Kendra Wilkinson has opened up about her career struggles, 17 years after moving out of Hugh Hefner’s infamous Playboy Mansion.
The 40-year-old real estate agent, who recently began using a GLP-1 for weight loss, vented about a work slump in a lengthy and candid Instagram caption on Saturday.
She admitted to her three million followers, ‘I don’t feel good. I have to smile like everything is ok when it just isn’t.’
Wilkinson wrote elsewhere in the note, ‘I love real estate and I love people but wow, I’m so beyond heartbroken today with how things are going.’
The former playmate explained that the job is about more than transactions, ‘it’s people,’ and revealed she’s ‘hit a major wall with people.’
Wilkinson, who shares son Hank Jr., 16, and daughter Alijah, 12, with ex-husband Hank Baskett, 43, added, ‘I signed up for real estate because I literally had no work and had to choose a career path after getting a divorce and being alone in the world.’
Kendra Wilkinson is opening up about her career struggles
It comes 17 years after she moved out of Hugh Hefner’s infamous Playboy Mansion; pictured in 2008
Wilkinson, who rose to fame on the E! unscripted series The Girls Next Door, moved into the Playboy Mansion at the tender age of 18.
She relocated from San Diego to Los Angeles to become one of Hefner’s three live-in girlfriends alongside Holly Madison and Bridget Marquardt.
Speaking with Fox News Digital in June 2025, she revealed the sole regret she has about that time in her life: ‘The only thing I can say I regret in my life is not starting my real estate career while I was living at the Playboy Mansion.
‘I was surrounded by everyone – every celebrity, every billionaire, and what was I thinking? But I’m now in real estate, so I’m good.’
In Saturday’s Instagram post, Wilkinson expressed feeling ‘tired’ and ‘lost.’
She pondered, ‘Will I quit because of people? Will I stay in this and rise up? I don’t know and I’m scared. As a single woman [with] 2 amazing kids, I don’t know what to do at this moment in time.’
The blonde pinup began her real estate career when she got her license in 2020 and joined fellow reality star realtor Mauricio Umansky’s The Agency.
A docuseries, dubbed Kendra Sells Hollywood on Discovery+, showcased her struggle as a new agent in the bustling industry. It lasted for two seasons from 2021-2023.
The former playmate explained that her real estate job is about more than transactions, ‘it’s people,’ and revealed she’s ‘hit a major wall with people’
Wilkinson seen on the cover of Playboy in 2009
Wilkinson was one of Hugh Hefner’s three live-in girlfriends alongside Holly Madison and Bridget Marquardt; Hefner and Wilkinson seen in 2006
Along with being a real estate agent in Los Angeles, Wilkinson is also mom to son Hank Jr., 16, and daughter Alijah, 12, who she shares with her ex-husband Hank Baskett, 43
In a recent Q&A shared online, the star answered a fan who asked what happened to her real estate reality show.
‘I have no idea,’ she responded. ‘It just got canceled, just thrown away. I loved doing it. It was really fun and we were getting places.
‘I learned real estate, I’m learning real estate and I wish I could show you where I’m at now. There’s so much to show.’
Days ago she told her Instagram followers that she ‘had a long day of travel, only to get turned down for a listing… Real estate isn’t easy and I sometimes feel like I’m walking in quicksand but it is what it is. Gotta keep moving and grooving right?’
This is not the first time Wilkinson has discussed her hardships in the industry.
In 2024 she announced she was temporarily quitting real estate to focus on her mental health and her children.
‘My relationship with real estate has come to an end at this moment and I’m on to new projects,’ she said online at the time. ‘I’m blessed and thankful for all the support and mentoring I was given. Real estate is hard and I might get back into it again down the line.
‘For now, its a little stressful in my life so I’m focusing on myself and kids and getting my mental health good again so I have the strength to get back in it with a good head.’
