Why ADHD Entrepreneurs Struggle With Boundaries (And How to Fix It)
As I sat across from Jabari, I could feel both the resonance and the difference in our experiences, and it was precisely this dynamic that made our conversation so rich.
Like so many entrepreneurs with ADHD, Jabari struck out on his own to escape the feeling of being boxed in, only to find himself recreating old patterns—overwork, scope creep, and that familiar feeling of being energetically drained.
Finding Alignment in the Uncomfortable: Navigating Expertise, Identity, and Growth with Jabari Allen
When I launched the ADHD-ish ™ Podcast, I always hoped it would become a space for honest conversations that stretched beyond the typical ADHD productivity hacks, and instead delved into the nuanced realities of building a business as a neurodivergent individual. One of my more memorable recent conversations took place with Jabari Allen, a tech consultant working at the intersection of artificial intelligence, regulated industries, and identity. As I sat across from Jabari, I could feel both the resonance and the difference in our experiences, and it was precisely this dynamic that made our conversation so rich. Working with him as a business strategy coach has taught me as much as I've believe I’ve taught him.
From the outset, I told Jabari what I'd already told him several times in the past—I don't play favorites with clients, but he is unequivocally one of mine. His willingness to self-interrogate, to challenge his own beliefs and blind spots, is rare and vital in a world that so often rewards conformity. As I opened the conversation, I asked him to introduce himself—not the way a LinkedIn bio would, not the rehearsed "elevator pitch," but simply: Who are you, and what do you do, if you were at a dinner party talking to a stranger? He told us, simply and clearly, that he helps businesses in regulated industries evaluate whether their AI systems can truly be relied upon. There's a humility in how he operates—he could go deep, could start "getting into the weeds with people," but chooses not to until he's invited.
Like so many entrepreneurs with ADHD, Jabari struck out on his own to escape the feeling of being boxed in, only to find himself recreating old patterns—overwork, scope creep, and that familiar feeling of being energetically drained. When he described "not feeling like he was practicing at the top of his license," (using a term borrowed from the medical field) I thought of how often I see this, especially for those of us whose talents are undervalued or misunderstood in more traditional workplaces. The pull to prove ourselves—by doing more, pleasing everyone, sacrificing our boundaries—is almost magnetic.
I've spoken often about people pleasing as something that can quietly swallow entrepreneurs whole. Many listeners picture the smiling, non-confrontational sort who never says no, but the reality in business is subtler. Jabari Allen's version was prioritizing the comfort of others at the expense of his professional intuition—pushing down that gut feeling that something was off, for fear of ruffling feathers or losing approval. He articulated a familiar sensation, that of "gaslighting yourself," continually second-guessing which direction is correct, all the while knowing, deep down, that your instincts are right but feeling pressured to ignore them for the sake of harmony. Our perspectives here were very much aligned: business strategy coaching work is a mental and emotional challenge as much as it is a practical one, and it requires a delicate balance of client satisfaction and self-trust. The need to please is both functional and fraught, often heightened by the specter of rejection sensitivity in ADHD and societal messaging that "the customer is always right."
But the conversation shifted to something deeper and, honestly, far less commonly explored. Jabari brings to his entrepreneurship a complex identity—he's Black, neurodivergent, and working in tech, a space that is often neither diverse nor especially welcoming to difference. When I asked about his comfort in sharing these truths, he told me it was unavoidable—not necessarily unsafe, but ever-present, "like talking about the water around me." This was not just a side note but a central axis around which his experience of business ownership spun. He described with clarity and self-awareness how being a "Black face in a white space," and being neurodivergent, creates a constant low-level hum of being othered, sometimes subtly, sometimes overtly, but always there. For those of us navigating rejection sensitivity in ADHD, this reality is compounded.
For me, growing up white, some doors have always opened more easily, and some doubts have simply never needed to be considered. But what struck me in Jabari’s narrative was not just the challenge, but the sense of affirmation he's found in entrepreneurship. In the fullness of running his own consulting business, with all its risks and uncertainties, he discovered a kind of validation that is uniquely his—clients come to him for his expertise, not despite, but because of all that he is. That feeling of being chosen for your whole self, in a world that so often asks you to fragment or conceal, is something I can celebrate even as I know I cannot fully embody it.
Both Jabari and I see growth as inseparable from discomfort. Whether it's pushing back on clients' unrealistic expectations, overcoming analysis paralysis, or refusing to default to overcompensation and self-doubt, the path forward is rarely comfortable but always clarifying. This is where business boundaries become essential—and where my role as a business strategy coach helps clients identify exactly where they're overextending. When Jabari Allen described his "circling the drain" sensation—overworking, overthinking, yak shaving—I recognized my own tendencies, and those of nearly every entrepreneur I know with ADHD. The difference, as he pointed out, is not that these feelings disappear, but that we learn to notice them sooner, release the pattern faster, and agonize less. That, I told him, is winning.
Perhaps the most powerful moment in our exchange was when Jabari described the breakthrough of seeing himself not just as a highly skilled technician for hire, but as an "emerging thought leader." This didn't come naturally—he admitted that seeing himself that way at first made him uncomfortable, that he wrestled with "who am I to be disruptive?" In our industry, challenging the orthodoxies around AI isn't popular—especially when it comes from a young, Black, neurodivergent consultant. Here, the exchange of opinions was clear, as we discussed the responsibility that comes with having a divergent perspective, the weight and the freedom of needing to create your own safety when others might be quick to delegitimize you. Strong business boundaries are what make that possible.
Throughout our conversation, the common thread was this: the hard work of building not just a business, but a new and more expansive concept of self. Jabari spoke openly of moments where he was tempted to overcompensate or fall back on familiar scripts, but instead chose self-honesty, business boundaries, and radical candor. He acknowledged the anxiety and the existential threat that can follow these choices—the risk of burnout, disappointment, or even failure. Yet, by trusting himself, by choosing discomfort over default, he found clarity, focus, and a sense of being "comfortably seated in himself."
As I concluded the conversation, I felt more certain than ever that, whether you are neurodivergent, navigating complex identities, or simply trying to bring more of yourself to your work, growth comes when we allow ourselves to question the obvious, to challenge the scripts, and to risk being seen in all our complexity. My point of view is deeply aligned with Jabari Allen: it is not in spite of our differences, but through them, that we discover our real power as entrepreneurs—and as humans. If you're curious about where this journey is taking Jabari, you can find his ongoing thoughts and work at Inside Voice AI, where he's demystifying the technology, advocating for skepticism and inclusion, and helping others realize that they too can hold all these truths at once.
For me, these are the conversations that matter. This is why I host the ADHD-ish ™ Podcast, and why I believe that exchanging opinions, sharing stories, and holding space for discomfort are the keys to building something far more valuable than just another business—we're building a life that fits. Whether you work with me as a business strategy coach or find your own trusted thought partner, the work of alignment is always worth it.
Feel free to DM me on LinkedIn or send me an email at diann@diannwingertcoaching.com. I'd love to hear your thoughts!
If you'd like to hear the full episode on the ADHD-ish ™ Podcast, you can do that here.
