Rewatching The Wizard of Oz as a Grown-Ass Woman

I had the power all along. But also? I’m tired.

Some women find spiritual awakening in yoga.

I find emotional clarity watching a teenage girl commit involuntary manslaughter via house and then politely apologize for the inconvenience.

I’m talking, of course, about The Wizard of Oz.

I’ve watched it so many times I could serve as a Dorothy understudy and tell you scenes that give me the same feeling as reading a condescending email from a co-worker named Jeff.

But watching Oz in middle age hits … differently.

When I was a kid, it was about adventure.

In my 30s, it was nostalgia.

Now? It’s a psychological thriller about a woman navigating a dysfunctional, patriarchal society where everyone wants something from her, and she’s supposed to fix it all without complaining.

Sound familiar?

Grab your basket, Toto. We’ve got some Technicolor baggage to unpack.

Dorothy: Patron Saint of Women Who’ve Had Enough

Dorothy Gale is the woman we should all aspire to be amid societal expectations to do it all, have it all, and not lose our s*it when it all hits the fan.

The girl gets snapped at by Aunt Em, threatened by a neighbor with canine homicide, and told she’s overreacting. So what does she do? Packs up her dog, storms out, and lets a tornado handle her exit strategy.

In Oz, she accidentally kills someone (iconic), gets handed literal blood diamonds for shoes, and calmly starts managing a group of under-functioning men through a journey of hostile vegetation, flying primates, and political conflict.

She doesn’t panic.

She pivots.

And she’s 16.

I’m three decades older and had an existential crisis when they discontinued my favorite mascara.

Lesson: Dorothy never asks, “Can I pull this off?” She just pulls it off. Gingham. Pumps. Witch murder. Done. The real magic isn’t in the ruby slippers—it’s in refusing to apologize for taking up space in them.

The Scarecrow, Tin Man, and Cowardly Lion: The Men You’ve Worked With or Dated

Dorothy doesn’t just collect friends on the Yellow Brick Road. She collects the living embodiment of every ex and annoying male coworker you’ve ever survived.

The Scarecrow: Charming and occasionally brilliant, but somehow manages to make every simple task a crisis. He never finishes fixing the sink, can’t figure out PowerPoint, and insists he has big ideas when really he’s just forgotten what he’s doing.

The Tin Man: Exterior? Shiny and appealing. Interior? Emotionally constipated. He nods politely in meetings or at dinner, rarely contributes to the conversation, and when asked how he feels? Requires metaphorical WD-40 just to function.

The Cowardly Lion: All bark, no bite. He’ll promise to handle a problem—home repairs, a big presentation—then disappear to “think about it,” leaving you to fix it yourself. Sweet, loyal in theory, but you know he’s secretly hoping you’ll just take the lead. Again.

Lesson: Dorothy didn’t rescue them. She redirected them. She proves you don’t need perfect people—just the ones willing to walk the road with you.

Glinda: Drama Queen or Friend Who Actually Gets It?

Initially I thought she was a glitter-covered, passive-aggressive drama queen who would notice lipstick on your teeth and fail to tell you. She knows the shoes work from the beginning. She could’ve saved Dorothy three days of trauma, tears, and horticultural warfare. But instead she lets her get kidnapped by monkeys, threatened by trees, and emotionally gaslit by men who smell like hay and rusty metal.

What changed?

I realized Glinda was in her spiritual coach era before Instagram was a thing. She’s the friend every middle-aged woman dreams of: supportive without being suffocating, empowering without enabling, and just snarky enough to keep things entertaining.

She doesn’t lecture, doesn’t care if you’re more bad witch than good witch, and doesn’t judge your questionable life choices. She’s the one who says, “You’ve got this,” and disappears until you need her again—always on your terms.

Lesson: Everyone needs a friend who reminds you that you don’t need anyone else to save you, but is there for the times that you feel like you do.

Bonus points if she gifts you really great shoes.

The Wizard: Patriarchy in Pajamas

That supposedly all-powerful figure who turns out to be a guy in a bathrobe, puffing smoke and mirrors. He’s every boss, ex, or authority figure who talks a big game, expects applause for doing the bare minimum, and has absolutely no idea how to handle a strong woman asking the hard questions. He promises wisdom, power, or solutions. But in the end? He’s just a man hiding behind a curtain, hoping nobody notices he’s full of crap.

Big talk. Big presence. Big disappointment.

And yet, like Dorothy, haven’t we all been in her (ruby red) shoes? We’ve waited for guidance, validation, or a simple answer that never came. But Dorothy doesn’t resent him. She just sees him, weighs her options, and then does the damn thing herself.

Lesson: You don’t need validation—least of all from a man in a robe telling you to believe in yourself.

The Flying Monkeys: Toxic People Who Won’t Go Away

As a kid? They were terrifying. As an adult? Still terrifying. The flying monkeys don’t just visit—they invade. You didn’t invite them, you don’t want them, and yet somehow, they’re everywhere: lurking in family group chats, at work functions, on your feed when you’re doomscrolling at 1 a.m.

They swoop in with unsolicited opinions, condescending comments, and the uncanny ability to remind you that people can be … exhausting. And no matter how many guardrails you set, they somehow find a way around them.

Lesson: Dorothy had it right. Set boundaries. Block. Mute. Delete. Not your circus, not your (flying) monkeys.

There’s No Place Like Home (Where the Snacks Are)

At this age, I mostly have exhaustion, creaky joints, and a craving for lasagna and silence. But as Glinda so sagely points out, “You’ve always had the power, my dear. You’ve had it all along.”

Because rewatching The Wizard of Oz for the 200th time isn’t about magic. It’s about power and recognition. Of how often we, as women, are expected to navigate chaos, emotional labor, and talking trees without complaint—and while wearing heels.

Dorothy didn’t try to defeat the system.

She just walked through it without becoming it.

She stayed kind. She stayed curious. She kept her dog alive and her friends together. She rejected the powerful. She trusted herself. And at the end of it all, when some man in a robe told her what to do, she literally turned away, clicked her heels, and left.

If that’s not the energy I need at this point in my life?

I don’t know what is.