‘Everything We Do Is Political’ Inside The Barbados Retreat Where Black Women Talked Money And The Midterms

Every generation of Black women inherits the same math problem: do more with less, and do it quietly.

This year the Support Your Girlfriends retreat took that math apart out loud. The itinerary read like a vacation, with a welcome dinner in hues of pink, a golf clinic, a yacht day, and a finale dinner in metallic chic. The conversation read like a boardroom, moving through Project 2025, new voter suppression laws, venture capital entry points, and how many women in the room were carrying an entire household on a single income.

For its 8th year, the retreat returned to Barbados in partnership with Barbados Tourism Marketing Inc., and spent the week on the two subjects most likely to determine what the next decade actually looks like for us: money and power.

The retreat, created by Dr. Nikkia McClain, founder of Support Your Girlfriends, gathered leaders across media, finance, real estate, healthcare, law, and advocacy. Some have been part of what is called the Glossy Posse since the very first trip. Others were new inductees. All of them arrived at a table where the conversation moved quickly from renewal to receipts.

“The success of every woman should be the inspiration to another,” Nikkia said, quoting Serena Williams, as she opened the welcome dinner. Her framing for the week was rooted in that concept and encouraged no gatekeeping, women investing in each other, growing together, and traveling together as sisters.

The financial programming, led by Sherkera Green, VP Senior Business Consultant at JPMorgan Chase and SYG NJ Chapter Co-President, did not begin with vision boards. It began with numbers.

“52% of Americans have under $500 in a savings account,” Sherkera told the room, before naming the thing that usually keeps that statistic in the dark. Shame. Nobody wants to be judged. Nobody wants to be asked for money. So the money conversation never happens at all.

To break that, she ran an exercise called Stand With My Sister. She read a statement, and any woman who identified with it stood up while the rest of us looked around the room.

You are the primary household breadwinner. Women stood.

You have seen a major increase in your household expenses over the last year. More stood.

You have borrowed from your 401(k) or an investment to cover cash flow. Still standing.

You feel extremely disorganized when it comes to your finances. Nearly the whole room.

What followed was an honest financial conversation that held space for vulnerability and strategy. One woman described receiving a seven-figure check and parking it in a business debit account, unaware that a money market account existed for exactly that purpose. “I could have made $30,000 on that just by putting it in the market,” she said.

The room debated real estate versus the markets, first-time buyer programs, REITs as an entry point, and the tax tradeoff between claiming low income and qualifying for a mortgage. Then Sherkera reframed the horizon: by 2030, women are projected to control 40 to 45% of all financial assets. Several studies have confirmed this. According to McKinsey & Company, by 2030 women will control an estimated $30 trillion in financial assets. 

“Imagine it’s 2030 right now,” she said. “Cash is rarely used. AI is handling jobs. Digital currency is common. How are women creating wealth?”

Answers came fast. Buying baby boomer businesses things like laundromats and coffee shops and delivery routes, and installing a manager. And Yandy Smith, TV Personality and CEO Yelle Skincare named a concept she called tree businesses.

“Creating businesses that are like tree businesses that have branches,” Yandy explained, describing how her restaurant, her skincare line, and her television presence each market the others. “Being able to create things that catapult each other.”

One member disclosed that a limited partner position she took in a venture fund in 2020 has more than doubled, and then opened the door for the group to split an entry into the fund’s second raise. That is the part that matters. Access like that usually travels quietly through rooms most of us are not in. She chose to say it out loud at the table instead.

“We are sitting here talking about investing, and everyone reacts with fear,” she said. She emphasized that we need to start coinvesting into each other’s projects and looking at that as part of our overall investment strategy as a norm.

The session closed with each woman naming one thing she would do differently. Run a financial audit. Take more calculated risk. Stop operating from scarcity. Learn what my financial advisor is actually doing. Stop making emotional decisions with my money. One woman committed to making no large discretionary purchases for a full year, starting August 1, and redirecting all of it into investments.

While the finance session established what we have, Tamika Mallory’s session established what is at stake.

