Elaine Williams, comedic motivational speaker, author, life coach, trainer, and comic, has had plenty of exposure to the business world. She has over 30 years of experience working with companies such as Hard Rock Café, Marriott, Miller, and Del Frisco’s Steakhouse (which is the highest grossing restaurant in the United States). Elaine’s comedic experience is equally as impressive: she has opened for Dane Cook, Darrel Hammond, Dwayne Kennedy, and twice voted comedic of the year, Spanky. She has also appeared on “America’s Got Talent,” the “Colbert Report,” “Saturday Night Live,” HBO’s “Lucky Louie”, “All My Children,” “One Life to Live,” and numerous commercials. More recently, she has been voted Up and Coming Comic at the New York Underground Comedy Festival.

Elaine also possesses the ability to use her comedic talent to teach others, both in the business and collegiate world. While she is often invited to talk to and train staff about the finer points of customer service, she is also asked to speak at colleges and universities about the struggles of stress eating and binge drinking. Through humor and her own life experiences, she engages younger audiences and helps them understand how to break bad habits and deal with stress through using certain tools and solutions.

7 Things I Wish I Had Known Before I Went Into Business (and Life)

Let me begin by saying that I am truly grateful for my life, my health, my support network, and for the work I am doing in the world. My life has taken some interesting twists and turn, and although there have been some PAINFUL lessons along the way, I also believe that for whatever reason, I needed to have these experiences. Maybe it was to add fuel to my comedy act. Or maybe it was so I could pass on my wisdom to you.

With that being said, I have made some “not-the-most-brilliant” decisions in my life. I am at a good place in my life with business and finance, mostly because I am stubborn, tenacious, and persistent. I have been a marathon runner literally and figuratively.

But let me cut to the chase, because we are all so busy with our lives.

My hope is that these tips are helpful to you so that you can learn from my mistakes.

1. No is a complete sentence.

I grew up in the South, where I was socialized to be polite and sweet. I have always worried about other people’s feelings way more than my own. Many females are socialized to listen and not be rude.

I believe that women are often taught to explain strong statements or opinions.

So, put this on a post-it on your computer or on your mirror.

No is a complete sentence.

You do not have to go into an entire explanation about why you can’t host the PTA meetings or take on another project at work.

There is so much freedom in saying NO. You can practice saying “No,” “No thank you,” and “Thank you, but I respectfully decline.”


Try it. You’ll like it.

2. Everyone has an agenda. Everyone.

This was really hard for me to admit and to accept. I honestly thought, for a long time, that once people heard my story and how I was trying to help save the world, they would want to help me… just because. I feel embarrassed admitting this, but this attitude has really bitten me in the butt, and so I hope that by sharing it, I may help others with “trouble childhoods.”

I will explain. I grew up in an addicted, violent family; and then, in turn, had 3 addictions that I was able to eventually overcome. And now I speak at colleges, telling my story, and educating students about alcohol and assault prevention and response.

I guess that I had some hidden self-pity and self-righteousness that ran me. Like: you don’t know what I’ve been through so you should help me for free because the world owes me or someone owes me. It’s not pretty. But this was an underlying attitude that did NOT serve me or any of my unfortunate business partners.

So if someone seems eager to “help,” it’s a good rule to check their agenda.

For example: when my “friend,” Rudy, was excited about selling me a house so I could invest in the same neighborhood where he was, he was not doing it because he believed in my vision.

He wanted to (and did) make money off of me. He made a commission when he sold me the house as a broker.

He made money with his construction crew when he double charged me for rehabbing the house. When other investors came to this Philly area and saw what a tough neighborhood my investment house was, they all said: Any experienced investor with any integrity never would have sold a new, inexperienced investor like you, a house like this in this kind of neighborhood.

Stay tuned for more tips and crazy fun stories from a sober, big dreamer, entrepreneur. But, bottom line, I should have looked further into his agenda. I should have been more honest with myself, instead of being all caught up in my “vision.”

On a personal note, while I have never been able to meet Elaine, she and my dad have become close friends through multiple business and motivational conferences they have attended. I have been hearing for years about how encouraging, motivating, and hilarious she is, and am honored to have finally gotten the chance to speak with her. She has had an enormous amount of experience in the business world in multiple areas, and is often asked to teach and motivate others through her comedic abilities. – Caitlin

Contributed by Caitlin Maiewski