Ep 1: Success and Getting What You Want in Life

Episode Summary

Bill Deresiewicz, bestselling author of Excellent Sheep, talks about the conversations he had with students that really had an impact when he was teaching at Yale and Columbia. His advice for how to do this with your own teen involves being non-judgmental.

Show NotesParenting ScriptsWorkbook ExercisesInterview TranscriptGuest Bio

Full Show Notes

Welcome to the Podcast

Hello! Welcome to the first episode of our podcast, Talking to Teens. I’m your host, Andy Earle, and I am so excited for you to come on this journey with us! My job is to explore what it means to be a teenager and to help parents like you find the perfect solution to ANY teenage struggle.

It’s natural for teenagers to encounter hardship as they live in a transitional period between childhood and adulthood. All this change can be overwhelming and difficult for even the most stalwart teen. However, with careful assistance we can guide teens to grow and flourish in the world.

The age-old battle between strict parents and rebellious teenagers has influenced our preconceived notions of parenthood. In so many coming-of-age stories, teens are depicted as wanting to explore their newfound independence recklessly, going against the will of their well-meaning parents. So how do this common movie and book archetype play out in real life?

On this episode of Talking to Teens, we discuss how to navigate the treacherous waters of parent-teen communication in the context of newfound independence with special guest, Bill Deresiewicz!

Bill lends his thoughtful approach to struggling parents by breaking down ideas of success and budding adulthood. Formerly a professor at Yale and Columbia, Bill is the author of the New York Times bestseller Excellent Sheep: The Miseducation of the American Elite and the Way to a Meaningful Life. From this interview you’ll learn one thing for sure: talking to teens is an art form of its own. Thanks to Bill’s years of experience as a mentor to teenagers and young adults, he can unearth knowledge about fostering discussions and supporting teens’ journeys to independence

Independence Can Invite Conflict

As a parent, you want to see your children grow up to be independent, make good choices, and live a happy and fulfilling life. However, conflict can arise when parents and their children have opposite opinions on what that future might look like. Without proper conflict management, families might run into heightened resistance, which often leads to a breakdown in communication. Easy objectives like talking to teens have suddenly become loathsome chores as frustration turns into anger and quick chats become heated arguments.

It is important to note that if you resort to commanding your teens to do what you think is right, your teen feels left out of the conversation. Parental control over teenage decision-making disenfranchises their voice and furthers their struggle to find their own identity. Inclusion in conversation is paramount to the well-being of an adolescent.

According to Bill, teenagers aren’t commonly included in parental decision-making—which can be problematic. The inability for parents and teens to talk about the transition to adulthood stifles growth. This is one of the many complex obstacles that parents face when talking to teens.

Mastering the Discussion

Bill has a solution to avoid communication breakdowns when talking to teens. He explains how sometimes the best way to assist your teen to be more hands-off. That doesn’t mean letting your teen run wild unsupervised, that won’t help at all. What does help, is assisting your teen’s journey to independence by creating the environments where your teen can succeed.

This might look like allowing your teen to choose an academic schedule, explore their own career ideas, or try out a new hobby without parental judgment. This way, you don’t have to instruct their teen to do “what’s best.” Instead, a growing adolescent can make more of their own choices and share their journey with you, conflict-free.

Talking to teens about their plans might be a little unfamiliar to some parents, because up until now, parenting was much more hands-on. Younger children need to have parents around to navigate the world around them. It would be foolish to let a 5-year-old determine what they want to focus on in school because they might choose to skip school altogether and play videogames all day!

Teenagers, on the other hand, are much more capable decision-makers and they should be treated as such. If you ask your teen what they would like to spend extra hour doing each day, it is more than possible that they can articulate what they really enjoy. If it’s caring for the family pet, you might have a conversation about ways your teen can volunteer at animal shelters, explore veterinary schools, and so much more!

The Mentor’s Approach

Bill’s approach when mentoring his students centered around asking his students questions about their past and their current trajectory. It gave students an environment to talk about themselves, away from preconceived notions of what others wanted for them. Bill found that this helped students express themselves and their own ideas freely.

It is great that Bill created this environment for his students, but how does a parent go about creating a space for this discussion? What sort of questions should parents look to ask when talking to teens about the future? Bill told me that “every question I asked that really helped students… was some version of, ‘What do I want?’”

It might appear incredibly simple to talk to your teen about what they want. The truth is, talking to teens about this in a meaningful manner is quite difficult. There is a vast ocean of possibility that lies beyond this question, ranging from what they want for dinner to the type of education they desire at college. And finding a way to sort through the chaos of a teen’s life to get these answers won’t happen overnight.

