
These Black Women Left Their Jobs To Turn Their Wildest Dreams Into Reality

“I’m too big for a f***ing cubicle!” Those thoughts motivated Randi O to kiss her 9 to 5 goodbye and step into her dreams of becoming a full-time social media entrepreneur. She now owns Randi O P&R. Gabrielle, the founder of Raw Honey, was moving from state to state for her corporate job and every time she packed her suitcases for a new zip code she regretted the loss of community and the distance in her friendships. So she created a safe haven and village for queer Black people in New York.
Then there were those who gave up their zip code altogether and found a permanent home in the skies. After years spent recruiting students for a university, Lisa-Gaye Shakespeare became a full-time travel influencer and founded her travel company, Shakespeare Agency. And she's not alone.
These stories mirror the experiences of women across the world. For millions, the pandemic induced a seismic shift in priorities and in desires. Corporate careers that were once hailed as the ultimate “I made it” moment in one's career were pushed to the back burner as women quit their jobs in search of a more self-fulfilling purpose.
xoNecole spoke to these three Black women who used the pandemic as a springboard to make their wildest dreams a reality, the lessons they learned, and posed the question of if they’ll ever return to cubicle life.
Answers have been edited for context and length.
xoNecole: How did the pandemic lead to you leaving the cubicle?
Randi: I was becoming stagnant. I was working in mortgage and banking but I felt like my personality was too big for that job! From there, I transitioned to radio but was laid off during the pandemic. That’s what made me go full throttle with entrepreneurship.
Gabrielle: I moved around a lot for work. Five times over a span of seven years. I knew I needed a break because I had experienced so much. So, I just quit one day. Effective immediately. I didn’t know what I was going to do, I just knew I needed a break and to just regroup.
Lisa-Gaye: I was working in recruiting at a university and my dream job just kind of fell into my lap! But, I never got to fully enjoy it before the world shut down in March [2020] and I was laid off. On top of that, I was stuck in Miami because Jamaica had closed its borders due to the pandemic before I was able to return.
Randi O
xoN: Tell us about your journey after leaving Corporate America.
Randi: I do it all now! I have a podcast, I’m an on-air talent, I act, and I own a public relations company that focuses on social media engagement. It’s all from my network. When you go out and start a business, you can’t just say, “Okay I’m done with Corporate America,” and “Let me do my own thing.” If you don’t build community, if you don’t build a network it's going to be very hard to sustain.
Gabrielle: I realized in New York, there was not a lot to do for Black lesbians and queer folks. We don’t really have dedicated bars and spaces so I started doing events and it took off. I started focusing on my brand, Raw Honey. I opened a co-working space, and I was able to host an NYC pride event in front of 100,000 people. I hit the ground running with Raw Honey. My events were all women coming to find community and come together with other lesbians and queer folks. I found my purpose in that.
Lisa-Gaye: After being laid off, I wrote out all of my passions and that’s how I came up with [my company] Shakespeare Agency. It was all of the things that I loved to do under one umbrella. The pandemic pulled that out of me. I had a very large social media following, so I pitched to hotels that I would feature them on my blog and social media. This reignited my passion for travel. I took the rest of the year to refocus my brand to focus solely on being a content creator within the travel space.
Gabrielle
xoN: What have you learned about yourself during your time as an entrepreneur?
Randi: [I learned] the importance of my network and community that I created. When I was laid off I was still keeping those relationships with people that I used to work with. So it was easy for me to transition into social media management and I didn’t have to start from scratch.
Gabrielle: The biggest thing I learned about myself was my own personal identity as a Black lesbian and how much I had assimilated into straight and corporate culture and not being myself. Now, I feel comfortable and confident being my authentic self. Now, I'm not sacrificing anything else for my career. I have a full life. I have friends. I have a social life. And when you are happy and have a full quality of life, I feel like [I] can have more longevity in my career.
Lisa-Gaye: [I'm doing] the best that I've ever done. The discipline that I’m building within myself. Nobody is saying, ‘Oh you have to be at work at this time.’ There’s no boss saying, ‘Why are you late?’ But, if I’m laying in bed at 10 a.m. then it's me saying [to myself], 'Okay, Lisa, get up, it's time for you to start working!’ That’s all on me.
xoNecole: What mistakes do you want to help people avoid when leaving Corporate America?
Randi: You have to learn about the highs and lows of entrepreneurship. You have a fast season and a slow season and I started to learn that when you're self-employed the latter season hits hard. Don't get caught up on the lows, just keep going and don't stop. I’m glad I did.
Gabrielle: I think everyone should quit their job and just figure it out for a second. You will discover so much about yourself when you take a second to just focus on you. Your skill set will always be there. You can’t be afraid of what will happen when you bet on yourself.
Lisa-Gaye: When it comes to being an influencer the field is saturated and a lot of people suffer from imposter syndrome. There is nothing wrong with being an imposter but find out how to make it yours, how to make it better. If you go to the store, you see 10 million different brands of bread! But you are choosing the brand that you like because you like that particular flavor.
So be an imposter, but be the best imposter of yourself and add your own flair, your own flavor. Make the better bread. The bread that you want.
