Sherri Shepherd Opens Up & Shares Her View on Regrets, Marriage & Motherhood (Exclusive Interview)

For seven years, Sherri Shepherd was a mainstay on one of the most successful daytime talk shows in television history. Rising from poverty and the ranks of the unknown, she became a recurring sitcom staple before bringing her quick-witted comedic voice to The View. Now that her tenure on the popular talker has reached a bittersweet end, Shepherd was gracious enough to sit down with Tinseltown Mom and open up about marriage, mommy guilt, life lessons learned from her son, and her unexpected departure from The View.

“When it was coming up on the seven year mark, God was like ‘it’s time.’” The sincere talk show host revealed. “And, I was like, ‘excuse me Lord? I can’t hear you…’ So, I gave notice, I left, and there was a lot of turmoil, but it’s interesting that with all of the conflict and turmoil that was going on at The View that God chose to pull me out before all of that.”

The Emmy-winner also discussed the uncertainty she felt about leaving a job that’s not only given her great exposure and stability, but has allowed her the opportunity to do the things that she desires. “It’s scary when you’re used to having a job that’s completely stable, and you know that you have a paycheck coming in every week, and going from that to stepping out on faith. When God told me it was over, and it was time, it was like, ‘now what?’ I got a child; I got school fees to pay; this boy’s got special needs, so he’s got therapy, and I live in New York City. It’s not like I live in Alabama, where the cost of living is low.”

Shepherd knows about instability; the actress made regular appearances on several sitcoms that didn’t make it past year one, and although she’s enjoyed a modicum of success on several primetime laughers, her star-making turn came in 2007 when she joined The View. Shepherd is an actress who understands that a steady gig is the exception, not the rule, and with that in mind, one would think that her decision to leave the popular daytime talk show would bring about misgivings, but Shepherd shares a different view. “Sometimes I look back and I say, ‘Are you sure you know what you’re doing, Lord?’ I know I’m going spiritual, but I want to be where He (God) tells me to be because if you stay in a place too long you get scared and it’s fear. For me, my mantra in life is run toward the very things that you fear because the blessings are on the other side. Do I have any regrets? No. I did seven amazing years. I didn’t leave with any bridges burned; I know I could go back at any time; I left with a good name, and I feel like I’ve gotten everything that I was supposed to have gotten. I’ve contributed everything I was suppose to contribute; I know exactly what I brought to The View, and I’m proud of what I did.”

There were other proud moments Shepherd shared with us, adding she’ll miss those once in a lifetime experiences she had. For example, meeting President Barack Obama on three occasions; sharing a couch with Colin Powell; sitting under Condoleezza Rice, and hobnobbing with all the artists she admired growing up. “Donnie Wahlberg called me the other day, and he was like ‘Jenny (McCarthy) and I were just thinking about you.’ And, I was like ‘is this Donnie Wahlberg from New Kids on the Block?!’ I never knew what I was going to get at The View. That flying by the seat of your pants is what I’m going to miss, and the excitement. When things happen in the world, like what’s happening now in Ferguson, MO and with ISIS, normally I would think ‘I can’t wait to get back on The View to talk about it.’ But, now I have no View. Now, I’m calling my girlfriends and I’m like, ‘Can we just have a Pow Wow?’”

Even though Shepherd has left the highly coveted chair on The View, she isn’t slowing down. Her popular, high-fashion wig collection, “Luxhair Now by Sherri Shepherd” is quickly making a name for itself; she has a New York Times best-selling book, Plan D, that’s getting glowing reviews, and her acting career is in full-swing. She’s presently filming Ride Along 2 with fellow comedian, Kevin Hart, and just wrapped a movie, Finally Famous, with comedic genius, Chris Rock. And beginning September 9th, the multifaceted actress will live out her fantasy when she makes her Broadway debut in Rodgers and Hammerstein’s Cinderella, playing the evil stepmother to Ke Ke Palmer’s title character. “Being on Broadway was always a secret dream of the heart that I’ve never told anyone about.” Ke Ke Palmer will be the first African-American to play the role of Cinderella on Broadway so she’s also part of history in the making.

