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How to prepare your teen for life after high school

Updated: Oct 11, 2022

College students across the county are in the throes of a mental health crisis. And those numbers keep increasing every year. Students at Stanford have an annual celebration each year called the "Stanford, I Screwed Up", specifically to help students acknowledge the fact that it's ok to fail.

Rising rates of mental health crisis in college

How are we raising a generation of students who somehow believe that anything less than "effortless perfection" is a failure? How have they not learned that struggling is a part of the normal routine of everyday life? Well, let's find out. What follows is a transcript of an interview that Josefine did for the podcast Mhourom's of Teens and Tweens with Sheryl Gold. In the interview, Josefine reveals what she's seen over the past nine years of working with students one-on-one, and shares advice on how to help students thrive not only in college but beyond. This transcript is on the longer side, so if you prefer to listen to her, head over to Moms of Tweens and Teens Podcast

Table of Contents


Sheryl Gold

Hey, friend, welcome to the show today. And I'm so glad that you're here. And before we launch into our awesome episode today, I want to ensure that you have signed up for our Free three-day workshop that kicks off next Tuesday, September 27th. And the topic is escaping entitlement and raising responsible, respectful, and kind teens in an entitled generation.

And moms have been begging me to talk about this topic, and I'm listening and it's gonna be awesome. And if you have a tweener teen and you're finding yourself worrying about their future or you're dealing with disrespect or a lack of motivation and don't know how to support them, or you're burned out and need some encouragement, support.

I encourage you to come and promise you will leave feeling so encouraged. I will share my personal story, experience, insights, and tools to empower your kids and build that strong, healthy relationship that we all desire. To check it out go to and get signed up.

And I hope to see you there. So let's go to the show. And my special guest is Josefine Borrmann, the founder of Strive to Learn, a tutoring and college prep service that provides students with 1 to 1 support from experts who foster accountability and teach them the skills they need to prepare for life outside of high school.

And in our interview, we talk about so many things, but Josefine really shines a light on what our tweens and teens need from us when they're preparing to leave the nest and the importance of mentoring versus monitoring, so our kids will learn the skills they need and how to do that so they learn the skills they need while they're still in our home, and we talk about so much more.

So let's dive in. Well, Josefine, welcome to the Moms of Tweens and Teens podcast. I'm so happy to have you on because we're going to be talking all about college, our kids applying to colleges, and the application process, and *sigh* parents are talking about it already and being stressed out.


So a lot is going on for both rising juniors and students who just graduated and rising seniors. So everyone's kind of busy in this in the summer before the next year, right?

Sheryl Gold

I know it's a really it can be a very stressful time. Well, I want to jump in. And first have you share a little bit of your story because you do have a story and what led you to doing what you're doing and working with students and being a professor and all the different things that you're up to.


Yeah, absolutely. So. So basically I founded a company called Strive to Learn about nine years ago. And actually, yeah, nine years was like wait, "is a ten?" No, it's been nine years. And our goal is to really help any student find joy and confidence in learning. So we started as a test prep company and tutoring company and then I realized that I really want to give all-around support to local families.

So seven years ago we also started offering college counseling and now we work with the Newport Beach Public Library. We work with a high school in Colorado and the college counseling department of a high school here in California. So we've expanded our knowledge base and the team quite a bit, which is exciting. But when I first started, it was just me.

I was a tutor putting myself through college with tutoring just because that was something I was able to do and relatively decent at. And so it started with just me, right? And I knew what I want to do with this thing, you know, not knowing anything about business or anything like that. I just really wanted to create a space in which students who have fears about their future or anxieties about their schoolwork can work with a mentor who really gets them.

And that comes a lot from my personal story. So I'm from Germany, born and raised, and I came to the U.S. for my undergraduate studies. I had to teach myself how to navigate this complicated university application system. It's really, really different in Germany. I had to do things like taking like statistics, which scared the hell out of me, and it made me realize that I really wanted to help guide others in their pathways with all of this knowledge that I kind of gained and accumulated over my first few years here in the U.S. So that took me on a couple of different paths. I became a math tutor, even though math had always been really hard for me growing up. I also taught several anthropology and sociology courses at Chapman University, and then I also built a team of college counselors at Strive to Learn.

So through all of this, I realized that what I feel like has the most profound impact on teens potential for growth is really that individualized, reflective mentorships, mentorship. And that's why we're here today. Right. How can we mentor teens, right? It's not just other people who are mentoring, it's parents who are mentoring as well. So I'm really excited to be here and talk about, you know, what can we do with mentorship when it comes to supporting our teens and our tweens. It's a hard time in life because we've all been tweens and teens, right? Some of us tend to forget. Others don't. And I think for me, the biggest thing that I remember from being both a kid and into teenager-hood, was I always felt like I'm a real human. I am, you know, a full-fledged human.

