Journaling Prompts for Midlife Questioning
Midlife questioning often gets dismissed as a cliché—the sports car, the crisis. But underneath the cultural shorthand is something genuine: the moment when you look up from the years of building and doing and achieving, and ask whether any of it has been pointed in the right direction. It can feel disorienting to question a life you've worked hard to construct. It can feel ungrateful. But it can also be one of the most important examinations you'll ever do, if you're willing to be honest about what you find. Writing is a private enough space to be that honest.
Journaling Prompts
What were you certain about at 25 that you are no longer certain about? What changed—experience, time, loss, something you learned about yourself?
If you could redesign your daily life from scratch, keeping only what genuinely matters, what would stay? What would you release without much grief?
What regret do you carry most quietly—the thing you almost never say out loud? Write about it. What would it mean to stop carrying it forward?
What do you want the second half of your life to feel like? Not look like from the outside—feel like from the inside, on an ordinary Tuesday?
What have you been waiting for permission to do, say, or be? Who has the permission to give it, and what would happen if you stopped waiting for it?