The Lives We Didn't Live

Each Saturday, I share a thought-provoking journal-writing prompt here on the blog. These weekly prompts offer a specific topic or question to encourage you to explore your thoughts, emotions, and experiences. You can answer them exactly as they're written, or let them serve as a starting point for a larger, more formal piece of writing. So long as you write something in response, anything goes. But by giving yourself a specific focus, you can delve deeper into your writing and uncover new insights along the way. Feel free to personalize the prompt and make it entirely your own.


This week, I want to write about the roads we didn't take.

Somewhere, in some parallel hour, there is a version of you who said yes when you said no. A version who stayed in that town, married that person, mailed that application, boarded that bus. We don't talk about these other selves much—it feels indulgent, or dangerous, like picking at a seam. But I believe our unlived lives walk beside us whether we acknowledge them or not. They show up in the sting of a certain song, in the career we still daydream about at midnight, in the strange grief that arrives with birthdays. This week, instead of turning away from those ghost-selves, let's invite them to sit down and talk.

Use these questions as starting points for your journal entry:

  1. Name a crossroads. Think of one real moment when your life could have gone another way—a decision, an invitation, a door that opened or closed. It doesn't have to be dramatic. Sometimes the whole current of a life turns on a phone call, a snowstorm, a class you almost took. Describe that moment as vividly as you can remember it.
  2. Follow the other road. Now write a day in the life of the self who chose differently. Where does she wake up? What does her Tuesday look like? Give her real details—her breakfast, her window, her worries. Resist the urge to make her life either perfect or ruined. Let her be as human as you are.
  3. Ask what she knows. If you could sit across the table from this other self, coffee steaming between you, what would you ask her? And what do you suspect she'd want to ask you? Write the conversation. Let her surprise you.
  4. Find the gift in the road you took. It's easy for this kind of writing to curdle into regret, so don't let it. What exists in your actual life—a person, a strength, a hard-won wisdom, a small daily joy—that could only exist because you chose the way you did? Write about what the road you took gave you that no other road could have.
  5. Look ahead. Not every unlived life is behind us. Is there a road still open—a dream you've quietly shelved but never quite thrown away? What's one small, real thing you could do this month to crack that door back open? Or, if the season for it has truly passed, write it a loving goodbye and let it rest.

Take one of these prompts, or weave them all together. Or simply write a letter that begins, "Dear self I never became..." and see where it carries you. You might let the art images guide you, too. So long as you're wandering your unlived lives in words, anything goes.

My challenges and prompts are not interactive. You don't have to come back to link up. No comments are required—just your creativity. 🌻