So why are people talking to me like I'm half of one or like I don't know what I'm saying?

Sheryl Gold

Wow. And you remember what that felt like?


Yeah, absolutely. Because I was like, why are you talking to me like I'm stupid? Or didn't think of X, Y and Z, you know, just because I made me don't have your life experience. Like, I can still think for myself. So I was, I always felt a bit outraged about that. And the people who had the most profound effect on me, I would say, as I grew up, were the people who spoke to me like I'm 100% human, not just 50%.

You know, and it's just so important to feel seen and heard. And I'm not saying that's people who, you know, said, yes, amen to everything I said, but it's people who called me out on things that I said who asked me to be responsible for the things that I said or did and that, you know, has a really profound effect because you can take that responsibility because you are also being seen fully as a full human.

And that's how I talk to my students because they are responsible for themselves, no one else is. They are. And so, you know, let's get down to business and talk about what's going on here instead of trying to skirt around issues.

Sheryl Gold

Wow. I love that we have to pause, like you said, so many good things. How to me? Well, first of all, I noticed how you use the word mentor. And I say that a lot of the parents that I work with that were no longer like trying to teach, although that's, you know, a big part of what you do.

But it was very interesting to me that you use the word mentor, because when our kids are teenagers and when they become tweens, there's this big transition that begins to happen. And we talk at. Rather than what you were saying when you were when you were a teenager, you remember that the people that you said that you felt really heard by. They were they were I'm imagining asking you questions. And they wanted to hear from what you thought about things rather than talking to you like you didn't know or, you know, you were not a young adult.

So I think that that that's really interesting for you to share that and how that, I'm sure, is impacting what you're doing with kids today and how you talk to them.


Yeah, absolutely. I mean, I recently went to a conference from the IECA, the Independent Educational Consultant Association, and one of their keynote speakers. I'm completely blanking on her name right now, but she said it's about mentoring, not monitoring. Monitoring is a lot easier. And again, these are not my words. I'm stealing them. Monitoring is a lot easier, right?

Saying yes or no to things and, you know, checking the location of your kid, seeing that they do their homework, things like that, mentoring and sitting down and talking about the why, the how, asking those questions and really having them become a part of the decisions that influence their lives. It's harder. It takes more time, but it's a lot more rewarding.

And it's really what gets teens to young adulthood.

Sheryl Gold

Yes. Yes. Say that again. What did she say? She said mentoring versus monitoring.


Yeah. Mentoring. Not monitoring.

Sheryl Gold

Which gets which leads into what we're going to talk about is the whole college application process. And I mean, we'll talk about other things, but that's what I see. And what I've experienced as a parent myself and working with parents is that it is so easy to try and manage and monitor and control things and especially when your kid is not seeming to be motivated.

So what are some of those things that you see working with teenagers that we should not do that actually backfires?


I think this may be a little controversial, and too many rules might not be the best thing. But again, also not too much freedom.

So I think, again, having the teen have a choice in the decision that's being made, can make a big impact. My parents were very strict when I grew up, but they also gave me a lot of freedom, which sounds really weird and it's hard for me to try to explain that they you know, I had the the most chore of all my friends.

I had the the smallest allowance, the earliest curfew. I definitely had those things. But I also, you know, both of my parents worked full time. I would do whatever I wanted after school. So between one and five, I would just have free range of wherever I wanted to go and whatever I wanted to do. This was pre-smartphones in your pocket.

And, you know, I think I really grew through that, through these open spaces where I could be bored and where I had to figure myself out. Yes. They locked the TV remote away so that I wouldn't, you know, just binge-watch all day, which in retrospect, I'm very grateful for. But that made me have to get creative and be a bit bored and figure stuff out.

So I hung out with friends a lot. You know, I read, I did my homework, whatever, did some stuff that probably isn't the best idea but learned from it. And I think if we shelter our kids too much from making mistakes, from doing, let's just say dumb stuff, right, then they don't have the opportunity to commit those mistakes and realize on their own, that was a really dumb thing to do.

I don't think I'm going to do that anymore. Right.

So if they can't have that experience, then I think that is really problematic because we see a lot that when kids get to college, they it's a lot it's a lot of freedom, it's a lot of independence. All of a sudden. It's a lot of drinking. It's a lot of figuring out your own schedule.

