For Parents For Educators For Schools GET ACCESS

How do I help a kid plan for their future? The 9 Mistakes Parents and Teachers Make.

Subject: How do you help a kid plan for their future?


Our oldest kid, our son, who’s now a sophomore in high school, has passed that inevitable threshold where the topic of his future is coming up a lot. His friends are talking about it, we’re talking about it, and he’s thinking it through. The clock is ticking, and he hears it loud and clear.

Recently in the car, he asked me a sincere, honest question: “How do I figure out what to do with my life?” Looking back on the conversation, I realize there are so many directions I could’ve taken my response. And most of them wouldn’t have been helpful at all. 

There’s no question young people need to make significant decisions about their future. The pressure, stress, and anxiety they feel about their future, plus their lack of life skills to problem-solve career decisions, can impact their mental health. We want to help kids grow in self-confidence, emotional intelligence, and discernment capacity so they can thrive now, as college students, and in their future careers.

So what are the ways parents and teachers can help kids figure out their future? Let’s start with the nine mistakes adults make when trying to help kids define their future.


Mistake #1: It’s not a career conversation


It’s not a career conversation (or a college conversation). It’s a conversation about all of life. He is asking me how to figure out his career path, but the mistake would be to only look at his future through that lens. Rather, we’ve found by working with thousands of teenagers and transitioning veterans the importance of planning for all of life. First, that involves looking backward and getting a clear sense of the trajectory your life is already headed. Next, you must look inward at your core foundations—your beliefs, values, principles, and priorities. Then, you need to look forward through a lens of imagination, to dream about the kind of person you want to become, the problems you want to help solve, and the mark you want to make on others. Once you do all that, you can see more clearly the options and paths that make more sense for you. 


Mistake #2: Transferring your anxiety


I remember the second he asked me that question, I felt a sudden surge of anxiety. What matters more in my life than who my kids turn into? I tend to live more in the moment as a parent, dealing with the current season we’re in and responding to the current challenges. I don’t think very often about five, ten, or twenty years from now. I trust it will all work out well—which sounds mature but quite naive. 


I don’t want my kids to ‘blow it’ with their lives. I want them to discover what they’re passionate about, take responsibility for their lives, and make us proud. When he asked me about his future, I realized in a split second that what matters most to me is barely in my control. His life is up to him. I can’t make him do anything anymore unless I try to use big threats or dangle huge rewards. 


Rather than pass along my anxiety to him, I took a deep breath. (And then made notes to write this article!)


Mistake #3: Forgetting how it all works


When I was a teenager, our school made us take a career assessment to help us figure out our career path. Like my son, taking the test and thinking about my future brought me anxiety and stress. So, I gamed the test. I answered questions like, “Do you enjoy working with numbers?” with a strong affirmative, and the questions that were more, “Do you prefer working with your hands?” I responded negatively. As chance would have it, my results popped out at the end, saying I should consider a career in finance or accounting. Surprise, surprise. The same career path that my dad, uncle, aunt, grandma, grandfather, and pretty much every adult I knew had taken with their lives. 


The problem was, that it wasn’t accurate. It made some sense, to be sure. I was good at math. I do like business concepts. I am attracted to a stable, secure income and respectable career. But, that wasn’t the whole story about who I am and what kind of person I wanted to become. 


It’s easy to forget that figuring out what to do with your life is an iterative, discovery process. The insights my son has now about himself, and his awareness of what’s out there in the world will continue to evolve. In other words, he doesn’t have a clue yet who he is or where he’s going, and if we commit to the right conversations and experiences over the next few years (see above), the process will work, and he will figure it out on time. 


Mistake #4: Shrugging your shoulders


I am 100% confident that my son has asked me that question before, as has my 13-year-old daughter. And I completely whiffed on the moment. It’s not that I don’t care about their future, but because of the anxiety their future success or failure brings up in me, I typically avoid dwelling on something that might go wrong. So, I shrug my shoulders. Or change the subject. Or try a little Jedi mind trick and say, “Don’t worry—you’ll figure it out someday.” 


When our kids ask us sincere questions about their future, don’t be like me. Help! Put your phone down, turn towards them, and get fully present. Read their expression, dig a little deeper for what’s motivating them to think about it, and ask a bunch of questions. Our kids don’t need us to be passive observers, they need us with them in the process.


