this waiting will you miss when the waiting is over?

15. What Am I Not Saying?

What am I not saying that needs to be said? To myself, to my loved ones, to my heart and soul.

(h/t Jerry Colonna)

16. Numerology Magic

Pick a random book off your shelf. Look at a clock and find the time. Use the numbers to find a word or phrase. For example: if it’s 2:38, go to page 23 in that book, to the 8th line, and select a phrase. There’s magic to being propelled by this serendipity.

For example, I just picked up a book off my shelf and looked at the clock (11:27). I flipped to page 27 and went to the 11th line. The only three words on the line: “in this system.” So much in there as a journaling prompt.

17. Presence via the Ear

Find someplace outside. Sit and listen, then listen some more. Write down all the sounds you hear. The hum of something electric. A distant voice down the way. A 2007 Honda Civic driving 5 MPH over the speed limit. Listen deeper still.

Exhaust the sounds, then the thoughts will be clearer.

18. Firsts

Describe a first, any first: your first apartment, your first car, your first movie, your first promotion, your first kiss. What were the circumstances, what did it feel like. Give all the details.

Or, imagine a first that’s yet to be: your first grandkid, your first day after retirement, your firstborn’s wedding. Who will you be? What will it feel like?

19. “The Truth Is the Kindest Thing”

Harriet Beecher Stowe talked about truth being a kindness we can give someone. Take this quote and work with it.

20. Shake Hands with the Demons

There’s a wonderful Sam Shepard quote that sums up good reasoning for embarking on a journaling practice. I’m including it here as the final invitation.

I feel there are territories within that are totally unknown.
Huge, mysterious, and dangerous territories.
We think we know ourselves, when we really know only this little bitty part.
We have this social person that we present to each other.
We have all these galaxies inside of us.

Catharsis is getting rid of something. I’m not looking to get rid of it.
I’m looking to find it.
I’m not doing this in order to vent demons.
I want to shake hands with them.

What demons can you shake hands with today?

Hoping you found this helpful. Have a sweet week.