If you want to build trust in your teen’s ability to determine their own future, it is beneficial to practice having conversations that encourage this. There are so many ways to ask teens questions about the future. But when doing so, it is crucial for parents to recognize that they should listen more than they talk. Turning the discussion in the direction of personal interests will give space for teens to openly explore their untapped potential. Hobbies and personal interests, along with subjects they enjoy in school, can all be areas where teens can find long-term interests that may influence what they pursue in the future.

Ideally, parents want to advocate their teens to pursue the genuine interests they have without restricting opportunities. It is so easy for external ideas and influences to affect the path to a teen’s self-discovery. Plus it is impossible for a teen to know exactly what they want to do when they’re just starting to find their place in this world. When parents take a step back and actively listen to their teen’s hopes and dreams, they can make a huge difference in encouraging long-term success and growth of a teenager into an adult.

There’s a lot more in store on the full episode! Bill and I discuss:

  • Creating non-judgmental environments
  • Common conflict traps for parents
  • No-conflict parenting
  • The biggest mistake when talking to teens

I’m so thankful you were able to tune in to our first episode of the Talking to Teens podcast! Thank you to Bill Deresiewicz’s incredible thoughts about parental roles, mentorship, and teen independence. I hope this episode helps make talking to teens about their future easier for parents and teens!

Parenting Scripts

Word-for-word examples of what to say to your teen

1. Encourage your teen to follow their passion

“It’s better to be a successful graphic designer–even if you’re not making a fortune–than an unsuccessful engineer. Because then you’re nowhere and there are going to be lots of other people who are better at engineering than you and you might even find yourself without a job. And then what?”

Bill Deresiewicz

2.  The most important questions to ask any teenager are all variations on the same theme:

(Members Only)

3.  How to help a teenager who is debating about whether or not to try something:

(Members Only)

Workbook Exercises

Step-by-step guides for applying the ideas from this interview

1.  Ask Your Teen About What they Really Want in Life:

One of the experiences that ultimately led Bill to leave his position as an Ivy League professor and write Excellent Sheep was talking to these elite students during his office hours and seeing how directionless many were. Over the years he developed a knack for asking the right questions at the right times. According to Bill, every question he ever asked that really had an impact on a kid was some variation of “what do you want?” or “are you doing what you want?” or “are you getting what you want out of college?” Try to start asking your teenager variations of this question as often as possible. On a piece of paper, jot down 5-10 different questions you could ask your teen that would get them thinking about what they want in life. Try to ask all of them over the next 2 weeks! Some other examples that Bill gives during his interview are: “What do you enjoy studying?” “What do you wish you could study?” “If something seems to be missing here in your college experience what do you think that is?” When you ask your teenager these questions, try to help them explore without imposing an answer on them.

Complete Interview Transcript

Andy: So there’s something going on today that I’ve noticed with a lot of parents and their teenagers that I think is interesting. If your teenager is really successful, is the captain of the football team, is the class president, it makes you look good. I almost want to call it like trophy children. And I think it leads to what you write about in your book, which is hoping that your child will fit into one of these prescribed routes to success. You go to an Ivy League school. You get a good education. You get a good job. A high paying salary, and your idea of a successful kid as a parent might be different from your teenager’s idea of what it would mean to them to be successful.

Andy: And so there might be these two conflicting views of what it means to do something meaningful. How do we reconcile that?

Bill: I think you’ve really touched upon the essential question, which is “What does success mean?” And I think what we need to help our kids do is to figure out for themselves what success means. Maybe it would be better if we didn’t use that word at all, because it has so many connotations. And in some ways it carries with it the very problem that we’re addressing, which is the sense that success means being successful in other people’s eyes. And that starts with your parent’s eyes.

Bill: The problem starts with kids who are taught to do what other people want them to do. Their parents, but not just their parents. I mean, there are all kinds of ways that these expectations get transmitted. They get transmitted at school. They get transmitted through peers. They certainly get transmitted through media and social media. So what we really need to do is to help create kids who are capable of deciding for themselves what matters to them.

Bill: And then it’s not about what choice they make, but how they make the choice. That’s not an easy thing to do. I mean, I think parents think that it’s much easier to just tell your kid what to do. Maybe on some level it is, but it generally leads to very bad outcomes. So we can, and should talk about how you help kids become the kind of person who can make their own choices.

