Stop Waiting for Permission to Dream Bigger

This episode is a conversation with my cousin Nikki The Jeanius, founder of All Things Ankara, the largest African print platform in the world, and now co-owner of VIBE Restaurant and Lounge, an Afro-fusion concept opening in Silver Spring. We talk about the email that changed her career before she had a business plan to back it up, what it actually costs to keep dreaming bigger once the first win arrives, and why rest is part of the ambition, not a break from it. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾 

You have an idea you keep circling back to. Maybe you've mentioned it once or twice, to a friend, in a group chat, in a note in your phone you reopen more than you'd admit. And you're waiting. For the market to feel more certain, for your following to grow, for someone with more letters after their name to tell you it's allowed. Nikki and I spent this episode on the version of that waiting that costs the most: the kind that happens after you've already had one win, when the next dream feels too big to say out loud.

The email that started a career nobody planned

Nikki's first big break came from a single email. She wanted a celebrity face for a ball built around ankara print fashion, back when the fabric was mostly worn to parties and nobody was covering it as a category. Her creative director, Troy, sent her a stranger's song cover on WhatsApp. She heard it once, decided the artist was going to blow up, and told Troy she wanted him to headline. Troy's answer wasn't a plan. It was "we're doing it, we're doing it, we're doing it," and within a week the reply came back yes. That artist was Jidenna, a week off his first single, before almost anyone knew his name. The ball went viral. Huffington Post covered it. CNN called too late to send anyone. And Nikki, with roughly 20,000 followers at the time, became the person people still ask about a decade later.

I recognize that shape of decision, because I made a smaller, quieter version of it in the same month the world was on fire. I started my own business in the spring of 2020, and the choice that mattered wasn't a big one. It was a decision not to overanalyze, not to wait for the right conditions, and not to ask anyone's permission first. I didn't announce it. There was no launch plan. I just tried it and let the outcome be whatever it was going to be. That decision eventually led to a client contract worth nearly half a million dollars and an innovation award we never applied for. Neither of us knew what we were building when we hit send. We just decided the asking was worth more than the certainty.

Everyone needs a Troy, and some people need a new circle

Nikki credits Troy for treating her idea as inevitable before it had any evidence behind it. "Everybody needs a Troy," she told me, and I'd add the harder truth underneath it: some of you have the wrong person in that role right now, someone who talks like a hype man but has never actually been a good steward of your dreams. I think about a retreat I attended with Arlan Hamilton, the venture investor who went from sleeping in an airport to backing companies with support from Mark Cuban. I sat in a room while other women described billion-dollar visions with total ease, and I realized, sitting there, that I wasn't dreaming big enough. Not because my goals were wrong. Because I had gotten comfortable inside a version of ambition that felt safe and doable, and safe and doable had quietly become the ceiling.

That's the tension underneath most stalled dreams. It's rarely a skills gap. It's proximity to people who only know how to mirror the size of the dream you already have.

The part that doesn't make it into the highlight reel

Nikki is a self-described "detailed" person, her preferred word for what other people call perfectionism, and she'll tell you plainly that it has cost her time on more than one project. But the section of our conversation that stayed with me longest wasn't about branding or trademarks. It was about her mother, a night-shift nurse who was diagnosed with cancer and chose to heal through diet, rest, and supplements rather than the path everyone expected. Nikki watched that recovery and drew a line straight from it to her own ambitions: "if I'm not here, there's no dreaming." One of my closest friends passed away in her sleep a few years ago. She was healthy. She was a doctor. She did everything right by the standard playbook, and life ended anyway.

"If you're not here, there's no dreaming." — Nikki

I want to be precise about what that story is asking of you, because it's easy to hear it and reach for the wrong lesson. It isn't asking you to buy a candle or block off a spa day. There's a real difference between self-care and comfort care, and comfort care is the version that lets you avoid what's actually depleting you. The deeper ask is a holistic one: mind, body, and whatever you'd call the thing that gives your work meaning past the metrics. Entrepreneurship will find every unhealed part of you and hand it back on a deadline. Building something meaningful was never going to be separate from the healing.

Dreaming bigger isn't the same as dreaming louder

Here's where I want to slow down, because "dream bigger" gets used as a slogan more often than it gets used honestly. It is not about the number. I once sat across from a woman clearing $25 million a year off a single offering, and what stopped me wasn't the figure, it was watching her keep expanding anyway: a TV show, a new partnership, ideas she hadn't stopped chasing just because the first ones worked. Bigger, in the way that actually matters, means refusing to stay in the version of your work that merely feels safe enough.

I use three questions to check myself on this, and they're worth sitting with longer than a scroll allows. Does this dream actually align with who I'm trying to become, or is it out of character for the sake of looking ambitious. Does this vision serve my community and the people I care about, or does it stop at my own doorstep. And am I building from abundance, love, and curiosity right now, or am I actually running from fear, scarcity, or ego wearing an ambition costume. That third one is the one people lie to themselves about most. Nikki put it more bluntly than I would have: if what you're building doesn't help someone feed their family somewhere down the line, you're not thinking about it deeply enough yet.

What actually moves an idea into motion

None of this works without a floor under it, and Nikki's floor is unglamorous. Build a product that solves a real problem, then advertise it with intention instead of just spending money and hoping. She proved that formula twice with almost nothing but two Instagram pages: a thousand dollars in a single day selling reusable face masks made from ankara cotton, then ten thousand dollars in one Black Friday weekend once she found the right audience for the innovation. GQ, Essence, and BET all found her because she kept showing up in the right rooms, not because she waited to be discovered.

The unglamorous floor also includes the paperwork nobody dreams about. Nikki learned the hard way, through a cease and desist letter that forced a full rebrand, that a domain name and a social handle are not the same thing as owning your business. An LLC, a trademark done correctly, the difference between a business and an asset you could actually sell if you walked away from it tomorrow. I've watched people build years of goodwill into something they don't legally own, and that's not a small oversight. It's the difference between building equity and building a very good hobby.

And underneath all of it sits pacing. The Navy SEAL line I keep coming back to is "slow is smooth, smooth is fast." Nikki's version showed up as five contractors and a restaurant investors kept telling her to just open already. Mine showed up as a decision to rebuild an app from the ground up, on a slower timeline, because the version we could launch right now wasn't the version our first customers deserved. Rushing isn't the same as moving. Sometimes the fastest path really does run through the slow one.

If there's an idea you've been sitting on, the invitation isn't to have it all figured out. It's to send the email before you feel ready to.

If you've got a pull toward something and the only thing standing between you and it is fear dressed up as caution, From Stuck to Starting was built for exactly this moment. It's a free tool for the space between sensing something and acting on it.

Originally aired as Episode 14 on the Choose Courage Inc. podcast.