Sheryl Underwood’s Tips for Success in Comedy and Business

Strategies for getting ahead, on and off the stage


Comedian Sheryl Underwood has been tickling our funny bones since she first appeared on Russell Simmons’ Def Comedy Jam, BET’s Comic View, and The Steve Harvey Morning Show, and on the big screen as Catfish Rita in Beauty Shop. Her career-trek represents a journey of breaking glass ceilings across multiple professional mediums with no signs of slowing down. had the privilege of sitting down with Sheryl to discuss key lessons that have helped her develop and expand her personal brand, from the comedy club to the corporate hub. Sheryl shared the personal and career development strategies that have equipped her with not just a repertoire of jaw-dropping jokes but the wisdom to have success on and off the stage.

[Related: Comedienne Sheryl Underwood Talks Health Challenge and Campaign for Advocacy]

Think like a headliner. Don’t let anyone keep you bound to their best version of you. “I love comedy. Comedy is my first love. But there was much more for me to accomplish beyond that scope—educationally and even professionally.” Whether it’s one profession that monopolizes your finances, or you have multiple talents and gifts that make a way for you, never stop striving to be your best self. Even if you work a nine-to-five or are self-employed, stay hungry for your next level of growth. “With growth comes unfamiliarity and, sometimes, even adversity. But it beats being stagnant any day.” By following this principle, Sheryl has allowed her career to evolve over the years to include being a radio and talk show host, serving as the 23rd international president for Zeta Phi Beta Sorority Inc., and being founder and CEO of Pack Rat Productions, Inc.

Know your material. Don’t just be in your field, know your field. From comedy performances to corporate contracts, Sheryl is always aware of how her time and talents are working for her financially.“When it comes to comedy, I negotiate directly with owners and vendors about how (my accompanying comedian colleagues and I) will be compensated. That’s rare for a woman in this industry.” As a CEO, Sheryl obtained professional certifications relative to business and finance, so she can know how her financial wealth is working for her.

Have a strong act to follow. Sheryl attributes her multifaceted success to divine guidance. “From my career to my personal life, whether in regard to opportunities that have presented themselves or even doors that have been closed, my decisions and choices are all made carefully by putting God first.” Spiritually and even naturally, Sheryl emphasizes that success is amplified by being willing to follow. Find mentors and confidants who will help you navigate your plans and offer encouragement, wisdom, and business advice.

Show up for showtime. A typical day for Sheryl includes waking up at 4:00 a.m. for meditation and prayer; getting some exercise; eating healthy (with an occasional treat), studio time for one of her several radio programs; CBS studio time for taping shorts, promos, and the actual live show, The Talk; meeting with her team about Pack Rat Productions and, sometimes, preparing to travel for comedy shows. Sheryl pushes through her relentless workload by “staying on go.” “Doing what you love is about showing up. If an opportunity comes along for you—especially one doing something that you love or are crafted to do, you owe it to fate to make the best of that opportunity.” Time is your greatest resource. Make the most of it.

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