Chelsea Handler's Costly Renovation Mistake, Career Regrets, and New Ventures at 50

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Chelsea Handler has been commanding the spotlight recently, balancing major career moves, candid interviews, and a dash of tabloid intrigue. The biggest news making headlines this week involves Handler openly discussing her most regrettable financial decision—she told MarketWatch her biggest money mistake was shrinking her five-bedroom Bel-Air home down to two bedrooms specifically so family wouldn't overstay their welcome. She admitted that not only did the renovation make the house less valuable, but it also forced her to spend even more when she eventually had to revert the change before selling. Handler bought the property back in 2010 and finally sold it in 2021 for over 10 million dollars, but now confesses the entire ordeal was a pricey lesson in familial boundaries and real estate timing. MarketWatch and realtor.com both highlighted that she currently lives in a lavish estate in Mandeville Canyon, purchased from Cheryl Hines, boasting five bedrooms and a chic California vibe that matches her evolving tastes.

This revelation coincided with a reflective moment about her career choices. In a recent appearance on Mike Birbiglia's Working It Out podcast, Handler admitted that her six-year hiatus from standup following the end of Chelsea Lately was a big mistake. She said she could have worked through her issues without stepping away and lamented the challenge of having to rebuild her audience afterward.

Public appearances are picking up as well, with Handler headlining a much-anticipated standup show at The Chelsea inside The Cosmopolitan of Las Vegas on August 30—ticket buzz suggests fans are eager for her return to the stage. Her year has also been busy with the release of her best-selling book, I'll Have What She's Having, and a new Netflix standup special titled Chelsea Handler The Feeling, showing that at 50, she's only gaining momentum.

Handler is expanding her brand yet again with a foray into the beverage industry, launching a boozy lemonade in partnership with Owl's Brew, touting it in energetic TikTok posts and citing her childhood lemonade stand roots as inspiration. Interviews in MarketWatch, QUE.com, and others are framing her not only as a comedian but also as a savvy real estate enthusiast and investor, offering advice to wannabe moguls and emphasizing the importance of evolving at any age.

On the gossip front, social media was abuzz after Handler was photographed leaving the Vanity Fair Oscar party arm-in-arm with actor Ralph Fiennes, prompting romantic rumors. Entertainment Tonight ran with the story before Handler quickly clarified nothing romantic transpired—they were part of a group, she doesn’t consider Fiennes marriage material, and she is already seeing someone else, a mystery man she’s been dating for nine months. Handler further underscored her commitment-averse philosophy, noting to PEOPLE and others that she’s more of a purpose person than a relationship person.

Handler has been active and unfiltered on social media, mixing promo for her standup and business ventures with irreverent humor about aging, family, and her latest real estate antics. Her charm and candor are clearly fueling another career renaissance as she straddles the worlds of comedy, business, and lifestyle stardom with absolute confidence.

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