Fathers Forum Presents
Parenting Scene 2025
School Heads in Conversation with Jennifer Wallace
April 29, 2025
By Melanie Wells
NYC-PIA Parenting Scene is an open discussion with parents, educators, and thought-leaders to delve into best practices for raising and educating children today.
On April 29, Heads of School Tom Kelly and Robbie Pennoyer, and journalist and author Jennifer Wallace sat down with NYC-PIA board members Oscar Bleetstein and Charles Harkness to discuss parenting in today’s world. How can parents best support their children to excel academically, socially, and personally? The panel discussed a variety of current topics, including anxiety, academic and social pressures, screens, and generally raising good humans.

Dr. Tom Kelly

Robbie Pennoyer

Jennifer Wallace
Speakers
Tom Kelly is the Head of School at Horace Mann School. He is a member of the Upper Division faculty where he has taught both Ethics in School and Society and Advanced Placement Psychology. Beyond the walls of Horace Mann, Dr. Kelly’s serves as a member of the Boards of Directors and advisory boards for multiple schools and organizations to support children and education.
Robbie Pennoyer is the Head of School at Grace Church School. He has been an educator for over 20 years and was ordained to the priesthood in 2016. Outside of his administrative duties, he leads weekly chapel services in the Early Childhood division and teaches classes in the Lower, Middle, and High School, and volunteers associate priest at the Church of Heavenly Rest.
Jennifer Wallace is an award-winning journalist and author of the book Never Enough: When Achievement Pressure Becomes Toxic – and What We Can Do About It. She is a frequent contributor to The Wall Street Journal and The Washington Post and appears on national television to discuss her articles and relevant topics in the news.
Moderators
Oscar Bleetstein, NYC-Parents in Action Board Member
Charles Harkness, NYC-Parents in Action Board Member
Moderator Oscar Bleetstein of NYC-Parents in Action introduced himself and Charles Harkless, Co-President of NYC-PIA. He noted that Parenting Scene provides independent school parents an opportunity to hear from from School Heads and guests on current topics, then introduced the panel: Thomas Kelly, Head of Horace Mann; Robbie Pennoyer, Head of Grace Church School; and noted author and journalist, Jennifer Wallace.
Tom Kelly: What do I see? It’s not easy to be a kid today. Our information-rich world puts tremendous pressures on kids to solve problems, even those we may have created. With pressure comes anxiety, but I see great hope for the future. This life matters, and these kids matter.
Robbie Pennoyer: As both School Head and Episcopal priest, I’ve felt a calling to service, and in deciding where to serve, in church or school, I’ve tried to do both: Grace is my job, but I volunteer at Church of the Heavenly Rest. And what do I see? I see parents, nervous, asking – am I doing enough? Am I doing too much? I see children, nervous, asking – will I be enough? Enough for the privileges and opportunities I’ve been given? Or for my parents and all they’ve done for me? This world presents turbulence, and internal pressures too, in raising these kids. At the same time, the work of tending to school is an immense privilege; it’s a joy to be part of a community with high hopes for the kids. I share your sense of hope, Tom; the students we work with are inspiring, as are our colleagues and families.
Jennifer Wallace: I recall, as a kid, throwing coins into a fountain to make wishes; I wanted to know everything about everything. I became a journalist, so I could hear and learn how people experience the world. I’m a parent of three teens who attended our independent schools, and I’ve noticed how different their childhood was from mine. In my youth, achievement mattered but it didn’t define my childhood the way it does for many kids today.
In 2019 I published an article for The Washington Post on studies looking at which children were most at risk for negative outcomes: the findings listed children of incarcerated parents; children living in poverty; children in foster care; children of recent immigrants; and, a new at-risk group, children attending high-achieving schools, public and private. These kids are two to six times more likely to suffer clinical levels of anxiety and depression, and two to three times more likely to suffer substance abuse disorder than the average American teen, from excessive pressure to achieve. It doesn’t mean your kids will suffer these problems, but something about their environment is putting them at risk.
This led me to write my book. After speaking with teens around the country, I’d say our narrative – labeling them the Anxious Generation – is not fair, because so are the parents! If you look at the data on youth mental health, you’ll see the same is happening with adults. The kids are canaries in the coal mines, telling us something is broken in our society. We should listen, not label. However, I’m hopeful, inspired by the teens I’ve met and the conversations we’ve had.
Charles Harkness: Anxiety levels have increased over the years: Tom, how are parents dealing with ambiguity? Does increased anxiety come with intolerance for ambiguity?
TK: I think there’s a sense of unknowing, or of feeling ‘less than’ that can drive poor choices or regretful moments among good people. We’re all feeling tension from ambiguity. Parents matter, kids matter – they all need to feel they have something to contribute. Conversations like this one are valuable. Parents are as fearful as the kids sometime – the college process never calms down. I hope schools have the bandwidth to acknowledge parent needs, too. At some point, too, we’ve got to turn the volume down. Ambiguity for kids and adults is producing worry – and life is too short for constant worry.
Oscar Bleetstein: I’m a product of these NYC private schools, as is my son, so, two questions: are we asking our kids to do too much? Are we asking parents to do too much?