Lisa-Gaye Shakespeare
xoNecole: Will you ever return to your 9 to 5?
Randi: I wouldn’t go back to Corporate America. But I don’t mind working under someone. A lot of people try to get into this business saying, “I can't work under anyone.” That’s not necessarily the reason to start a business because you're always going to answer to somebody. Clients, brands, there’s always someone else involved.
Gabrielle: I went back! I really needed a break and I gave myself that. But, I realized I’m a corporate girl, [and] I enjoy the work that I do. I’m good at it and I really missed that side of myself. I have different sides of me and my whole identity is not Raw Honey or my queerness. A big side of me is business and that’s why I love having my career. Now I feel like my best self.
Lisa-Gaye: I really don’t. For right now, I love working for myself. It's gratifying, it's challenging, it's exciting. It’s a big deal for me to say I own my own business. That I am my own boss, and I'm a Black woman doing it.
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Featured image courtesy of Lisa-Gaye Shakespeare
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'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Are You & Your Partner Financially Compatible? Here’s How To Tell.
With nearly half of all marriages that end in divorce citing finances as the nail in the coffin to deading their relationship, financial compatibility is one aspect of long-term compatibility that doesn't get talked about enough. Beyond the circular 50/50 discourse and whatever hot-button issues regarding providers and the like, at its core, financial compatibility is about how well your financial behaviors, values, and long-term goals align with those of your partner.
More than it is about how much money a person makes or doesn't make, financial compatibility focuses on how you think about money, how you spend your money, and most importantly, how you plan for the future with your money. Think, questions about money mindsets, spending habits, debt, budget, etc. Are you a saver and he's a spender? Do you see money as a tool for freedom? Does he see it as something to hold on tightly to as a means of survival? Can you talk about your financial goals and plans openly?
Knowing if you and your partner are financially compatible can save a lot of heartache, a lot of headaches, and a lot of money in the end. Keep reading for a few key indicators to pay attention to and learn whether or not you and your partner are truly aligned financially.
Signs You’re Financially Compatible
1. You can talk about money without judgment.
Conversations about money aren't something you dread. You're able to talk to your partner freely and openly about money matters, like debts, bills, the budget, etc., even when it is uncomfortable. There is an understanding that talking about money doesn't have to be something you're on the defense about, instead it's an opportunity for transparency, clarity, and solutions.
2. You respect each other's money personalities.
What is a money personality? According to Ken Honda, author of Happy Money, a money personality is our "approach and emotional responses to money" and there are seven money personalities we can fall under. These personalities can help us understand our own relationship with money, as well as our partner's. For example, maybe you're someone who likes to treat yourself to a fancy dinner once a month and your partner is someone who believes ordering takeout and not cooking meals at home is a cardinal sin.
When you can respect each other's money personalities, neither approach is subjected to judgment and shifts can be made in each other's spending habits as needed and from a place of love versus guilt or shame.
3. You agree on what it means to have "financial security."
Whether it’s building a stacked emergency fund, paying off debt before putting a downpayment on a home or being able to splurge on a baecation without checking your account balance before the bill arrives, your definitions of what it means to be financially secure are in sync, or at least compatible enough to reach a compromise.
4. You are not each other's "financial parent."
You’re not constantly teaching, fixing, or stressing out over what the other person is doing with their money. Although I fast-forwarded through a lot of the most recent season of Love Is Blind, I did pay attention to Virginia and Devin and money seemed to be a recurring theme in their conversations. It was clear Virginia had her ish together when it came to money and her financial plans for the future and Devin was not quite on her level.
Though she said no at the altar for additional reasons, I could also see how sis could eventually get very tired of being her partner's second mama, so to speak. And that's the thing about being your partner's "financial parent," eventually, you could end up feeling like you are one-half of a "parenting" or "teaching" dynamic with your partner instead of feeling like you're equals in a partnership.
5. You make financial decisions with each other in mind, not for each other.
Whether it’s booking a trip, deciding which debt to tackle first, saving up for a big purchase, or planning out your next move, there’s a mutual respect for each other’s input. Those shared goals might look like wealth, freedom, stability, or just a debt-free life that feels soft and secure.
You don’t have to be chasing the same bag in the same exact way, but you do need to be aligned on the vision. What you're building should feel like a joint venture with shared effort and purpose, not one of y’all making major money moves like you're still single. Making financial decisions is not just about where the money goes, it's about where you’re going together.
6. You're aligned when it comes to the big stuff.
Financial compatibility extends to the long-term of money management. The legacy, structure, and shared responsibility that comes with decisions like shared accounts, estate planning, having babies, or even blending families. Will you split bills or combine income? Who’s taking time off if you have a child? How do y’all feel about generational wealth or investing for your family’s future? You and your partner have had the real conversations.
These conversations can’t wait until after the wedding or until after a baby’s here. They’re the foundation for how you function as a unit, and if you're not aligned, or at least willing to get on the same page, that incompatibility can cause friction in the end that love alone can't fix.
Love is cute and all, but building an empire together? That’s the real flex. Tap into our new series Making Cents to see what financial compatibility really looks like when love and legacy go hand in hand.
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Featured image by pixdeluxe/Getty Images