The Questions I Wish I’d Asked Sooner: Hard-Earned Lessons from Helping My Teens Plan Their Future

In previous posts, I have shared a bit of my journey—the ups, downs, and wake-up calls that led me to write College Is Not Mandatory. But today, I want to take it a step further.

Because here’s the truth: If I could go back in time, there are a few key questions I would’ve asked sooner—both to myself and to my teens.

Not because I had all the answers.

But because asking the right questions can open the door to the right conversations.

Four Hard-Earned Lessons from Helping My Teens Plan Their Future:

Lesson #1: College Shouldn’t Be the Default—Clarity Should Be the Goal

What I wish I’d asked: “What do you actually want your life to look like after high school?”

Too often, we focus on what comes next—college, job, trade—without first asking what our teens value. What do they want their daily life to feel like? What lights them up? What drains them?

I didn’t know how powerful that question could be until I started asking it—and saw the relief on their faces when the pressure was taken off “having it all figured out.”

Lesson #2: Struggling in School Doesn’t Mean They’ll Struggle in Life

What I wish I’d asked: “What are you good at that school doesn’t measure?”

With my daughter, I didn’t realize how many of her strengths—creativity, empathy, resilience—weren’t reflected in her report card. I kept pushing her toward a college-bound plan because I thought that was the only path to a good life.

If I had paused to recognize the ways she was succeeding outside the classroom, we might have had a very different (and much less stressful) experience.

Lesson #3: Your Teen’s Confidence Isn’t the Same as Clarity

What I wish I’d asked: “Are you choosing this path because it excites you—or because it’s what people expect?”

My son was confident in his post-high school plan—but looking back, I wonder how much of that confidence came from his desire to be “on track” or avoid disappointing anyone.

We can support their confidence while still checking in on what’s driving their choices. Teens are excellent at looking sure of themselves—even when they’re unsure underneath.

Lesson #4: We Have to Be Willing to Let Go of the Timeline

What I wish I’d asked: “If you had more time, what would you do differently?”

Gap years, work experience, internships, apprenticeships—there’s no rule that says they have to have it all figured out by 18.

I now know that giving our teens space to explore before locking into a path is a gift, not a delay.

You Don’t Have to Figure This Out Alone

Every question I wish I’d asked, all my hard-earned lessons from helping my teens plan their future is now part of the book I wrote for parents just like you.

If you’re looking for:

• A more confident way to support your teen

• A way to open real, non-judgmental conversations

• A resource to help you explore all the options (not just college)

  
  

…then College Is Not Mandatory was written with you in mind.

Grab your copy here and let’s keep building a future your teen can feel proud of.