1: What is your greatest fear, and how do you manage it?
My greatest fear has definitely changed over time. As I've gotten older, and as my kids have gotten older, my greatest fear has really become creating mediocre work rather than solid and concrete work that I’m proud of. I reflect on how I’m utilizing my time more now and if I’m really maximizing it on the right things. How am I stacking the minutes, days, weeks and months to add up to a legacy for myself and my family that I can be proud of. I believe that mediocre work stems from distractions, chasing too many things, and having too many goals. So I manage this fear by ensuring that I’m putting things in my daily routine that add value to and fulfill my life. Making sure I exercise, sleep and eat well. Making sure I spend time with my wife and kids, and that I prioritize activities outside of work, like hobbies.
2: How do you define success?
This may sound cliche, but I define success as finding a sense of gratitude and fulfillment. I chose those words intentionally because I do believe there is a difference between feeling content and feeling fulfilled. Entrepreneurs, or anyone in business that’s striving to reach the next level, inherently have a drive inside of them. I think the worst thing you could do for yourself is try and suppress that drive. And just placate and say, I should be happy, I should be content, I should be grateful. Where that fulfillment stems from for me is the ability to look at anything in my life and understand that each small moment in time had some reason or purpose, even if these were hard moments that simply made me stronger or taught me a valuable lesson.
"...success is being able to see your value as a human being. Knowing that you are valuable enough to be loved and cared for unconditionally."
Also, success is being able to see your value as a human being. Knowing that you are valuable enough to be loved and cared for unconditionally. A lot of people don't seem to understand their value at that level - that they are lovable independent of the condition of their business, career, success, and bank account. When you reach a point where you understand that you are worthy of being seen and heard, by yourself, and by others, that feels like success.
3: Who are your real-life heroes?
Definitely my wife, who I’ve known since I was 16. She’s a phenomenal, kind, and strong individual, and the CEO of our family, but the reason she’s my superhero is because of the way she approaches life. She is someone who is constantly learning, constantly curious, objective in her viewpoints, always helping other people, and ruthlessly passionate about our kids - ensuring they’re always set up for success. Those qualities are really hard to find in people.
Then there’s my mom who was such a great mix of fire and quiet. She always knew what she wanted, had a lot of wisdom to share, was extremely kind, and had a great sense of humor. My mom just navigated life and life’s challenges with such wit and kindness. Something she instilled in me was her approach to challenges - breaking it down and tackling it in small steps. Don’t try to solve it all at once or even map it all out - just focus on one thing at a time and keep moving.
4: What is the best gift you've given yourself?
I want to say, permission to fail, but I don't know if I've fully given myself this gift yet, it's an ongoing effort. I think this gift stems from the idea I shared earlier about viewing yourself as valuable and worthy, unconditionally. It’s about giving yourself permission to not equate your value as a human to the day in and day out “successes” or “failures”. When you truly believe that your successes and failures do not define you, it becomes easier to see the value in failing. Life then becomes a series of learning experiences.
"When you truly believe that your successes and failures do not define you, it becomes easier to see the value in failing. Life then becomes a series of learning experiences."
I’ve spent a lot of my career being hyper competitive and somewhat of a control freak, and when I first started Human Design I leaned heavily into “Madison Avenue Agency” optics. Our industry is historically pretty vein and it’s easy to get caught up in the optics. We signed a 7 year lease in a beautiful, 14,000 square foot space, and then COVID hit. The pandemic really challenged us as a business, but it also helped me realize that a lot of things in life will be out of my control and it’s ok to pivot - it’s ok to change. It helped me realize that what really mattered in this business, and to me, was the work we were putting out into the world to meet our original purpose of moving the human race.
5: What was the last win you celebrated?
I don't know if I'm great at celebrating wins, like in big ways. I think how I celebrate wins is by reflecting on and being conscious of all the small wins that turn a day into a total win. I remind myself daily that my day is going to be made up of many moments and I don’t need to “win” at every moment to have a day worth celebrating.
"I remind myself daily that my day is going to be made up of many moments and I don’t need to “win” at every moment to have a day worth celebrating."
I’ve also been intentional about celebrating more with my family, and more dates with my wife. Even just sharing small wins with my wife and kids, or the challenges I’m encountering have really helped me to process and reflect on my own experiences. I think it’s important for my kids to hear me celebrating my wins verbally, especially the small ones, as it helps me build a stronger connection with them.
About John Weiss:
For the past two decades, John has been an entrepreneur, investor, founder, designer and, all along the way, student of human behavior, both online and off. His latest company is Human Design, which he co-founded with the purpose to “move the human race” through purpose driven outcomes. His work is guided by purpose, passion, simplicity, beauty, innovation & surprise.