Bill: But that’s the essential thing. And again, I mean whether a parent’s conception of success is getting their kids into an Ivy League school or something else. I mean maybe their hippie Bohemian parents who want their kids to follow in their path. That’s not any better. I live in Portland, there are a lot of parents like that, who I think wouldn’t be very happy if their kid wanted to go to a great college and become a lawyer. But if that’s their path, that’s what they should do.

Andy: That is so interesting. And I think it’s exactly what I was saying before, that we can have different view of what success is for our kids. And it’s like we are trying to force our kid into this idea of success that we have, so that they will be successful in our eyes, so that we can feel like we did well, which is why I’m just calling it trophy kids.

Bill: Yeah I don’t actually think this is such a new story. I think people have been writing about this for a while. I mean really the classic book about this that I encourage everyone to read, it’s called The Drama of the Gifted Child. It’s basically about what you call the trophy kid. About the kid who’s a narcissistic extension of their parents’ expectations, instead of their own person.

Bill: Listen, I think it’s a hard thing for parents if they have a narcissistic personality, to have fears for your kids, to have hopes for your kids, to want to make everything right, and smooth their way in the world. And I think letting go of your child is really hard. I mean it’s the hardest thing that a parent can do, I think.

Bill: But as Julie Lythcott-Haims who wrote this wonderful book called How to Raise an Adult, says the goal of being a parent is to raise an adult. To raise someone who’s autonomous, and an autonomous person may very well make choices that you don’t like. And raising a child who has the strength to defy you if necessary, and certainly to disregard what you expect of them really should be the goal of a parent.

Bill: Parents say that they want their kids to be happy, which is perfectly reasonable. Who among us knows what makes another person happy? As if any of us have discovered the secret to happiness. I mean I think it’s the work of a long life just to figure out what makes you happy. But to be able to say that you know in advance, before a person even is really much of a person, what it is that’s going to make them happy, I think is absurd.

Bill: And I think if we were talking about anybody but your own child, you would realize that it’s absurd. So all you can do is equip them to figure that out for themselves.

Andy: Also, of course then the million dollar question is how do you do that?

Bill: I was a college professor and I’ve talked to a lot of students who were my students, who were students at other schools. I’ve talked to high school students. I am not a parenting expert.

Andy: Sure.

Bill: But I think it’s clear, it seems clear to me, that you start to do it by giving your child autonomy, age appropriate autonomy, as early as they can start to handle that. Starting from when you’re teaching them to tie their shoelaces, to I don’t know, walk down to the end of the block and mail a letter. Whatever is appropriate for that age I think kids should be given as much autonomy as they can handle, so that they learn how to make and exercise choices. And they learn the consequences of their choices, and that sometimes their choices are bad choices, and they’re going to regret their choices. That’s part of life.

Andy: Right.

Bill: There seems to be a big drive among parents today, and I think this is relatively new. I don’t think parents projecting their desires onto their children is new. I think what is relatively new is this sense that the best way to go about things is to protect your child from any kind of risk or failure, which is obviously ridiculous because life is full of risk and failure.

Bill: And what you need to do is help them learn how to handle risk and failure. And the only way to do that is to allow them to take risks, and allow them to fail. And then help them process that failure after it happens, as it inevitably will. Then you build kids who are resilient and have “Grit” which I know is a big buzz-word now and all that jazz.

Andy: Do you put yourself in this situation as a parent where the more you affirm their autonomy to make their own choices, inevitably you’re going to come to a situation where they make a choice that you don’t agree with. So what is it that you’re looking for there? Is it that they made the choice for the right reasons versus the wrong reasons? Or how do you respond?

Bill: I think you can start by not having such specific expectations about the choices that they’re going to make, and be open to not only listening to who your kid actually is, but even more importantly helping your kid listen to who they actually are, and what they actually care about, instead of telling them what to care about.

Andy: Sure.

Bill: And I think you can have expectations in terms of doing your best, trying hard, giving it a real shot, not giving up too easily. Those are all reasonable expectations to have. You want your kid to have a strong character. You want your kid not to just slack off. But again, to help them get into the direction that’s the right direction for them.

Andy: Well in the educational psychology literature, they would call this metacognition. You’re helping them to work through what it is that’s important to me in this situation, and it’s thinking about thinking. Working it through with them. It’s that self awareness.

Bill: Yeah I would think that that involves talking to them about it. Yeah, being self aware. I mean there’s this, obviously we all know about helicopter parents, blah, blah, blah.

Andy: Sure yeah.

