This Journaling Journey

Category: journal prompt

Thoughtful, authentic journal prompts for personal growth

More than just standard, generic journal prompts.

Each prompt on this page is inspired by my own journaling journey. Shaped by real-life experiences, deep reflection, and wide-ranging reading in psychology, philosophy, and personal development. They’re designed to go beyond surface-level questions and help you uncover what really matters to you.

Whether you’re seeking clarity, purpose, emotional insight, or a stronger sense of self, these prompts are here to support honest reflection and meaningful growth. They’re not about ticking boxes or chasing productivity, they’re about helping you develop a deeper, more authentic relationship with yourself.

Feel free to explore. Use one or more prompt or just allow them to inspire your own writing.

  • Journaling prompt: Always think with your stick forward

    Journaling prompt: Always think with your stick forward

    Prompt: Always think with your stick forward The phrase Amelia Earheart painted on the side of her plane ahead of flying across the Atlantic were, “Always think with your stick forward.” I think it’s easy to misconstrue the wisdom here and assume the phrase means, just keep heading in a given direction, no matter what,…

  • Journaling prompt: How do we forgive ourselves for the things we did not become?

    Journaling prompt: How do we forgive ourselves for the things we did not become?

    Prompt: How do we forgive ourselves for the things we did not become? This is a line from the Doc Luben poem, ‘14 lines from love letters or suicide notes’ It speaks to me on a deep level. We all have things we wanted to be or wanted to achieve or do. Goals we set…

  • Journaling prompt: Put your arse where your heart wants to be

    Journaling prompt: Put your arse where your heart wants to be

    Prompt: Put your arse where your heart wants to be Put your arse where your heart wants to be. I think about this quote a lot. It’s so simple and so effective. If you truly want something, you need to be present and putting in the work every day. The quote is from American author,…

  • Journaling prompt: Why should I fear death?

    Journaling prompt: Why should I fear death?

    Prompt: Why should I fear death? “Why should I fear death? If I am, then death is not. If Death is, then I am not. Why should I fear that which can only exist when I do not?” Epicurus A beautiful philosophical exercise in logic and mortality. Why should we fear the things we don’t…

  • Journaling prompt: A drier form of drowning

    Journaling prompt: A drier form of drowning

    Prompt: A drier form of drowning I stepped out of my comfort zone in 2022 by joining a reading group. Not only was it an uncharacteristically social move on my part, but I also found I was challenged to read outside of my comfort zone. There was barely a mention of dragons or wizards in…

  • Journaling Prompt: We are all opsimaths

    Journaling Prompt: We are all opsimaths

    Prompt: We are all opsimaths In the last installment, I spoke about a manager at a previous job. I’ve been lucky to have some really good bosses in my career. Going back to my first manager though, and one thing I’ll always remember. An early task I was set was to send him three interesting…

  • Journaling prompt: The homebrewers mentality

    Journaling prompt: The homebrewers mentality

    Prompt: The homebrewers mentality My first proper job out of University. I worked in marketing for a homebrew alcohol company.  Normally, when I tell people that (and when I elaborate that the job involved traveling to beer festivals around the world) they say something along the lines of, “Dave? Why would you ever leave that…

  • Journaling prompt: Other people’s expectations

    Journaling prompt: Other people’s expectations

    Prompt: Other people’s expectations I can’t stress enough the influence this interview with David Bowie has had on me (and just Bowie in general!); Bowie on creativity I’m ashamed to admit, I didn’t get in to Bowie until after he died.  He had always been ‘old people’ music – and a little bit novelty in…

  • Journaling prompt: Throwing away the alarm clock

    Journaling prompt: Throwing away the alarm clock

    Prompt: Throwing away the alarm clock and have met some strange, wonderful people one of whom was myself—someone my father never knew.’ “Throwing Away the Alarm Clock” by Charles Bukowski, from The Flash of Lighting Behind the Mountain. © Harper Collins, 2004. Read the full poem. I love this poem. Today’s prompt is fairly simple, but…