Jeff Jacobson

Jeff Jacobson

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Coach 🤝 Author 📚
🙋‍♂️ Human Rights Advocate 🏳️‍🌈

Lover of
Magic 🧙 Halloween 🦇 Jump Rope 🦘 Jeffrey A.

Jacobson, CPCC, PCC, is a professional coach and facilitator with 29 years of experience in the coaching world. He works with clients to manage change, enhance performance, discover cutting-edge solutions, and create sustainable working environments. Prior to coaching and training, Jeff studied Asian culture and language for years throughout East and Southeast Asia and went on to teach Mandarin Ch

07/09/2026

Imagine what becomes possible when boys don't spend their whole lives reining themselves in.

Leaders who can stand shoulder to shoulder despite their differences. Men who don't have to police themselves or each other. Future generations who get to live the full range of what it means to be human.

That's what this series has been pointing toward. Not just naming the problem but imagining what's on the other side of it.

I have read the following book, and highly recommend it if you are interested in this topic:

Terry Real — I Don't Want to Talk About It
Real's brave approach looks at how boys and young men are encouraged to be driven, ambitious, and dominating, but to eschew community-building emotions, supporting others, etc. He also makes an equally compelling argument that girls and young women are taught just the opposite: to downplay their desires for individual success and drive, and to cultivate connectivity and helping others. He then argues that when so many men hit what is often referred to as a mid-life crisis, it can be good news, if treated respectfully, for it signals that all the tricks and tools men used to suppress essential parts of themselves stop working.

The following books are ones I haven't read, but am interested in. Anyone want to join me?

James Gilligan — Violence: Reflections on a National Epidemic
Gilligan's work focuses on shame and how it leads to violence, based on his work as a psych in prison systems.

bell hooks — The Will to Change: Men, Masculinity, and Love
hooks tackles young boys' emotional mutilation as the first victims of the patriarchy, leading to misogyny and the inability to love.

Niobe Way — Deep Secrets
Way asserts that young boys and teenagers are capable of intimate friendships but are socialized away from them, leading to confusion, loneliness, and isolation.

07/07/2026

Nobody designed this system. Nobody sat down and said, let's teach little boys to police themselves and each other before they can even read. It just built up over time. And then we inherited it.

Isabel Wilkerson writes about this in her book, Caste. She talks about inheriting a house with mold and rot in the walls. Nobody built the mold on purpose. But it's there. And you can keep living in it, passing it on to the next generation, breathing it in. Or you can do something about it.

That's where this series has been heading all along: Doing something about it.

07/02/2026

This stuff is hard to hear, but I'd invite you to sit with it for a minute and think back. Were there moments where you were told not to be a baby, not to be a girl, not to act a certain way? And did you push back? Did you say no, I'm going to be exactly who I am no matter what?

Most of us didn't. Most of us contracted. Quietly. Without even realizing it.

I know I did. I policed myself. What I said, how I talked, what I let myself enjoy. And I policed the boys around me too. We all did it to each other.

06/29/2026

By the end of elementary school, most boys have already spent years learning what not to be. Don't need anyone. Don't do the soft things. Don't get too close. Don't like the wrong things. Don't sound like that.

Nobody sat them down and explained the rules. They just absorbed them. And what gets lost in all of that isn't just confidence or emotional range. It's the natural, yet remarkable experience of just being a person.

We're not raising boys. We're restricting them.

06/25/2026

Nobody has to enforce this message for very long. Little boys start doing it themselves. Policing each other. Watching for anyone who steps out of line, even when none of them know where the line actually is.

And everything goes through that filter. Music. Hobbies. How you laugh. The color of your backpack. All of it becomes a question. Is this okay? Is this going to get me in trouble? By the time a boy is old enough to understand what any of this actually means, he's already had years of quiet terror trying to figure it out.

That's the runway this message creates.

06/22/2026

I love conversation, and I've been thinking about what actually makes one good.

Here are three things I keep in mind:

🎉 Be a good host. When you're hosting a party, you're enjoying yourself AND keeping an eye on the room. Is everyone good? Is the energy right? You can do the same thing in a conversation, even while you're fully in it.

🗣️ Pay attention to quantity. Who's talking? Who's gone quiet? Am I taking up too much space? Sometimes the best thing you can do is slow down and ask someone else what they think.

🥊 Keep it above the belt. When things get heated, go after the idea, not the person. You can disagree, debate, push back...without drawing blood.

These are the things that keep a conversation humming for me. What would you add?

06/17/2026

Most people think this message is about sexual orientation. It's not. At least not yet. At that age, it's about something much simpler but still so damaging.

A little boy starts pulling back from his brothers, his friends, the kids he used to just play with, because somewhere there's a line and he doesn't know where it is. So he plays it safe. He starts watching himself. And without anyone saying it directly, he learns that there's something in him he's not supposed to love.

That's a heavy thing to carry before you're old enough to understand why.

06/15/2026

We talk a lot about protecting children from adult content. But nobody talks about this. Telling a child 'don't be gay' is introducing sexuality before they have any concept of what that even means. They're not thinking about love or attraction or marriage. They just like what they like. This message lands way before they can make sense of it and way before it's appropriate.

There's a lot to sit with here, but it's worth discussing.

06/11/2026

"Don't be a girl." Here's where it gets really complicated. Little boys don't understand the rule. They just know there is one. So they start running everything through a filter: Is this too girly? Am I allowed to like this? Art. Asking for help. Being too close to people. All of it gets flagged.

And for heterosexual boys, there's a painful double whammy. The person they fall in love with is also someone they've been taught is less than. You can't build something equal on that foundation. It was never set up to be.

What part of this hit closest to home? I'd love to hear it in the comments.

06/11/2026

In case you missed it, here's a look at what we explored in May's Kind Lab.

We dove into the pathway of Vulnerability. We explored how to stay open and undefended while holding complexity, so we can deepen our connection with clients.

Join us next week for our final Kind Lab of the season (before we break for summer). We will be reviewing the pathways we've covered together. It's the perfect time to step into The Kind Lab.

🗓️ Thursday, June 18, 2026
🕛️ 12:00–1:30pm PT / 3:00–4:30pm ET
💻️ Virtual via Zoom
🔗 https://jeffjacobsoncoaching.notion.site/thekindlab

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