Many of us grow up knowing that we are not meant for the cubicle life. Some of us know that we are best suited for careers like speaking and coaching, that allow our personalities to shine and inspire others to reach their full potential, but don’t know where to start.

Cheryl Wood, CEO of Personal Power Enterprises, LLC was one of those people. EBONY had the opportunity to speak with her about her life and journey, and what it took for her to build a successful speaking career from scratch. Here’s what she had to say.

EBONY: What inspired you to begin a speaking career?

Cheryl Wood: After starting my t-shirt business, Moms R The Best, I was contacted by Morgan State University (MSU) and extended my first opportunity to speak at a women’s conference with over 200 attendees.  When I finished that first speaking engagement on September 18, 2010, I knew that I had discovered my unique gift – inspiring others. Speaking has made me feel internally fulfilled, allowed me to serve and help transform the lives of other women, and offered the opportunity to connect with other aspiring entrepreneurs. I began assertively pursing speaking as a full-time career, and I started to receive frequent requests from groups, associations, companies and conferences to share a message of empowerment with their attendees.

Years later, I was still trying to juggle the business and my full-time job, but I came to a fork in the road where I had to choose. And I chose to give up my full-time paycheck to take a chance on my speaking business.  It was extremely challenging financially, but I stayed committed to figuring out a way to make it work. Ultimately, my speaking led to my coaching practice.  After speaking on stage and opening people’s eyes to the possibilities of walking in their passion and purpose, I needed to have a way to teach them and offer them the tools needed for implementing their ideas.

EBONY: What do you think are three of the major misconceptions that Black women have about pursuing a career in speaking?

Cheryl Wood: I think the three biggest misconceptions are that their past and what they’re lacking will prevent them from achieving massive success as a speaker on large platforms, that their “voice” as a speaker will never be acknowledged because they’re a “little fish” in a “big ocean,” and that they will never build wealth through speaking.

EBONY: Share with us one of your biggest business failures and how you overcame it.

Cheryl Wood: One of my biggest business failures was not having confidence in my worth. I struggled financially in my business for the first few years because I couldn’t see my value.  I focused more on what I was lacking than on my strengths.  I spent too much time second-guessing whether or not people would even listen to me. I felt growing up in poverty in the inner city of Baltimore, Maryland, being a product of a single-parent household with limited financial resources and no college degree would count against me. As a result, I struggled with sticking to my speaker fees, increasing my coaching rates, and constantly giving the “homie hookup” (when clients talk you down on your pricing or try to negotiate your fees instead of paying the full price).  Essentially, I was running from my truth because I felt that it devalued me.

EBONY: How did you overcome your insecurities regarding the business?

Cheryl Wood: By starting to look at the bigger picture. All the things I had experienced in my life that I was trying to run and hide from were the very things that made me extraordinary, because I didn’t allow them to make me a statistic.  I claimed my personal power to determine what my future would look like and to create the reality I desired.  I was fearless enough to step outside of my comfort zone to do what was unfamiliar and uncomfortable, and to take risks that didn’t have a guaranteed result.  And that’s what I began teaching others – how to fearlessly pursue, and create the reality you desire.  I began to realize the value I was delivering was worth far more than what I was charging.  Once I embraced the results I delivered, I shifted my mindset and start sticking to my fees.

EBONY: For those of us who follow you, we are familiar with your much used phrase, “Playtime is over.” Where did the idea originate?

Cheryl Wood: “Playtime is over” was birthed out of my realization that as a full-time entrepreneur, time management is a critical component of success.  One day, I was in my home office and noticed that I was wasting valuable time on the internet instead of using my time to actually grow my business.  In that moment, I said to myself, “Cheryl, playtime is over.”

It was self-talk to remind myself that I needed to get laser-focused, stop procrastinating, and eliminate distractions that were preventing me from success.  Thereafter, I began sharing the expression, “Playtime is over” on social media and it literally took on a life of its own.  The expression resonated with women nationwide and it became a movement designed to empower women to put in the work for their dream and eliminate excuses and distractions.

EBONY: “Playtime is Over,” has evolved into an annual conference (now tour) where you bring women together who are interested in growing professionally. Tells us about it. 

Cheryl Wood: The Playtime Is Over Tour (PTIO) was created as an extension of the two-day Playtime Is Over Women In Business Conference that is held in November each year.  The PTIO Tour was designed to help more women to start breathing life into their dreams and to connect them with women of like minds, who are on a similar path.  Each tour stop includes networking, a full lunch, an exclusive presentation by me to empower women to think outside of the box, and strategies to equip entrepreneurs to grow their businesses to new levels.

I was never under the impression that I could succeed alone, so I linked arms with women in various states to plan the tour.  I utilized my strong social media following to enlist tour hosts who supported the initiative and located venues that would fit our needs. The response was overwhelming.  For pricing, I was intentional about keeping the ticket cost below $50 to make it an easy “Yes” for any woman who was hungry for growth in her life.

At each tour stop, women leave feeling transformed and ready to achieve their goals. Women of all ages, races, and backgrounds stood up at the end of each tour and expressed how the content and environment shifted their mindset to want to take bigger risks, and stop playing safe.

EBONY: What advice would you give to a novice speaker about branding, pricing, and creating a name for themselves?

Cheryl Wood: I would advise novice speakers to invest time and energy into developing four ongoing elements that will position them to succeed as a speaker: Consistency, Visibility, Credibility and Authenticity.

CONSISTENCY as a speaker means repetitiously doing what fuels your speaking business – educating and informing prospects, sharing your expert advice, networking and building relationships.

VISIBILITY is mandatory if you want to stay relevant.  I remind my clients that, “Visibility always trumps ability.” It doesn’t matter how great your ability is as a speaker, without visibility you will remain a best-kept secret.  If you want to be a speaker, get out from behind your laptop and speak.  Sometimes in the beginning that will mean waiving your fee, speaking to small groups, or investing in opportunities to speak.  But the more visibility you have, the more opportunities you gain for future growth.

CREDIBILITY is the reputation you develop based on the results you help others to achieve.  As a speaker, ask yourself: What benefits do audience members gain from hearing me speak?  What are the tangible results?  How are the participants transformed? Start to concisely articulate these benefits and results when speaking to event planners who are considering hiring you to speak at their event. Credibility leads to increased profitability.

AUTHENTICITY is the thing that will separate you from every other speaker.  Don’t waste your time trying to imitate any other speaker.  Just be YOU.

If you know that you’ve been called to speak and inspire, then don’t let these powerful tips go to waste. Just like Cheryl said, “playtime is over” and your life of passion and purpose are waiting for you to claim.

For more information on Cheryl Wood visit,

Kara Stevens is the founder of the personal finance and lifestyle blog The Frugal Feminista, an online home for financial empowerment, girl power, and juicy living. Connect with her on Twitter @frugalfeminista.