"Just Be You"—A Career Coach Shares Her Best Advice for Entrepreneurs

In 2014, Angelina Darrisaw Cheeks slid into my DMs after she’d made her first purchase from my stationery line, Mae B. Next thing we knew, we forged a friendship and spent hours texting about the ups and downs of our journey as entrepreneurs. Before long our digital friendship became real when we ran the RUN 10 FEED 10 race in New York City.

What was your first job out of college? What were the most valuable lessons you learned?

I was a sales and marketing associate at ESPN. It was essentially a rotational program that helped me gain insights to the two key revenue streams of the company (ad sales and affiliate sales). This helped me be thoughtful about where I wanted to land in my next role. It was like having an additional year of business school. My network throughout the company grew from having access and exposure to so many departments. This was definitely an advantage.

Did you always know you wanted to be a career coach and entrepreneur?

No, I always knew I wanted to contribute to my community in some way, but it took me time to recognize what that contribution would look like. The one theme I will say was recurring as a passion was wanting to do something that involved working towards racial/socioeconomic equality. That stemmed from seeing disparities as a child (commuting from a low-income neighborhood in Brooklyn to the wealthy Upper East Side for school) and witnessing the dynamics of inequality firsthand. Having worked with over 2,500 business owners, I can’t say I hear the same story all the time about knowing entrepreneurship is for you. There are definitely some people who have been selling lemonade and girl scout cookies or whatever else since they were five and will always be inventing and creating and owning a business. Then there are those who have a very big idea and want to see it to fruition because they believe they have something good that will solve a problem. I definitely fall in the latter half.

There are those who will always be inventing and creating and owning a business, and there are those who have a very big idea and want to see it to fruition because they believe they have something good that will solve a problem. I definitely fall in the latter half.

What was it like transitioning from a corporate career to building C-Suite Coach full-time? Did you face any challenges? How did you overcome those challenges?

It was terrifying. Leaving the comfort of a biweekly paycheck, benefits, routine… all of that was very difficult. Also, though well-meaning, everyone in my circle didn’t understand the unique challenges of entrepreneurship. I maintained my circle, but had to build new connections. I needed to have other business owners I could turn to who could understand and say, “Girl, that is totally normal. In my first year, this happened.” I also recognized my needs — for instance, I prefer to work in an office vs. from home and I like a routine. So apart from two months, I’ve been in offices or coworking spaces since I quit and it’s more productive for me. Self-awareness is key.

One of your roles includes being a Google Digital Coach. How do you manage and determine the partnerships you take on?

I leverage my personal mission as a rubric for decision making. My personal mission is about economic empowerment of people from underserved backgrounds. Essentially, I want to help more people of color, women, and LGBT people thrive and succeed in their work. Therefore, when I come across opportunities and partnerships, I always ask myself, will this help me further my personal mission. If the answer is yes, then I move forward, and if the answer is no, then I push myself to say no, no matter how appetizing it looks.

What is one key piece of advice you give small business owners at Google events?

Often as business owners, we spend the bulk of our time with our existing clients. But for our businesses to grow, we need to spend some time thinking about how to attract new clients or expand our offerings for our existing clients. That requires reflection and time for strategy. I challenge business owners to schedule in time for planning and roadmapping how they will scale and grow their business.

I am also a huge advocate of using data to drive decisions, vs. solely gut. So I always suggest to business owners that they spend time with the data they have available to gain insights about their business and use that to guide action.

You gave over 75 speeches last year. Do you ever get nervous before your speaking engagements? How did you become a seasoned public speaker?

Yes, I still get butterflies every single time. While I am always clear on what I will say and how, how the audience will react and connect is an unknown and that can make me anxious. Two things I’ve learned and think are very important. 1) Preparation eases anxiety. Over-prepare so that if something throws a wrench in things (an unexpected audience question or some sort of scene happens), you know exactly how to bounce back. 2) Always be you (more about this here). I’ve frequently seen people change up their whole act because the audience is quiet or because a previous speaker did something that got a great response, so they are trying to elicit the same response.

Just be you. So much can go wrong as a speaker when you try to be someone else. Furthermore, if speaking is a tool you are using to grow your business, the more you are “you” in your speaking style, the more you will attract the right clients for your business.

Just be you.

Women are paid seventy-six cents to the dollar of men, and that number significantly drops for women of color (sixty-four cents for black women and fifty-six cents for Latina women). How can women advocate for higher pay and feel empowered to speak up when they know it’s time for a raise?

Get a strategy for negotiations and be knowledgeable about your marketplace value. Don’t wait until you are asked, “What’s your desired salary?” to think about what your salary range should be. Regularly research the ranges in your industry and consider where your skills and experiences put you in that range. Never feel obliged to disclose your previous salary (it’s now illegal in some states for your new salary to be based off that). Make calendar reminders weeks before your review to check in with your boss and where you are in terms of likelihood of getting a promotion/raise. If you’re met with “not likely,” get them to give you specific and measurable actions that need to happen for you to get one. Plan a check-in date for evaluating your progress.

