Sherri Shepherd Says Motherhood 'Is My Biggest Insecurity': 'I Always Feel Like I'm Doing It Wrong'

In a talk with PEOPLE Every Day podcast, the comedian revealed she's started casually dating and learned appreciate "what I want and just be happy at not trying to rush anything"

Sherri Shepherd is an open book.

The former The View co-host, 55, appeared on Friday's episode of the PEOPLE Every Day podcast where she talked about her experience being a mom in the spotlight and her excitement about her own new daytime talk show.

When Shepherd first heard the news of the show, she could barely believe it herself. "It was literally like when you win a beauty pageant," she says. "It was something that was such a blessing because it's been a dream of mine since I was a little girl."

And though she'd hoped for a talk show for ages, she thinks it came at exactly the right time: "I wasn't ready when I wanted it. I was ready when the offer was presented to me. So I was ecstatic."

"I'm excited to bring my brand of humor and lightness and fun to the daytime talk show space," she adds.

Sherri Shepherd/Instagram

When she was offered the role, Shepherd had one thing in mind: her son Jeffrey Tarpley Jr., 17. " I was like, 'Can my son get a job at the show?' That's the first thing I thought," she says. "Now this boy is going to be a working and contributing to my household."

Shepherd, who is a single mom, also embraced the hours of the show to allow her more time with her teen. "Doing a daytime talk show is such a great thing for me because we do it and I'm off by a certain time," she says. "Now I still gotta do my research and all of that, but I still can be home."

With that said, the excitement of spending more time together might not be totally mutual. "I don't know if he really will want me at his extracurricular activities," the comedian says, joking that her son has been planning his move away from home pretty much since high schools started. "He is trying to find his independence as a young man and I support that."

Though Shepherd says she sometimes thinks, "Where did all my time with my child go?," she's proud of the young man he's turning out to be.

"He's got a very dry sense of humor, he's funny as all get up and he's a compassionate person," she said. "[With] boys it's raising them to be respectful and to be compassionate. Those are the qualities that I want."

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Parenting for Shepherd, like most parents, has been far from easy. "Being a mother is the biggest accomplishment that I've ever had in my life," she says. "It's also my biggest insecurity because I always feel like I'm doing it wrong."

But she hopes that following her own dreams will encourage Jeffrey to do the same: "I'm hoping that my son will see that I am doing what I love and then he will pursue his passion because he sees that his mom is doing it. And I try not to take on that guilt."

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Fellow comics Niecy Nash and Kym Whitley, among others in her life, have helped her work through the "mom guilt" she experiences, she says: "They're my village of people that I go to for advice that I go to when I don't feel like I am everything that Jeffrey needs me to be ... I think creating a village is really important."

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And as for her own life as Jeffrey looks to leave the nest? Shepherd says she has "started dating" with the intention of doing it for fun, as opposed to the serious relationships she's been in the past.

"I wanted to date to see what it felt like to just somebody take you out and treat you to dinner and you laugh and then you can say it was great, and move on," she says. "This is my year of saying yes. So if you wanna go out, as long as you ain't no serial killer, let's go out and have a good time."

Dating has also given Shepherd a newfound appreciation for herself. "It has really allowed me to appreciate men, to really know what I want, and just be happy at not trying to rush anything."

For now, she's enjoying her time with her kid, especially with Mother's Day on the horizon: "He's gonna make me breakfast and we're gonna go to the beach and we're gonna sit at the beach together and watch the because I love being at the beach," Shepherd says, choking up a bit. "That's my favorite place and it's just gonna be Jeffrey and me."