
From Dropout To Self-Made Entreprenuer, Pauleanna Reid Paved A Lane All Her Own

Women empowerment isn't a game for Pauleanna Reid. As the co-founder of New Girl on the Block, a mentorship program that reaches over 200 women across 10 countries, the Toronto native ushers millennials into lives of their own creation. It's a mission that is deeply personal, especially when the senior contributor at Forbes and Business Insider retraces her steps to success.
As a target for bullies throughout her K-12 experience, Pauleanna once questioned her space in the world. "Since I can remember, I always felt misunderstood," she tells xoNecole. "I always felt like I did not fit in. I always felt like I was reaching for validation. I always felt like I had to prove something to somebody."
Courtesy of Pauleanna Reid
"I always felt like I was reaching for validation. I always felt like I had to prove something to somebody."
In the midst of isolation, she found solace in notebooks. Toting blank pages with her everywhere she went, Pauleanna discovered a love for words and dared to dream beyond the classroom. However, when she decided to articulate her desire to be a writer at the end of high school, her parents and guidance counselor were quick to point out that she failed English her junior and senior year. In their eyes, her choice didn't add up. "My philosophy is that your parents don't always know what's best for you. Sometimes they project their own fears and doubts on you, and they put you in a box and put a label on you because they were too afraid to pursue their dreams themselves," she points out. "My parents wanted me to play it safe."
Steered by opinions outside of her own, Pauleanna enrolled in a business administration program instead. "I absolutely hated it," she remembers. What should have been a launching pad for her dream career became a graveyard where her vision was laid to rest. The depression that loomed throughout her childhood crashed hard. She didn't socialize, turn in assignments, or attend class for weeks at a time. "The classroom was somewhere where I did not feel safe," Pauleanna reveals.
During her sophomore year, she attempted to commit suicide twice.
"When I recovered from both attempts, I took it very seriously," she reflects. "I believe that God was telling me that second chances do exist and that there was a purpose for my life, and that was the moment I decided that I was going to dedicate my life to figuring out what my purpose was. I immediately dropped out of school."
Courtesy of Pauleanna Reid
"I believe that God was telling me that second chances do exist and that there was a purpose for my life, and that was the moment I decided that I was going to dedicate my life to figuring out what my purpose was."
Pauleanna hid her decision from her parents for a little over a year. "I wanted to have receipts before I told them I dropped out of school," she says. "I wanted to have experience under my belt."
She made her next move with careful thought. "If I was not going to pursue a traditional education, that meant I had to turn the world into my classroom," she explains. "In addition to life experiences, I also knew that I needed to stand on the shoulders of giants. I knew that I had to acquire mentors."
In 2009, Pauleanna met sex educator Shannon Boodram and media professional Shannae Ingleton Smith. "They've been my big sisters for the last decade, and they really catapulted my writing career to be honest," she expresses with humility.
While Shannae encouraged Pauleanna to start her own blog, Shannon guided her through the process of penning her debut novel Everything I Couldn't Tell My Mother. The book, which mirrors 90 percent of Pauleanna's life, faced 22 rejections from publishers before she opted to cut out the middleman and self-publish. "I understood that I wasn't going to let someone in a corner office who had no idea who I was dictate the next steps of my career," she stresses.
Everything I Couldn't Tell My Mother went on to become an Amazon best-seller and 2014 Top Summer Read on the Queen Latifah Show. The personal tale, which tackles date rape, abusive relationships, and deep-seated insecurites, also gives way to reflection, growth, and self-love. "The one thing I really wanted to convey in this book is in order to achieve the success that you want, you have to either let go of resentment or anger or deal with the issues you've been bearing head on," Pauleanna says. "If you're carrying emotional baggage, you will not give yourself the opportunity to open your hands up and catch a blessing."
The full-time entrepreneur also notes that this process takes time. "The only way I know how to climb out of any hole that I'm in is gradually," she maintains. "I think you have to give yourself time. You can't put so much pressure on yourself to heal in a specific timeframe."
Since being diagnosed with depression and anxiety in 2010, Pauleanna gave herself permission to try everything from medication to therapy. While implementing lifestyle changes were key to her progress, tuning into self and connecting with God reigned supreme on her road to wellness. "When it has been necessary, God has always shown up. It's been very evident. Whether it was a job opportunity, removing people from my life, or helping me recover from my suicide attempts, He has always shown up on time," she muses. "I want people to know that there is life after disappointment. Everything that we experience is for our greater good. It may not always make sense, but we have to understand that God is not obligated to tell us the details. He has a greater plan for our lives, and it doesn't include crying at night or believing that we're broken."
Courtesy of Pauleanna Reid
"Everything that we experience is for our greater good. It may not always make sense, but we have to understand that God is not obligated to tell us the details. He has a greater plan for our lives, and it doesn't include crying at night or believing that we're broken."
She is a testament to this thought. After dropping out of college, she fulfilled her childhood dream of becoming an author, launched the celebrity ghostwriting agency WritersBlok, and elevated to senior contributor at Forbes and Business Insider. In the process, she also collided with a deeper calling. "After looking at my career, many people would assume that my purpose is writing. My purpose is not writing," the public speaker says with clarity. "My purpose is I'm here to help people see beyond the limits of their circumstances."
As a mentor to millennials, Pauleanna encourages the hundreds in her program and the thousands tuning into her moves on social media to play it smart instead of throwing blind darts in hopes that they'll land on a goal. Before stepping into full-time entrepreneurship, she held down a corporate job for a decade and used her free time to sharpen her business acumen, build a proven track record of selling products and services, and slice her debt by $45,000. "Don't let the Internet rush you," she warns. "It took me 10 years to figure out the formula, and I was totally OK with that. I think the reason why my transition was so successful is because I'm very patient with myself and like Jay Z says, I play the long game."
And while she could hoard the gems she's accrued along the way, Pauleanna is completely fulfilled paying it forward, the same way her mentors continue to come through for her today. "They believed in me on days I didn't believe in myself. I can screenshot any conversation, and they always tell me I'm a bad b***h," she says. "They always tell me I can do anything."
For more of Pauleanna, follow her on Instagram.
Featured image courtesy of Pauleanna Reid
Shanice Davis is a writer from New York, dedicated to illuminating women of color and Caribbean culture with her pen. Follow her on Instagram and Twitter: @alwayshanice.
'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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