E42: Supporting Your Child Through the College Essay Process with Carter Osborne

Shelley:
Hello and welcome back to Raising Thinkers. It's Shelley and I'm so glad that you're here with us today. Today we have a very special episode. We have our second guest podcaster here and I'm excited to introduce Carter Osborne. His focus has been with working with students in the college admissions process and he's going to be able to tell you a little bit more about that. I know often we've been more focused on our younger students, our younger learners, both in elementary, and even toddlers sometimes, and then going into things that could be helpful for you as parents of middle schoolers. But we haven't focused as much on the high school sector. And so I'm really excited to have this conversation with Carter today and how he's going to enlighten us on how to help raise thinkers. But as we're thinking towards the college direction and higher education. So welcome, Carter. Really glad that you're here.

Carter:
Well, thank you, Shelley, and thanks for having me on. You know, I am a total nerd about the college application process, but most people don't want to hear me talk about it. So I appreciate you having me on to share a little bit more. Yeah, you know, I got my start in the college application business after my undergraduate experience. I had just finished a lot of creative writing courses at Stanford where I did my undergrad, came up to the University of Washington where I'm now at home in Seattle and needed a way, frankly to make a little extra cash on the side, help out with tuition. So I went to a college admissions consultant in the Seattle area who I actually went to back in the day when I was a high schooler to seek some help. So it sort of a full circle experience. She was very kind and kind of gave me my first batch of clientele, let me apprentice under her and helped me kind of find my foothold in the industry. Those clients told their friends who told their friends and eventually I became a full-time consultant. It's been quite the sort of roller coaster ride, but today, you know, working on college applications and particularly the college essay process is a real passion. I love it and I love helping students succeed through that process.

Shelley:
That's amazing. So what would you say inspires you to help develop students, especially our older students, as thinkers?

Carter:
Well, so most of what I'm gonna talk about is routed through the writing process and particularly the creative writing process. I mentioned that I got my start in this whole field when I myself was going through a fairly rigorous creative writing set of courses during undergrad. And that was a real awakening for me, a way for me to kind of realize that writing is not just a way to complete an assignment or something that my teacher is asking me to do. It really is a deeply important self-reflective exercise that I think almost everyone can benefit from. I got a lot of joy and introspection from the writing process when I was going through it myself. And I still do today with my writing outside of my work. So for me, being able to channel that into an educational format to help other students embrace creative writing, introspective personal writing as a way to learn more about themselves, as a way to grow. And then by the way, to help them navigate the very opaque and complicated college application process. That was kind of just two wins in one for me. And so that very quickly, it was sort of an educational drive that very quickly and naturally became a job for me. So it's a niche sector, but it's one that I love being in.

Shelley:
That's really helpful because as a thinker, as a learner, as a human, we have to reflect. We have to go through that introspection for us to then continue to grow. Right. So something that sometimes I talk about is just reflection or something that I talk about with my own students is reflecting, reflecting upon whether it's your choices and maybe you need to make a better choice, but also reflection through writing. And I think a lot of students shy away from that. I know that's something that I've recommended to students before, like keeping a journal about what you're reading, know, just writing down notes here and there. I think there's a certain element of that that's becoming a dying art form in society today. I don't know if you see that as well and if it's become harder for you over time to work with students or not.

Carter:
This is such an interesting question. I fear that you might be right, that writing is kind of falling by the wayside. I really don't want to have this opinion, but pessimistically, think I do. know, anecdotally, so I've been working on college essays with students for, this will be my eighth year. And when I first started, I have to say the quality of the writing that I got from my students was notably higher than it is today.

So it seems that, it seems at least in my sort of narrow world, it seems that the quality of writing has gone down somewhat significantly. And no surprise, COVID was the real barrier that separates those two worlds. And today I find that I have to spend some extra time with my students, just helping them understand, here's how you write a complex essay. Like here's how you write something that is not just the five paragraph structure you've been taught in school, right? So there's some baseline education happening in my meetings with students today that didn't used to happen.

I don't know what the firm cause is there. I can't give you like a full explanation, but that is certainly what's happening. And so I think your assessment is correct. The thing is, I think that we're in agreement that that's a challenge not only just from a productivity standpoint, but from an emotional and a reflective standpoint for students as well. Writing is an incredible exercise to translate the sort of fuzzy thoughts that we have every day into something clear and coherent and often we discover things about ourselves while we're writing. It's not just a form of expression, it's a form of discovery as well. This is why I love encouraging my students to do free creative writing at home, not for an assignment or a test or something as big as the college application process, but just to have fun, just to learn about themselves. When we lose that, we lose some way to learn about ourselves that I don't know is replicable in any other medium.

