From Class President to Flying First Class as Leslie Jones' Makeup Artist (with Lola Okanlowan)

In this episode of How I Got Here, Dreena welcomes Lola Okanlawon to speak about her journey to becoming a highly sought-after Professional Makeup Artist, from the elevator ride that led to her first celebrity client to the words of wisdom and guidance she has for aspiring makeup artists and people in the beauty industry. 

Reflecting on her younger years as class president in high school, Lola once aspired to be an attorney. She talks about the transitions she made in her subjects of study at college and how the influence of her Nigerian parents guided her to make changes in her life.  

Lola’s experience working at a hair salon sparked her interest in beauty and helped her develop a deeper connection to femininity and the comradery within the back and brown communities. She broke into the industry by landing a job at M.A.C. and shares the challenges and benefits of navigating a new world of learning while getting her MBA. She shares her candid thoughts on working in retail versus working as a freelancer and gives insight into what led her to pursue freelance makeup artistry professionally, noting what it takes to be successful in a highly competitive service industry. 

She touches on how her parents feel about her career path now, the only misstep she feels she had in her life, and what path she may have taken if she didn’t go so deep into makeup artistry. Lola addresses the importance of unionizing and the many reasons why makeup artists want to join a union, as well as how Leslie Jones has been her biggest champion and the power in choosing loyalty over opportunity. 

After having worked with top A-list celebrities and at countless major networks and events, Lola shares with us what’s next in her journey, including a potential move across the country and a few entrepreneurial ventures that are in the works. She also sheds light on what a day in her life looked like pre-covid and during covid, noting the changes that have happened to the beauty industry as a result of the pandemic. 

Want to see connect with Lola and see her work?

Follow her on Instagram: www.instagram.com/lolasbeautymark

About the Host:

Dreena Whitfield has a proven ability to create tangible outcomes that helps clients exceed expectations. Her diverse career has led her to spearhead the communications and marketing efforts for leaders in the nonprofit, corporate and political sectors, as well as small businesses internationally.

With more than a decade of experience, Dreena and the WhitPR team have a proven ability to spot opportunities for our clients to grow their brand recognition in saturated markets that are in alignment with their overall objectives.

The Huffington Post listed Dreena as one of their “Top 25 African American Millennials in PR to Watch.”

Follow Dreena & WhitPR on all the socials:

@Dreenawhitpr & @whitpr

Join The WhitPR Collective: www.whitprcollective.com

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Creators and Guests

Host

Dreena Whitfield

Dreena Whitfield-Brown is the Founder and CEO of WhitPR, an integrated strategic communications agency with 15+ years serving clients in the nonprofit, corporate, and political sectors. Recognized as one of PRWeek's 40 Under 40, a PR News Top Woman in PR, and named to Inc.'s 2025 Female Founders 500 List. She created How I Got Here to have the raw, honest conversations about entrepreneurship that nobody has on the record.

Producer

Keena Williams

Keena Williams is the founder of Struxa and the Executive Producer, Writer, and Creative Director of How I Got Here.

What is How I Got Here with Dreena Whitfield?

How I Got Here with Dreena Whitfield goes beyond the highlight reel with Black women founders, executives, and leaders. Real conversations about the pivots, the setbacks, and the purpose behind the work. From bootstrapping a beauty brand with $500 to leading a professional sports franchise, each episode explores the moments that shaped who they became and the cost of building something meaningful.
For women navigating leadership, business ownership, career reinvention, and the cost of ambition.

New episodes biweekly on Wednesdays.

Host: Dreena Whitfield
Executive Producer, Writer & Creative Director: Keena Williams / Struxa
howigotherewdreenaw.substack.com