Ajayi's foray into entrepreneurship was almost accidental. She had been an entertainment blogger on the side for years but only started doing it full-time after losing her marketing job at a nonprofit in a company layoff. As she tells Krawcheck, it wasn't until other opportunities failed to materialize that she considered moving full steam on her own site, Awesomely Luvvie.
"Creative positions can feel frightening because it's hard for people to take them seriously, so it was difficult for me to conceptualize the idea that I could actually become a writer and make a living at it," she tells Refinery29. "But I thought okay: If I have to work for myself, how does all of it work? I don't think it's about waiting for signs because sometimes you might not have one."
Not waiting around until the moment "felt right" involved taking on opportunities as they came her way — being invited to big events as an interviewer with more traditional outlets, writing a book (which became a New York Times best-seller and was optioned by Shonda Rhimes), and building a team to help her with some of the financial matters that can accompany success.
"I made sure that if I brought more money in, I also had more structure to manage it."
"I figured that if I was in a room, there was no other option but to come correct," Ajayi says of fighting off imposter syndrome. "That was important — to keep doing what I'm doing. I'm not going to change who I am because of whatever room I'm in."
When it came to managing her money, Ajayi says she sought out help on matters she didn't know. She read as much as possible ("You have to be a lifelong student," she explains), and got a financial advisor and accountant that understood the nuances of entrepreneurship.
"I made sure that if I brought more money in, I also had more structure to manage it, and I got more people on my team," she says. "As somebody who runs her own business, I realized that I had to create my own structure and maintain it. I couldn’t do it by myself, so it was a process of knowing what to outsource."
Knowing what's right — and what is possible — is key, Ajayi adds. Although many people casually toss around the idea of entrepreneurship like free candy, she says that being thoughtful about building toward that goal is just as important. Some parts of dropping everything on a dime to launch your own business aren't glamorous, but it can lead to a meaningful payoff just as often.
"It's not about taking a leap blindly. I was able to not have a full-time job for a while and still be okay because I didn't have another person depending on me for survival," Ajayi explains. "Going after our dreams doesn't stop bills from being there and doesn't stop you from having to pay your rent, so make sound decisions for what's best for your own life based on where you are."
"And if you can’t quit your job and go full out on your side-hustle or your passion," she continues, "plan toward it. There's nothing wrong with collecting a check from somebody else because that check can actually help you build your dreams, and that's perfectly fine."