Shelley:
I wonder about the just social media usage as well. And just the the pulls on children's time that I know I didn't have in the same way as I was growing up. And so, well, you could write, you could produce artwork, you could find ways to occupy yourself... I recorded myself on a tape recorder, sometimes just talking or reading poems out loud. I think we don't have as much, I guess, boredom that is allowed for children to then be able to find those creative outlets in different ways. And there's lots of amazing things that kids are producing through social media and technology as well. I wonder if that's a part of it, but I'm not sure.

Carter:
I wish I knew, you I think we could probably go a full hour back and forth trying to find the cause of this whole thing. But I agree with you, there is a shift towards short form these days in terms of consumption and production of content and you know, done in a deep and reflective way, writing is challenging and it takes a while and often you kind of just have to sit at your desk with a notepad or a computer and just wait for a while for an idea to strike and then you can start exploring it. So it's an exercise in patience is writing and I think that that's one of those skills that goes away when we have the constant sort of addictive tug of social media in the background.

Shelley
Yeah, for sure. So let's talk about AI as well, because I know as an educator, I'm using AI are the school that I'm working at. We're also trying to figure out how that's transforming the face of education and how this is a part of our students future, regardless, like it's not going away. But I think that's been really huge. I think there's valid reason for hesitations. when you think about AI and the challenges but the opportunities as well, how would you suggest for a parent or for a student, a high schooler or even a collegiate student to navigate those challenges and changes that are coming?

Carter:
I wish I had an easy answer for you here, Shelley. This is a complicated one. And I feel like by the time someone listens to this, it may have changed because AI is sort of evolving so quickly. I am gonna resist my instinct to be a total curmudgeon with new technology and try to, and the thing is, I think you're right. AI is developing and right now it's virtually unregulated, which means it's everywhere and it's advancing very quickly. We all get the latest update of it.

So think you're right, it's permeating culture and society, particularly among young people, and it's around so we should figure out how to use it properly. I'll start with my kind of curmudgeonly critique of it, and then I will evolve hopefully into something more constructive. the challenge with AI, and I've increasingly seen my students using this in their college application essays, which is a whole different sort of kettle of fish. I think generally speaking, the overarching challenge with using tools like ChatGPT or Gemini or Claude or whatever it is, to write a long form essay is that it functionally outsources part of our critical thinking to a machine that can do it for us. I mean, the common comparison is like a calculator, right? A calculator does things so we don't have to do them by longhand, but there's a reason that all of our teachers in third grade taught us to do long division by hand first so we could understand the mechanics of mathematics before we have a machine do it automatically.

The thing that's deeper and more challenging with generative AI tools is that it's not just adding or subtracting or dividing numbers, it's critically thinking on our behalf. And if we don't flex that muscle, we will start to see it atrophy over time. Or in the case of young people, they haven't even fully built that muscle yet. That's what they are in class to do. That's what they're working on college applications to do. And if we outsource it to AI, I feel that we lose an opportunity to build it up in some more robust way. So there's my kind of like philosophical critique. But I do think to your point, it is both prevalent and can be used as a constructive tool if used properly.

So what I tell my students, at least my college essay students is this, if you're gonna use AI in the process, use it for brainstorming, because I do find that bouncing ideas back and forth off of a tool like ChatGPT can actually be quite constructive to the process, can help you kind of see ideas where you wouldn't have seen them before. So use it for brainstorming, and if you need to, use it to help with your outline.

So take maybe like a rough set of ideas that you've already outlined and use AI to kind of build them out into something more full and then you can write your first draft based on those more robust notes. So long as it's following the ideas you have already laid out, like you have done the critical thinking yourself, I find that to be a perfectly valid use. So that's what I encourage my students to do. Realistically, some of them cut corners and they don't use it that way, they use it to write their drafts. Here's the thing, here's my message to any parents out there who have a student who's applying to college or soon to have a student applying to college. Right now, as of April 2025, AI tools cannot write a good college essay. The products that they produce are simply bad. They're low quality, they're very obviously written by AI, and admissions officers can pick up on them easily and they punish students accordingly. please do not use, know, students out there who might be listening, do not use AI tools for any of your college essays.