Mistake #5: Being a cheerleader (rather than a guide)


I love my kids, and I see many signs that they’re on the right path. I figured myself out towards the end of college, and I’m sure they’ll figure themselves out, too. I understand the discovery process of adolescence and how it all works. Besides being successful in life, I want my kids to feel supported by me. I want them to feel my favor towards them and know that I have their backs. 


The mistake I see a lot of parents making is to be exclusively a cheerleader to their kids. “You’re doing great!” “You’re going to crush it!” “You always dominate!”


They want you to be positive, encouraging, and nurturing, but it eventually becomes vapid noise. Kids need affirmation—we all do—but even more so, they need a guide through the journey. They need someone to point them in the right direction, act as a mirror and sounding board, and hold their hand when appropriate. They need someone to support them as much as challenge them, revealing the next step they can take and putting the burden on them to take it. 


Mistake #6: Having the conversation once


Most kids hold their thoughts in their heads as a rule of thumb, especially from their parents. Adolescence is a time of individuation, a fancy term for figuring out life for yourself. They carry a lot each and every day, from school to friends to work to home, not to mention sports, activities, and social media, and by and large, their narrative voice is an internal one. You might hear, see, or feel the spikes like big reactions, intense feelings, or listen in on their conversations with their friends, but the little toddler who used to sit in their car seat behind you and talk your ear off is now with a hood on, earbuds in, and quiet as a mouse. 


That doesn’t mean they don’t need your help, though. 


It’s a mistake to only talk about their future every once in a while, like when their report cards come in or a new semester or quarter starts. It’s a mistake to only talk about it when they bring it up. They need frequent, ongoing opportunities to reflect on what they’re discovering and be shown the steps to get the insight they need. 


Mistake #7: Neglecting your resources


Typically, high schools have a lot of resources for our kids. From teachers to specific classes to counselors and PSAT prep opportunities, your kid will likely sit through multiple presentations and assemblies, receive handouts, access college prep software, and meet with their assigned counselor.


But it’s a mistake to leave our kid’s future planning for their lives up to their school. Most schools are overwhelmed enough, don’t have a strategic leader at the helm, and can’t give every kid personalized attention. But you do. You have resources to share, from personal stories to friends to introduce them to. You probably have family members doing interesting things with their careers who would be delighted to talk with your kid. 


Most importantly, your life is your primary resource to share with your kids. The parents who take the time to reflect on themselves, recall their past, dig into their core foundations, and share them with their kids are the ones who provide the best support for their kids. They are living role models, whether with a “do what I say and not what I do” vibe or not. 


The fact remains that your kid needs you. They will figure out life independently, but it will probably take a lot longer and be much more painful without you. 


Mistake #8: Try to relive your life through them


You made mistakes, didn’t you? You could’ve been more courageous and confident and said yes (or no) earlier. But that’s history. Unfortunately, many parents try to relive their lives through their kids. They aren’t pleased or fulfilled with how their lives have turned out, so they pressure their kids to do things differently. 


That’s a mistake. Your kids are a reflection of you, but they aren’t yours. Don’t try to relive your life through them. 


Mistake #9: Try to get them to live your life


Perhaps you’re content with your life and happy with your choices. You pushed through big obstacles to get where you are, and now you want your kids to experience the same thing. 


I see this most often in families with parents who are wealthy. They had extraordinary drive and ambition, which is what enabled their success. They gave their kids opportunities they never had when they were growing up. But now, they don’t see their kids' same drive or ambition. Now, they must let go of control and release some pressure. Kids thrive under high expectations as long as they get an equal dose of nurture and support. Don’t make the mistake of pressuring your kids to follow in your footsteps. For one, they’ll resist. Also, they need to carve their own path—no matter how good yours has been. 



  • Which mistake are you prone to?
  • What work will you do to give your kids what they need?
  • What would you add to this list?




Do you know?

For years we’ve been studying what a young person needs in order to transition into a healthy, thriving adulthood.  

They're uncommon sense ideas, really.

Download this checklist and use it with your students (or kids).

50% Complete