Desirée Rogers on New Orleans Roots, Harvard MBA, Chicago Powerbroker to the White House and CEO of Black Opal and Fashion Fair
Do you feel pigeonholed in your career? Do you struggle to see how your diverse experiences across corporate, government, and non-profit sectors connect? In this inspiring episode of No Boxes: Just Verses, we go beyond the bios, beyond the titles with Desirée Rogers—renowned strategist, connector, and co-owner/CEO of Black Opal and Fashion Fair. Desirée shares her "unboxed" playbook for strategic career pivots, revealing how lessons learned from managing utilities and insurance giants prepared her to revolutionize the White House Social Office and, ultimately, revitalize iconic Black beauty brands. If you want the blueprint for weaving seemingly unrelated experiences into a powerful Masterpiece Mentality that leads to massive impact, this is your must-listen episode.
Desirée Rogers is a renowned leader, strategist, and connector who has redefined every role she has held, from corporate boardrooms to the White House. Currently the co-owner and CEO of Black Opal LLC, she oversees the iconic Fashion Fair and Black Opal Beauty brands, which serve multicultural audiences and are sold nationwide at retailers including Sephora and ULTA. More than beauty companies, these brands are cultural touchstones—Fashion Fair in particular has long celebrated and elevated Black beauty.
Her career spans transformative leadership in business, media, and public service. As Social Secretary for President Obama, she brought the administration’s values of inclusion, transparency, and diversity to life through experiential events. She revitalized Ebony and Jet magazines as CEO of Johnson Publishing, positioned Chicago as a top global travel destination, and drove growth at Peoples Energy, Allstate, and the Illinois Lottery. A graduate of Wellesley College and Harvard Business School—and recipient of HBS’s 2024 Alumni Achievement Award—Rogers serves on the boards of Stagwell, Inspired Entertainment, and the American Cancer Society.
Key Takeaways:
Academic Discipline is the Equalizer: Early competition in academics built her core discipline and confidence.
Build a Generalist Tool Chest: A deliberate career strategy across regulatory, ops, and marketing was key to leading smaller organizations later.
Align Values to Culture (Formation): The White House role was a lesson in brand management, ensuring events reflected the administration's values of inclusion and diversity.
Persistence Outlasts Resistance: Pursuing a target business owner for three years proves that patience and persistence are crucial for achieving a long-term goal.
Embrace Your Authentic Self: She stopped trying to hide her identity in "safe" jobs (utilities, insurance) and found purpose by fully leaning into beauty for her community.
Desirée's entire journey, from New Orleans to the White House to the front of the beauty industry, is proof that all of your experiences, even the difficult ones, are building your unique tool chest. Your diverse path is your strength.
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Your Superpower: 5 Simple Steps to Connect All Your Different Career Experiences
Why Your Diverse Path is Your Biggest Advantage
Have you ever looked at your resume and thought, "Wait, how do these jobs even fit together?" Maybe you worked in government, then in a big company, then started your own thing. It can feel messy, like a puzzle with missing pieces. You might worry you don't have a clear career story.
This article is for you if your career is full of twists and turns. We're breaking down the journey of a super successful CEO, Desirée Rogers, who went from working at major energy and insurance companies to serving at the White House, and now leads iconic beauty brands. She proves that all those different jobs are not problems—they are superpowers. You will learn the simple steps to connect everything you've ever done so you can lead with confidence and purpose.
To make this strategy work, you have to stop seeing your job history as random. Instead, you need to see yourself as building a specialized tool chest. You are ready for this if you are tired of limiting yourself to one industry and want to find a way to make a huge impact using everything you’ve learned.
Here's what you need to be successful:
A "Man in the Mirror" Moment: You need to look at yourself and decide to take ownership of your growth.
Curiosity: You must want to explore new challenges and industries.
Belief in Your Mission: You must know that your work is important for your community or the people you serve.
Step-by-Step Guide: Your Strategic Ascent
1. Use Discipline (Not Sports) to Build Your Core Strength
Most people think of sports when they talk about discipline, but if you weren't an athlete, you can build that same core strength in other ways. When you are the one who looks different, or you feel like an outsider, it can be scary. The common mistake is to shrink back and try to hide. The new and better approach is to use that feeling to drive your performance in a visible way. For one CEO, this meant making academics her competitive field. She was constantly challenged to be smarter and better, which built a foundation of confidence and discipline. This discipline becomes the fuel you use to take big career risks later.
