We caught up with the brilliant and insightful HOLLY JAI a few weeks ago and have shared our conversation below.
HOLLY, looking forward to hearing all of your stories today. What’s the best or worst investment you’ve made (either in terms of time or money)? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)
The best investment I’ve made was one I didn’t fully recognize as an investment at the time and honestly, that’s what made it so powerful.
As an undergrad studying Mass Communications with a concentration in PR at a STEM-centered university, I was surrounded by people who had very clear, conventional paths. Mine felt less defined, but I always trusted what felt authentic over what felt expected. That instinct led me to sit in on a speech hosted by USF where a professional spoke about the importance of personal branding and building a portfolio. Something clicked. I didn’t have a roadmap, but I started building anyway and that’s how I launched my first digital community, The It Gal.
I poured everything into it. Event planning, copywriting, editing, interviewing, website building. I was doing the work, learning the craft, growing a community. Then March 2020 happened. Months away from hosting my first annual Project Prom event, COVID shut the world down. I had just landed my first real job, and suddenly everything paused.
But the pause was a gift I didn’t see coming. The world slowing down gave me space to ask a question I’d been avoiding: *what about me?* I’d been building for a community, but I’d always had a deeper dream of building a personal brand centered around myself. I just hadn’t lived enough life yet to feel ready, or so I told myself.
COVID removed that excuse. I pivoted. I invested that time into honing every skill I’d picked up and redirected them toward building something of my own, starting with YouTube. Then came the moment that changed everything. I purchased a Canon G7X Mark II. What felt like a simple camera purchase turned into the single biggest tangible investment I’d made since choosing my major. That camera gave me the tool to create, and I used it, producing five plus viral videos that positioned me as an affordable fashion creator and fashion DIY creative.
And somewhere in that season, something else crystallized. I started looking at the people around me, not for comparison, but for confirmation. Out of everyone in my orbit, I could think of maybe 30 people. Every single one of them could see the potential in content creation. But none of them wanted to do it. None of them felt called to it. Except me. That quiet realization turned a light switch on that hasn’t gone off since.
The lesson? Your best investments rarely announce themselves as such. Sometimes they look like a camera. Sometimes they look like a quiet season you didn’t ask for. And sometimes they look like a speech you almost didn’t attend that plants a seed you spend the next several years learning how to grow.
HOLLY, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I’m Holly Jai, fashion content creator, lifestyle curator, and founder of Planet Holly, a digital fashion ecosystem built for the it girl of her circle. I call her “The Holly.” She’s the one who always stands out, always shows up, always makes the room take notice in her own way. I create for her because I am her.
My path into this space was self-built from the ground up. I studied Mass Communications with a concentration in PR, taught myself editing, copywriting, website building, and content creation, and launched my first digital community, The It Gal, before I had a blueprint for any of it. When COVID hit in 2020, I pivoted from building for a community to building for myself, something I had always wanted to do but kept waiting until I felt “ready” for. A Canon G7X Mark II and five plus viral videos later, I was established as an affordable fashion creator and fashion DIY creative, and I haven’t looked back since.
Planet Holly is the evolution of everything I’ve built and everything I know myself to be. It is a universe curated by Holly x Jai, for The Hollys of the world. A space where fashion, lifestyle, and culture collide with intention and editorial perspective. I specialize in making the it-girl aesthetic accessible, proving through curated finds, outfit inspiration, and creative content that style is about point of view, not price tag. Planet Holly is not just a destination. It is a world The Hollys can see themselves in.
What sets me apart is simple. I’m not here to chase trends. I’m here to build a universe. And I want every woman who finds Planet Holly to leave feeling like exactly what she already is. The Hollywood of her circle.
How can we best help foster a strong, supportive environment for artists and creatives?
In my honest opinion, the greatest thing society could do to support creatives is simply slow down.
That might sound simple, but it is the most radical thing I can ask for. We live in a world that moves at a pace that was not designed with the creative mind in its consideration. And for most creatives, especially those of us still building toward the point where our art sustains us fully, we are also operating inside that same rat race. Day jobs, deadlines, obligations. We are trying to create meaningful, intentional, thoughtfully curated work in the margins of a life that was structured around everything but that.
I know this personally. Some of my most impactful content, the work I am most proud of, the pieces that actually connected and resonated, did not come from my busiest seasons. They came when life slowed down enough for me to actually hear myself think. There was a particular season where the world outside grew quiet, and in that quiet I was finally able to create in a way that felt true. That experience showed me exactly what is possible when a creative is given space, and exactly how much we are leaving on the table when we aren’t.
What I want people to understand is that creativity is not just something we do. It is part of who we are. When we are not given the space to create, it is not just a professional loss. It is a personal one. Creating is regulating. It is how many of us process, heal, and make sense of the world around us. When society moves too fast to make room for that, it is not just art that suffers. It is the people behind it.
So support creatives by valuing process over output. By understanding that the best work takes time and stillness to arrive. By not reducing what we do to content and product while forgetting that behind every piece is a human being who needed the right conditions to make it. Give creatives room to breathe, and watch what they build for the world.
What’s a lesson you had to unlearn and what’s the backstory?
The lesson I had to unlearn was that there is a right path, and that I should be on it.
I grew up in spaces where the blueprint was clear. You study something practical, you secure something stable, and you measure your success by how well you follow the program. And for a long time, even when I knew deep down that I was wired differently, I kept trying to fit myself into that framework. I would look at what everyone around me was doing and quietly wonder if I was the problem. If maybe I was just convinced I was supposed to be something I wasn’t.
What changed was perspective. I started paying attention not for comparison, but for confirmation. I looked at the people closest to me, friends, coworkers, peers, and I noticed something. Every single one of them had found their lane. Nursing, law, filmmaking, healthcare. Beautiful paths, all of them. And when content creation and building something of your own would come up in conversation, they could all see the potential. But none of them wanted to do it. None of them felt pulled toward it.
Except me.
That was the moment I stopped trying to unlearn my ambition and started trusting it. The lesson I had been living under was that wanting something unconventional meant I was being naive or unrealistic. The truth I had to replace it with was simpler and a lot more freeing. Not everyone is called to the same thing. And the fact that I kept being called back to this, through self-doubt, through detours, through seasons where it would have been easier to let it go, that wasn’t a coincidence. That was confirmation.
I’m not the one out of thirty who couldn’t figure out a conventional path. I’m the one out of thirty who was never meant to walk one.
Contact Info:
- Instagram: hollyxjai
- Facebook: https://www.facebook.com/planetxholly
- Youtube: https://www.youtube.com/@HOLLYJAI
Image Credits
@mindofjr Trenton Butler
@blkbookstudio Kaylyn Fudge
@themodelfactory_ Daijah Jackson
@hollyxjai Jaiya Williams