So, you know, not knowing when to do your homework or not because you're not being as handheld by your professors as you are by your teachers and high school. You know how to do your laundry, when to eat food, how to cook your meals. It's just very simple things where putting them all together can become very overwhelming for students.

And a lot of students report very high levels of stress and anxiety and depression in college. I think it's about 75% of college students. Now, at some point in their college career report, clinical levels of stress and anxiety. So that is- I'm throwing that out there. That's not set in stone. It's something I read in multiple sources. Sorry, I'm a, I'm a research methods geek.

So just throwing out a percentage like that makes me feel like, Oh, man, I need to go check my sources now. But I do believe it's somewhere around there and how do we avoid that? Right? How do we avoid these mental health problems in college? It's that we have it can't be all or nothing. It can't be this scheduled out life that you live only to get to college.

That's the whole reason you're doing all these sports. You're doing the volunteering and this internship that you really don't want to do, but you feel like you have to. You're taking all the APIs, you're getting all the good grades, you're doing test prep, right? I mean, looking at these team schedules, I'm just, wow, I'm floored. Some of my students, sleep 4 hours a day and that is just so detrimental to the development of your brain, to your emotional growth, and anything else.

And then they arrive in college and they're just so burnt out and suddenly have all this freedom and maybe they're homesick, etc., and it can be, you know, quite, quite the disaster sometimes. So I think it's of utmost important to not shelter our kids too much while, yes. Having firm rules that, you know, everyone knows about, they're mutually agreed upon.

Hey, if you violate this rule, this is what happens. But also giving that independence is not over, sheltering and letting go bit by bit. Maybe even saying, okay, you know, every year I'm going to go let go of something else. So looking at my kid is in sixth grade. By 12th grade, I want my child to know how to do X, Y and Z, to be confident in X, Y and Z situation.

Right now, they're here in six years. I want them to be there. What can I let go of as a parent every year? You know, a responsibility, any type of monitoring, whatever it might be. What can I give back to my kid in that year so that my kid can learn that skill, that confidence, that independence bit by bit, and I'm here to support them.

And that way maybe we can get there.

Letting kids fail

Sheryl Gold

Yeah. I love how you connect and I'm, I teach this so often to two moms, primarily moms and parents, about how to let go and think about it from the lens of what skills do I want my kid to develop? And we are a culture of parents and I think I could say the safely, even though we don't want to admit it. And I've been one where we don't want our kids to make mistakes, you know, we're protecting them and we want we love them and we want them to do well.

But with that, we're not allowing for them to learn from mistakes. And so we have to remember how do we learn skills? Most of the stuff I've learned is often from the mistakes I've made.

The big, you know, the big lesson.

Josefine Borrmann

Saying, oh, yeah, that's who you are, right? It says growth opportunities, basically. I think maybe that's a good way to kind of start tapping into that is rephrasing the word mistake and to growth opportunity. I know it sounds really cheesy, but really thinking about it, a mistake is never a failure and I think a lot of kids see failures. Right? I see it. I mean, the easiest example would be a math tutoring student. Right. I failed this quiz, so I suck at math, which means I'm not smart. That's just like, no, no, none of these things are true. First of all, you made some mistakes on squares, which means you have an opportunity to grow. So let's talk about how you can take this opportunity and grow and move forward from this, because it is not a failing or dead end ever.

I think people who have made giant mistakes that they interpret as failures in their lives and now look back on how they grew and how that shaped who they are now. I think most of them will agree that, hey, you know what, I would never be who I am now and would never have learned what I did learn by doing that.

And so that's why I really like that rephrasing of, Hey, this is an opportunity to grow. Let's figure out how we can grow here.

Sheryl Gold

Yes, it's the growth mindset with being a Cal California gal. You, I'm sure, are familiar with Carol Dweck.

Josefine Borrmann

I was going to say shout out to Carol Dweck, of course, of course.

Sheryl Gold

But for from our listeners, it's such a good book and that's exactly what you're saying. And I love thinking of it that way because mistakes sound - what she calls - so fixed mindset. Like, I don't want to make mistakes, so I'm not going to put myself out there. I'm not going to go out for that, or maybe I'm not even going to try very hard because if I try hard and I don't do well, then I'm going to feel stupid versus this is a growth opportunity and a learning opportunity. And what did you learn from this rather than, "how did you get this grade in that paper?"

Josefine Borrmann

And what did you and I think one of the easiest ways to wrap your mind around the growth mindset without it feeling all cheesy and weird because it can it can do that, right?

It can sound like, oh, everything is rainbows and I'm going to grow from the worst mistake of my life. Well, you probably will, but it's hard to think that in that moment.

