This morning I accompanied my niece to a workshop on entrepreneurship. She walked in with her notebook and nerves. I stayed outside with my book and my firm belief in boundaries.
Within minutes, I was approached by two well-meaning adults who looked at me as if I had forgotten my shoes or left the child in the parking lot.
“You’re not going in?”
“Wouldn’t she feel more confident with you beside her?”
I declined. First with a smile, then with the kind of practiced patience only a seasoned caregiver can manage.
What I didn’t say—but deeply wanted to—was this: She needs to build her own confidence, not borrow mine. And I need to know that when she walks into a room, she believes she belongs there without me having to hold her hand.
I’ll take her to the doorstep. But she steps in. She stumbles, asks questions, makes her own notes. She learns. Then she comes back and knows, without a doubt, that I’m here. Not in the room, but with her all the same.
Ironically, this workshop was on entrepreneurship—the art of taking initiative, managing risk, learning from failure, and creating value. And yet the behaviour of the outreach team hosting it was anything but entrepreneurial. There was no curiosity, no tolerance for alternative approaches, no openness to a different model of support.
Which got me thinking—parenting and caregiving might just be the most under-acknowledged form of entrepreneurship. A form where people need the quiet kind of support that makes people nervous. And when people are nervous, they judge.
It’s not new to me. I grew up watching my mother face it. She had a certain way of raising us—calm, reflective, not prone to panic or performative parenting. And she was judged for it constantly.
I remember her coming home, seething after a relative had given her unsolicited advice. “You should do this,” “Why aren’t you more strict?” or the dreaded, “If they were my kids…” She would vent for hours, then fall silent, reliving the indignity long after the words had passed.
She hated it—not just the advice, but the assumption behind it. That someone else had understood her children, her choices, better than she had. That they had permission to instruct her on how to mother.
Now, decades later, I feel that same fire rise when I’m politely cornered by someone else’s certainty about my way of caregiving.
Because here’s the thing: We parents/caregivers know how easily intent can be misunderstood. We’ve all had moments twisted, gestures misread, love mistaken for neglect or fuss mistaken for care. And yet, we turn around and do it to each other with remarkable efficiency.
And yet we cling to the idea of the “parenting community.”
In theory, it’s a noble idea. In practice, it often resembles an unlicensed AA group—except instead of alcohol, the addiction is control. We gather to confess our frustrations, share our latest failures, whisper our fears. And yes, there’s comfort in the chorus of “Same here,” “Mine too,” and “You’re not alone.”
But once that circle ends, we sometimes turn on each other—subtly, with raised eyebrows and veiled questions. A competition wrapped in empathy. You’re struggling? Me too—but look how well I’m handling it.
We’re desperate to know we’re not the only ones flailing—but equally desperate not to look like the one flailing the most.
It’s a curious contradiction. We crave solidarity, but often weaponize similarity. If my child throws a tantrum, and yours doesn’t, am I failing? If you hover, and I don’t, am I cold? If I stay outside the room and your instinct is to go in, must one of us be wrong?
Why is it so hard to allow another parent the benefit of context?
I don’t want to do to others what I saw done to my mother—or what’s been done to me. I want to step out of the judgment loop, the “I-know-best” carousel that seems to run endlessly in parenting circles.
I want to raise a child who questions everything—including me. Who doesn’t accept second hand opinions as fact. Who knows that curiosity isn’t disrespect, and debate isn’t rebellion.
Parenting, or being any kind of consistent adult presence in a child’s life, is a daily bet placed on a very long game. There’s no user manual, no clear ROI, and plenty of quiet failures. Every day brings the question: Did I do the right thing?
Many days, we don’t. Some days, we do. The failures are loud. The successes are whisper-quiet.
The toddler doesn’t say, Thank you for letting me scream for ten minutes without giving in.
The 10-year-old isn’t going to write you a note saying, Thanks for holding the line on screen time.
And the teenager? Well, if they acknowledge your existence without rolling their eyes, it’s practically a standing ovation.
Rebellion is the dominant dialect of youth. And as caregivers, we wait—often decades—before we hear the echo of our effort. If we’re lucky, we see the success not through their words, but their choices. We see it when they become kind. When they hold space for someone else. When they choose integrity over ease.
By then, we’ve usually become grandparents. Or ghosts.
Still, we try. And try again. Because we didn’t ask for the child. We asked for the relationship.
That’s what struck me most today—not just as someone who chose not to walk into that workshop, but as someone who chose to walk into my niece’s life.
I’m not her parent. I’m her aunt. I made the choice to be involved. I wasn’t asked. She didn’t sign a consent form. She’s dealing with my presence as much as I’m shaping it. That’s the strange beauty of caregiving—it’s built on a mutual unfolding. We don’t choose the person; we choose the bond. The meaning of that bond reveals itself over time.
And like all true entrepreneurship, it involves risk, effort, ambiguity, and the occasional sense of being in way over your head.
So no, I didn’t go into the workshop. I waited outside. She walked in on her own. She came out brighter, louder, full of questions. She crossed that space herself. But she knew exactly where I was.
Right where I said I’d be.
At the doorstep. Not beyond.
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