Making mistakes is one of the ways we grow as people. What mistakes have you made that taught you a valuable lesson that you’ve applied to how you navigate your career?

There’s not only a single mistake I think of, but I think in terms of missed opportunities. When I’ve yearned for things badly and didn’t get them, there often were reasons why. Sometimes it was timing and fit, but other times it was me. When I feel like it was me, I spend a lot of time reflecting on what I could have done differently, so I’m never in that position again. I want to always know I’ve done everything I can to be on point, and if I have, and still don’t get the yes I want, then I’m okay blaming it on timing and fit.

I want to always know I’ve done everything I can to be on point, and if I have, and still don’t get the yes I want, then I’m okay blaming it on timing and fit.

It is often said, when you’re a person of color, you have to be twice as good. What inspires you to get up every morning and bring your best to your tasks of the day?

I am inspired by the sacrifices of my mother and other elder women in my family. I have so much I could say about this, but generally I know that where I am is a blessing and a gift and that it required the hard work of those who came before me, so that makes me want to do well and excel with the opportunities I’ve been given.

Have you ever struggled with imposter syndrome? If so, how do you overcome it?

Unfortunately, yes I have and far too often. I overcome it by reminding myself of what I’ve had to overcome to get in the rooms that I’m in. I also listen to feel good music, take time to hype myself up, and hit up the people in my network that will help hype me up. I also actively work on reminding myself to be proud of how far I’ve gotten, even when I know there’s a lot further that I want to go.

How do you find new clients, and how do you cultivate client relationships?

I find clients primarily through networking and referrals. Networking can be difficult to make time for when your to-do list feels never-ending, but it’s key and there are so many people who don’t know you who want to help you further your goals — they have to meet you in order to do that. That’s part of the strategy around attracting new clients — get out there and meet people and joyfully share the work you do and what sort of clients you’re looking for. In terms of cultivating relationships, the best way is by solving their problems and providing value. Apart from that, I recommend hand-written thank you notes and sharing relevant information with them.

What’re your favorite things about career coaching?

I feel really full/fulfilled when I see my clients achieve a new awareness or feel empowered to commit to a new habit that is going to help them find the success they want professionally. It’s delightful — that’s the best way I can describe to see the happiness on a client’s face when they’ve identified a blind spot or have uncovered something new they want to take action on.

Entrepreneurship requires a lot of time and dedication. Do you take time to recharge with self-care? What are your favorite things to do to give yourself a positive boost?

Not always, but I am working on it more and more. I try to do something I like (could be a cocktail with close friends, a manicure, online shopping, whatever…). It’s really hard to find time for any of those things, so when I do, I feel like it’s a win! And when I’m doing it, I shut down conversations about work. I eat, sleep, and breathe my business, and it’s always on my mind. I know my circle is often asking because they care, but when I’m trying to relax, it makes me think of a reason I shouldn’t be relaxing… It makes me want to go back to work, so I tell them I’m off the clock and would rather discuss their hot date or latest marathon than chat about my upcoming contracts.

Walk us through a typical day for you.

There really isn’t a typical day for me, but there are a few things I try to keep consistent — like to be moving by 6am and start my day with positivity. That could mean a podcast, a good song, or reading something uplifting. I also try to eat a healthy breakfast, and on the good days, I’ve worked out. From a work standpoint, I am often presenting or working on new partnerships or new content. My days are long and very full, so I am very pointed in meetings and push to have an agenda before taking meetings.

What advice would you give your 22-year-old self?

Do that thing you are afraid to do or don’t feel ____ enough to do. Do it anyway.

Love on yourself and eliminate any relationships that make you feel you don’t have all the reasons in the world to love on yourself.

Angelina Darrisaw Cheeks is The Everygirl…

Starbucks order?

Unsweetened Skim Green Tea Latte or Skim White Mocha

Favorite way to relieve stress?

Running Outside

Favorite guilty pleasure song?

“Fight Night” by Migos

If you could have lunch with any woman, who would it be and why?

Bozoma Saint John. I am moved by how she carries herself openly and freely, especially in corporate spaces. She is a beauty queen mixed with Oprah mixed with marketing genius all in one. I feel like our conversation would flow from innovative ideas I could take to my own business to new ways at looking at self love to an exchange of testimonies (we might stop to stomp and shout) to fun girl time and chatting about fashion and music over a cocktail. In any case, it would be one of the better lunches of my life.

“Just Be You”—A Career Coach Shares Her Best Advice for Entrepreneurs