Reigning Men with Jonathan Jackson

Jonathan Jackson is hilariously real. I think that’s one of the first things we noticed about him and is something you’ll absolutely see in this interview. He keeps it all the way 100 but his opinions don’t cause you to hate him or anything even if you disagree because you know he’s genuine in his meaning and intent. Writer, speaker, maker, Jonathan operates at the intersection of media and culture. Here he provides thoughts on where we are today, what “for the culture” even means and why Black women aren’t his mule. Get into it. You can keep up with him on Twitter and Instagram or let him milly rock into your inbox (linked below).

Reigning Men Jonathan Jackson

Photo: No Signal Creatives

Tell us a little bit about your background: Who are you and where are you headed?

I grew up in New Hampshire, I did gymnastics for a decade, and I have an older brother. By origin, my family is split between Trinidad and Mississippi, so I feel like that colored a lot of my perspective on history, culture, and family.   

I’m pretty introverted, which people fight me on because a lot of my work is public facing. I’ve learned recently that I am actually extroverted around people who bring me peace and joy, or environments where I can do my work. It’s been fun to finally understand myself a bit more on that level.  

I’m headed to wherever helps me bring the fullness of my gifts nurtured, magnified and expressed. I don’t care about being right as much as I care about being whole. If you’re into seeing me whole, please, come thru. If you’re not, the demands I have of myself, and the life I intend on living will remove you by force or circumstance.

How did you get your start in writing, speaking, and making? Who or what inspired you?

I’ve had a hyperactive imagination since I was really little and learned how to memorize before I finished learning how to physically write, so I like to think I’ve been taking snapshots of things with my mind much longer than I’ve been putting pen to paper. I had some trauma growing up, so I spent a lot of time in my head as a mechanism to protect myself. Writing is how I come alive. Speaking is how I communicate my feelings. Making is the combined action of both those things. As I get older, I realize that I’m agnostic to the vehicle I use to communicate. I just want to touch your pulse every single time. That’s my aim.

I was inspired by what I read and the stories I saw come to life. The Souls of Black Folk, Autobiography of Frederick Douglass, Native Son, The Bluest Eye, Beloved. Those were my connection points to how literature can shape your ideas of the world.

Reigning Men Jonathan Jackson

Photo: Quinnton Harris

You work at the intersection of media and culture. What trends are you seeing in our current moment? What does “for the culture” mean to you and how can or does one best operate there? (If we presume there is a best and place at which to operate of course).

Brands treat creators like labels, and we get surprised when the splits aren’t equitable. They will take from you whatever you allow them too and give you the equivalent of a 360 deal. All this influence, and no ownership? Issa no for me dog.

The other thing I’ve been fascinated by, is the fatigue people have with media, but their insatiable appetite for transmedia. Given how we consume media, the ability to share narratives across platforms in different ways isn’t going to be a nice to have, it is a necessity. You don’t have to love Instagram. You should know how it works though so you can use it to your benefit if it’s a part of your media mix.  

“For the culture” occupies the same space for me as people who put “diversity and inclusion” in their bio but don’t use systems thinking, and would rather be professional panelists then functional operators; it doesn’t mean anything depending on who is saying it, and what their track record of execution is. If for the culture doesn’t involve equity all in my deals and ownership from the onset, you can keep it. That’s not for me, and it shouldn’t be for us. For the culture would mean telling people how to get it in a way that doesn’t make them compromise their art for cash they could have made on their own. It would mean not selling us your $29.99 ebook and masterclass for four easy payments of $99 on how to a be a 6 figure infopreneur when you just did that for the first time in 2017. Doing something once is absolutely worth clapping for and celebrating, but depending on the context, I’m not sure it makes you an expert, and it definitely doesn’t make you an effective coach. You need to earn me into your funnel, not demand it because you think I’m operating at a loss. We win when the ecosystem is self-sustaining, not because there are individual successes that get touted as models.

