As Former First Lady Michelle Obama's Assistant, Here's What I Carried in My Bag
I’ve always been a little envious of women who show up with a little purse, just large enough for keys and perhaps a cellphone. How do you slide through life with a bag that small? For as long as I can remember, I’ve carried a bag; even as a young girl, I never left home without one. It equipped me with all the random tools I needed—but little did I know that one day, it would come to represent much more.
For my job, I carry an oversized black bag with me every day. In it, between purse dividers, I have Sharpies, a palm-sized battery operated fan, sticky notes, floss...you name it. It's cute, yet durable, with ink markings and water spots telling its story through the years. Whenever it’s opened, a floral scent from the fragrances of the lotions and oils inside permeates the air. All in all, with its straps, sturdy zippers, and contents, the bag weighs in at a whopping 5 pounds.
You wouldn’t carry a bag like this for just anyone. But I work for Michelle Obama. Whether you know her as a woman, a friend, a mother, author, style icon, Hugger-in-Chief, or the nation’s first Black First Lady, she represents the epitome of what is possible with hard work, tough skin, and ambition.
As an assistant, you're expected to be prepared for any and everything. But as an assistant to a First Lady—even, now, a former one—preparation means something totally different. You have to anticipate your boss’s every move, playing out every imaginable scenario in your mind, and ensuring that nothing will distract her from the task at hand. You’re the problem solver. The first line of defense. The one organized enough to think of others before yourself. It means having a “ready for anything” mindset...and bag.
When I took over the position of Trip Director and Special Assistant to the First Lady in 2015, there were a few things that my predecessors noted I should always have: Various types of ink pens, hand sanitizer, straws, tissue and challenge coins, which are typically given to service members. But I took it to a whole new level, expanding from a list of five simple items to a plethora of supplies to anticipate the First Lady's unique “what if’s." I began carrying around what I then called my FLOTUS bag—a black Lo & Sons purse with never ending compartments. If you’ve watched Veep on HBO, you’ll know a guy by the name of Gary Walsh, who was special assistant and personal aide to the Vice President. Gary always carried a bag that seemingly weighed down his right or left shoulder. That bag sure looked heavy—and trust me, it is. That’s what happens when the goal is perfection.
While Mrs. Obama was the First Lady, I had to think of everything and consider each possible scenario. I knew her bag had to be different—because as the United States of America’s first Black First Lady, part of my job was to help her deal with the nation’s baggage around the notion of what she and her family were supposed to represent. So I filled it with 3 different kinds of lotion: A lighter one for her feet, so that they wouldn’t slip and slide in her heels, a thicker one for her body, and an ultra-thick one for those ankles, knees and elbows, all in an attempt to prevent any possible ashiness. There would be no lack of moisture on my watch. I also carried hair spray for the flyaways and an edge brush, just in case, for smoothing down fine hair near the temples or around the hairline. (This was probably the first time that a First Lady ever had to be concerned about laying edges.)
Of course, there was also a pair of flats. She’d sometimes greet hundreds of people in photo lines, and walk hallways the length of a football field, or stand behind a podium for hours on end. Imagine the pain of walking in heels for extended periods of time, and then multiply that by 100.
My bag also included straws because we know the value of a “good lip,” and a lint roller. I added bra clips and double stick tape to avoid any attire mishaps, and room temperature water, because a sip right before hitting the stage will help eliminate a slight cough. There were mints, because first impressions stick, and hand sanitizer, long before it couldn’t be kept on the shelves. I had tons of it so she could work a rope line, during which she freely engaged with supporters after a speech—hugging, taking selfies, holding babies, shaking hands, and talking to a crowd that spanned the length of a stage.
I had chargers and extra sets of headphones, because she always needed to be connected, and you never know when she might need to drive out the noise and focus. I kept a nail file for those unexpected breaks, and a sewing kit that came in handy during one White House Correspondents Dinner when a celebrity who shall remain nameless had a tear in her gown that I was able to fix with a safety pin from my FLOTUS bag. This bag has come to the rescue for many, not just our forever First Lady.
To this day, even assisting Mrs. Obama post-White House, I’m still equipped with a first aid kit, stain removers, deodorant, a sponge to remove deodorant, oil blotting sheets, cough drops, and extra earring backs. Any time my boss needs or asks for something that I don’t have in my bag, I add it by our next trip. Mrs. Obama has lovingly teased me about my bag and why I feel the need to haul around so much stuff, but it’s because I never wanted the story about her to be about the one hair that was out of place, or the one mark on her dress, or the earring that fell, instead of the legacy the Obamas were creating. During their time in the administration, everyone around them strived for perfection because there was no other option. There was too much on the line.
