Raising Boys After 2020: 10 Parenting Practices That Helped Me Stay Connected, Grounded, and Hopeful

I’ll preface this listicle by saying this: I’m a solo mom.

My son’s brother—who spent every other weekend with us before moving in full-time at 15—lost his mother to mental illness when he was just four years old. I could not have raised these beautiful men without the powerful, co-parenting model organically grown by my best friend and me. Our four boys, their friends, and their moms, created a community that to this day is still the most exemplary model of “the village” I could possibly imagine and I remain deeply grateful for that time.

In retrospect, I can see more clearly what actions and behaviors helped me navigate those teenage years—especially when racism, misogyny, homophobia, and right-wing ideologies began knocking at the proverbial front door.

These are the practices I learned, tested, and refined.

1. Listen and listen. And then, listen again.

I spent a lot of time talking—explaining, and teaching. In hindsight, I wish I had listened more.

When I came to this awareness my boys were about 15 and I realized I had to switch up my strategy if I was going to have any resemblance of a relationship with them. As they grew into young men, they needed space to try on ideas, challenge perspectives, debate, and observe their impact. They needed a place where they could say things—sometimes offensive or misinformed—without being shamed or shut down. A place where even if they sounded ignorant or immature, they would still be loved.

Even when their ideas were regurgitations of the toxic masculine that has now become mainstream fodder once again, I kept my mouth shut and said things like:

• “That’s an interesting perspective—tell me more about how you came to believe/think/know this.”

• “I hear your point. I’ve had a really different experience.”  (Do not share said experiences unless curiosity is present or they seem open to listening.)

• “You seem passionate about this—can you give me some examples so I can understand better?”

These types of responses allowed me to gain a more detailed and nuanced understanding of what they were learning and, by staying curious instead of reactive (which is really hard!), I could hear what was underneath: fear, confusion and the fragile emergence of their fledgling identities.

It also helped me prioritize the most harmful rhetoric and allowed me to choose my battles strategically.

2. Consistently reiterate your values

After hearing some of the appalling, offensive, uninformed and historically incorrect utterances from my children, there were moments when I needed to step away, take a breath, or hit a pillow.

Social media is powerfully influential—and nearly impossible to regulate. So I focused on what I could control: clearly and consistently naming and reiterating my values and the values I hold for our family. I repeated them often. I wanted to embed, engrave, and brand them on their little evolving hearts and minds! I’d say things like:

• I believe in equal rights for all people.

• I believe women should be valued for what is in their hearts and minds, not how they look.

• Trans and queer people deserve the same respect, love, and freedom as anyone else.

• Anti-Blackness is real, historical, and must be actively challenged. It must be eradicated entirely at the individual and institutional levels.

• Is that language/behavior loving, respectful and kind? These are our family values and they are important to me.

3. Model thoughtful, reflective language

I said:

• “I’d need to think more deeply about that and learn from others and read what some of the great thinkers of the past have said, or review what we’ve learned from history about that. Would you be open to exploring it together?”

• “I’m feeling defensive and angry by what you’re saying—it feels disrespectful and harmful. I need to take a break, but can we talk about this later?”

• “I don’t know a lot about this topic but it seems really important to you. I’m going to learn more about it so we can discuss it in more depth. It's really important to me that you understand our family history and values and I’d like to put my thoughts together so I can be clear.”

  
  

This approach models intellectual curiosity, emotional awareness, and accountability—all at once.

4. Don’t let racist, sexist, classist, homophobic language go unchecked

Listening does not mean allowing harm.

When something crossed the line, I named it clearly:

• “That language/behavior is harmful and could potentially cause violence.”

• “I don’t allow that kind of language in my home. It’s hurtful and disrespectful and can cause harm to others.” 

• “We can talk about this, but not in a way that disrespects others.”

Consistency matters. Letting something slide—even once—can signal acceptance.

Often, I followed up with context. Many young people simply don’t know the history behind what they’re saying—especially those with historically, privileged identities.

