Question 1

What kinds of students do you work best with?

Accepted Answer

Over the years, I’ve found that the students I seem of most help for have one or more of the following characteristics:

They don’t think they have any stories worth telling.
They don’t feel confident in their writing skills or essay ideas. 
They have learning differences like dyslexia or ADHD, and may have seen learning or behavioral specialists in elementary or middle school. 
They work better with structure—clear homework assignments and expectations on what “done” means, actionable feedback, and me setting the weekly agenda. 
They consider themselves to be underachieving or indistinguishable from their peers.

I’m a good match-up for students who identify with these traits because I’m a creative person and I see potential in ideas that students might dismiss. I’m also upbeat, optimistic, and I enjoy cheering my students on and affirming who they are.

Question 2

How are you different from other essay coaches?

Accepted Answer

Based on what my graduates have told me about their friends’ experiences with other counselors, I’m more approachable and easier to get real with. I work collaboratively rather than in an authoritative, top-down manner. I try to have conversations that are a two-way street: I might modify a homework assignment to suit a student’s schedule or working style better, editing decisions are open for debate, and if I don’t initially get why they want to write about a certain experience, I’ll make the effort to dig in further so I can understand why that thing matters to them and help translate that for an audience.

Because I work 1:1 with so few students and see them at least once a week for up to 9 months, I usually get to know them very well and I do feel an emotional investment in my students’ success. More personally, it’s a matter of pride to turn out quality writing and improve my processes each and every cycle.

Question 3

What happens during private sessions?

Accepted Answer

As you might suspect from a college essay coach, we do a mixture of brainstorming, outlining, writing, and revision. I think what sets my approach apart is the depth with which we work through each of these steps—I typically push students to devote more time to each phase than they might invest themselves.

During the initial brainstorming phase, I spend Zoom sessions grilling my students so I can get as many pieces of essay material on the table as possible. I want to know what they’ve been up to for the last 3-5 years, what they’ve struggled with, loved, and learned. Students often lack the perspective to fully appreciate their strengths and overlook so many rich and interesting details about their lives.

Brainstorming can run for 2-4 weeks depending on how willing and able a student is to write a lot and reflect a lot. Once we have a decently-sized pile of raw essay material, we start outlining and strategizing around what to highlight about the student, and in which essays. Just as an example, the University of California, has a prompt about a challenge you might’ve faced. You could, however, choose to talk about that challenge in the optional additional comments section and share something else about yourself in one of the required essays.

Once we hit the writing phase, sessions can look very different from student to student. Some bring in rough drafts that they’ve written on their own time, but many others struggle to write, period, so we might spend our sessions focusing on just getting something down on the page:
Rather than have students churn out a full-on essay, I give them a series of short writing prompts they can work through in 5-10 minutes, and we eventually piece those responses together into an essay.
If a student gets stuck, I’ll offer up different options for word choice or phrasing.
If they’re struggling to explain something complex, I might call a time-out and give them a mini-assignment to write 3 iterations of the same sentence. 
Writing is cognitively challenging, and I help students make progress by breaking the process down into more manageable action items.

During revisions, we work with the essay like we’re molding clay. We’ll chop certain anecdotes, rework the flow, emphasize and de-emphasize certain events and reflections, nudge the wording so it leans more in one direction or another. I check in with students and confirm whether the essay aligns with what they truly wish to express, then proceed based on their response.

Once when we finally land on something we’re happy with, we’re usually way over the final word count limit. One of the most valuable skills I have to offer my students is my ability to trim and condense without oversimplifying. As one of my former students put it, “I didn't realize how complex I was and how many things were important to me that I couldn't fit into the word count—you really helped me balance that out and mention every single part.”

Question 4

How do you measure success if admissions are unpredictable?

Accepted Answer

Many of my students have beaten the odds and gained entry to schools where their stats on paper don’t quite measure up. Outside of admissions, I consider our time together successful when a student walks away with improved writing (and thinking) skills that they can apply in AP classes, future application cycles, and life in general. I also consider myself successful when they tell me they found moments of enjoyment while writing their essays. Finally, I consider myself successful if a student says they’ve learned new things about themselves that they wouldn’t otherwise have had they not gone through the college essay process.

Question 5

What makes a “good” college essay, really?

Accepted Answer

Lucid thinking, a sincere effort at reflection, and hyperspecificity to the point where no one else could’ve written the same essay.