Congrats on heading to Harvard as a Nieman Fellow. Talk to us about the process of getting to this step. You mentioned you had it bookmarked as a later when I feel ready thing. What does that mean and how do you decide what opportunities to pursue and when? How does your penchant for asking good questions tie into trust of yourself about what your next step should be?

Asking questions was something I used to get penalized at school for until I found the environments that nurtured that. I’m fortunate that my parents never dissuaded me from asking questions, and never pretended they had the answers, but they encouraged me to go out and search for them. That searching is something I take seriously because it means I refuse to settle for something simply because it’s presented to me. It’s saved me from believing other people’s definitions of who I could be and helped me ask “what if”, even if I was scared of the answer.

In hindsight, my framework for pursuing opportunities is less about the thing, and more about the capacity I have to learn new things. I have serious demands of myself, and I don’t like when I get close to stasis. Once I start feeling that, I have to shock my own system, which hurts, but being disrupted by something else that you could in fact plan for, is much worse to me.  

Nieman was really a dream that’s about to be a reality. I didn’t apply because I’m scared of my own capacity for greatness. I’m contrarian by nature, so when someone tells me something, I’m usually not trying to do it. It’s something I’m learning to balance because it has been a detriment in my personal life when left unchecked. I knew I could get to Nieman intellectually, but emotionally I had excuses for why it wasn’t my time yet. I have a strong sense of self-belief, I just thought I should be waiting for the right moment, so everything would line up. I’m grateful my parents are around to see me do something I didn’t think I was worthy of. Now that I have a better love for myself, I’m going to be fully in my bag, and I plan on exiting much better than I came in. I want everything that’s mine.

Black men and women are in some ways in a crisis. Crises of understanding and communication as a community, in addition to all the ways racism, sexism, and sexual orientation discrimination amongst so many other axes of oppression impact our everyday lives. Talk to us about how you see and understand the state of Black men today? What’s on your mind? What issues are most pressing to you? What triumphs are you seeing? Where do Black women fit in?

I don’t think Black women need to fit in anywhere. That’s not the right framing. I think a better question is what kind of future are we imagining and working towards? What issue is in your circumference of influence to engage with and push against, so that it doesn’t have to remain a norm?

I had a good friend call me a few weeks ago. I picked up the phone, and he said, “I think I’m having an anxiety attack, and I don’t know what to do.” We talked, I walked him through some processes and techniques I had learned and been taught by some professionals, and he was able to make it through that. That’s an isolated example, but because we have a relationship, he didn’t try to survive that himself.

I don’t know our state, but I do think there are critical conversations we need to be having about what’s keeping us from actually living our best lives. Jonathan’s been hurting for a while. Jonathan would make excuses for his insecurities instead of calling them what they were; manic episodes of anxiety compounded by the need to fulfill unreasonable expectations he placed on himself, so he could prove he was worthy of things that were already his birthright.

I have had to do some serious work in and on myself, to unmask and really get to the root of some of my own issues that scared me. No one can do that emotional work for me, nor should they be a casualty of it. If anyone’s heart work infringes on your safety or peace of mind, they are not for you in that current state. Doesn’t mean you have to cancel them, but it does mean your boundaries need to be enforced. Those are the kinds of conversations I’ve been having more of with black men in my life, which has given me a measure of optimism that we aren’t hopeless and unsalvageable, which I think a lot of the rhetoric can reinforce. There’s a need for consistent and ready accountability, but I think that can be tempered with people understanding how to do the work they need too and marshaling the resources that will support them in doing that. Black women are not that resource, and it isn’t their job to do that for me, or lead me to the water, or teach me at a detriment to their wellbeing.

Reigning Men Jonathan Jackson

Photo: Jarrod Anderson

Every day it seems like I see a tweet along the lines of “Support Black Women” “Believe Black women” “Pay Black women” or “Black women I hope you have a great day today,” and often from Black men. As great as the tweets are, I often worry that the other shoe is going to drop and/or the support/love/whatever for us is superficial. Why do Black women matter to you? What can our men be doing to uplift and encourage us in ways that aren’t just clickbait or temporary? What can Black women do to return the favor?

