This is my friend Mary.

She has been known to hold me accountable—and occasionally cradle me in the air by one leg.

So when we decided to try another 30-day journaling challenge together, I assumed accountability would not be our problem.

This was our second time doing the challenge—and one of my favorite ways to stay close across state lines.

Instead of relying on the usual “How was your day?” texts, we respond to prompts and send each other small windows into our inner worlds—what we’re remembering, questioning, avoiding, and beginning to understand.

Recently, after reading one of my responses, Mary said something I loved:

“I loved learning something new about you.”

Who knew that after three decades of friendship, we could still surprise each other?

That may be the real gift of writing alongside someone we trust. A thoughtful prompt can move us beyond the stories we have told a hundred times and reveal something that has never quite made it into ordinary conversation.

The plan for our challenge was simple: respond to a prompt, share what we wrote, and encourage each other along the way.

But we agreed on one important rule: no pressure.

Neither of us wanted this to become another obligation or another opportunity to feel as though we were falling behind. If one of us missed a day—or several days—there would be no guilt trip waiting in the text thread. We wanted to be there for each other, not police each other.

It was a kind approach.

It may have also been our greatest logistical flaw.

Because life kept happening.

There were workdays, appointments, responsibilities, distractions, and all the ordinary things that quietly push something meaningful to the bottom of the list. Without structure or regular check-ins, I began to falter.

This is a familiar pattern in my life.

I love a good challenge. I can begin with genuine enthusiasm, but if there isn’t a date on the calendar, a routine, or some kind of skin in the game—financial or otherwise—the practice can slowly drift out of sight.

I’m calling it goal-stale syndrome: when something still matters but gradually gets crowded out by newer, louder things.

It isn’t that the goal stopped mattering. Wanting something and creating a structure that helps us return to it are simply two different things.

Mary and I intentionally removed pressure from our challenge. That made it safe and generous—but it also meant neither of us was going to send the dreaded, “Excuse me, where is Day 17?” text.

If I wanted pressure, I have family for that.

Then something interesting happened this week.

As soon as I knew I wanted to write about our challenge, I felt a little bounce return to my pen. Suddenly, the words came more easily. I probably wrote more this week than I had during much of the previous 30 days.

Apparently, encouragement helps me begin. Structure helps me return.

That is why setting aside intentional time to write can feel so different from telling ourselves we’ll journal “when we get a chance.”

We don’t necessarily need more discipline or pressure. Sometimes we need a protected stretch of time, a thoughtful prompt, and people who understand that showing up matters more than producing something perfect.

This experience reminded me why I created Writing Bravely™.

On September 19, I’m offering a four-hour, in-person Writing Bravely™ experience in Richmond. The date, time, prompts, and supportive container are already waiting for you.

We’ll explore guided expressive writing, reflective storytelling, Inner Active Cards, quiet reflection, meaningful conversation, and an optional nature walk.

You don’t need to call yourself a writer. You will never be required to share what you write. You only need to arrive with a little curiosity about what you might discover.

And, unlike Mary, I promise not to cradle you in the air by one leg.

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📝 Your Writing Bravely™ Prompt

What is something true about you that even someone who has loved you for years might still be surprised to learn?

Set a timer for ten minutes and follow the first answer that appears. If it feels right, share what you wrote with someone you trust.

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Want more writing prompts? Download a free sample of the Writing Through Grief and Loss Journal to get IFS journal prompts.

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With courage and acrobatic moves,
Adina

P.S. If something meaningful keeps getting crowded out by life, Writing Bravely™ offers four protected hours to return to yourself—with thoughtful prompts, supportive structure, and no pressure to perform or share.

​Explore the Writing Bravely™ Experience​

September 19 · Noon–4 p.m. · Richmond

Early-bird registration is $129 through August 17. Space is intentionally limited.

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