On following the path in front of you

Your CV includes writing, speaking, branding and advertising work, and your popular social media affirmations—a pretty diverse and unique combo. How did you get to where you are today, and what are the most important things you’ve learned along your path?

I’ve never felt 100% sure about exactly what needs to happen next, but I’ve always been willing to pick up different skills along the way. My initial goal as a creative, as an entrepreneur, was to run a rap blog, so I was studying different ways to understand SEO basics, bring in traffic, [and] conduct quality interviews, and I immersed myself fully in that world. That progressed to me finding new interests creating content on social media, building a personal platform about things that I care about, that pertain to mental health, productivity, healing.

Because I’ve been able to grow my platform, I became sought after as an advisor or coach for people looking to grow their business or their personal platform on social media. I didn’t plan for the next transition per se, but I got there, I saw what it was, and started studying, started trying to figure things out and learn both through research and experience what the best way forward was.

I think I have a healthy degree of obsession with whatever my current creative project is. My work is largely passion-based, so it’s never too hard for me to find something new to immerse myself in and learn about. Oftentimes, the work I’ve done in previous chapters ends up translating to help me have a unique spin on what I’m doing in the moment.

You were expelled from college a month before you would’ve graduated, yet here you are, making a career out of your creativity. How did you create a path outside the usual system?

I had to. I went to a military academy and I was expecting [that to be] my career path until at least 27. I found out a month before I graduated that that was no longer the case. It put me back almost in this kid space of, “You have to think about what you want to do for the first time. You’re about to be done with school, and you have to figure out what your next step is.” That was not true of any choice I’d made before that point.

I found myself in a space where I was drawn toward what I was most passionate about in that moment. My interest in music and writing about music had been a really helpful side hobby. I launched a blog when I was a 19-year-old college sophomore, and it was a fun place to play around with things I didn’t get to talk about or think about at the military institution. I followed the interests I had developed. I gave myself free rein.

I was broke when I was in college. I worked a part-time job but spent a lot of time going after things that interested me, like interviewing underground artists and legacy artists in hip-hop. That was just the path I chose. It was very much interest-based. It was based on a belief that I could build something from scratch and eventually make money off it with the skills I acquired from building it, and that took longer than expected, but I got there.

Circling back to what you said about the kid space, the more I speak with creatives, the more I’m convinced that being childlike and not being afraid to be silly and do things adults might not always do is key to creativity. I’m wondering if that kid space comes up for you still.

I use my desire to learn more about writing, to push myself to explore different forms of communication and creativity. I’m not going to do it anywhere in public, but I’ll play around with freestyling, with improv, with all different sorts of communication, and give myself license to be a complete rookie at some creative form of communication or some form of art, not to produce it or profit from it, but just to learn about and understand it.

I also have, generally speaking, childlike curiosity. I’m following ventriloquists and chefs with a focus on very obscure cuisine on [social media], not just other writers. Having that broad view of the world, being willing to be a rookie at almost anything, and doing things that interest me, as almost little side quests, gives me more room to play and feel childlike, and to experiment both in and outside of writing.

To what extent do you treat your creative practice like a business? Is there a line you draw between the two, or do they bleed into one another?

I’m fortunate that I’m starting to build more leverage as a creative [and] can do more things that feel like I’m committing to art, to creativity, and not focused aggressively on business. I have a talent manager who [thinks] about those things for me while [I] reckon with capitalism while living in Brooklyn. There’s no easy way to not think about that entirely.

I don’t think I’m profit-obsessed to the point that I’m changing the nature of what I do. I give myself time to play around with different things and do things I enjoy, and to figure out…how to monetize that, if I want to monetize that, and I allow myself to go from there. I think I have a somewhat healthy balance when it comes to the fun, creative aspect and the business aspect.

How did you initially figure out how to make a living for your creative work?

Luck. Lots of…work, feeling my way around, and luck.

My first attempts to make money with a specific income stream failed miserably. I wanted to run this rap blog. I wanted to be a full-time freelance journalist, and I wanted to build a lot of income as a full-time content creator, all the photoshoots and product reviews and things like that. None of those things worked out for me. I built a lot of knowledge, a lot of leverage, but not for the thing I was looking to build. In my time running a hip-hop blog, which was not profitable in any way, I leveraged [my] interest in music to give me interesting things to talk about and different artists to feature on reels as background music for the content I create now.

Journalism gave me more confidence in my writing than any other period I spent writing. My editor when I wrote an interview series for MTV News was the most impactful editor I’ve ever worked with, and she pushed me to get more comfortable with constructive feedback and made me a lot more confident in my ability to dig deeper as a writer, thinker, and creator. That gave me increased confidence in my ability to write, function, and create on the fly.

The time I spent as a content creator forced me to push past my tendency to overthink…because so much with building a social media audience is both quality and quantity. There’s so much to compete with on any feed, so if you’re looking to use an audience for leverage, you have to be sharing very consistently. For the first time in my life, I had chosen a goal that required me to publish things not based on the cadence I wanted, but based on the cadence that had to be true. I had to lean into that.

