The star, whose new Netflix talk show Chelsea debuts on May 11, told PEOPLE and Entertainment Weekly Editorial Director Jess Cagle recently that she isn't always sure of herself.
Brian Bowen Smith
Handler, 41, also admitted, "I don't think I'm a good host. I'm not a good host. I'm terrible at hosting. That's my problem. I can talk and have interviews, but I'm not a host in that sense."
Handler also opened up to Cagle about another deeply personal topic: the unexpected death of her brother, Chet, when she was just 9 years old.
"Seeing your parents fall apart is really rough," she said. "I wouldn't wish it on anybody."
"In hindsight it really kept us as a tight-knit group, because it was so tragic and awful," she says. "Ultimately, it was kind of a beautiful gift because we all value each other so much."
Of her five older siblings, she says, "They took care of me. They took me everywhere, and I was a little rascal. They'd go to their high school parties and bring me because I had this attitude. I was their little entertainment wind-up doll."
Courtesy Chelsea Handler
"We're going to open the show a lot like we open the documentaries where it just kind of fades up and you're coming in on a conversation," Handler says. "Everything's coming in halfway through a conversation. A lot of the things I loved about the documentaries we were able to implement into this show, like the dinner parties. "
For more on The Jess Cagle Interview with Chelsea Handler, check out People.com all week and pick up this week's print issue of PEOPLE, on newsstands Friday
"I said, 'I can't do the same thing – have the same five-minute, 10-minute, 15-minute intervals of the show. It's got to be different and not regimented."
She added that "it's got to have a fluid feeling so that some nights you turn it on and maybe we're talking about one topic for the whole 30 minutes, and then the next night we have a guest and we have a musical performance."
"It just can't be regimented," she reiterated. "I'm not good with routine."
Chelsea will debut on Netflix every Wednesday, Thursday and Friday beginning May 11.