Podcast Summary: The Tamsen Show

Episode: How to Do It Scared (and Still Succeed) with Sherri Shepherd
Host: Tamsen Fadal
Guest: Sherri Shepherd
Release Date: November 19, 2025

Episode Overview

In this inspiring and deeply personal conversation, Emmy-winning journalist Tamsen Fadal sits down with comedian, actress, author, and talk show host Sherri Shepherd. The discussion centers on the theme of “doing it scared,” as Sherri recounts her tumultuous journey from hardship to Hollywood stardom—offering wisdom on grit, faith, resilience, and the importance of a supportive circle. The episode is a heartfelt road map for anyone facing self-doubt, reinvention, or daunting life changes, especially women navigating midlife challenges.

Key Discussion Points and Insights

1. The Hollywood Walk of Fame: Full Circle Moment

• Sherri reflects on receiving her star ([03:27]):
  • Surreal sense of legacy and gratitude, quipping about being “number 2,882” to get a star.
  • The star stands on the street she once lived on while struggling in LA.
  • “I just knew the heartache and the tears and the grit… I still have tears in my journal.” ([05:33])

2. Hardships and Early Lessons

• Struggles with finances, housing, and legal troubles ([07:45], [09:47]):

  • Recounts sleeping on couches or busses, getting evicted, and being arrested for unpaid tickets.
  • Unvarnished honesty about youthful mistakes and the consequences.

• Importance of her early support system ([13:31]):

  • Friends and coworkers from her law firm became her first audience and believers.
  • Secretaries at the law firm pooled $600 for her first standup comedy class.

    “All of those secretaries… put the money in and paid for my six weeks of comedy classes.” ([19:56])

3. The "Do It Scared" Origin Story ([16:07])

• Pivotal night at The Comedy Store:

  • Encouraged by a female audience member and advice from Eddie Griffin/Andrew Dice Clay:

    “Just do it.”
    “But I'm scared.”
    “Then do it scared.”
    — Sherri Shepherd, paraphrasing both comics ([16:41])

• Mantras that fueled her:

  • "If you don’t try it, you’ll never know." (Advice from friend Donetta, [19:15])
  • Doing it scared remains her life’s philosophy.

4. Barriers and Breaks in the Industry

• Early acting gigs and racial barriers ([32:17]):

  • Sherri’s memorable bit role on “Friends”—obtained after her agent begged for her audition when the role “wasn’t supposed to go to a Black woman.”
  • Attempt to inject humor and awareness with her “Friends finally got some color” postcard, which ended up offending producers.

    “I think it kind of triggered them. And I never was on Friends again.” ([34:42])

• Navigating typecasting:

  “I used to be known as the black girl who was on all the white sitcoms… Stealing the scenes.” ([35:08])

5. Turning Points: Comedy, Acting, and Motherhood

• Breakthrough with “Suddenly Susan” and persistence

  • Recalls finally feeling some stability, only for the show to be canceled after one season ([37:24]).

• How standup became sanctuary amid chaos ([24:51]):

  • Balanced comedy nights with exhausting family and caretaking responsibilities.
  • "Being on stage was the only thing that made me happy."

6. Motherhood, Trauma, and Healing

• Jeffrey’s premature birth and challenges ([43:02]-[45:14]):

  • Shares her son's birth at 25 weeks, a period marked by marital infidelity and depression.
  • At one point, doctors recommended removing life support, but a last-minute change saved Jeffrey’s life ([51:02]-[52:00]).

  • “He didn't die that day… They said he wouldn't be able to talk… When my son says to me, ‘Mom, bruh, I love it,’ because they said he wasn't gonna be able to do all of that.” ([53:42])

• Motherhood as fuel ([55:53]):

  • Sherri wakes up “worried a lot” and everything she does, she does for her son.
  • On why she works out:

    “I'm always picturing Jeffrey at a finish line… So everything that I do… is for Jeffrey.” ([56:07])

7. Evolving as a Talk Show Host

• The winding road to The Sherri Show ([63:49]):

  • Numerous rejections due to age or not being “what talk shows want,” including being told “we need younger people in the talk show space.”
  • Emotional toll and perseverance:

    “It hurts too much to have this dream… I can't, I'm tired of the no's…” ([66:07])

  • Managers/agents who stood by her side for a decade.

• Why success came at the right age ([75:54]):

  • “If I got a show in my 20s… I was not ready. I was not mature enough. I was too much of a people pleaser in my 20s and my 30s.”