We were in a unique situation. This was the first Black administration in the history of this country. It mattered so much to me, but it came naturally. I come from a rich matriarchy: A great grandmother, grandmother and mother—four generations strong—who made sure the next would be better than the last.
Growing up, my mom taught me that everything was in the details. She was a single parent who worked the graveyard shift for years to be available to me during the school day. That took planning. Mom always kept a small yellow legal pad on her nightstand near the phone and filled it with notes. I’d watch her work on our finances, brow furrowed as she calculated bills—every so often with a glimmer of worry in her eye. When she talked to our mechanic or our handyman or even the teller at the bank, she took notes. To this day, I can see the piles of paper filled with details that seemed so trivial at the time: Who she spoke to, the exact time, and everything that was discussed.
So it was Mom who taught me to always be prepared. That you need a plan B through Z, because sometimes plan A doesn’t always work out. She knew this world wasn’t going to be fair and in order to take it on, I would also have to learn how to be prepared, especially because being a Black woman in America means being born with two strikes constantly working against you: your Blackness, and your sex.
Both are things you have no control over, but have to figure out how to navigate. There’s the continuous struggle of yearning for identity and combating racism head on—realizing that as much as you try to conform, you can’t fully, because your Blackness sets you apart. So you allow the lack of not being able to conform to shape your personal view of self, struggling with body image and needing to look a certain way. Dealing with so many folks along the way that make sure you feel every bit of the fact that you don’t belong. Having your abilities doubted, talked down, and written off at every other turn.
On top of that, there are the undercutting microaggressions that you’re forced to swallow as compliments, like “You’re so articulate,” or “You’re so pretty for a Black girl,” or “Your hair...it’s so fascinating.” As a Black woman, you know all too well how the undertones of those “compliments” sting. You’re constantly working overtime and twice as hard, never allowing yourself to be satisfied with anything less than the best, because it’s what’s required of you. And yet, this world causes you to doubt the essence of who you are every day. Not even the most perfect preparation can protect you from the horrors of racism.
My mother taught me this lesson early on, and she made sure that I respected her as my mom and an elder, and that I valued her opinions, even though I used to fight her so much. But she understood exactly when to give me that little extra, “Well I’m your mom and this is the law,” to get me to make better decisions for myself. And every time she did, it worked out for my good. From having me attend a predominantly white elementary school so that I could get access to better resources and exposure to the “green grass of the other side,” to pushing me to attend an awards ceremony senior year of high school, even though my friends couldn’t get tickets. That night, my mom wasn’t having it. She put her foot down. Once again, she was right. I worked hard for this award and deserved it, and she knew if they were my true friends, they would want me to soar and not hold me back. (Thanks to her insistence, I won one of the most prestigious awards of my young life on May 16, 2006, The Miami Herald Silver Knight Award.)
In hindsight, I owe so many of my greatest decisions to my mom. In fact, it was my mother who was the driving force behind my decision to accept the job as Mrs. Obama’s Trip Director and Special Assistant (Bodywoman). When I was offered the position in 2015, I had just hit my two year mark working for the Walt Disney Company’s Government Relations Office in Washington, D.C. Given that it had taken three years to find a sound job with good pay, I was hesitant to give up that position—especially given that the Obamas only had two years left in their administration. But as always, my mom stepped in right on time, reassuring me that she was my safety net, and reminding me that I should refuse to let instability interfere with being able to dream.
A decade later, I know exactly where that award is. In my closets, I have soccer trophies, honor roll certificates, pageant sashes, countless yearbooks and concert ticket stubs, and more lanyards that I can count. I refuse to throw away little objects, convinced that my future kids will need them to take to show-and-tell at school one day. I also hold on to these things because I want my children to look back with pride at who I was and what I have done in life. These little scraps add up to something bigger. They represent my legacy, and the contributions to history that I’ve been blessed to be a part of thanks to two women: The mother who laid the foundation for the person I am today, and the boss and mentor who recognized that good foundation.
To this day, I carry my bag with pride. It represents everything I’ve learned from childhood and until now. It’s all in that bag: My attention to detail, my knack for covering all of my bases, my ability to always prepare for life’s what if’s and see around corners, anticipate needs, read the atmosphere, be nimble and pivot on a dime, and acknowledge mistakes—and learn quickly from them.
When your bag is full of everything you need both physically and spiritually, it’s easier to handle the weight of the world. I learned that from my mom, in the White House, and through following Mrs. Obama into her new chapter.
My journey isn’t unique—it’s just one that I’d been preparing for all of my life. Witnessing the day a Black man would serve as this nation’s Commander in Chief, then serving in that administration, and supporting its Forever First Lady. But sometimes, you have to see something to know it’s possible. And now, so many more generations will be born understanding that, too.
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