And yes, sometimes I incentivized reading together and learning:Extra screen time. No chores. An hour past curfew. Even cash. 

Whatever works.

5. Keep dialog open and ongoing

Trying to control or eliminate platforms like Discord or social media can be a futile effort. Like sex, drugs, and alcohol—they will find a way to engage. What matters more is staying in conversation so they are more willing to share what they are experiencing.

I asked questions like:

• What are you talking about (on the app)?

• Who are you talking with?

• What do you think about it?

• Is it harmful to anyone or yourself?

• How do you think it impacts others?

The goal wasn’t interrogation. These questions gave them structure when they were experiencing the negative content online. I listened to their answers, tried to stay curious and did my best not to react.

There are no guarantees they will grow out of radical beliefs. But, with consistent parental interaction in an engaging rather than punitive and shaming way (unless they are showing signs of depression, isolation or self harm which requires more support), we all know that being radically different from our parents is an important part of growing up. 

Being annoying, reactive, and angry is normal (for them and us!). Noticing feelings, naming feelings and giving feelings a space to live can allow the feelings to play out without suppression or acting out. Ongoing and intentional dialog creates space for reflection and

6. Check in—and circle back

Growth doesn’t happen in one conversation.

Revisiting moments—language used, ideas expressed—keeps things alive for deeper understanding.

It’s okay to be redundant. In fact, it’s necessary.

7. Trust them—and learn from them

Our kids are growing up in a world vastly different from the one we knew. Access to AI, social media, and the internet are becoming more aggressively available through apps and platforms that creates a dynamic where it's hard to keep up.

Instead of positioning myself as the expert, I invited them to teach me:

• What they’re seeing/hearing online?

• What excites them, what is boring and why?

• Reiterating my “trust and belief in their ability to make good decisions for themselves, their family and the world” —it’s a powerful mantra to embed into their psyche.

Trust matters.

8. Let love be the foundation

Love must be at the heart of everything (pun intended!).

Love isn’t passive—it’s active, intentional, and consistent.

If we name and remind and reiterate and circle back to love, we will install in our son’s a sense of vulnerability and sensitivity that the masculine has currently turned away from.

Love creates the safety needed for vulnerability—and vulnerability is something many boys are taught to suppress.

9. Offer a framework: Share with them the 3 stages of the Hero’s Journey (Joseph Campbell)

I shared the concept of the Hero’s Journey—the idea that life unfolds in stages: Departure, Adventure, Return.

They are preparing for the “departure.” The “adventure” is still ahead and they need tools for what the world will challenge them with. Help them choose their tools and remind them of the prolific impact of curiosity, love and justice. When they “return” they will bring great learning to the village.

10. Be open and present to their shadow

They are struggling to make sense of an often scary, violent and misogynistic world. It's also a world of beauty, love and creativity. Allow for the balance, create a space where they can be unapologetically themselves, the good, bad and ugly.   

Where We Are Now

My sons are men now. They are out in the world, living their adventure. I miss their sweet, curious vulnerability. I rarely glimpse the silly boys that loved to wear capes, traded Pokémon cards, and jumped into my arms when a spider appeared.

My son’s brother has encountered the generational schizophrenia passed down from his mother. He has left us and is now out in the world on his own. Learning to relinquish worry—and the illusion of control over his mental health—has been some of the deepest soul work of my life. I’ve come to understand that “helping is the sunny side of control” (Anne Lamott), and I’ve turned to my spiritual practice to trust and accept that he is on a path that no longer includes me.

This painful process of letting go has strengthened my ability to step back a bit in my other son’s life as he works to find his passion, navigate decisions around college or entrepreneurship, and understand what it truly means to commit to a woman with his whole heart.

Now, when we talk, I see how he has softened and grown. He’s beginning to understand that some of his more unpopular views haven’t served him well—whether in professional spaces or in relationships with women. And slowly, I see our family values reemerging in him—quietly, almost shyly—in the stories he shares about the world he’s navigating. Sometimes he looks at me, those big blue eyes searching for my recognition that he’s come full circle—back to love, back to justice… back home.