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.
BlackEnterprise.com 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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Become “one” with your audience. Sheryl abides by the principle: It is better to give than to receive. She looks for ways to use her talents for philanthropic endeavors. One particular area she is passionate about is education. Through her Pack Rat Foundation for Education HBCU Initiative, Sheryl is
raising awareness and money to support the 105 Historically Black Colleges and Universities and students committed to pursuing a higher education. “There’s a whole generation on the rise and they are going to be our next leaders, politicians, and the like. … That’s why I’m passionate about [supporting] higher education, particularly HBCUs.â€Sheryl also supports the efforts of the NPHC Greek letter organizations and partners with HBCU radio stations, providing Sheryl Underwood Radio at no cost to the stations. To support new talent, the Sheryl Underwood Radio app will provide a platform to break new music and showcase original radio theater. The app is also a home for her original and archived programs, which her fans love. Sheryl’s advice: Find an entity, group, or organization where your influence has the power to make a difference. It doesn’t have to be financial. Give your time, your expertise, and your support to communities and causes that have helped you get to where you are, or that exemplify positive initiatives and interests in general.
Respect and honor your team. When you’re around Sheryl, it’s clear that she not only values the asset
of having a strong team by her side, but her team also reciprocates that view. Two fellow comedians, members of Sheryl’s team, reinforce the idea of how important it is to keep good company. Michael Washington, one of Sheryl’s longest team members, says his experience has been rare.”Sheryl is more committed to the team than money.”Sheryl also invests in the future of comedy by mentoring her protégée, Kyle Erby. He has been her mentee for seven years. The one word he uses to describe her is “go.” Their time together taught him that, no matter what, he must continue to “go.” “Be better than you were the day before†is the standard she sets for herself and the team,” says Erby. Never underestimate the need to build your team.
Sheryl, who was recently the subject of the TVOne bio-documentary series, “UNSUNG Hollywood: Sheryl Underwood,” can be seen daily on CBS’s Talk, which averages over three million viewers and, during Sheryl’s tenure, received its first of many Daytime Emmy nominations. Her radio show can be heard regularly on numerous HBCU Radio Stations, and she continues to be an in-demand entertainer who gives back.
Connect with Sheryl on Twitter @sherylunderwood, Facebook (Sheryl Underwood Fan Page), and Instagram @sherylunderwood.