Revisited – True Fiction Favorites: A Case Study on Anna Delvey/Anna Sorokin

In this revisited episode of the True Fiction Project, I speak with Diann Wingert, psychotherapist turned business mindset coach and the host of the Driven Woman Podcast. 

Why are people so fascinated by Anna Delvey/Anna Sorokin, who bilked her way through the New York social scene? As a psychotherapist, Diann was particularly intrigued by her motivation – what drove this seemingly successful young woman to engage in such fraudulent behavior? Interestingly, much of Anna’s motivation can be traced back to her childhood. She was always a bright and imaginative child, but she was also drawn to the finer things in life. This combination of factors likely contributed to her later sense of entitlement and her willingness to take whatever she felt she deserved – even if it meant breaking the law.

Tune in as Diann Wingert explains where Anna’s personality pathology starts to develop, personality of entrepreneurs vs signs of narcissism, and the real reason audiences like stories where humans are missing morals. Later in the episode, we hear a fictional story written by Parker James.

Shifting Weight – A Fictional Story in Print 



  • [03:42] Anna Sorokin’s personality and what was really the driving force behind her?
  • [10:23] Creative people need to go where creative things are happening. For Anna, that was Paris.
  • [14:00] Diann Wingert explains Anna’s personality pathology starts to develop in New York
  • [18:40] Someone called Anna a sociopath and she considered it a compliment. 
  • [24:00] Why do we like stories where humans are missing morals?
  • [31:55] Diann talks about age and maturity
  • [34:40] The common ambition shaming of women 
  • [38:18] FICTION: Shifting Weight written by Parker James
  • [40:34] Justin James sauntered into the house
  • [41:50] I need you to wire me $2,000, please



  • Celebrities who came from humble beginnings knew that their hometown was not where they belonged
  • Most people will continue to live a lifestyle and have very close expectations to what they grew up 
  • The flaw in her psychological makeup is that she didn’t have empathy for the people that she was taking advantage of 
  • People are drawn to flawed characters because every one of us has the potential to be arrogant, manipulative, to be an opportunist, to be dishonest. Although we like to watch them fall so we can be reminded that we in fact are not, reassuring us of our own morality
  • Diann Wingert talks about age and maturity. Does it come as a result of being incarcerated or as she aged and matured 
  • We admire, applaud, support, and encourage ambition in males. But girls are supposed to be modest. We are supposed to accept what is offered to women. But men do. So why is this?



Diann Wingert is a psychotherapist turned business mindset coach who serves the growing number of female solopreneurs who struggle with self-employment after successful corporate or nonprofit careers by helping them identify and eliminate the obstacles that hold them back so they can embrace their full potential for success. She is an expert in the mental health challenges of entrepreneurship and how ADHD presents in adult women and entrepreneurs.


Diann Wingert is a psychotherapist turned business mindset coach who serves the growing number of female solopreneurs.





HXGO – New Delhi Song 

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