JW: There are many reasons childhood is more competitive today, but the story resonating for me is an economic one. In our early years everything was more affordable, with more slack in the system. Parents could be assured that even if kids got B minuses they could replicate their parents’ success. But we’re facing a different reality – millennials are NOT doing as well as their parents. Our kids know this. Look at the price of apartments or at school costs. These kids are paying attention. It’s not a psychological problem, it’s a sociological and economic problem. We and our kids sense fewer and fewer guarantees. Parents are trying to weave a safety net for the kids, and it’s not getting easier – now we have competition from AI. There’s a lot of uncertainty.
RP: We live in a society that treats success as a proxy for worth, so parents feel the need to set up kids for success. Nothing wrong with that, there is good in that. But in your book, Jenny, what I thought was immensely tragic was the divide between parents wanting their kids to believe in their unconditional love, and just not getting that message through. Kids hear static in the message, “You are worthy just as you are,” so that they also hear, “If I don’t get into this school, that team, I’ll let my parents down.” We must ask: how can we help our children feel our unconditional love?
CH: Academics aside, what are top life skills to prepare our kids for life beyond high school?
TK: Inclusiveness. Some will say that’s ‘woke,’ but a sense of belonging, being valued in a group, being able to speak and listen in a group – I can’t think of a bigger gift to give a teen than joy in being with other people, including people who are profoundly different. Our kids are capable – they’re the Navy Seals of academia. Give them the resources, they’ll figure it out.
RP: I think belonging is exactly right – especially a sense of belonging that’s not passive, that doesn’t just happen. We can teach our kids skills to give them a sense of control: How to forgive someone? How to forgive yourself? How to be rigorously kind instead of just ‘nice’? How to have humility? How to acknowledge people who see complex matters differently than you? We want our kids to have the experience of mattering so they can thirst for it later on and build communities of belonging and have joy in belonging. We have a sign in our Kindergarten play area: ‘Stand here if you want someone to play with you.’ Our Kindergarteners learn to scan the room and find ways to help.
JW: I’d echo this, and add: If I were to name a skill I want for my kids it’s ‘mattering.’ Here’s the secret sauce I got from an Ohio school I visited, St. Ignatius. They have a Jesuit motto: ‘Not better THAN others, but better FOR others.’ To backwards-engineer success, teach kids how to matter to others, with chores, in being a good neighbor. I co-founded something the mattering movement: now Harvard is piloting a mattering movement on their campus because many students struggle with a sense of belonging. Find a genuine need in your community, and ask how you can meet it. That’s how you matter. Mattering is a meta-need, encompassing belonging, self-determination, connection, mastery – all these are embodied in it. Show your child both how to matter, and that they do matter.
TK: This is doable – discuss it at family supper. Kids like these would be the kind of kid that anyone would want at their table, on their team.
OB: What percentage of your students rely on outside tutoring and how do you reconcile this with a prevalent no-tutoring push, especially for lower grades?
RP: We surveyed families – we phrased it as, how many of you have tutoring the school did not recommend and does not know about? I’m guessing about 30 percent. We have tutoring built into our high school, through a math center, learning center, and writing center. We hear from families that it does a pretty good job of helping.
TK: We have a policy that began this year: if you’re an employee at Horace Mann you’re not allowed to tutor a current student. You can have a tutor if the school recommends it, and we’ll pay but that’s the only way you can have our employee as tutor. In the lower division it’s usually from a fear of not reading or writing at the level of the class. It’s probably 10-15 percent. Sometimes the parents are the tutors, but parents should parent. If you include parents as tutors it’s 70 percent. If we’re talking about real tutors, it’s 40-50 percent.
OB: Kumon, test prep and tutoring companies are on every corner. On tutoring, Jenny, you write about a scarcity mentality. How do we break out of that?
JW: We can’t convince everybody the pressure is too much. But try to find people who share your values. We tried to make our home a haven from pressure. We instituted, in my son’s senior year, dinners with families aligned with our values, so our kids could hear that. If you feel yourself pulled off course, anchor yourselves with those who share your values.
Q and A From Audience:
Q: How do we speak to our kids about polarizing issues?
TK: I’d flip it and say, listen. If you listen, the greatest gift you can give kids, they’ll tell you how to meet them. If you really listen you’ll know where they want you to begin. Ask yourself to allow time for listening. Find the right moment and listen first.
JW: A concept picking up lately is intellectual humility. I’m a huge fan of it. In my childhood, my dad was intellectually humble with me. He didn’t lecture down at me. Be open to learning from your kids, too. We want relationships with them to last many years.
RP: We have a GCS parent who has a taxonomy of disagreements: we can disagree at the level of taste, the level of opinion, the level of belief, or the level of identity. It’s challenging if people disagree from differing levels, like an opinion landing to challenge someone’s identity. I went to our high school community meeting, post October 7, ready to land a short sermon, but the student leaders of our Jewish and Middle Eastern-North African-Muslim groups spoke first, and said, ‘This is going to be really hard and it’s going to get harder. We’ve decided we’re going to care more about loving each other than about being right.’ So, listen to the kids – they understand how people around them matter, and they understand that cherishing each other’s humanity builds tolerance for passionate disagreement. We have to teach our kids to be comfortable engaging in the muddle, through focus on love.