A lot of it is around knowing the space you are in, and what privilege looks like, given your sphere of influence. For me, a lot of it is access and proximity to power; who I get to know, the rooms I get to be in, the side conversations with money involved, the discourse I’m privy too that other people might never know about, the moves I hear about a year in advance.

You don’t read Alice Walker and get to call yourself womanist, no less than a white person reading Between the World and Me gets to tell you that “they get it now”. That’s not how understanding or dismantling works. You can’t microwave the unlearning you have to do.

We do a lot of theorizing, but I’m not sure we understand that the lived experiences we will never have and can’t fully comprehend, not only deserve to be heard, but are critical to bridging the gap between what we think is happening based on how we’re socialized, and what actually happens that we choose to ignore or find ways to not believe. Just because you read the think piece, doesn’t mean you get to proselytize your thoughts as if the things you read actually happened to you. There are consequences for those assumptions that people pay for with their lives. Just because you practice your empathy, doesn’t make you an expert on the realities of someone else, it just means you have the capacity to understand what they are saying. That capacity has limits, and we would do well to understand what those are.

We cannot have convenient conversations and say we are committed. Convenience says, “I felt like doing this.” Commitment says, “I did it even when it was uncomfortable, and I will continue too because I have the agency to do so.”

I don’t really have a turnkey solution for what Black men can be doing, but I think less tweeting and more listening is a starting point that you can at least move forward from. This freedom we discuss so casually is cool until it requires something of you. Every one of us has the chance to not be neutral in a situation where a black woman in our vicinity has been violated in some capacity. We know what it looks like, we know what happens, and we know it doesn’t get better because we think about it. Equity is a noun, but it’s also a verb if you’re serious about it.

As it relates to Black women and why they matter to me, you don’t have enough unlimited scroll on your website for that. I talked to God about it, and I’m fairly certain I’ll marry one. The who is still very much unknown, but I’m not tripping off that right now.

Reigning Men Jonathan Jackson

Photo: No Signal Creatives

What can we expect from you moving forward? How can we be of support?

I’m doing a lot of healing right now, so I sometimes don’t even recognize myself. It’s like an IOS upgrade every week, and I’m addicted to it. I’m trying to learn how to receive the quality of love I push myself to give. You can expect me to only be surrounding myself with people who love and care about who I am more than what I do. A lot of people enjoy saying how much they don’t care about things and how much of a savage they are. That’s cool, but it’s not my ministry. I wear my heart on my sleeve, and I’m not going to do less of that because it makes people uncomfortable. I was changing for the wrong things. Now I’m growing towards the right ones. I just want to be found doing my work.

I’m a believer in moves over announcements, but I’ll be doing more writing this year. A young brother has a newsletter though, so come through and let me millyrock in your inbox every now and again. People don’t really know me outside of the image I’ve carefully crafted and maintained, so I’m working on getting free of that. Art helps.

Also looking for a sweat suit sponsorship. You send me clothes, I adorn them and look comfy while doing things like cooking, speaking, and walking under street lamps. If that’s you, pull up in my inbox.

In the end, how do you want your story depicted? What legacy do you hope to leave behind?

I want to leave life with nothing left. I want to do work that outlives me.  Every interview, every podcast, every speaking engagement, it’s all part of a body of work. If I die, you should be able to look at the portfolio of my life and glean exactly what I cared about inside of whatever I left. That’s what I’m imperfectly fighting for.

Just for kicks:

  • Kendrick or J. Cole? That’s like asking if I prefer the oxtail more than the gravy. You need both for a complete meal. I need that collaboration album they hinted at a few years ago though.
  • Podcast or blog? Thoroughly enjoying podcasts right now, but I enjoy a good long read from time to time.
  • Football or basketball? NBA
  • Advice to other writers, speakers, and makers? Meetings are fun, Contracts are dope, invoices are cool, but confirmation emails of deposits and wires being sent are a love language.

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