Helping Your Teen Choose What to Do After High School

by Roberta Whitney Hughes, Founder of PeaceFull Living and PeaceFull Living TV


This blog is for all of the parents out there who are beginning to have conversations about college with their teens.

The Back Story

My son Connor graduated from high school in May 2017. I always saw Connor as a brilliant boy. He could put together puzzles beginning at 14 months old. By 18 months, he could put together a puzzle of the United States. State by state, I could ask him to find the piece, and he would find it and place it exactly where it belonged. He knew the entire alphabet and loved for me to read books to him. By age two, he had memorized most of his books from cover to cover and could “read” them out loud word for word, page by page. At the age of four he was reading chapter books. I was pretty sure he had a photographic memory.

The Early Years

When Connor began kindergarten, he was reading chapter books while other kids were just learning their ABCs and phonics. It was his kindergarten teacher that realized Connor had a gap. He saw words as pictures. He knew what sounds each letter made, but he didn’t seem to understand how the sounds built words. Connor’s teacher discovered that while he could read the word “discover,” he could not verbalize how to sound out the word cat. Thankfully, she helped him fill this gap.

Elementary School

In elementary school, Connor was a great student. He excelled in Language Arts, although he had a very difficult time holding a pencil. The feedback I received most often from his teachers was that he preferred to keep to himself and would only answer a question if asked. Teachers wanted him to freely participate without being asked, but that wasn’t Connor’s style.

Middle School

In middle school, Connor began to struggle. Having many teachers with different expectations was tough for him. Keeping track of homework was a challenge. He would come home, do his homework, and somehow most of it never ended up back in school with the teacher who needed to see it. His student account always showed missing assignments, and his grades began to slip. I thought it would help to do some testing to figure things out and help Connor. After much research, I couldn’t find any testing that was covered by insurance, and his dad refused to pay for specialized testing. So, instead of testing, we hired a tutor to work with Connor. He did very well with her; his grades began to improve. While Connor still struggled with organization, his work was getting turned in and he seemed to be managing things pretty well.

High School

When Connor transitioned to high school, the struggles resurfaced. It took him time to get to know a new school and new teachers. I could see his joy for reading, and it carried him through high school. Aside from reading, I didn’t see any indication that Connor was happy at school. As I look back now, I wish I had paid more attention.

Because I see Connor as a brilliant boy, I always thought college would be his next step. I never considered that college might not be for him. The one time Connor had the courage to tell me he didn’t want to go to college, I didn’t listen. I brushed it off and told him he would be a sign spinner on the side of the road if he didn’t have a college education. I can’t believe I said that to him and still have regrets about it. 

You see, Connor is a very agreeable person. He will do almost anything you ask of him. So, I said he was going to college and he went.


Connor went to CSU his freshmen year. He wasn’t too far away and was able to ride the light rail home on weekends. Each weekend he came home, I could see that he was unhappy. During his first semester, Connor became very quiet and withdrawn. His grades were low, even in language arts. Although I tried to talk to him many times, he wouldn’t say much. Finally, over Christmas Break, I asked him to write to me and clear his mind. I didn’t want him to hold anything back and asked him to be completely honest. 

Connor finally revealed that the only reason he went to college was because I wanted him to go. He pointed out what I had said about being a sign spinner and how much it hurt him. He was angry with me and had every right to feel that way. I didn’t listen to him, nor did I give him the opportunity to choose what he felt was best for him.

A Lesson Learned

As I look back now, it is hard not to feel regret. I didn’t know how to have an authentic conversation with Connor.  My ideas  clouded my view. I thought I knew what was best for him, and instead of listening to Connor, I told him what to do. In hindsight, I would have been a better listener and helped Connor create what was best for himself.

Talking to Your Teen About What to Do After High School

Had I known what I know now, these are the questions I wish I had asked Connor. I hope these questions help you begin a healthy conversation with your teen.

  • What are your thoughts about college?
  • What do you see yourself doing after high school?
  • What have you liked about school?
  • What haven’t you liked about school?
  • If you don’t go to college, what is your plan?

Healthy Communication and Conversation

I urge parents to use these questions as conversation starters. Here are a few things to remember when you open the conversation:

  • Be an active listener. 
  • Keep your ideas to yourself.
  • Give your teen the freedom to express themselves. 
  • Be kind in what you say to your teen.
  • Help your teen create what they want for themselves. 
  • Ask questions.
  • Resist telling your teen what to do.


For more information about helping your teen decide what to do after high school, read this article

Share Your Story and Questions

I invite you to share your questions and stories in the comments.

  1. Robin Palmerston
    | Reply

    Roberta, your recommendations are very appropriate for grandparents to learn from, as well! Thank you.

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