TL;DR: Subscribe to receive a journaling prompt delivered to your inbox every Sunday, and a discussion on that prompt on Friday. It’s worth it. Especially if you’re a dude.
I sucked at journaling
I wrote like I was afraid I would get Alzheimer’s.
Every time I tried to pick up journaling in the past I’d fall into the same pattern. My pencil (yes, I write in pencil whenever I can) would scratch across the page as I committed to paper the minutia of my day, detailing how I knew the players involved in every story, what they (and I) were wearing, how we are arrived at wherever we were, and other superfluous backstory that left my wrist tired by the time I was to go from playwriting to processing.
So look back at my old journals and you’ll learn exactly how I know my friend Joe: where we met, when, what we’ve done together since. But if you’re looking for me to talk about my feelings, well, there’s not much to be found.
Because of that I could never sustain a journaling practice. What was supposed to be a place for personal connection and self-reflection became a Farmer’s Almanac-like retelling of my life, one nobody asked for or needed.
Enter: 2022.
Finally, something clicked. I went from abandoning journals by the fourth or fifth entry to filling the pages of notebooks. Just look at my output from the past year alone.

So what’s the secret? What unlocked my potential as a journal-keeper, and could it do the same for you?
I have no fucking clue.
If I go back and look at the first entry in my journal from last year, there’s nothing on the page that would lead me to believe this was the start of a new writing habit. No grand statement of intent, no change in style, no new format. It’s just little old me, doing some silly little writing for my silly little mental health.
But 365+ days later I’m more committed to the practice than I’ve ever been. These pages have proof that how I process and identify my feelings has evolved because of this habit, and writing has become as important a part of my day as drinking water. And just like drinking water, when I skip journaling I get a terrible hangover can feel a difference in my headspace and emotional health.
Getting to the Point
So this is my way of telling you that journaling changed my life, and that it has the power to do the same for you.
Yes, I KNOW it sounds hokey. I KNOW you’ve seen countless InstaTherapists and Influencers take their aesthetically-driven shots of their #DailyPages and groaned under your breath. I know you think journaling isn’t for YOU. But I am here, telling you, you’re wrong.
(Sorry, did you think I wouldn’t call you out? Absolutely not. Don’t like it? Read another newsletter, see if I care.)
If you’re afraid to journal or think it’s not for you, then humor me and drop your mental block for just a week or two and give it a shot. Journaling isn’t like weightlifting. There’s no proper form, there’s no best practice. Journaling is YOUR practice and it can look like whatever you want. What works for me (writing in pencil, putting on jazz, writing before bed) may not work for you. In fact, I hope it doesn’t. That’s my thing, get your own!
But what I want to try to offer you is a starting point. In that spirit, you can expect to find a weekly prompt delivered to your inbox every Sunday. My suggestion is that you use this prompt to guide your journaling for the week, alongside processing whatever conflict and/or situation come up in your daily life. These won’t be questions to hit with a Ronco-style approach. These will be ones for you to ponder, sit with, answer, second-guess, and then answer again. Questions that will hopefully provide answers you’ll keep coming back to.
And then on Friday, I’ll share my answer with you, and hopefully some of yours (if you want to anonymously share a snippet of your answer, feel free to email me at Jonathan@JonathanJacobs.com or DM me on Twitter). Plus, maybe I’ll throw in a little bonus treat to thank you for participating.
For the Dudes
And just to be clear, these prompts will be for everyone (at least, I think they will be). But if you identify as a male, then I want to really lean on you to subscribe. My mission is to have more honest conversations with men about mental health, and I hope this can be a space for just that.
Disclaimer
In case anyone assumed otherwise, let me be as transparent as possible: I am not a trained mental health professional. I am not a member of the clergy. I am not a spiritual guru. I am not a doctor. I’m just a guy who is on his 63rd re-watch of The West Wing who likes to journal and wants to talk with others about it.