1. There is always a "third way."
One of my first days working at Idea Booth, Ron asked me to research how to get something posted for a brand within Flipboard. I poked around on Google for about 10 minutes and then came back to tell him, "I looked, and it's impossible. You can either do this, or this, but what you're asking for can't be done." He smiled and said, "There is always a third way. Go find it." He was right. Twenty minutes later I figured it out. And to this day, whenever I fall into the trap of saying "I can't figure it out," all he says is "Flipboard," and I am reminded there is always another answer--a third way.
2. If someone likes your idea the first time you explain it, your idea isn't risky enough.
I've come to learn that the ideas most quickly praised are actually some of my weakest ideas. People praise them because they "make sense" and don't push boundaries--they don't "threaten" anyone. This was something I didn't understand until I really started sharing my own ideas with the world. The valuable ideas are the ones people question, because where there is a question there is room to explore. The ideas that people immediately validate, that make them say "Sure! Love it!" are the safe ones, and tend to lack the risk needed to be truly influential and groundbreaking.
3. Titles are meaningless.
This is a lesson I thought I had learned earlier in life, but it needed to be learned again. When I first started working at Idea Booth, I fell into the trap of wanting "more." I was a kid fresh out of college, and looked around at some of my peers who were in high-paying positions and had fancy titles next to their names, and I wanted that. I wanted that feeling of validation. I wanted people to know I was "successful." But whenever I would spend time with Ron, practically asking him how I could have my own title, his only response was, "Titles don't matter. Focus on doing great work instead." It took me a long time to understand how valuable that lesson is--and even more so, how many people use a title as a way to cover up how little they actually know. They let their title speak for them, instead of their skills and working knowledge. And they expect people to listen to them because of their title, not because of what they actively bring to the table.
4. Rewards are fleeting (and do not bring fulfillment).
Another thing I would do (as an ambitious young creative) was ogle the sports cars, nice clothes, and gorgeous women who frequented the Chicago hot spots Ron would take me to. I would look around and say, "I want that. I want that. I want that," to which Ron would say, "If you judge your success off the things you have, you will never be fulfilled." Being a 23-year-old staring at a jet-black Ferrari parked outside of a fancy restaurant, those words are not easy to encode. But I see now how much those words have stuck with me. Because once you get one reward, you want the next one, and the next one, and ultimately they lead nowhere. Real fulfillment comes from being in love with what you do, and always pushing yourself to create your next best piece of work.
5. Great ideas don't happen sitting behind a desk.
The interesting thing about our dynamic is that Ron and I are both very similar and very different. I am obsessive about my repetitive daily routines, and he is fearless in his willingness to try new things. In many ways, this is something we taught each other. For me, this meant stepping outside of my comfort zone and being willing to ride the waves of life. What I learned from Ron was that as much as daily discipline is required for long-term, sustainable progress and growth, moments of inspiration and creative freedom rarely happen in a closed room. They happen when you're out in the world being exposed to new things. They happen over dinner at some crazy concept restaurant, or while watching live music in a grungy blues bar. They happen at an art museum, or while walking through a park. They happen on a roller coaster, or in a yoga class. They happen when you step outside what is familiar to you, and your senses are exposed to something different.
These days, I try hard to do something I have never done before at least a few times a week--because I see the value.
6. Say yes, then figure out how to do it later.
One of the fundamental changes I have witnessed in myself over the past few years has been my willingness to say yes to what is 100 percent unknown--and I attribute that to having spent so much time watching and learning from a seasoned entrepreneur. Very rarely do you walk into a situation knowing all the answers, and this ambiguity used to keep me from saying yes to a lot of opportunities. Unless I knew exactly how I was going to do something, I would avoid it. What I have since learned is that the unknown is nothing to fear, and the only question you need to ask yourself is, "Do I believe enough in myself to be able to figure it out?" That's it. If the opportunity intrigues you, say yes. Figure out how you're going to pull it off later. But get yourself in the trenches. Get your hands dirty. And know, deep down, that you have what it takes to get it done.
7. True creatives are unapologetic in their work.
This is, hands down, the biggest lesson I learned from Ron, as well as the hardest.
Every creative person's fear is rooted in judgment. "What will people think of me? What if no one likes what I create? What if I'm wrong?" These fears are what keep many people from ever creating anything of value--and simultaneously, force them to lean on the title "creative." They call themselves creative more than they perform the act of creating, while the truly creative are the ones who are too busy working on their craft to care one way or another how people refer to them.
For me, the manifestation of this lesson came through the publishing of my first book, Confessions of a Teenage Gamer. I had just started writing when I began working at Idea Booth, and it took me almost five years to complete and publish. The reason it took me so long was because I cared a lot about what people thought. I feared how people would take it and worried it wouldn't be "good enough." I wondered if people would understand or appreciate it.
Publishing this book showed me I had finally learned the lesson Ron had explained to me time and time again. "You create for yourself," he would say. "Your work is an expression of you. And you can't live your life in fear."
This wasn't a lesson Ron sat down and "taught" me. It wasn't explained once or twice, and then I "got it." This was a slow progression over several years, the result of my being in his presence and feeding off the energy of someone who was 100 percent confident in his ideas and willing to face the criticism of others.
That is the value of a mentor, and what a true mentorship is. It's the opportunity to learn firsthand. It is not a class. It is not "I teach you and then you're done." It is an experience. And the greatest lessons come from simple being in the presence of someone who possesses the qualities you hope to one day embody yourself.
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