How would your relationships be different if you could experience the world from the other side of the gender divide, and understand how a man or woman (whichever you are not) feels and experiences life? Would it bring more compassion for the things that irritate you?
Today’s guest has something very few people can offer: a real life perspective on living as both a woman and a man.
Since Jason Hill transitioned he has experienced radical shifts in how people perceive him, how he’s treated professionally, how much emotional vulnerability feels accessible, how his sex drive changed, and even how much physical affection is available to him.
In this fascinating conversation, we explore what those experiences reveal about men, women, love, sex, emotional intelligence, and the invisible expectations we place on each other.
We talk about:
- How Jason has been treated as more intelligent and receiving more professional opportunities as a man
- The pressures men can carry with the expectations to provide, earn, protect, and prove their worth
- Why having male privilege doesn’t mean life is always easy
- What women usually don’t see about men’s vulnerability to violence, rejection, and emotional isolation
- Why so many men are touch-starved, and how sex can become one of the only socially acceptable forms of affection
- The surprising ways we’re socialized differently as men and women
- Why emotional intelligence can be learned
- How to make the goal of conversations understanding what is actually happening for another person, rather than winning the argument
- What greater empathy across genders could make possible in our relationships
Jason’s story invites us to hold multiple truths at the same time: men benefit from systems of privilege and still experience profound pain, loneliness, objectification, and pressure. Women suffer from discrimination and often have assumptions about men that can make it harder for men to feel loved and understood.
The more we’re willing to get curious about those contradictions, the more possibility we have for love.
Because emotional intelligence isn’t about becoming better at arguing your side. It’s about becoming better at seeing the person in front of you.
Links:
Connect with Jason
Connect with Shana James
Best love and sex of your life quiz
Get a Free copy of Honest Sex: A Passionate Path to Deepen Connection and Keep Relationships Alive.
Whether you’re dating or in a relationship it shows you how to take the self-doubt, struggle and shame out of your love life.
If you’re looking for love:
Take this quiz: Find Love With More Ease and Joy
If you’re dating or in a relationship and you want more connection or intimacy:
Take this quiz: What Keeps You From Having the Best Love and Sex of Your Life?
Each quiz only takes a few minutes, and give you a personalized report of how you can have more of the love and intimacy you want.
Bio:
Jason Hill helps men stop blowing up the relationships in their lives.
For years, Jason delivered gender, sexuality, and workplace culture training for HR teams and employees at organizations including Disney, Sony, AEG, Trader Joe’s, Starbucks, UCLA, and On Board Experiential.
His trainings addressed gender equality, sexual harassment, LGBTQ+ competency, and more ethical hiring practices for marginalized groups. But the deeper Jason went into this work, the more he noticed a critical gap.
Organizations were talking about how women and marginalized people experienced the workplace. Very few were talking directly to men about how they had been conditioned to communicate, respond to conflict, exercise power, or protect themselves when they felt criticized, embarrassed, rejected, or disrespected.
Men were expected to know how to build trust, navigate difficult conversations, repair misunderstandings, and lead people who experienced the world differently than they did. But most had never been taught how.
Instead, many had been socialized to hide uncertainty, suppress vulnerable emotions, avoid asking for help, become defensive when challenged, and treat conflict as something to win. These patterns did not stay inside individual men. They shaped entire teams, management cultures, and prevailing definitions of “professionalism.”
Many workplace conflicts were not caused by a lack of intelligence or good intentions. They were caused by relational skill gaps nobody had named, combined with protective patterns nobody knew how to interrupt.
Jason launched Beyond The Man Box to directly address that missing piece.
For the past five years, Jason has also coached men one-on-one, helping them understand the reactions that damage their relationships at work, at home, and within themselves. His work helps men recognize what happens inside them before they become defensive, aggressive, controlling, withdrawn, or emotionally unavailable, then gives them practical tools to respond differently.
Through Beyond The Man Box, Jason is turning his experience in organizational training, advocacy, enterprise sales, and one-on-one coaching into a practical methodology for understanding the connection between male socialization, relational intelligence, conflict, leadership, and trust.
Previously Published on Shana James Coaching