Conclusion: Where You Compete is Where You Grow
Find your personal competitive field, whether it's studies, hobbies, or skills.
Use challenging environments to build your discipline and strong work ethic.
Know that your earliest support system (family, teachers) helps boost your confidence.
Remember that the energy you put into learning now helps you take bigger chances later.
2. Build Your "Unicorn" Tool Chest Across Different Industries
It's common to hear advice that you must stay in one lane and climb one corporate ladder. But the problem is that if you do that, you only learn one way to solve problems. The smart approach is to be intellectually curious and jump into totally different, mature businesses—like energy, lottery, or insurance. This lets you gather skills in regulatory work, operations, finance, and marketing all at once. This diverse set of skills is called a "generalist understanding," and it’s why one person was perfectly ready to take on big, "unicornish" roles in public service later on.
Conclusion: Collect Skills, Not Just Titles
Look for challenges in mature businesses that need to be twisted around and improved.
Seek roles that let you learn big skills like operations, marketing, and government relations.
The goal is to become a generalist with a deep understanding of many different business parts.
This "tool chest" is essential when you move to a smaller organization later in your career.
3. The Highest Levels of Service are About Brand Management
When you get a high-profile role, especially in public service, people think you are just in charge of logistics or events. The mistake is to treat it like a party-planning job. The real job is much bigger: it's about making sure everything you do aligns with the values and mission of the people you serve. The new and better approach is to see every event, meeting, or decision as a chance to reinforce the brand and the mission. For example, when running events at the White House, decisions about who was invited and how they got tickets were used to promote inclusion and diversity to the whole country.
Conclusion: Values Must Be in Formation
See your role as a brand manager for your leader or organization.
Every public action must align with the core values you represent.
Use simple things—like how you handle a ticket lottery or who you invite—to create huge, powerful experiences for people.
Understand that serving a bigger mission requires huge stamina and dedication.
4. Be Persistent (and Patient) to Get Your Goal
When you have a big vision for what you want to achieve—like running a specific company—you can't just send one email and quit. The problem is that many people give up after the first "no." You need to remember that the timing might be wrong, or the other person just isn't ready. The smart strategy is to be quietly persistent. The successful CEO wanted a certain beauty company, and she pursued the owner for three years. She kept showing up, kept asking, and was patient until the owner was ready. Her long-term goal finally came to her.
Conclusion: Never Let a "No" Stop Your Vision
If you have a clear idea and passion, be very persistent.
Stay in touch and keep showing up, even if the answer is "no" for a long time.
Patience is key; sometimes, you just have to wait for the right moment.
Know that your tenacity proves you are the right person to take over the mission.
5. Find Your Purpose by Leaning Into Authenticity
It’s easy to try and hide parts of yourself that you think people might judge. For this CEO, she ran from being known as "fashionable" or "cute" by taking highly technical jobs (like utilities and insurance) so people would respect her mind. The problem is that running from who you are limits your real purpose. The breakthrough is realizing that your unique interests and passion—even beauty—can be the very thing you need to serve your community. By finally leaning into beauty, she used her skills to provide high-quality products that help Black and Brown women feel fantastic and confident, which takes a "load off" so they can focus on their own missions.
Conclusion: Your Passion is Your Mission
Stop letting the judgment of others dictate the jobs you choose.
Realize that your unique passions can be used to serve a higher purpose.
Find ways to help people feel confident so they can pursue their own mission.
The most rewarding work is when you align your passion with your community's needs.
Your Next Steps: You Are in Control
The big idea from this incredible journey is that your messy, interesting, unboxed career is your biggest asset. Stop worrying about what you should be doing and start looking at all the amazing skills you have collected.
Here is your list of steps to implement these ideas successfully:
Define Your Discipline: Identify the one non-sports area where you are the most competitive and disciplined (e.g., studies, learning a skill). Commit to using that discipline this week.
Audit Your Tool Chest: List your last three jobs. What three unique skills (Ops, Regulatory, Marketing) did you collect from them?
Find the Pivot Clue: Think about your biggest goal. Who do you need to meet, and how can you be persistent (without being annoying) for the next three months?
Embrace Your Authentic Self: Identify the one passion (e.g., fashion, writing, fitness) you tend to hide at work. Find one way to intentionally bring that passion into your professional life this month.