If you’re not familiar, she’s a social justice leader and co-founder of Until Freedom. She opened by connecting the entire week back to itself. “Every single thing that we do is political,” she said. “We talked about money, we talked about family, we talked about careers, we talked about our own entertainment. Even talking about hair.”

Then she made it physical. “Policy is not something written on paper. It’s human. We are walking policy. Everything about us, the decisions being made about what’s on our bodies, about what’s in our bodies, is all political.”

Her case was built on numbers most of us had not sat with:

• At least a million Black women have been pushed out of the workforce through the rollback of DEI, “and Black men are right behind us.”
• There are 426,000 Black people across six states who are not registered to vote right now.
• [Close to] 90 million people did not go to the polls in the election Donald Trump won.
• Only 34% of Black people hold passports, a detail that matters enormously under the proposed SAVE Act, which would require a matching ID and birth certificate to register or update a registration.
• Roughly 69 [million] of women do not have the same last name on their identification as on their birth certificate.

Official reports support what Tamika brought forward in the discussion. The Brennan Center for Justice found that 21.3 million American citizens of voting age do not have ready access to a document proving citizenship, with 11% of citizens of color affected compared to 8% of white citizens, and reports that two-thirds of Black Americans do not hold a valid U.S. passport. The Center for American Progress puts the number of American women whose birth certificate does not match their current legal name at roughly 69 million, because 84% of married women change their surnames.

“What they are doing is creating a situation where Black people and women, all women, will be disenfranchised,” she said.

She was blunt about proximity to power in her own state. “New York is rapidly becoming a Republican state. We’re probably two elections away from a Republican being able to become governor of New York State.”

The turn came when someone asked whether the strategy should be to win over other voting blocs. Tamika’s answer was a strategic redirect that reframed the whole conversation.

“We do not need anybody else at all. The numbers are on our side,” she said. “If we increase the group of people within our own communities showing up as educated voters, we can beat them every single time. And they know that. That’s the reason why they want to disenfranchise our communities.”

The number she is organizing around is roughly a 4% bump in Black voter participation. The method is hyper-local and unglamorous. Going into states like Michigan, North Carolina, Georgia and leading with mutual aid, because it is easier to talk to someone about the polls after you have fed them. And bring the entire household along, year-round.

“We want to force our children to go to the polls the day before the election, but not tell them what’s going on leading up to it,” she said. “You cannot stay in my house and not be politically engaged.”

She also made a direct funding ask on behalf of Until Freedom, noting that Black-led organizations across her network are struggling to keep doors open, and that recurring support at $10 a month is meaningful at this stage.

Out of that conversation came a commitment. The Glossy Posse is drafting a shared political action plan, convening on Zoom to assign states and roles, and pooling resources for on-the-ground turnout work between now and November.

The economics thread ran through Bershan Shaw‘s session, “Nourishing the Future,” which asked each woman to recall herself at six, seven, or eight years old, before fear got a vote.

Bershan, who is the CEO & Founder of URawarrior, reframed fear as false evidence appearing real, and grounded it in her own history. She was diagnosed with stage four cancer 18 years ago, she described the turn from asking ‘why me’ to asking ‘why not me.’

Her challenge to the room was economic. Black spending power is measured in trillions, yet money cycles out of the community in roughly 20 minutes. There are no Black women on the cap tables of the platforms we built the culture of. By her math, the women in that room were sitting on a collective half a billion dollars and still playing small.

Then she went around the table and made everyone say the biggest dream out loud. One woman is working to mentor young dentists into practice ownership, which she named as the only real path to income in healthcare. Another is raising a first-phase investment fund built specifically for women business owners. A founder with 35 years of cultural contribution behind her wants a multi-category global lifestyle company with licensing deals, because as she put it, the money needs to match the legacy. One woman intends to own skyscrapers in Manhattan. Another is turning her family’s land in Honduras into a heritage space that preserves Honduran native culture for younger generations. One is building toward a billion-dollar company at the intersection of content, commerce, and community.

“Talk is cheap,” Bershan said. “We’re becoming.”

