Having the ability to apply emotional intelligence to sync ideas into tangible outcomes is a rare skill in a saturated digital market. Marketers love the word "millennials' for behavioral habits. Nonetheless, adding cultural context to this demo makes us one of the smartest markets to tackle. For this Millennial Monday, we’ve highlighted Jonathan Jackson for his ability to articulate and leverage the “why”. Recognized for launching and content-branding platforms like Blavity and The Night Shift, Jonathan’s versatility in creating content while offering insight beyond surface level factoids positions him as a standout creative in media. We caught up with Jonathan and got the tea on his perspective on what we care about. Check it out below: Co-Founder, Writer, Speaker — How do you describe the work that you do? I work at intersections of people, relationships, and opportunities. Intersections are difficult because, just like NYC traffic in real life, it’s possible that you can get hit from multiple directions–even if you’re in the right of way. The risk is high, but the reward is there if you learn how to direct from different angles and adjust for variables. That’s where the fun comes in. What’s one thing you’ve found to be true about being a millennial in media that most people would disagree with? Our influence isn’t based on the fact that we are digital-first. But, that our agility can transform our careers before market disruption does it to us. Externally, none of this makes sense. Because we don’t have the luxury of explaining our moves, this concept isn’t as palatable for other people. If you’re getting your hands dirty and getting your stripes, the least you can do for yourself is set aside time for yourself. Think about what it is you actually want. Optimize for that. While launching Blavity, you've transitioned into entrepreneurship while working as a full-time employee. What was that experience like for you? I learned more about myself during that process, than any formalized training would ever have given me. The lessons I have now are going to serve me for the rest of my career, regardless of where I am and what I do. It also forced me to be mindful of things you can take for granted working in a structured environment. Just because it’s “stable” doesn’t mean you’re safe, and taking risks is the prerequisite for any success on your own terms. "Taking Click To Tweet What are some of the biggest mistakes you’ve made that have impacted the way you conduct business? Lack of decisiveness. There are many things worse than making a “bad” decision. Not making one is chief among them. I try to make less decisions daily that can be decided ahead of time. It’s critical in having a routine and activities that I do regardless of circumstances. [This] helps me conduct better business. Not doing the pre-work required to have on opinion. One of my worst professional moments I’ve ever had was being asked why I thought something, and being unable to answer. I couldn’t answer because I didn’t have a reason of my own, just a bunch of annotations of other people’s thoughts. That petrified me, and since then I’ve made a commitment to have my own thoughts about anything I bring up. This means I inherently listen more, because I want to learn and absorb as much as possible. Reputation is cool, character is more important. My reputation is controlled and managed. My character requires investment. The latter feeds the former, because it’s what happens when no one is around, and when you have the access to a different realm of opportunities. Whether I am what I say I am, or I’m not, will get revealed through time or circumstance. I can pay someone to manage my reputation. There isn’t enough money available for someone to construct my character for me. My family and friends don’t care about whether or not I’m popping on the Internet. They deserve the best of me, because they love me unconditionally. Chaos isn’t always indicative of errors. Sometimes it’s a flag to keep going. It’s May and I’m having the most personally trying year of my life thus far. The irony is that the hardest decision I’ve had to make has been to surrender, so I could get stronger. I used to conflate any type of surrender with weakness. But, it actually takes a different measure of fortitude to look objectively at something and say “Nah, that’s not for me” while letting go of the false sense of security I used to attach to it. It’s the hardest personal and professional lesson I’m learning right now. Being careless with how I talk to myself. There is no one who can have a more disrespectful conversation with me, than I’ve had with myself. I’ve had to unlearn and discard the negative dialogues I used to have with myself, and replace them with more care and affirmation. That’s allowed me to remain balanced internally through a lot of difficult external situations. It took me most of my life to actually start loving myself, but I’m glad I decided to start when I did. There's usually a critical point for everyone that foreshadows how they might envision their career path. What was that moment for you? The day I realized that who I want to be is more important than what I want to do. I have friends with five, ten, and fifteen-year plans and I’m excited for them. They’re going to become incredible people and I’ll probably ghostwrite their autobiographies, because they’ll be too busy working. But that’s not how I think about my career. I’m serious about planning, but I also know that what I have been gifted with isn’t for use in a solely a job. It’s more attached to experiences I have to pursue to create the kind of life I want. I want a big one, so I can bring the people I love into it, and envelop them. I have a vision for my life that continues to expand, and I’m grateful for that. That’s much more important to me than where my career could go, because it keeps me mindful of opportunities that I’d overlook because they don’t fit inside of _____. "The Click To Tweet What is the biggest factor pushing you to strive for success? I want to persistently test my limits. There are a lot of people who have ideas about what they think I’m capable of. I don’t care about that, because I have to be Jonathan after that deal, this event, or that opportunity. I made some promises to people who aren’t here anymore, and some other ones to some people who did everything so I could be here. I intend on seeing those to fruition. Any upcoming projects? Tell us about it and how we can keep up with you. I’m always up to a few different things. For now, I’m working on being transparent via my email list, called The Night Shift. I’ve fallen off a bit, so the more people that know about it, the more accountable I am to giving them consistent value. Plus, it gives me a reason to make full use all the stock photo sites I’ve been compiling for the past two years.