All those different things I did led me to finding my way as a writer on social media platforms. That probably is the thing people know me for the most. Miraculously, I’ve been able to find a bunch of opportunities from the clients we have in our agency, to the books I write, to the different types of content I create for brands, as a result of different things I learned during different phases of my career. It was never planned.

Given the number of creative pursuits and income sources you balance, what exactly does your work look like day to day? Can you talk about your process, any rituals you have, things like that?

I’m actually working to shift that and lock in on a more consistent process. I start almost every day writing something to share on social media. I do my best to stay consistent with that. That gets my brain going, gets me moving. Mind you, I’m doing that if I can get out the door. My daughter is a toddler. She’s not yet two years old, and she’s the most important thing in my wife and I’s life right now. Sometimes, we leave home and go to the co-working space a little bit late if she needs us. We’re fortunate enough to have that privilege, so we put her first.

I start my workday at nine. I look to publish something on Instagram, a quote and a caption for the day. From there, I’m prioritizing client needs, handling any creative work that has to be done, and doing my best to get a better feel for the systems that are and aren’t working so I can always be refining and iterating on what I do and how I do it.

Why are you looking to shift?

I realized I have ADHD last year. I realized I wasn’t just forgetful, that my brain actually couldn’t work in the way I was trying to make it work. The reason a lot of different ventures and jobs didn’t work out was because I was trying to approach planning and process from the vantage point of what would work for somebody who is neurotypical and can operate in a different way. I’m doing my best to give myself more grace, not be hard on myself for the things I can’t control, to account for them and structure my day in a way that’ll minimize overwhelm [and] allow me to function and be efficient without feeling like I’m always in a frantic space.

How do you make time for each of your creative pursuits? How do you figure out how much attention you want to give any one of them on any given day and attend to them as necessary?

The biggest thing is being clear on deadlines, what’s due when, and what that needs to look like. I’m experimenting with giving myself more time to just think through what appeals to me.

For example, if I have two deadlines next week and, today, my mind is screaming at me, “Write this thing,” I’m going to write that thing, I’m going to focus on that, and I’ll block off time, as a compromise, to do the other project I have to get done the next day. I’m giving myself guardrails that allow me to get multiple projects done in an efficient way while saying, “If I have space before both these things are due and I want to do this thing today, I’ll focus my energy there.

What are the most valuable creative resources you seek out for each of your types of creativity, or just in general?

Right now, I’m pretty big on Asana, and I leverage Slack as well. Getting clear on the role of each platform, as far as each different creative workflow, has been huge for me. I know where to go for what, I know what to check for what, and I know how to make sure I haven’t missed anything.

[Talking through roadblocks with] my creative community and peers, fellow writers, strategists, content creators, and people who are interested in mental health is a huge support that allows me to not feel alone and to work through things and understand things in a more nuanced way than I might on any emotionally taxing or generally fatiguing day. That additional perspective is priceless.

What role does collaboration play in your creativity?

The biggest form of collaboration for me as a writer, given that we’re communicating, is conversation, hearing people talk about things they care about, people who are in similar spaces getting their thoughts out and exchanging insights and ideas getting feedback on different things that I’m thinking about. All those types of conversations I couldn’t ask the average person, but can ask people who I’ve built connections with because of our shared interests and passions, are huge for me. The people I’ve talked to the most shape my thinking, and my writing is my thinking on the page, so it’s invaluable to have those conversations with different people every day.

Besides the money your creative work brings in for you, what are the rewards of all your creative pursuits? What have they taught you about yourself?

My creative pursuits taught me that I can envision something and bring it to life. My creative pursuits taught me that it wasn’t arrogant to believe I could pursue a non-traditional path of sustaining myself and working, living, and existing. My creative pursuits taught me that people care about my perspective and vantage point. They taught me about the value of slowing something down and allowing it to coalesce into what you want it to be, even when the details feel fuzzy at first.

How much, if at all, did you know beforehand that there would be an audience for what you wanted to do? Where did you find the bravery to try your hand at something that you weren’t sure would pan out?

I’ve always believed that something would pan out. I was more scared of being forced into a traditional career path that didn’t excite me and having to show up for that every day than sharing things online and investing energy into that. I’ve always had a belief that this would work out in some way, shape, or form. It was more so a matter of me continuing to do that work and figure things out, as opposed to whether or not it would work out.

That’s all I wanted to ask you, but if you have anything more you want to say about creativity or anything more you wanted to say to my questions, the floor is yours.

I want to expand on the conversation about community. I was…always scared to ask for help, to reach out, to build bridges with other people doing things [I was] interested in. I would [tell] anyone in any phase of their career that, if they want to have more friendships and professional connections, to be the catalyst for those, be the one to reach out, be the one to put themselves out there. That type of connectivity is better than the actual stuff you create sometimes, because you feel seen in different ways. To have people who understand you creatively [and] are working on similar things know what you go through to create what you create is possibly the best gift of creativity.