While true that Shepherd is living out her dream, and rubbing elbows with the biggest names in the world, the compassionate mom makes it clear that her 9-year-old son, Jeffrey, is priority number one. Because Jeffrey was born at 25 weeks, and weighed a mere 1 pound 10 ounces he has developmental delays. “I’m trying to teach Jeffrey to learn the rules, learn the techniques and push through things… He went to his first track meet because I really wanted him to work on his socialization skills with children who didn’t have special needs…”

She explains that loud noises affect his sensory system. “There was a lot of people, a lot of chaos, and he wasn’t handling everything well, and they don’t let the parents on the track…. I could see that he was looking lost, and I’m crying, and he looked at me and screamed, ‘Mommy, I’m scared but I’m going to be brave,’ and I started balling. They shot that gun; he covered his ears and he started running and everybody finished and my son’s still running around the track. He fell, he skinned his knee, but my baby got up and kept running and he went through the finished line and raised his fingers with the victory sign. He said, ‘Mommy, I fell and came in last, but I’m still a winner, right?’ And, that taught me so much about pushing through… not quitting when it gets rough. So, my son, with his delays, really taught me about facing fear.”

When asked what was the hardest part about being a working mom in the entertainment business, the down-to-earth mother said it was guilt. “And, I don’t think it has anything to do with being in entertainment. I think people think it’s a different kind of thing we go through, but my guilt is probably the same guilt as Sarah, who works at Bank of America. It doesn’t matter if you’re working on a movie set or you’re working at The View, mother guilt is the same. Now, it might be a little bit more glamorous because I’m feeling guilty standing next to Kevin Hart… I had to do a stand-up gig in the Bahamas, and I thought Jeffrey’s assembly was at a different time, and he said, ‘mommy it’s today.’ And, he had been working on the song, Frère Jacques for three months, and that’s all he talked about. Do you know, that I cried on the way to the airport? I cried on the plane; I cried with my opening on the stage, and as they were saying, ‘welcome to the stage, she’s been on Dancing with the Stars; she’s been on The View’, I was crying. The only time I didn’t cry was for the hour that I had to make people laugh. But, when I said thank you, goodnight, I went to my room and I cried. That guilt… but I knew doing this gig, I had to pay the bills.”

Even with all the success Shepherd has enjoyed she’s also endured her share of challenges. One of the most difficult being her public divorce with second husband, Lamar Sally, and the unsubstantiated rumors concerning the custodial status of a baby boy born via surrogacy. Legally, Shepherd can’t discuss these matters, but the comedian gets sentimental when asked if she’ll ever marry again. “I think I need to find a chair and sit down and heal. Do I love being married? I love being married. Is it worth being married? It is worth being married. Absolutely, and I hate that my marriage ended, but right now when I think about being married, I think, I have a child; I have a son, and for the very same reason it was hard for me to get married a second time, I don’t want my son to see a man coming in and out of my house…I have my son’s heart in my hands and I cannot allow his heart to be broken. My choices have nothing to do with Jeffrey, yet my choices affect Jeffrey. So, when you say, do you want to be married again, yes I would, but for my son, I need to sit down and heal, and have it be about Jeffrey and Sherri. I don’t want him to be in therapy for a bunch of issues because his momma couldn’t get it together.”

With Shepherd’s effervescent personality and infectious smile, people often misconstrue what’s really going on deep inside. “I think people see that you smile and you make people laugh and they don’t realize that when you go home at the end of the day, you’re just human.  You hurt like everybody else. You have those moments when you’re scared, or you’re just like ‘what am I supposed to do?’ And, my thing is I just trust, and everyday you just get up and you do it… As long as you can get up you got another chance to get it right. People say to me, ‘you’re so strong, you’re so strong,’ but it’s not so much that I’m strong, I just know how to smile through it. I smile through…”