For the past few months, I’ve been creating and sharing monthly journaling prompts as a way to create some structure around reflection. I’ve always kept my own answers pretty private because journaling has been this quiet, personal practice for me… something I do for myself and no one else. But recently I started thinking that maybe sharing how I actually use these prompts could be helpful. Not in a “here’s the right way to do this” sense, but more as a demonstration of what’s possible when you sit down with a question and let yourself follow it wherever it goes.
If you’ve been reading my work for a while, you might be familiar with THE DAILY 5, my practice of writing for five minutes each day without stopping or editing. It’s stream of consciousness, unfiltered, and it’s become one of the most valuable tools I have for processing thoughts and emotions in real time. That same approach carries over into how I work with prompts like these. I sit with the question, I start writing, and I see what comes out. No overthinking, no trying to make it sound good. Just following the thread until something clicks (although, there are days when nothing does, to be honest).
The prompts I share each month are designed for private reflection first. They’re meant to help you check in with yourself, clarify what matters, and notice patterns you might otherwise miss. But I also know that some of you are writers yourselves, whether you’re building your own Substack or just looking for ways to share more of your own story—and these prompts can absolutely serve that purpose too. They’re great fodder for personal essays, or for exploring your own experiences in a way that might resonate with your readers. But whether you use them privately or publicly, the goal is the same: get honest with yourself and see what’s actually there, what’s happening under the surface.
November’s theme is grounded gratitude, and I put together 30 prompts to explore that throughout the month. One of the prompts from Week 3 really stuck with me: What’s something that happened this year that felt like a setback but turned out to be redirection? I wanted to work through it myself, so I jumped ahead and figured I’d share my answer. Think of this as a demonstration of what engaging with these prompts can look like when you give yourself permission to be honest.
Here are the September & October prompts ICYMI or would like to revisit.
Turning setbacks into redirects —
Thoughts from my reflection to the prompt: “What’s something that happened this year that felt like a setback but turned out to be redirection?”
Earlier this year, a friend suggested I apply for a writing position at a media company I really admire. It wasn’t a formal job posting or anything like that, just an informal recommendation. A “hey, you should reach out” kind of thing. The owner was looking for another cultural and politics writer, and my friend thought I’d be a good fit for the role.
So I sent an email with a few clips and a quick explanation of why I thought I could contribute to what they were building. Within 72 hours, I had my answer: thanks, but no thanks. (Ouch.)