Wednesday brought the annual giveback with I AM A GIRL. This year the girls came to us at the villa, where Yandy Smith turned a skincare routine into a life-skills curriculum for a group of Barbadian teens.

Cleanser meant writing down what you need to release, then ripping the paper up. Toner meant setting the tone in every room you walk into. Serum meant being selective about what you allow to seep in, whether that is music, media, friendships, or jobs. Eye cream meant tightening your goals and releasing the bags weighing you down. Moisturizer meant staying elastic, because you will bend and you cannot break.

The last exercise was a mirror. Each girl looked at herself and named the first thing she noticed. Almost every one of them named something she loved. Her eyes. Her skin. Her cheekbones. Her glow.

Anyone who has run programming for young women knows how rare that is. Most rooms default to flaws.

Candis Grace, founder of global marketing firm The Brand Group, led a session on why social media is no longer optional infrastructure for a serious business.

“It’s no longer a kid’s toy,” she said. “It is your business card. It is your face card.”

She audited the room’s profiles in real time, which was as uncomfortable as it was useful. Her framework: name the three things you want a total stranger to understand about you, then make sure your pinned posts and your bio deliver exactly those three things.

“If you have 97 different things in your bio, it looks like you’re not serious about anything, even if you are,” she said. “You have to assume that people don’t know you at all.”

She also made the case for restraint, and for understanding that a post outlives by years the moment that produced it. Brand partners and clients do go looking. “Once it’s out there, it’s out there. It could be used against you,” she said.

And she named the thing that stops most people from posting at all. “When you overthink it, you get overwhelmed, and then you just don’t post.”

Her counter to overthinking was going with your gut. “If it feels fly, just trust it.”

The detail that stayed with me: Candis pointed out that when Bershan asked the room to name the biggest dream imaginable, an overwhelming number of women described something involving media. Which is to say, the ability to shape and control our own narratives showed up as a prerequisite to nearly every other ambition in the room.

Sandra Garcia Green, founder of Encounter Your Potential, closed out the week with a session on owning your confidence, structured around a framework she calls P.O.W.E.R.

Preparation, because armor is real and you decide what you put on before you walk into a room. Own your confidence, which means marrying your skill set to your innate self-worth rather than waiting for a title to confer it. Worthy of success, found by paying attention to what people consistently praise you for, because monetization usually hides inside the thing you already do for free. Engage and advance, because growth lives past comfort, and boundaries are what protect the energy required to get there. Refine and recalibrate on a quarterly cycle: review, revisit, revise.

She landed it with the airplane oxygen mask metaphor we’re all familiar with. You have to encounter your own potential before you can empower anybody else.

We closed with hands on hearts and a mantra led by Dr. Nikkia:

We gather in gratitude, grounded in truth. Strengthened by sisterhood and renewed in purpose. We will not leave this retreat unchanged. We commit to doing the work, even when it’s hard. We will show up for ourselves and for our girlfriends. And so we rise. Together. Accountable. And unafraid.

The finale dinner brought the announcement of a Barbados chapter, extending a relationship with the island that has now spanned years rather than trips. Support Your Girlfriends is a 501(c)(3) with a paid membership of $104.00 annually and active chapters in New Jersey, New York, and Atlanta.

On the final morning, before flights, the group gathered to feed people experiencing homelessness in Barbados. Six in the morning, on departure day, after a week of dinners. Women got up.

This retreat sent us home with a financial audit to run, a state to organize, an ask to fund, and a mantra about not leaving unchanged. Aside from the sessions detailed, we experienced workshops from Lucinda Cross of Activate Worldwide who hosted the LeadHer Pow(H)er Dinner, Modupe Rouse of Finally Free led the Sacred Circle, Charreah Jackson of Shine Army led “Stop, Beach, and Shine!” on the sand, and Bershan Shaw had us up walking most mornings for Morning Breath. Barbados Tourism Marketing Inc. gave us the island itself, including the rum tour and the yacht experience.

The pictures from this week are beautiful, and they will (and have) circulated. The work behind them is what shows up in November.

The 9th annual Support Your Girlfriends retreat returns in 2027. For information about joining visit https://www.supportyourgirlfriends.org/.