I recently caught up with my friend Fleur Hassan-Nahoum, former deputy mayor of Jerusalem, for coffee and a stroll through the Rova (the Old City’s Jewish Quarter). By the time we made it to the rooftop of Aish overlooking the Western Wall and the Temple Mount, we’d covered leadership, aging, and showing up as a woman in spaces that weren’t always designed for us.
What started as having coffee together turned into one of those conversations that reshape how you think. Grab a pen – this is the kind of stuff your soul needs to scribble down.
Getting older is actually your superpower
After the hugest hug and a few sips of coffee, Fleur flat-out told me she is living her best life. “When I turned 50,” she said, “I felt that even if given the choice, I would never go back to being 40 or 30.”
I’ll admit, as someone who used to cry at every birthday since my 20s because I hadn’t achieved all the milestones I had set for myself, I’m finally feeling different in my 40s. I was brought up in the culture obsessed with youth – where women, especially, are made to feel like we’re on a countdown clock. But Fleur’s point is one I’ve come to believe deeply: Confidence comes with experience, and experience only comes with time. There’s no shortcut.
I still get teary on my birthdays, but at least now they are tears of joy. With age, maturity, perspective, and experience, I have come to recognize my accomplishments, struggles, and even seeming shortcomings as part of the tapestry of my life that I accept and embrace. And I no longer want to go backwards. I loved meeting someone who feels the same and can articulate it so confidently.
The real work isn’t about accomplishing everything you set out to do in your 20s: It’s about embracing the woman you never even dreamed you could become. Maybe it’s finally accepting who you actually are and building a life around that truth.
Female leadership isn’t male leadership in heels
This is where the conversation got super interesting.
We both agreed that women don’t need to adopt masculine qualities to lead effectively. It’s instinctual to mimic the characteristics we’ve seen modeled as displays of power, but that’s not the answer. Instead, we should bring our feminine strengths to the front: emotional intelligence, listening, and intuition. “All the new management books and videos tell you that listening is vital,” Fleur said. “That’s a feminine trait we need to utilize more.”
I agree, but I’d push it further. It’s not just that women aren’t using these qualities: It’s that organizations still don’t value them the way they should. Emotional intelligence gets praised in leadership seminars but overlooked in boardrooms. Listening is applauded in theory and ignored in practice when it’s time for promotions.
In a world that often mistakes volume for authority, emotional intelligence isn’t a consolation prize. It’s a strategic advantage. The answer isn’t for women to lead like men: It’s for organizations to recognize that the qualities women bring are exactly what’s been missing.
Jewish history offers a powerful precedent for this kind of leadership. Again and again, women shaped the destiny of the Jewish people not through force or title but through emotional intelligence, intuition, and deep listening. From Miriam sensing when the people needed song and hope, to Devorah leading by wisdom rather than domination, to Esther reading the emotional moment and acting with precision, Jewish women led by understanding people and timing – not by outshouting anyone. Their influence didn’t come from adopting masculine power but from leaning fully into the strengths our tradition has always recognized as transformative.
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“Marriage proposal syndrome” is that thing we do where we work harder than everyone else and wait for recognition to find us. Spoiler: It won’t.
“When men look in the mirror, they see something more than they are,” Fleur said. We finished the thought together: “When women look in the mirror, they see something less than they are.”
I’ve seen this play out countless times in my career. Qualified women wait to be invited to the table, while less prepared colleagues simply pull up a chair. The discomfort of advocating for ourselves feels somehow immodest. But that’s a mistake. Self-advocacy isn’t arrogance when it’s based on self-knowledge and skill.
The sooner we stop apologizing for taking up space, the sooner we actually change what leadership looks like. At the same time, there’s an important Jewish concept: If you chase after honor, it will run away from you. So, it’s a delicate balance between advocating for yourself with confidence and voice, versus bulldozing your way in and trying to grab it. That never works (I’ve learned this the hard way).
Public failure is part of the story
As public women, Fleur and I have both experienced very public losses. For me, after losing student body president in high school (which was soul-crushing), I’ve endured the loss of a million-dollar contract for my signature product line, a few very visible endorsement deals, and had to close my namesake magazine business and personally contact and refund all current subscription holders, to name just a few. Fleur experienced public loss the first time she ran for city office. These are the kinds of losses where everyone is watching, and everyone has an opinion.
Fleur’s approach? Give yourself three days to mourn, listen to Joni Mitchell songs, and then get back up.
Public failure can be paralyzing. But we both agreed that after a brief pity party, we pick ourselves up (with the help of our hubbies, our biggest fans), dust ourselves off, and try again. Better to try and fall than to spend your life wondering what might have happened if you’d taken the chance.
So, we talked about aging into confidence, leading like women instead of imitating men, advocating for ourselves without apology, and getting back up when the whole world watches us fall.
By the time we left the rooftop, the coffee was long gone, but the conversation wasn’t. Some talks just stay with you. This was one of them.
The writer is a bestselling cookbook author, former TV producer, and global spokesperson and chief communications officer for Aish, a Jewish Orthodox educational organization.