So, you what I encourage my students to do is like, look, you have this unique opportunity through the college essay process to write very personal, self-reflective, introspective essays that you aren't assigned in school, you're not asked about by your parents. You know, this is sort of a, this is a unique opportunity to dig into some part of your life you may not have dug into otherwise.

Don't outsource that to chat GPT. Like this is cool. You you get to tell your story for the first time in a, you know, in a new way. Let's, let's have fun with it. Let's do something unique and interesting here. Usually when I frame it that way as like a form of personal expression, students will leave the tools behind or they'll use them in the way that we talk about using them, which is for brainstorming and outlining the kind of initial part of the writing process. And then we can move forward with more authentic drafts together.

Shelley:
Those are some great suggestions. And I appreciate that thinking about the thinking process because it can rob students of that. And I think that's one of the main things that I see as well. I'm an instructional math coach right now at my school. And so I see it more on the mathematical side. And I'm still finding that whatever tool I'm using, if I'm trying to use it as an AI tutor for students, it still allows it right now making errors. And then the students or I have to step in and kind of argue with the AI and say, hey, you're wrong. We're right. This is why. And then it will apologize for its hallucination. And it's fun and it's funny. But at the same time, I don't want my students to come away with a misconception or thinking that they're wrong when they might already be struggling in math or whatever it might be.

I think as well, just thinking of how we can use it and plug in a whole bunch of data and have it do data analysis and observations and whatnot. But if we haven't taught our learners how to go about the process of doing analysis for themselves, then they're just going to take whatever gives them and say, OK, this is great. Now I have this tool that does it quickly for me. But then they go into some board meeting later when they're at their job and they're presenting this and somebody in there is going to say, this doesn't make sense and they would have never double checked it. Now, we might get to the point that it does all make sense and that's great, but if we haven't learned how to do that analysis for ourselves or that thinking process and the creation and the reflection, then we're robbing them and they're robbing themselves of that opportunity to become better human beings by going through the process.

Carter:
Yeah, that's that's exactly right. You know, actually just this morning I was reading a Wharton study Wharton school study from last year on high school students It sounds like you might be familiar with this but your instruction in math reminded me of it It was of a group of math students who used AI virtual tutors to prepare for their final exams versus a group that did not use it and lo and behold the group that used it got lower scores on their final exams because they had been using as sort of like a bootstrap rather than learning the entire sort of depth of the content they needed themselves. I completely see what you're talking about.

Shelley:
Yeah, so it's that balance of using it as a tool versus a crutch. And when does a tool become a crutch for you that you become dependent on? And I think if we could get students away from that and being able to step back and say, is this an appropriate time to use it or not, that's going to be a key piece in their future.

Carter:
Yeah, yeah. You know, this is one reason why I really enjoy the college essay and college application process though. When I work with students, the prompts we answer are things like, you know, name a time when you were deeply involved in your community or talk about part of your identity that's particularly significant for you. Or, you know, talk about a leadership experience where you helped other members of your community achieve some vision that they had.

These are questions that you cannot outsource to chat GPT. I mean, it doesn't know the answer. You have to do some really deep reflection of your own life to be able to come up with the right topic for those. I kind of, that's why I like the college essay process. It has this unique reflective aspect to it that I don't really find anywhere else. And that forces students to kind of look inwards and really get used to that kind of critical thinking.

Shelley:
Absolutely. And that just makes me think about how AI is learning from everything that's input into it. So if we go and we take that information about yourself and you're giving it to AI, then they can it it not a day. I don't know. Can then take it and then use some of that to later try to answer that sort of question for somebody else. And like you're losing or letting go of some of your identity into the ether.

Carter:
Yeah, what a sad day when somebody types into chat GPT, what is a significant part of my identity? You know, I hope that that doesn't happen out there. I'm sure it does, but I hope it doesn't.

Shelley:
So true. I also think about different articles that I've read about just assessment for students and how with AI, we need to be thinking as teachers or as instructors about the types of questions that we're asking of our students. And if AI could just answer them, then what's the point at this point? We need to be asking better questions. We need to be developing better assessments than what you said about the college essay process and the types of questions that they're asking, I think of that as well in terms of they're giving a question that can't just be replicated and duplicated. It's not like a high school English essay where they're analyzing Shakespeare versus Lord of the Flies. AI can figure that one out, but it cannot figure out your own personal life and your experiences.

Carter:
Right, yeah, personal writing versus analytical writing, which is more what they do in school. Yeah, personal writing is a whole different exercise. Although that's often why my students are so, I suppose, frightened by the process and why I get a lot of calls from nervous parents saying, we need your help. know, often the college application process is the first time any of my students have done personal writing. They literally have never done it in any other part of their life. And of course, it's at a time when the stakes have never been higher. They're trying to get into college.

