You might know Chelsea Handler from her late night show Chelsea Lately that ran seven years (from 2007-2014) on the E! channel. Even if you didn’t watch her show, you may have been aware she had one from the promo commercials that would play while you were watching your favorite reality television show (hello Kardashians, Girls Next Door, and Dr. 90210—don’t act like you don’t know). This was the case for me. I wasn’t a big fan only because I was a probably a little too young in 2007 to relate to her jokes and content. Plus, as a fan of sleep, I’ve never been able to stay awake for late shows.

I became reacquainted with Chelsea Handler after she went on a year-long sabbatical only to come back to Netflix with a 4-part docu-series called Chelsea Does and now another talk show, done her way, appropriately called Chelsea. And you guys—I can’t get enough. And after listening to Anna Farris (another boss crush) interview Chelsea on her podcast, Unqualified, I was officially crushing. She shared the story of taking a year off to explore the world before she committed to creating another show—this time done her way and on her own terms. If everything about that isn’t boss, I don’t know what is.

Here are some more things I think makes Chelsea Handler so boss:

Chelsea Handler brings out the “realness” in her very famous guests by setting up her show in an authentic way
From having her dog wandering around on set to not sitting behind a desk when she’s interviewing her guests, to busting out the wine, or even inviting her celebrity friends over to dinner—Chelsea is able to highlight her guests for who they are and what they really want to talk about. The interviews are longer than the typical 3 minutes most late night shows give and Chelsea asks curious questions that get to the heart of who they are.

Chelsea Handler is unapologetic and says what she means
Chelsea Handler is not bullshitting around. I think it would be really easy to know where you stand with her at all times. But at the same time, she’s not a bully, overly cynical, or unkind. She’s the kind of boss who asks for what she wants, won’t settle for less, and works hard to make her vision real. I love that Chelsea is aware that she’s not for everyone and is 100% okay with someone not liking her—not because she doesn’t care, but because what someone else thinks of her is none of her business.

Chelsea Handler isn’t afraid to live out loud and be curious about what she doesn’t know
When Chelsea first launched her show, she stated her intention, admitted that she didn’t have it all figured out quite yet, and was open to letting the show evolve into what it was supposed to turn into along the way. This was so incredibly inspiring to me. It is so easy to want your website, your offering, or your business plan to be picture-perfect and bulletproof before launching, but Chelsea launched on a platform like Netflix (!!!) before she was 100% ready! I also get the sense that Chelsea Handler is committed to doing her best, and at the same time, isn’t afraid of sticking her foot in her mouth or saying the wrong thing.

Chelsea Handler has style
This might be a bit silly to say but I love Chelsea’s personal style. She’s been rocking things like high-waisted sequined skirts with worn-in vintage rock t-shirts and she just looks really cool and relatable. She’s not wearing the kinds of things you see other late night hosts wearing. You can tell that her “work” clothes are probably not far off from her “play” clothes.


Who do you have a #bosscrush on right now? Let us know in the comments below!

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Kathleen is the co-host of Being Boss Podcast, helping creative entrepreneurs learn how to run their own creative business while being their most authentic selves. She also co-owns Braid Creative, a business visioning & branding agency for people- and purpose-driven businesses.