So one of the phrases that she uses is, you know, I don't know that yet or I'm not there yet, but so I think that's you know, you can use that as a parent. Oh, my child doesn't know that yet. I get parents sometimes who are like my kid is know anything and like I don't even understand, he's 17. He can't even do his own laundry.

I'm like, well, let's add a yet to that and then let's figure out why and now have you ever taught him? And then like, well, I showed him once, like, okay, so then what happened when he was supposed to do it? And they were like "well, it just kept piling up, so I just did it for him."

Like, Okay, so he hasn't done it. He's only watched you do it. You tried to teach him. So kudos to you for that. But you know, he doesn't know it yet because he hasn't done it yet. And we can only learn if we do it. I mean, I definitely cannot learn how to do laundry by never doing laundry, by only watching other people. You have to do it a few times yourself, right?

So let that pile of stinky socks and workout whatever, you know, especially if they're doing a team sport. I know it can get crazy and musty, let it grow until they have no other choice than to do their own laundry, because then they will learn how to do their own laundry.

And I love that you said when you think back about everything you've learned, it usually came from something that wasn't super easy, right? Something that you had a speedbump and you had to get over the speedbump, right? And I think that's so important for parents like, hey, how did I learn thins lands let me think back how I learned this because I just think that adoption notice so my kid should know this, but how did I actually get to knowing this?

Because all of that is learned. Even culture is learned. Right. And so how did you learn that? It's you have to dig a little bit deep on that.

But if you can connect with that in yourself, if you can reflect on it, it'll get a lot easier to understand where your teen is coming from and to meet them where they are and to meet them as a human, not just as a kid.

Sheryl Gold


Mentoring, not Monitoring

Josefine Borrmann

And we're learning, right? We're learning all the time. That's what I say to moms is we expect our kids to know these things, but they're developing. They're not adults. They're learning. This is such a process and developing new habits and things that they have never done before, an increased responsibility and having to manage so many things that are going on in their lives.

So let's talk a little bit about we talked about what not to do. So not too many rules, not micromanaging, not, you know, mentoring rather than monitoring. What are a few of the things that are helpful that we can do? I mean, allowing them to have growth opportunities is what what else have you found helpful to the kids that you work with.

Being...making sure they know you're there to support them. So making sure they know that it's okay to make a mistake so that they're not scared out of their wits to tell you, but instead can come to you and say, "Hey, Mom," I don't know if I'm allowed to cuss on this. "So I F*** up, Is that okay?"

No. I mean, you know, that's that's the one time that word is warranted. I did X, Y and Z and I may have just, you know, really made a made a big mistake. So making sure they know they can come to you and talk about that, I think that's really important, that they're not too scared to come and seek help from you when they really do need to.

Because, like you said, they are learning. Right. And we're learning to we might call ourselves adults, but I know plenty of adults who are still waiting to feel like adults after 20 years of officially being adults, everyone is always continuing to learn and grow. And, you know, I'm 35 and in ten years I'm going to be 45 and I'm not going to be the same person I am now.

Right. A lot of me will be the same, but a lot will also have grown and learned more. Right? So we're always in that way. Very similar to teens were also always growing.

Why is mentorship important?

But yeah, I guess supporting them, making sure that you're there. And then another thing that I have found really helpful because I am that person, is finding someone else who can mentor your kid in a way that you simply can't because you're the parent.

And it's not anything you're doing. It's just that kids don't want to hear it from their parents sometimes. I, as their tutor or as their college counselor, I can say things to kids and be heard by them, that their parents can also say, but not be heard. "Oh, Mom, you don't even know how that how it is out there."

Like, you know, you don't even know like you went to college like 20 years ago and, you know, and then they're like, Oh, let me go ask Josefine. And then Josefine says the same thing. They're like, Oh, my mom kind of mentioned that. And I'm like, Yeah, you know, maybe maybe you can talk about that or maybe you can learn something from her.

So I do acknowledge that, you know, you can't always be your kid's mentor. You're also their parent and you have to find a balance there. And sometimes it's just it's not sometimes I think it's extremely, extremely valuable. And I think it's a must for every single teen to have at least one mentor who is neither a teacher nor a parent who is someone outside of that.

That could be a professional mentor. It could be someone like a college counselor, a tutor, someone with whom they can let their guard down and discuss some of those fears that they may not be really showing to anyone else in their world. Because I have some conversations with students where we dig deep and I am not a therapist, and if it ever goes there, I tell them I'm not a therapist and I really recommend that you get a therapist.