By lucid thinking, I mean that readers are given sufficient context to follow the story being told, and any reflections/assertions/conclusions from the student feel earned because supporting evidence has been presented in a logical sequence.

A “sincere” effort at reflection means doing the uncomfortable, sometimes scary thing of confronting yourself and your choices. The student essays that resonate even years later are those where a student has grappled with complex and oft-conflicting feelings about a certain experience. Those essays find a way to balance melancholy, regret, and pain with humor, acceptance, and growth.

Hyperspecificity is important because the ultimate goal of a college essay is to help you differentiate yourself from other applicants. Your personality should pop off the page and the reader should feel your humanness through the page. I help my students achieve this by drawing unexpected connections between their various pursuits, highlighting unusual details, and editing to keep in any idiosyncratic turns-of-phrase.

Question 6

When should we start the essay process? Is it too late to start in [month]?

Accepted Answer

For students who aren’t confident writers: if you want to reduce stress, spread out the workload, and/or anticipate having a busy summer, I would recommend starting to brainstorm and research colleges in March of junior year—we don’t need weekly meetings, but one session every two weeks would be helpful to ease into the season. It simply takes time to sort through years of memories, and it’s not uncommon for students to suddenly recall some buried detail months into the writing process. If you’re a rising senior, reach out to me before July and we should still be able to do the Common App, UCs, and a few private school supplemental essays together.

If you are a confident writer but want some one-off help, reach out anytime before September of senior year and I’ll let you know if I have room on my calendar.

Question 7

Do you work with transfer students / gap year students / international students?

Accepted Answer

I work with both transfer students and gap year students. For international students, it would depend on where they’re based.

I’ve helped students transfer from both community college and from 4-year universities, and I myself took a gap year in Germany through the State Department-funded Congress Bundestag Youth Exchange program. I did this right after high school and it was a period of massive growth—I’d be happy to assist on the essays involved in applying to study abroad programs.

As for international students, I’m based on the West Coast of the United States (GMT-8) which may limit our range of call times depending on where you’re at. But if you’re interested in working together, reach out! jessica[at]craftyourcollegeessay[dot]com

Question 8

How much does coaching cost? Do you offer packages or payment plans?

Accepted Answer

For the 2026-27 cycle, my 1:1 coaching packages start at $6,000. I do offer payment plans with an additional processing fee.

Question 9

Do you do refunds? What if I hate my essay(s) halfway through?

Accepted Answer

I do not offer refunds, but personality fit between me and the student is important, so I offer free introductory calls, which you can book by clicking this link. You can ask questions on the call, and we can talk through previous student work as well.

As for hating your essay halfway through—every essay has a growing pains phase and I consider it a normal part of the creative process. It’s common for beginner writers (and painters, dancers, singers, etc.) to have tastes that are more refined than their skills. It’s also super common for students to draft something in early summer, work steadily into the fall, find that they have new insights into whatever it is they wrote about earlier, and want to revise.

The way I handle whether to do light modifications or a gut renovation or total rewrite of an essay is to get really specific: what isn’t working for you? Why? What is working for you? Do you want to talk about something else entirely? Are we overemphasizing and underemphasizing certain facets of your being? Is the current draft not really getting at the heart of what you felt and took away from the experience?

Because we’re limited by word count, trade-offs are inevitable, but I believe in being intentional about those decisions.

Jessica Cao

Frequently
Asked
Questions

What kinds of students do you work best with?

How are you different from other essay coaches?

What happens during private sessions?

How do you measure success if admissions are unpredictable?

What makes a “good” college essay, really?

When should we start the essay process? Is it too late to start in [month]?

Do you work with transfer students / gap year students / international students?

How much does coaching cost? Do you offer packages or payment plans?

Do you do refunds? What if I hate my essay(s) halfway through?

My students reflect on their journey

Ethan, USC Marshall '30

Jessica Cao

Frequently Asked Questions

What kinds of students do you work best with?

How are you different from other essay coaches?

What happens during private sessions?

How do you measure success if admissions are unpredictable?

What makes a “good” college essay, really?

When should we start the essay process? Is it too late to start in [month]?

Do you work with transfer students / gap year students / international students?

How much does coaching cost? Do you offer packages or payment plans?

Do you do refunds? What if I hate my essay(s) halfway through?

My students reflect on their journey

Ethan, USC Marshall '30

Frequently
Asked
Questions