How to Best Prepare your High Schooler for the Big Bad World

Prepare your high schooler for life after high school

How to best prepare your high schooler for life out of the nest can be a terrifying thought.


Take it from me – the father of a 3-year-old who hasn’t quite approached that stage yet but experiences a 10% rise in blood pressure just as I write this sentence.


Sure, there’s research and logical thought on best practices, but how can you know if that’s what actually works – in the real world?


Well, we are incredibly fortunate to have 2!! people here today that literally work with 14-20-year-olds as they prepare for and enter life after high-school.


These two – collectively – have 3 degrees and double-digit years of experience helping kids just like ours make this transition successfully. There may not necessarily be one “right way” to prepare your teenager, but there are some great general concepts and the two below have graciously offered to help us all out… And they don’t hold back. Take it away, Team!


(Photo courtesy of MKulp Photography)



Hey Team, I’m Robin!  


After earning my Bachelor’s of Social Work (debt free two years after graduation thanks to some money-wise parents and AmeriCorps NCCC), I dabbled in service learning, applied behavior analysis & special education, marketing & fundraising, and outdoor education focused on social-emotional development.  


I currently work in student life for an all girls, 9-12 boarding school.  When Mike asked me to write something on how to prepare high school aged kids for life after high school, I figured it would be easy, right?  That is literally my job. But the more I tried to nail it down, the more elusive it became. That’s when I decided to phone a friend.


Hey, MikedUp Blog readers! My name is Nicole! 


I have a Master’s degree in Educational Administration. For the last eight years, I’ve worked in various areas of higher education from admissions and student involvement to career services and financial aid. I currently work in university housing and oversee about 3,000 residential students at a large, four-year institution.


R: We’ll do a little Q&A and pick each other’s brains.  Tell us what you think in the comments!


N: Robin, what do you hear high school students worry about as they look toward their transition to life after high school?


R:  In my current role at a college prep school, most of the student anxiety centers around the college application process.  But once they have committed to a school or a gap year, I hear the girls (finally!) acknowledging the support system that our school provides and their concern about navigating the world without that system in place.  


In other high school settings I’ve heard students worry about the financial burden that college will place on them or their families, getting along with their roommates, making friends, wondering if college is even right for them, or just making it to their high school graduation without really being able to think about what comes after.


How do these worries stack up against the challenges that you see students dealing with in their first few months of freshmen year?


N: More and more, we’re seeing students struggle with balance and mental health during their first year. In most cases, they are in a new place surrounded by new people, and it feels like starting over.


They are trying to find their place while managing more challenging coursework, a new job or extracurriculars, personal finances, etc. without that structure and support they had in high school that you talked about. It’s a lot of transition at once.


What do you do to prepare your students for life after high school?


R:  Working in student life, all of our programming is geared toward preparing our students to be thoughtful, kind, adventurous, and ready for what comes next.  We work with them on managing their finances, managing their physical, emotional, and mental health, developing healthy relationships both romantic and platonic, and most importantly we urge them to know themselves really well so they can recognize when something isn’t right.  


Each school and organization I have worked with is different, serves different populations of kids and those kids have very different goals.  However, all of the work really boils down to dialogue and processing.


A school counselor gave me a small piece of advice that has changed the way I interact with teenagers (and, honestly, adults too).  He told me, never ask “how was your day?” Instead, say “Tell me about your day.” Asking “how,” jumps directly to the processed result i.e. how they feel.  Asking a kid “what” gives them the opportunity to reflect from a distance to speak objectively about the events of the day.


Most days this is just a way to keep the airways open, but other days may result in a teachable moment.  As a teacher, parent, or trusted adult you get an opening to help your teen develop those processing skills to get from what, to how, to what now.  


But maybe I’m getting a little abstract.


What kind of skills have your most successful students had that others were missing?  


N: The most successful students I’ve seen ask questions and seek out resources. It may sound funny to call asking questions a skill, but so many don’t ask for help or utilize resources. Between time and financial management training, success coaching, study tips, and counseling sessions, there is so much available for free on college campuses and in local communities to support them.


In addition, I’d say the most successful students stay busy and take self-care seriously. They schedule time for exercise and relaxing around their classes, join a club, and get a job, without sacrificing sleep.


Most young adults don’t know what to do with the excess time they have after high school, and that lack of routine impacts their ability to focus, eating and sleeping schedules, and overall ability to function at their best.


Again, these seem like simple things, but they are overlooked and so critical!


We’ve talked a lot about the student’s transition, but it’s important to acknowledge that this is also a huge transitional time for our parents and advocates out there. I’ve talked to so many who’ve shared their fears and anxieties – most of all, they want to know their student is going to be OK.


What thoughts would you leave them with?


R: I think a huge thing to remember is that with transition comes the unknown and with the unknown, anxiety is always normal.  Helping your kid develop skills like problem-solving and self-advocacy are important to their success after they leave the protection of your nest.  


There isn’t any single right way to work on these skills together and not every kid needs the same type of guidance, but here are a few key things you can keep in mind as you prepare your high school aged kid for life after high school:  


3 big little things you can do to prepare your teen for life after high school.


1- Never ask them “How was your day?”


Instead, say “Tell me about your day.”


2- When they come to you with a problem, ask questions.


Do your best to avoid providing or even suggesting a solution.  Ask questions instead. Validate: “whoa, that’s a tough one” Question: “What are your next steps?”  “Where will you start?” “What do you want the result to be?”


3- Teach them to ask for help by letting them know help and resources are out there.

Validate: “whoa, that’s a tough one”  Question: “What are your next steps?” Support:  “What can I do to help?” or “What kind of help do you need?”



Reader’s Input


Have you sent a high schooler into the big bad world? If so, what have you done that worked well or what would you have done differently? If you are preparing for this stage, what plans have you made for a successful transition?


Let us know in the comments below and both Robin and Nicole will keep an eye out to answer any questions or comments you have!


Thanks for reading!


If you’re interested in discovering a better version of yourself – whether with fitness, finance, or family – then subscribe below to MikedUp Blog’s FREE newsletter and let’s improve together!


I’m glad you’re here. Thanks again and talk soon!


– Mike

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