It was 10:30 on a Thursday morning, two Decembers ago, and Jennifer Hill was dead sober. A friend in Lisbon, Keith Hodges, had offered her a session as a thank you for the connections she is forever giving away. She had carried the same weight since she was five: a recurring dream that she had to save humanity, and kept failing. He began to intone and chant, and space and time fell away. The first thing she heard was giggling, the gentlest laughter she had ever heard, and it was the universe, and the universe was telling her there was nothing and no one to save.
Then it gave her a mirror. In it, she did not see her own reflection. She saw every human she had ever met or would ever meet, reflected back as herself.
“then your only purpose is to look for and listen for the spark of light in every human you meet and reflect it back to them when they’ve forgotten”
This is the work Jennifer Hill does now. People call her the fairy godmother of human connections, and she gives away thousands of connections a year the way other people give directions. She founded the Jen Hill Tribe, a global community of several hundred entrepreneurs, thought leaders and creators, and OptiMatch, a matching platform built to help people find one another across the world. She keeps 180 tools she developed for herself, and she has made every one of them public. Watch her for an hour and you understand what she means: her intuition lights up like a net of small fires, and she feels the invisible thread of connection that runs through every human life.
The blank book, and the girl who tried to earn her way in
Jennifer describes childhood as being handed a book on how to be a human and opening it to find every page blank inside, while everyone around her seemed to have one that was filled in. She tried to earn her way to love by formula: get straight A’s, do the right thing at the right time, and love would arrive. Both her parents were working two jobs and drinking, and she was largely raising her younger sister. She speaks of them with love now. She and her mother talk every day, and her mother has stopped drinking for the most part, which Jennifer calls the happiest she has ever seen her. Her father passed away a few years ago.
The good-girl formula did not earn her the belonging she was after, so she went, in her phrase, to the dark side. There was a long, dark stretch through her late teens and early twenties that she has spoken about openly and writes about in her book. She came close to not surviving it. Around 2018, an autism diagnosis arrived and finally explained to her how differently her own brain had always worked.
The woman who called her Godzilla
She was about twenty-three, dragged to a three-day personal development class by her boyfriend, wearing a t-shirt that said Von Bitch to make it perfectly clear who she was and why she was there. She spent the weekend, by her own account, sitting in self-righteousness, a “judgy bunny” toward everybody getting their breakthroughs. At the close, one of the facilitators asked if she could be really straight with her. What she held up was a mirror Jennifer had spent years avoiding.
“You are one of the most powerful women I’ve ever met in my life, except you know what? You’re like Godzilla with a huge tail swishing behind you, knocking down buildings wherever you go. Except guess what? Those aren’t buildings. Those are people whose lives you’re destroying.”
The next morning she went into her office team meeting and asked whether she had ever been mean or condescending to any of them. The room went silent, and then somebody laughed and told her she was the most condescending person they had ever met and they had no idea how she was so successful. She marks that as the moment her life changed, from before she realised she was an asshole to after, and she has been in the twenty-year transformation ever since. Her forthcoming book is called The Recovering Asshole. Its real subject is gentler than its title: that we are hardest of all on ourselves first.
“until we can first repair that relationship with self, we’re never going to be able to have deep intimacy with others”
What she found when she finally stopped
About fourteen years ago, three influences arrived close together and began to genuinely change how she lived: transcendental meditation, Kabbalah, and a coach who taught her to regulate her nervous system. She had had the dream life before that, three homes, matching cars, two golf memberships, and felt her soul shrivelling inside it. Now she spends two hours a day in prayer, meditation and reflection, and she means it literally. Every night she does what she calls spiritual accounting, asking how she could have lived the day better, what caused pain, what she is proud of, what she is grateful for. It is a nightly mirror she holds up to herself with tenderness rather than blame. She and her husband ask each other three questions before sleep. Whether they did enough spiritual change that day. Whether they would be happy if today were their last. And, gently, whether one caused the other pain.
What she has built, and who it is for
The Jen Hill Tribe began as a birthday gift. A friend built her a WhatsApp group and dropped in thirty-six people she loved, to thank her for referrals. It has grown to several hundred members across Canada, Australia, Bali, the UK, Europe and Brazil, with twice-monthly socials and member-led trainings on everything from meta ads to building an app in fifteen minutes. OptiMatch grew from her intuition made into an algorithm, work she built for five years with her teacher and business partner Julian Adler, who died the very night their acquisition offer arrived. She carries his memory into the platform still. Inside the matching she uses a fruit typology, lychee, apple, mango, pear, for how people are motivated, and a “plus two” method for reading your own energy after a conversation. Underneath the tools is one finding from twenty years of connecting people: when two people are motivated adversely, they speak the same language and still cannot hear each other.
What her life is asking us to see
Katherine noticed something and named it. She had watched Jennifer’s mind and its extraordinary reach, and she said she did not sense a stitch of fear, and asked whether Jennifer knew fear at all. Jennifer thanked her, and said no one had ever asked her that before.
What followed was the account of a woman who has sat with the fear of death so many mornings that it has loosened its grip, and who now, when a plane shudders, notices she is at peace. Jennifer went right to the crux of her own transformation in the first minutes of the conversation. Katherine heard the arc she listens for in every life the moment Jennifer named the shift from before she realised she was an asshole to after: a collapse, and then the long, unfinished work of waking up, again and again, never in a straight line.
Both women, it turned out, had been meant to be in the Middle East as the conflict broke out, and both were turned back, one by a friend, one by an inner knowing. Jennifer read the wish she had written the day before her birthday. If peace is to ever exist in the world, she wrote, it first must exist within us. Katherine met it with her own words for the same truth: inner harmony is the pathway to outer harmony.
That is the whole of it. The magical mirror was never only Jennifer’s vision. It is the offer she makes to everyone she meets: that you carry a spark of light you may have forgotten, and that the peace you long for out in the world begins in the only place you have any authority, your own heart.
This is the kind of leadership our moment requires.
It is the kind of leadership Sincerely was built to honour.
A few hours with Jennifer
Settle in for a little over an hour with Jennifer and Katherine. Jennifer’s mind moves quickly, and it will surprise you into laughing, then it slows near the end when she reads aloud the wish she wrote the day before her birthday, that if peace is ever to exist in the world it first must exist within us. You may want to hear that part twice.
There is no hurry. The library is always here.
The lines Jennifer left me carrying
“your only purpose is to look for and listen for the spark of light in every human you meet and reflect it back to them when they’ve forgotten”
“instead of seeing my own reflection, I saw the reflection of every human I had ever met or would ever meet reflected as myself”
“If peace is to ever exist in the world, it first must exist within us.”
About Jennifer Hill
Jennifer Hill, known to many as J-Hill, is the founder of the Jen Hill Tribe, a global community of hundreds of entrepreneurs, thought leaders and creators, and of OptiMatch, a platform that connects people around the world by reading how they are motivated and pairing them accordingly. Over a career that began in recruiting, she has connected an enormous number of people, and she runs twice-monthly socials and member-led trainings across her community. She keeps 180 self-developed tools for self-regulation and inner peace, and shares them publicly. She has helped build schools in Nepal and Senegal, and her book, The Recovering Asshole, is forthcoming. She lives in Lisbon.
Find Jennifer: jenhilltribe.com · om.app/survey · LinkedIn · The Recovering Asshole (forthcoming)
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