Bill: Some of the adolescent psychologist who I’ve found most useful, and I mean they’re the famous ones, Madeline Levine, who wrote The Price of Privilege. William Damon, who wrote The Path to Purpose. They talk about how parents of “High achievers,” These sort of helicopter parents who are very focused on creating “Successful kids.”

Bill: That communication is not a two-way street. And if you ask the children of those parents, they will say, “My parents actually don’t really know what’s going on with me.” It’s like they are intrusive, but they’re not connected. They’re both there and not there at the same time. So talking to your kid, or at your kid, all the time might create an illusion that you’re connected to them, or that you’re having a dialogue with them. But what you need to do is you need to listen. And sometimes listening means asking the right questions.

Bill: I certainly found this as a professor. I mean not one of the things, but the thing that set me on my path to writing about this stuff is that I was the kind of professor who really cared about being a mentor to students, and that didn’t mean telling them what to do. It meant listening to them, but listening can often require eliciting the stuff that you want to listen to. In other words, asking questions, asking the right questions.

Andy: So you’re saying it was something that students would say to you, or?

Bill: I also just had students, any student I had, I would when I first saw them in office hours, and I would always insist that they come and talk. I would just ask them about themselves. And I actually often found that students were not used to being asked about themselves, and didn’t really know how to answer. And I had to make them feel comfortable, and I had to, “Where are you from? What do your parents do?”

Bill: And sometimes it wouldn’t go beyond that, but sometimes they would end up realizing for the first time that they weren’t necessarily feeling a hundred percent about the path they were on. So they didn’t always present that way, but as I talked to them and sort of gave them the permission to think about what they were doing with college, they would sometimes end up that way.

Andy: What is it, do you think, that made students feel okay to open up to you in these situations about what was going on with them?

Bill: Well look, I mean I don’t think there’s anything magical about this. I think that if you show people that you’re interested in what they have to say, and this goes for whether they’re talking about themselves or not. If you ask a question that shows that you’ve been paying attention to what they’re saying. If you listen in a way that shows that you’re interested, and you have to actually be interested, you can’t fake it. People want to tell their stories.

Bill: And then of course, obviously the other thing is to listen and respond in a way that’s not judgmental. And that can also include disarming the judgements that people assume you’re going to have about whatever it is. If it’s high achieving kids, or even not just high achieving kids, people often feel like they’re going to be judged if they reveal that they’re struggling, that they’re having difficulty. And if you create a non-judgmental listening environment, then people are, and not everybody, I mean not every student would have these conversations with me and that’s totally fine, but the ones who needed to were able to.

Bill: And I should say that I think that they were not encountering a lot of teachers in college who were willing to do that. So when they found one who was, they were, I think, eager to engage that.

Andy: You talk about giving them the permission to open up. What do you think it was about you, or about the environment that you created, that made them feel that they had permission to open up and to talk about this stuff?

Bill: Well look, you can only create a non-judgmental environment if you’re actually not judging people. You can’t fake that. I mean, for me I think this was the outcome of a very long process of working on myself, because I grew up in a very judgmental environment, and a very judgmental family, in a very judgmental world. And I of course internalized those judgments, and a very big part of my own development had to do with relieving myself of those self judgements.

Bill: And it was not easy, and it was not quick, but it brought me to a place where I’m able to not be judgmental, because I’ve learned not to judge myself that way. And I have enough life experience to know that most of these judgments of people, of other people also were superficial.

About Bill Dereziewicz

After spending the first half of his career as an English professor at some of the most prestigious universities in America, Bill left academia in 2008 to become a full-time writer. He met fast success with his first book, A Jane Austen Education: How Six Novels Taught Me About Love, Friendship, and the Things That Really Matter.

Bill’s second book, Excellent Sheep, examines the ways in which the most prestigious universities in America fail to prepare students to find meaningful and fulfilling careers after they graduate.

He argues that we may be raising a generation of kids who are incredibly good at doing what is asked of them but who often lack to ability to decide what they want for themselves.

Essays written by Bill have appeared in publications such as The New York Times, The AtlanticHarper’sThe Nation, and The New Republic.

He was awarded the Hiett Prize in the Humanities, the Balakian Citation for Excellence in Reviewing, and a Sydney Award. He has also been nominated for a National Magazine Award three times.

His work has been translated into at least 15 languages and anthologized in more than 30 college readers. He has spoken at over 70 colleges, high schools, and educational groups and has held visiting positions at Bard, Scripps, and Claremont McKenna Colleges.

Click here to visit Bill’s website and here to watch his TED Talk.