Journaling Prompts for Self-Discovery
41 prompts to help you figure out who you are and how to build your dream life.
The first journal I can remember writing in was a tiny yellow hardcover Scooby Doo journal with a classic lock and key, most likely purchased at a Scholastic book fair when I was in first or second grade.
Having been a fan of Nancy Drew, Harriet the Spy, and later on, the Amelia’s Notebook and Georgia Nicholson books, I was scribbling in that thing constantly.
Over the years, I had many intense relationships with many journals and notebooks, most of which still live under my bed. I enjoy reading through them from time to time, if only to remind myself of the specific agonies of adolescence (one favorite entry discusses my despair at finding the love of my life in freshman Spanish class, only for him to barely know I exist. The next entry, dated only an hour later, catalogues my Guitar Hero high scores).
Since college, though, my relationship with journaling became spotty and strained at best. I think there’s something to do with the fact that I discovered blogging and, like any millennial Lena Dunham devotee, I started treating the entire internet as my diary instead of keeping some thoughts to myself where they belonged.
I’d really like to get back into the practice of journaling, or morning pages, or whatever I decide to call it nowadays, so I put together some prompts to help me and figured I’d share them with you as well.
Part One: Past
These questions are designed to help you reflect on your past and who you were before you learned to play within society’s rigid rules.
What’s something you were told you were good at as a kid that you’ve never really tried as an adult? Why do you think you stopped?
Think about a version of yourself you’ve quietly grieved – a path you didn’t take, a person you almost became. What does she want that you’ve stopped letting yourself want?
What did you love doing before you knew you were supposed to be productive? The Saturday afternoons. The obsessions that felt embarrassing. The things you made for no reason.
Name a compliment you’ve received more than once that you’ve never fully believed. What would have to be true for you to accept it?
What’s a book, film, album, or place that felt like a hand mirror when you first encountered it – like it was showing you something true about yourself? What was it showing you?
Who is a person from your past whose opinion you still carry? Are you carrying it accurately?
What did your childhood bedroom look like? What did it say about who you were trying to be?
What’s something you used to do that you dropped because life got busy? Do you miss it, or did you outgrow it? Be honest.
Think about a time you felt most alive. Not happy, necessarily. Just fully present and undisguised. What were you doing? Who were you with?
What’s a choice you made that you’ve never fully made peace with? Not to relitigate it – just to name it clearly for the first time. To release yourself of the guilt, if you’re still carrying it.
What story do you tell about your childhood that you’ve told so many times it’s become fixed? Is it true, or has it become a script?
Who did you want to be when you were twelve? What parts of that kid are still in you, and what parts got quietly buried?
What’s something from your past you’re embarrassed to still want? The apartment you used to imagine. The relationship template you’ve never found. The version of your career that felt possible before it didn’t.
Part Two: Present
These questions ask you to see your life as it actually is.
Look at your physical environment right now – your home, your workspace, even your car. What is it reflecting back at you? Is that accurate?
Where in your life do you feel most like yourself? What conditions make that possible, and how often do you create them?
What are you tolerating that you’ve convinced yourself is fine? Be specific. No one is reading this but you.
What do you spend money on impulsively vs. what do you put off indefinitely? What does that gap tell you about what you actually value?
What are you waiting for permission to want? Who do you imagine giving it?
What’s a feeling you’re currently avoiding by staying busy?
What does your ideal Saturday look like? Now describe your actual last Saturday. What’s the distance between them, and what’s causing it?
Who in your life makes you feel most like yourself? Who makes you feel like a slightly worse version of yourself? What does that tell you?
What’s something you say you care about that your calendar and bank account don’t reflect? What’s something you say you don’t care about that they actually do?
What’s a role you play – at work, in your family, in your friendships – that has never quite fit? Have you ever said that out loud to anyone?
What are you proud of right now that you haven’t let yourself acknowledge? Write it down without immediately undercutting it.
What’s the last thing you made, built, cooked, wrote, or created that made you feel good? How long ago was that?
If you could change one thing about your daily life tomorrow, big or small, what would it be? What’s actually stopping you?
What’s a conversation you’ve been putting off having? What are you afraid will happen if you have it?
What do you do when you have an unexpected free hour? Is that what you actually want to be doing, or just what you default to?
Part Three: Future
These questions are designed to help you uncover your dream life and start taking steps to build it.
What does a day in your life look like two, five, ten years from now? Write it down hour by hour. Be specific about what you’re feeling.
What would you work on if time or money wasn’t a constraint? What does that tell you?
What’s one thing you want to stop doing in five years that you’re still doing now? What’s stopping you from stopping?
What kind of person do you want to be known as by the people who love you? Are you living in that direction?
If your 60-year-old self could send you one sentence right now, what do you think it would be? (Don’t overthink it. The first answer is usually right.)
What’s something you’ve told yourself you’ll do “eventually” for so long that the word has started to lose meaning?
What does your home look like in the life you’re working toward? Describe it specifically – the light, the objects, the feeling of walking in the door.
What kind of work do you want to be doing in ten years? Not just the job title. The texture of the days. The routine. The outcomes.
What’s a fear that’s been making decisions for you without your full consent? Name it plainly.
Who do you want in your life in a decade that isn’t in it now? What kind of friend, community, or relationship is missing?
What’s one thing you’re currently building, even slowly and imperfectly, that your past self would be proud of? Have you acknowledged that?
What would you have to let go of to become the person you actually want to be? A belief, an identity, a relationship, a habit – any of the above.
If you stopped waiting for the circumstances to be perfect, what would you start?
If these prompts are doing something for you, you’d probably like the Well-Designed Life curriculum. It’s the paid-subscriber series built around exactly this kind of excavation work – twelve months of prompts, essays, and exercises organized around six pillars of an intentional life. Less “optimize your morning routine,” more “figure out what you actually want and start building toward it.”
Parenthetical is a newsletter for women who dog-ear pages, overthink their seasonal wardrobe, and want to make their ordinary days more magical. Paid subscribers get access to the full resource library, plus The Well-Designed Life curriculum.
About the Author
I’m Lizzie Campbell – a Chicago-based designer and writer who’s spent the last decade working in almost every corner of the creative industry. I did the whole pastel-pantsuit-girlboss thing and lived to tell the tale (barely). Now I spend my days building brands for a variety of clients and my nights writing about books, personal style, and the art of romanticizing the everyday.
Off the clock: I’m an obsessive reader, 90s sci-fi junkie, canned rosé enthusiast, corgi mom, and someone who believes ordinary days deserve a little beauty.
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Lena Dunham devotees uniiiiiiite! Excited to give some of these a try :)
Whew these prompts are GOLD! Just what I needed. Thank you 💕