Dear Peter, You're Not A Lost Boy Anymore
The 90’s parenting tagline, “I want my kids to be happy,” created a generation of opportunists. Parents saw their college-educated peers’ earning potential as they climbed corporate ladders and wanted those opportunities to their children. Millennial college attendance soared, with 40% of Millennials earning a college degree compared to Gen X (32%) and Boomers (26%), according to Pew Research.
The “college experience” meant living in a four-year bubble where students had minimal responsibilities, survived overcrowded frat basement parties, and delayed real adulthood with the inevitable full-time job. Seeing our youth through their rearview mirror, our elders would give advice like “Go have fun,” “You have plenty of time,” and “Enjoy it while it lasts.”
Millennial college students lived like the lost boys of Neverland, thinking we had all the time in the world, endless job options, and could be whoever we wanted to be. Before we knew it, remote work made it possible to live anywhere, expanding possibilities. Lifestyle businesses created a cultural movement that freed us from desks and locations. We have options and opportunities aplenty, but are we happier or just more lost? What is the price of endless options?
Peter Pan’s Dilemma. We all know of the famous lost boy who defied growing up. As discussed in Dear Wendy, Wendy represents the nurturing presence that grounds Peter, while his shadow symbolizes all that he is avoiding. His wild imagination and active defiance of norms are endearing qualities, yet create instability. The story lives on in real life. You know Peter Pans who:
Are constantly on the move with travel, adventure, skydiving, and move through hobbies rather quickly
Throw themselves into making more money, value freedom, and nothing will hold them back
Use substances to take themselves out of reality, further avoiding emotions and responsibilities
Have a childlike, endearing essence, or “golden retriever energy,” leaving those around them to hold down the seriousness of life
Ambivalent about their competing desires in valuing their independence, but want a relationship
The internet exposes kernels of truth that validate-and exaggerate- our lived experience. Anecdotal data can be found on dating apps, Instagram reels, and in conversations with friends who share similar stories. There are common lost boy archetypes in 2026 that, in some ways, are not new. There are archetypes such as:
Unsure Lost Boy: The 35-40-year-old, unsure about wants kids and is figuring out dating goals. Not choosing gives the illusion of freedom.
Successful Lost Boy: The one who is chasing money, status, and job importance in hopes of feeling freer. Often has lavish hobbies (usually involves flying a plane), and lives for adventure. Values freedom and money, and doesn’t want his independence encroached on.
Ambivalent Lost Boy: The one who says he straddles wanting security- belonging, relationships, family, grounding- but travels all the time, finds importance in work, and “barely has time.”
The reason why these archetypes skew more male is that women’s biology doesn’t afford time as a luxury to be unsure of the future they want. However, these archetypes aren’t new, don’t exist only in singlehood, nor only to men. For couples, I’ve heard women say, “My husband just does what he wants, when he wants,” or “Maybe one day he’ll grow up.”
In Peter Pan, the story begins with Mr. Darling agitated by having to attend a work event, annoyed at his children’s play, and appearing miserable with life’s demands. This character deeply contrasts Peter, whose boyish charm reminds us to play and chase life’s adventures. When given these two options: Be tied down and miserable, or chase happiness to no end, it makes sense why the ladder is chosen. While male loneliness remains a public health concern, given the rates of addiction, violence, and suicide, I also wonder if the lack of purpose, direction, and male role models who intentionally form quality relationships impacts the crisis we’re seeing. The norms serve a self-centered approach to life, leaving more men and boys feeling lost and lonely. Freedom comes with a hidden cost.
The Neverending Chase. Chasing freedom is like chasing a ghost: you can sort of see what’s there, but you’ll never really catch it. Freedom offers aspirational ideas, but lacks direction. Purpose offers direction, and encourages belonging. Typically, purpose demands we think of others and not only ourselves. This comes with responsibilities, conflict, hard confrontations within ourselves, and it holds much greater value. The act of choosing means you are more involved in your life and get to move towards something greater. If you’re struggling with understanding what you want in life ask this:
What matters to me? How do my actions align with my values?
When’s the last time I thought about someone else’s wants, needs, or did a kind act? What can I do for another person today, tomorrow, this week?
If I were to write the story of my life moving forward how would I want it to go? Write for the next year, 5 years, 10 years. What actions do you need to take today to get there?
What do I need to tolerate to move towards purpose? Purpose is not easy, and it comes with responsibility.
Fulfillment is the path to freedom as it frees us from the chase.
In an upcoming podcast episode, I speak with Vince Benevento, owner of Causeway Collaborative, an agency created for mentorship and therapy for young men, and author of the book Boys Will Be Men: 8 Lessons for the Lost American Male regarding his work with young men. We talk about what how lost looks different today than it did 15-20 years ago, and how to help lost boys and men find their way. The episode comes out Thursday on the How to Relate Podcast.