Q: Regarding phones being harmful: Even the Governor is talking about banning them in public schools. Why are independent schools not taking a lead on this?
TK: A Harvard study says your phone, on or off, is a distraction unless it’s in another room. Kids don’t need this device for school work, but we don’t want kids to be isolated or alone. Phones are part of our lives. Kids must learn to put them away (not down) but it’s a complex issue – research shows the most critical time is after 6 p.m. Kids may have parents on a night shift and need to stay connected. We don’t see phone abuse during the day. A student can tell me at the beginning of class, I’m expecting a call from my mom, then excuse himself, take the call, and come back. It’s part of our lives.
RP: One of the joys of NYC independent schools is that we are different. Each school should approach this in ways that feel right for their values and mission. Phones are never part of JK – 8 at GCS. At our high school building, we have a central stair case that is intentionally inefficient because we think friction is an important part of daily life, but I hate passing a student on the stair and seeing them realize halfway down that it was the Head of School they just snubbed for their phone. I’m not popular with the high school because we ban phones and put them in pouches. There’s an argument that they’ll leave school and not know how to tolerate the distractions of their devices, but we feel that attention is another word for love. We want to equip kids to pay better attention to each other and their time here.
JW: I appreciate the national conversation we’re having on social media, and we should hold companies accountable, but I fear parents just blaming all issues on that. Kids’ problems predated social media. Big Tech saw a need and filled it. The research shows social media is an accelerant and a magnifier. If your child has sleep, distraction, or loneliness issues, they may be using social media in unhelpful ways. But if your child is functioning well, sleeping well, has interests, and does well with school work, then banning social media may hurt. Yes, we should take interest in our kids’ online life. But it’s a more nuanced conversation than the one we’re having right now. Researchers are pushing back on the narrative that social media is THE cause of kids’ problems.
TK: But that doesn’t mean you shouldn’t ask for help. If you’re feeling it’s a disruptor for your child, you can talk to the school. We have to learn to live with the devices, but can ask for help.
Q: What are you seeing that blows your mind, fantastic things you see kids doing, which means the kids will have a bright future?
RP: Children write their own prayers for our weekly chapel. They’re most achingly sincere, like: ‘I hope no one is hungry today’ or ‘I hope no one gets hurt by a poisonous dart frog.’ Our 10th graders do an independent study, asking a question and spending the year answering it. One student asked, ‘how do you solve climate change?’ After a month he was carrying around power tools. Then he started talking about carbon capture. Then he got a grant, and asked to attend a conference in Sweden. He went, and was advised to patent his idea. He took his carbon capture with him to Cal Tech, now he’s helping understand air quality in the aftermath of the LA fires. In your book, one piece that stands out is the value of service – how kids can feel a sense of profound mattering through service. As we help kids discover their beautiful individuality, they can find how the precise person they are is needed, and find their mattering there.
Q: What is research showing in terms of high character outcome in schools religious vs. secular?
JW: It’s not necessarily religion, but a sense of spirituality, of something bigger than ourselves. A self-focused lens on getting my resume, being the head of the team – that can lead to mental health struggles. Being a humanist, religiously or spiritually, with something outside the self, puts struggles into perspective. Face the lens outward – that’s how we have healthy kids. It’s an ethos saying, I’m part of something bigger than myself.
OB: Are you seeing changes in intensity of spirituality in our families?
RP: Yes, there’s some evidence of that. We don’t tell kids what to believe about God, but tell them what it means to be a human being, a creature of dignity and worth. Scientists encounter problems in hard data and ask, why is it that spirituality has a protective value for families? Attention to experience of transcendence is important. I understand that to mean a connection with something more than ourselves. Independent schools seek to do that whether religious or not. Every school has a ‘chaplain’ – perhaps it’s that teacher who helps you perceive something greater than ‘just you.’
JW: An Army study showed mental health struggles. The chaplain started a program to build a spiritual core in every incoming young soldier, defining it as a place to talk about existential questions. College campus crisis is often about struggling with these questions. We used to address this in places of worship, but often now have no place for it. You can show your child how you cope with big questions, and talk about it. This is protective.
TK: Give kids a sense of purpose, of something better. Our schools can provide the bandwidth to have conversations about these things.
Q: If you could give our parents one practical tip, what would it be?
TK: When they’re at their worst, you have to be at your best. Kids learn in a crisis. Teaching takes place when it’s rawest, and most meaningful.
RP: We often believe that what we feel is result of what has happened to us. Be aware of how stories we tell ourselves can shape our emotions. If you buy that when it’s raining you feel bad, you then buy that you have to make it stop raining to feel better. Attend to the stories kids tell themselves, particularly around how you value them.
JW: Underscoring both those solid pieces of advice, I’d say prioritize your own well-being, resilience and support system. You cannot help them if you don’t shore up your own deep, nurturing relationships. Our children’s resilience rests on our own resilience.