And it's at a time when students are generally not happy to have their parents intervening with suggestions about what part of their identity actually is significant to them. Do you know what I mean? So, you know, this is the kind of like cocktail of variables that lead people to call me, but it's challenging for students to step into the college application process and go, they're asking me to do this thing that I've never done before. And I'm trying to do my absolute best to get into college. It's a tall task to overcome. And so that's part of what we work on as well.

Shelley:
That's great. So related to that, what would be some of your top tips for parents for helping their kids now, even if they have young kids or, you know, think of elementary and middle school, high school, like in those different levels? What would be some of your tips for them to help prepare them for that process already and to be successful?

Carter:
Well, for parents of young kids, it's interesting. I mainly talk with parents of high schoolers for obvious reasons, people who are preparing for the application process. Although these days it feels like parents of elementary schoolers are preparing for the college application process. maybe we're all in the same boat. But for parents of young students, elementary school or younger, I really do believe in the power of a family sit down journal write time and this, doesn't have to be a reflection on your life or something deep or significant that way. It can be what happened today. It can be tell a story, make up a story based on your favorite cartoon characters or something. It can just be a little like, you know, 10 minute written assignment. I think very important for parents to do it with their kids and to share their work afterwards if they're gonna ask their kid to share their work. Right, it's basically like a little family time to sit down and get used to the idea of reflecting on your life through writing.

And again, writing, I think the medium of writing here is important rather than just sharing orally about your life. think writing is important because it forces you to take the thoughts in your head and write them in a very clear and coherent and linear way. Like that's the unique part of writing versus speech. I mean, you can tell in this answer, I'm kind of going around in circles and going off on tangents. That's what we do when we talk. When we write, it's a little bit more clear and cohesive. So that's why I think that's a powerful exercise. So basically, let's start building those strong reflective personal writing skills early. I think that that holds broader sort of cognitive development benefits in addition to preparing students for the college application process along down the road.

For parents of teenagers or students who are already approaching the college process there's, let's be honest, a limited role that parents can play here, right? It's kind of like, I saw one college counselor wrote recently that, you know, when it comes to college applications as a parent, anything you say to your kid can and will be used against you in the court of teenage opinion. Do you know what I mean? Like, it's just very challenging. Students are trying to write about a really vulnerable part of their life, which is already a tough place for a parent to intervene. And then it's also really high stakes and nerve wracking, because it's around college. It's sort of a perfect storm of things for parent input to be rejected.

So I find with parents, the best thing that they can do to encourage their students to embrace the kind of writing or reflective thinking skills that they need for the college application process is just to encourage them to storytell as much as possible, right? And I know this is hard and everyone's unique relationship with their kid will be different, but it's a matter of saying like, instead of just, how was your day today? It's like, hey, you told me about this thing that happened. Can you tell me a little bit more about why that was important to you? Or like, you know, it seems like you really value your friendships this year more than you did last year. What's, you know, what's causing that change? Yeah, have curiosity. I've just seen that in you. It's this kind of curious questions and maybe they get brushed off and maybe they don't, but the kind of curious questions that lead students to reflect more critically about their lives rather than just give updates about what's been going on. That kind of stuff I think can prepare students for the mindset that they need to prepare for college essays.

Shelley:
Yeah, that's great. We've had some episodes related to questions that parents can ask and it's not the typical question of, you know, how was your day today, to which they can say, fine, good, bad, whatever. And then it's over and done. It's, know, what was a great question that you asked today? And what did you learn from that? Or how were you a good friend today? Like those reflective questions, because even if they are brushed off, they still cause that child to be thinking.
And they may never tell the parent, they may never answer it, but they're thinking about it. So you've prompted that thinking through those questions.

Carter:
Exactly. You know, I remember when I was in high school and I was a sort of disgruntled teenager, kind of sick of my parents, my dad and I had a time every morning, I have breakfast. I had like a 30 minute window during breakfast when I sat down at the table and my dad was there and we would just chat for, you know, however long it was until I had to go off to school, 20, 30 minutes, whatever it was.
In hindsight, I recognize the pattern of our conversations. I didn't at the time, because I was sleep deprived and 17 and I didn't really get it.

