Stepping Stones

A Mini-Program

Only available Summer 2025. Space is limited.

When students first come to me, they typically have a problem with writing. Often, they:

➡️ Haven’t ever gotten feedback that highlights their real strengths as writers (because we all have them, even if we don’t know it).

➡️ Lack confidence to voice their ideas…or even more “cringe” (as the kids say), to write them down for all to see.

➡️ Feel intimidated by an assignment, from college essays to NYC admissions essays to a homework prompt—and get stuck before they even begin.

These students need support and guidance to unlock their voice, ideas, and creativity—and to learn a strategy to move forward. Sometimes, however, Write Well Brooklyn’ full coaching programs present a commitment students or parents just aren’t ready to make.

I created STEPPING STONES (and the STEPPING STONES BUNDLE) because I wanted to offer students confidence, strategies, and support along their writing journey…

…but in a low commitment offer that let them explore writing coaching with ease.

In three powerhouse sessions (that fit easily in a busy summer schedule), students will:

✏️ Connect with me, Ashleigh—a positive, supportive mentor, writing coach, and New York Times-reviewed author with 20 years in education.

✏️ Learn the Messy Model strategy and apply it to a writing project of choice—whether an admissions essay, a Scholastic essay contest submission, a New York Times essay contest submission, or an assignment I provide.

✏️ Practice my mini-prompt strategy to access voice, ideas, and creativity.

✏️ Walk away with a messy first draft—and a personalized plan of where to go from there.

✏️ Receive one free round of feedback on the assignment in the two weeks following the program’s end. Feedback provided via a ~5 minute video made just for the student.

And guess what else?

Parents will receive $100 off any WWB program purchased within 48 hours after their student’s completion of Stepping Stones. (Review additional programs here.)

Purchase Options:

STEPPING STONES: $1,495. Includes 3 sessions of 1-1 coaching with Ashleigh.

STEPPING STONES BUNDLE: $1,800. Includes 3 sessions of 1-1 coaching with Ashleigh PLUS an in-depth Six Trait Assessment with a parent update (total saved: $190).

Let's goooooo! I'm ready to book Stepping Stones!

I want to save & book a Stepping Stones Bundle!

How do you know if Stepping Stones is for your kid or teen?

✏️ A big English essay is due, and a high school junior feels anxious that any step forward will be the wrong one.

✏️ In preparation for their bar mitzvah, a sixth grader needs to connect a portion of the Torah to their personal life—but doesn't know where to begin.

✏️ A freshman is eager to be accepted to a prestigious study abroad program, but has no experience writing personal essays.

These are all real-life challenges my coaching students have navigated—but in each session with me, they:

✅ Reflected on what they needed to move forward.

✅ Received encouragement and actionable next steps.

✅ Employed tools and strategies rooted in the Messy Model.

✅ Accessed their voice, ideas, and creativity—creating momentum and concrete progress.

✅ Left my sessions feeling uplifted and more confident.

Stepping Stones and my Stepping Stones Bundle will help students overcome the common hurdles when faced with an unfamiliar or daunting writing task—but with a lower commitment than a full-on program!

Content for Stepping Stones may be an assignment the student brings with them or an assignment generated by me. Once you book, we’ll reach out to explore the best approach.