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Grayson Stepanek

Subscribe to my newsletter - the Step Up! You'll get an inside look into my thoughts, mental models, and ways of going about life - with the goal of helping you do the same. Take the first step and join me on this journey. Newsletter every Thursday at 4:30pm CST.

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The Step Up - Vol. 26: The Becoming

Vol. 26: The Becoming I used to tell myself “I’m not a runner.” I’d say “I don’t know why anyone would ever do a 5k.” Much less a 10k, half-marathon, or full. Or shall I even say… an ultra. I used to tell myself “I’m not a runner.” But one day I ran. Then I did it again a few days later. And again a few days after that. Like adding one grain of sand to another and to another until you’ve got a heap. But you don’t know exactly when you crossed that threshold to be considered a “heap.” You just...

Vol. 25: Vulnerability is Strength This week I watched this great TED Talk from Brene Brown on vulnerability as pre-work for my Goodwill Senior Leader Program, and it made me reflect on vulnerability as a strength. I pride myself on my vulnerability. I aim to be an open book (at least as much as I reasonably can). The ability to be vulnerable - to open up to others about who you really are and how you truly feel - takes more strength than bottling up. It's easy to hunker down. It's hard to...

Vol. 24: Building Strategic Relationships Ruben and I after our presentation Ruben Henderson and I had the opportunity to co-present at last night's the705 Member Meeting about building strategic relationships, and I want to talk about that a bit here. Relationships are critical in getting where you want to go, both personally and professionally. Building strategic relationships is a step deeper. It's the intentional practice - grounded in authenticity and integrity - of building...

Vol. 23: What is Productivity? Deacon Ed, Chris Messner, Ken Stansbury, and myself at our GoodPrints ribbon cutting last week - a huge project I viewed as very productive I'm blessed to be undergoing executive coaching through Goodwill, and a lot of our discussions have touched on my enjoyment of doing tasks/projects and my personal view of productivity. I've been thinking about this question a lot recently: what is productivity? I have a high personal drive. I love getting things done and...

Vol. 22: You Can Mentor - Now! 2026 the705 Mentor Mixer Last night we had the705’s Mentor Mixer - the kickoff event for our flagship mentor program that brings 705 members together with community and business leaders so they can learn more about each other before being paired up. ’m a massive advocate for mentorship. It’s truly changed my life. I’m blessed to have multiple mentors from Dr. Valerie McGehee (my first mentor) through UL, Deacon Ed (my CEO), Rickey Heroman (a Sigma Chi alum), and...

Vol. 21: Adaptability is a Superpower Justin, Glen, and I This week we’re going to pivot between cross-functional and multi-dimensional personal and professional modalities to leverage synergies and capitalize on low-hanging fruit. I’m kidding. Please don’t unsubscribe. Last weekend I went to San Diego to facilitate the servant leadership curriculum at Sigma Chi’s San Diego State chapter. My original plans before leaving that Friday morning were to go on a long run, shower, grab my bags (that...

Vol. 20: These Trying Times I'm not going to lie y'all. It's been harder to just go about life recently with everything going on. It's hard to be happy in your personal life when you see so much pain in the world. When you smile when you look up at your own life, but frown when you see others. I guess that's empathy, right? I don't have all the answers. I won't, and no one person will. In fact, this newsletter is my active way of thinking through my thoughts on how we move forward. In trying...

Vol. 19: The Price of Love Whiskers (table), Oliver (chair), & Buttons (rug) This week has been a sobering reminder about love and it's painful yet worthwhile price. This is not a pity piece, but it will be darker, longer, and more vulnerable than usual, and I hope you can find solace in it. My Mom texted me on Tuesday to stop by the house when I could. She had a feeling our cat Buttons wasn't going to live much longer. This wasn't the first time I got this text from her - the same happened...

Vol. 19: What is a True Leader? I'm blessed to hold various leadership positions where I have the opportunity to guide, empower, and inspire others. So obviously, I think a lot about leadership. It matters a lot to me. It matters a lot to the world. True leaders drive humanity forward. They make progress. They empower others to achieve unthinkable things. We owe the progress of humanity to great leaders throughout history who took it upon themselves to guide and empower others. But false...

Vol. 17: The One Thing You Can Always Control As we embark on our goals this year, I'd love to help focus our energy on things that drive us forward. Namely, things we can control, and not things we can't. In this chaotic world, there's a lot of things we can't control, both good and bad. Unexplained tragedies, unexpected opportunities, and everything in between. It's important that we recognize what is in our control and what isn't so that we can best allocate our time and energy to create...