8. Barbara Walters’ Mentorship and Lessons ([43:43], [76:27]-[79:27]):

• Taught Sherri to deepen her voice, speak with confidence, and project her beliefs.
• On learning to express why you believe in something, not just what you believe.
• Touching story of Barbara’s support for Sherri and Jeffrey.

• “You couldn’t pay to get the lessons that I got for free from Barbara Walters.” ([77:51])

9. The Power of Resilience, Taking Risks, and “Doing It Scared”

• Advice for women and younger listeners ([83:48]-[86:49]):

  • Encourages taking big risks, moving out of comfort zones, meeting new people, and embracing failure as growth.

  • “If you can get past the fear… that's where the treasure trove of opportunities are.” ([86:49])
    “So do it scared. Run towards that thing that causes that… jittery feeling. Run towards it.” ([86:42])

• Learning to say “no”

  • “At this age, I go, no. It'll be so much silence. We can keep looking at each other all day. I said what I said.” ([88:05])

10. New Directions and Creativity

• Writing a Blasian Romance Novel ([88:57]):
  • Sherri is learning Korean, collaborating with writer J.C. Lee, and blending Black and Korean cultural experiences, inspired by her love for K-dramas.
  • Injects authentic humor, life experience, and steamy romance into the narrative.

  • “I want people to be on the subway like 50 Shades of Grey going, ‘I can't let y’all see what I'm reading.’” ([93:08])

Notable Quotes and Memorable Moments

• On her gratefulness for the journey:

  “It’s overwhelming to know that that’s forever… my heart is so full of gratitude.” ([05:14])

• On believing in yourself:

  “If you don’t try it, you’ll never know.” (Donetta’s advice, [19:15])

• On the impact of friendship and sisterhood:

  “All of those secretaries… they all believed in me.” ([19:56])

• On mentorship:

  “Barbara Walters sat me down and she said, ‘You’ve got to project more confidence… If you don’t start interrupting and start saying what you believe, tell me why you are saying no.’” ([77:24])

• On perseverance:

  “I've had people believe in me… A person's belief in you will carry you further than an agent getting there, going, we can get you all this money, and we can. That's not it.” ([67:41])

• On overcoming imposter syndrome:

  “That thing, the hand got over my face and I was like, they're gonna find out that you're not deserving… But what keeps me calm is making people laugh.” ([90:37])

• Her ultimate mantra:

  “Do it scared.” (multiple segments; originated at [16:41], reiterated throughout)

Important Timestamps

| Time | Segment/Quote | |----------|----------------------------------------------------------------------------------------------| | 03:27 | Sherri’s feelings on receiving her Walk of Fame star | | 07:45 | Early industry struggles and her agent getting her on “Friends” | | 16:07 | The night at the Comedy Store and birth of the “Do it scared” mantra | | 19:56 | Friends pooling $600 for her to take comedy classes | | 32:17 | Breaking into “Friends” and industry typecasting | | 43:02 | Becoming a mother, Jeffrey’s premature birth, and personal trauma | | 51:02 | Deciding to “pull the plug” on Jeffrey and the last-minute miracle | | 55:53 | How motherhood changes Sherri | | 63:49 | Finally launching her own talk show after decades of rejection, ageism, and heartbreak | | 76:27 | Barbara Walters’ mentorship—teaching confidence and unique voice | | 83:48 | Advice to younger women and the value of embracing risk and failure | | 88:57 | Writing a Blasian romance, K-dramas obsession, and venturing into new creative territory |

Tone and Authenticity

The conversation is raw, humorous, and unfiltered—true to Sherri Shepherd’s signature blend of honesty and comedic timing. Sherri moves fluidly between laughter and vulnerability, revealing her setbacks, lessons, and hard-won wisdom. Both Tamsen and Sherri foster an atmosphere of encouragement, relatability, and deep respect for resilience, making this episode both touching and motivating for listeners at any stage of life.

Takeaway

Sherri’s Story = Proof of Possibility:
Whether you’re chasing a dream, weathering setbacks, or facing fear, Sherri Shepherd’s path proves you can “do it scared”—and succeed. Lean into faith, laughter, friendship, and the wisdom of mentors. Take big risks, refuse to let fear paralyze you, and surround yourself with the people who believe in you.

Follow-Up

For updates, behind-the-scenes, and future episodes:
@thetamsenshow

Sherri’s new projects:

• Children’s book: The Sunshine Queens
• Upcoming Blasian romance novel (stay tuned for title!)

“If you can get past the fear, that’s where the treasure trove of opportunities are. So… do it scared.” — Sherri Shepherd ([86:49])