But in hindsight, I look back and I go, what he was doing in these conversations was really engaging with the topics that I found interesting. So he would say, you're in debate class this year, what's one of the topics you've been talking about? And I would tell him and he'd say, well, I think, you know, my perspective on that is this, I don't know what you're arguing in class, but here's what I think about it. And then I would kind of go back and forth with him a little bit, you know, or he'd ask me about, I was a runner in high school and he'd ask me about the strategy that I was using in the race that's coming up the next week, right? It was just a time when nothing else was going on, where we could just talk in a little bit more depth than we otherwise would. You know, by the time I got home from school, it was all, how's your day? It was good, how's work? It was good, right? The kind of updates. For some reason in the morning time, there was just that space to get a little bit deeper. I'm not sure how replicable that is for other sleep deprived teenagers, but at least for my dad and I, that was a good strategy.

Shelley:
Yeah, I know. My dad, when I was growing up and still when I go home to visit, we often get breakfast together and he'll take me out, a daddy-daughter date still. And I think about just those times like little bits of time, whether it's the 20 or 30 minutes or a more intentional time to just have that time to sit and be with your child. And even if they're about to become an adult, you know, or they already are an adult, it still matters. That's relationship building.

I also wanted to just pop back to what you talked about for the younger learners and like sitting down as a family. I think that's a really great idea too, because that's something we've talked about also is like your children see you as their first teacher and as their first model. And so if you model, know, practice what you preach, if you want your kid to do this, then you sit down and do it too. Whether it's family reading time or like you said, the family writing time, just building that practice that this is something that we value. This is something that we do as a family. It makes a difference.

Carter:
Right. Well, and I'd emphasize too for parents, you know, we frame this as something that's constructive for kids, which it absolutely is. But having a family writing time is a great space for parents too. I mean, you know, talk about a hectic and busy life, lots of information every day, kind of flying around you often don't have time to sit down and process it. What we would all give for 10 or 15 call minutes to just sit down and journal a little bit, right? One page to talk about something that happened that day you're grateful for, or something that annoyed you or something that you just want to think through.

And yeah, if it comes, if you wanna practice sharing out afterwards, you you go around the circle and everyone shares what they wrote or something, all that does is show your kid that you're willing to be open and honest with the stuff going on in your life too, that the things in your head don't just stay there, you can be sort of transparent with that as well. So I think it's valuable for kids, it's also valuable for parents, right? This is why I believe in writing so much, it's just a constructive exercise for everyone.

Shelley:
For sure. And I think of people like myself, who right now we have really young kids. There are two and almost four. And they're not going to sit down and write per se yet. But you could still start modeling that, even if you're someone that has young kids, where this is family writing time. They can still pretend to write, or they can draw, or something like that. But you're just starting to build habits, which later you're able to turn into something deeper and more reflective.

Carter:
Right. You know, Shelley, if your kids are two and four, I think it's about time you started prepping for the college application process. I can put you on my list if you want. mean, you know. Yeah.

Shelley:
I know, right? All right. For a few years from now, right? Good deal. Well, speaking of that, where can parents find out more about you, Carter, and what you do? How could they reach out to you if they need to?

Carter:
That's a great question. Well, I wish I could say I'm popular enough that you could just Google my name and it would come up. I'm not sure if that will actually work. So my website is CarterOsborneTutoring.com or I'm sure if you Google Carter Osborne College Essays, I'll pop up too. And yeah, this is, know, my services specifically are for people preparing for the college application process. But every year I talk with parents of younger students or parents who are just interested to learn more about what college essays are. They have no interest in actually working with me. They just want to learn about the process.

You know, if folks out there are just curious about what it means to approach the college application process or what college essays are, or, you how can I inspire some better writing practices in my kid, I'm always happy to talk with people. Like I said, this has been a sort of transformative, actually not sort of, it has been a transformative practice in my life. And so that's why I love sharing it with others. And if we work together in a formal sort of like a working capacity, that's great. If you just have questions and wanna chat informally, that's great too.

Shelley:
That's awesome. Well, I'm sure there will be plenty of people who will benefit from your services and your expertise. And I've definitely learned a lot from you here today. So thank you so much for being on. Any last words you want to leave us with or anything else you'd like to share about what you do?

Carter:
I knew I should have prepped some nugget of wisdom or something. I should have pulled a quote to share or something like that. No, I don't know if I have any sort of pithy quotes to end on, but I'll simply share one more thank you, Shelley, both for this conversation and for all the hard work you do with this podcast. I mean, there's hundreds, if not thousands of parents out there who have gotten a lot of value out of this. So thank you for all that you do.

Shelley:
Thank you.