But if it's just you know, "regular fears" , regular in quotation marks here, very real fears that they just didn't know what everyone else is experiencing. So they didn't know if it was okay to talk about it. So having that and also having really positive role models who have that mentorship impact, where it might not even be conversations, it might just be observing them just being around someone where the student looks up to.

And can you know, learn a lot through observation of like, wow, this person does that. And it resulted in that, you know, there's a lot going on in our minds, right? So why should we think that's not the case for teens? What I hated the most was when people always told me, you're not thinking, you're not using your brain.

And I was like, but I was. And I still made this choice. Like, What does that say about me? Why are you pretending or saying that I am not using my brain even though I was you know, I'm I'm a person. I was thinking and I just, you know, made a choice that I kind of knew was dumb, but I wanted to try it out.

I'm right. However, we all done that as teens, so I think that's really, really important to know. There's a lot going on emotionally and cognitively in any teen's mind and body and not to assume, Hey, there's not much there. They're not thinking about much. They are. Even when you can't see it, they really are.

What should parents ask their kids?

Sheryl Gold

What do you think? As you think back, what would you have rather heard than you're not thinking?


I think a question. So not what were you thinking? Not in that to answer, but hey, so like why? You know, let's get to the bottom of this. Like, why did you end up doing what you did? Like, it's okay. It's okay if you don't have a good reason. I'm just, you know, I just want to just only have a conversation about it.

Something like that.

Sheryl Gold

Yeah. Being it, being curious about it.

Josefine Borrmann

And not dismissing the what, whatever answer you get. So I think that's hard. When, then, when then you muster up the courage as a teen to answer that question, even though it feels very uncomfortable to answer that. And then your answer is dismissed. You think that that's really hard for teens?

Sheryl Gold

That's very hard. Or judged by what you're not thinking, very judgmental. And it's easy, I know, to say that to your kid when you're scared as a parent, you know, you feel scared and you're like, Oh, my gosh, they could have really hurt themselves or something bad. And it's like, What were you thinking? But then they're not going to come to you and they're not going to talk to you because they're going to be they're going to be worried that they're going to be judged.

Josefine Borrmann

And I.

Sheryl Gold


Josefine Borrmann

I think sharing your own human moments is really important, too, because you can say, you know, out of fear, what are you thinking? And then you could say, okay, you know, I was I was scared. That's why I said that. Yes.

Sheryl Gold


Be Vunerable

Josefine Borrmann

Let's talk about this and then maybe sharing something stupid you did and showing that you were not always the saint that you might proclaim to be or not and sharing you know, a learning opportunity you had when you were their age. You know, if they were caught drunk when they really shouldn't have been and they're under age and they're doing something stupid with alcohol as an example, because I believe, like any parent at some point might deal with this, you think of yourself.

I mean, maybe you don't drink or maybe you haven't. But I think a lot of adults have done something similar in their teens. I sure did. And them being open and honest about that, hey, like, let me tell you about a time that I did something dumb and just kind of peeling back that mess of parents or they're just separate because they're adults and they're different.

Josefine Borrmann

And someday I will be an adult because it makes you think as a teen that there's this switch that's going to flip. And usually they think, Oh, that's not going to happen. When I go to college, like it's going to flip over and suddenly I will be an adult and have adult thoughts and feelings. I'll be super in control of myself and I will have everything figured out.

And that's not how it works for anyone. So showing them that human side of yourself where you were between having nothing figured out and having most things figured out what are some things that happened in between there that helped you figure things out? I think that can really help teens become kinder to themselves as well, because feeling like a failure is really, really tough and it affects the rest of your future.

It can affect your academics, it can affect your love life, can affect your career. And so many things, right? So being human and sharing some of your own faults and maybe weird experiences with your kids, I think can relate not all the time, but, you know, especially in situations where you were scared for their safety or when you really need to make a point just to show them, hey, that door is open because I do get it.

You think I don't get it? But let me show you the story that shows you. I do get it because I used to be you, and now I'm here to help you out.

Sheryl Gold

I like how you said also, you know, I was feeling scared. And if we do freak out as parents, I have to say this to the moms that are like, oh.I've said that. It's like we can always go back and say, You know what? I thought about it and I was just feeling scared, you know, I was scared and you know, I've also done those things. And because I really what I have experienced as a mom is some of the things that my kids have done that I did that were really dumb.

Those are some of the things I freaked out the most about.

Josefine Borrmann

Right? Yeah.

Sheryl Gold

Not not wanting to do some of the same dumb things. I did because I knew that.

Josefine Borrmann

They have impact.

Sheryl Gold


Josefine Borrmann


Sheryl Gold

And and you.

Josefine Borrmann