Meet the ‘Michael Jordan of babysitting,’ Chelsea Anderson, and her quest to support play

Chelsea Anderson knows playtime. And bedtime. And teeth brushing. And all the things you’d want in an ideal babysitter.

The 33-year-old Denver native is known as the “Michael Jordan of babysitting” a self-bestowed but well-earned title.

“The skills, I think, come from me having a really strong memory of what it was like to be a kid, and I also still deeply relate to kids,” Anderson told PauseRewind’s Elizabeth Stanton. “I love stickers, and I don’t want to brush my teeth either. And I wish that boring things were more fun, and so because I have to make things more fun for myself to do them, like grown-up things, it’s a natural skill to make them more fun for kids, which came in very handy for babysitting. I think I’m also a good storyteller, and I’ve found with kids, if you add a little bit of story to anything, you can make it much more compelling.”

She added, “As far as the title, it is self-appointed. But I have been told by many, if not maybe even all, the kids that I’ve ever babysat that I was their favorite.”

Anderson began babysitting when she was around 12 in her neighborhood and now dispenses tips, tricks, hacks, and ideas on Instagram and TikTok, with over a million followers between the two.

One of her primary passions in supporting parents and children is encouraging imagination, which is why she partnered with Pirate’s Booty for Captain Bob’s Summer Quest, a collection of fun activities designed to inspire creativity, curiosity and family connection. Activities include things like playing dress up, creating a treasure map, and creating coded messages.

“It was such alignment when I heard their idea for the campaign because my whole channel is about providing concrete ways that parents could play right now, or caregivers in general could be babysitters, could be grandparents, and I think it’s such a value add when you don’t tell someone, ‘Hey, just be creative,’” Anderson said. “You give them actual activities to do that do not require a lot of prep, do not require a lot of supplies, and that’s exactly what Captain Bob’s Summer Quest is. Is it’s a million jumping off points that I do believe any family could do tomorrow, and it’s free, which I also love.”

As Anderson explained, “imagination is really the backbone of so many things. Problem solving of imagining a better future, imagining how you want your life to go, and I think some adults think that imagination is something that you either have or you don’t. But after working with hundreds of kids, I know we’re all born with imagination. We all have it, but it’s like a muscle. You have to work it. You can make it stronger, and it can atrophy if you don’t use it for a long time. So I think that’s why it’s so important because it’s really a lifelong skill that we need.”

Ellie Kemper partnered with Pirate’s Booty to encourage a summer’s worth of imaginative play. (Courtesy: Pirate’s Booty)

Anderson is okay with screens (that’s how she makes a living after all) and supports shows like “Bluey.”

“I think there’s a lot of emphasis on play and the parents joining in on what’s silly or interesting, which I think is important because it can be a family thing,” she said of the hit children’s show. “It doesn’t just have to be play for the kids, and I think when parents find that they can add play to even kind of difficult situations. It can even make them fun for everyone. So I like that ‘Bluey’ encourages that.”

She continue, “Besides that, I think tutorials on how to do a craft with stuff you have around your house. Like I love watching those on Instagram. Just like the simple, hey, pick this up, and it really inspires you to kind of set the phone down because what they’re showing you looks so enticing that you want to go do that.”

Anderson has a book coming out next year, titled “Do As I Play,” expanding on her imaginative suggestions and ideas.

“I think that honestly, this Captain Bob’s Summer Quest Guide is like a perfect taster for what my book is all about. It’s stuff that can be implemented immediately. It’s quick instructions. It’s not like opening a board game and you’re like, oh, we have to figure all this out. It’s also stuff that I think works across ages and can be adapted,” she said.

Anderson continued, “I think sometimes parents think, especially when kids are different ages, it’s going to take a lot to keep them all entertained when kids can kind of naturally do that on their own. So my book contains a lot of stuff like that, but in the meantime, you can download this one at pirateswoody.com and it’ll hold you over at least for a little bit.”

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