Finding Answers in Stupid Questions – My Journey to Understanding, Acceptance, and Growth

I just recorded episode 91, and in a lot of ways, it’s the best one yet. It ran for 90 minutes and challenged me in a way I haven’t been challenged in a while.

How did it challenge me?

I just passed 32 years of age, and as many of you know, it’s marking the division of time I have been living with and without my father, Charles. For many reasons, this is a moment I’ve been reflecting on for a long time because, for some strange reason, I feel as if just now I am stepping out of my childhood self and into manhood for the first time.

You see, I have been interviewing for a long time. While in college, I started a small business making insulated hammocks. I was 21, and during that time I was mentored by many men and women I greatly admired. When I received an introduction to someone in the business community of Chattanooga, I would ask them if I could buy them lunch or coffee. I would meet and ask as many questions as I could, sometimes lasting more than two hours, in hopes of learning “why” they were “who” they were. 95% of the time, after those conversations, they would ask me, “How can I help you?” I was confused by that question because I honestly felt like they already helped me a great deal. But in an effort to have an answer, I began asking if they knew anyone I could learn from, and so, for four years, I met with person after person, interviewing them.

Looking back on that time, I realize now that what I was truly seeking from many of these people, mostly men, was for them to tell me what I should do next, which hardly ever happened. So I continued on this journey.

As time went on, I realized this deep desire within me and began to verbalize it to a few close mentors. I met with one man who was worth at least several hundred million and simply told him, “Look, if you tell me what to do, I will go and do it. I just need direction. I have the drive to make it work, I just want someone to tell me what to do.” In his wisdom, he simply said that even though that is what I thought I wanted, it is not what would bring me happiness. So I said to him, “Okay, well how am I to figure out what I am supposed to do?” He simply said, “You will know. It’s what gives you life, it’s what you are good at, and it’s what you look forward to.”

I went away from that meeting pretty upset and confused. But now, all these years later, 16 years after losing my father, 91 episodes into a podcast I call Stupid Questions, I am no longer confused. I know what I am good at, what I can continue to grow at, and what gives me life. It’s asking questions. It’s getting to know the human across from me. It’s sitting down with the guests across from me, giving a new pair of glasses to the audience, and turning the lights on to who the person they are listening to is and why they are the way they are.

Episode 91 challenged me, not because the guest was difficult to carry a conversation with—in fact, I could have gone for hours. You see, it challenged me because I realized that part of my intense fascination with asking people questions comes from a deep desire to understand why people make the good and awful decisions they do. It made me confront something I hadn’t fully acknowledged before: my need to understand why my dad took his life. For a long time, I felt a subconscious drive to probe the human mind and heart for answers—not just out of curiosity, but out of a personal need for resolution.

This episode illuminated something I had been wrestling with for years. It wasn’t because of something I didn’t do. It wasn’t because of something I did do. It was simply because he made his choice. He was hurt. He was lost. He saw no way out. Through that conversation, I came to realize that his tragic decision wasn’t a reflection of my actions or something I could have controlled—it was a result of his own internal struggles. And in that moment, I found clarity and acceptance.

This understanding has reshaped how I view not only my father’s decision but also the choices we all make. It taught me that people’s actions, especially the ones that seem inexplicable or painful, often stem from battles we cannot fully see or comprehend. We are each shaped by our unique set of experiences, and ultimately, we are responsible for the decisions we make.

The conclusion I reached isn’t just about my father’s story. It’s about learning to let go of the need for control over the things that aren’t ours to change. It’s about finding peace in acceptance, both of others and of ourselves. For me, the questions I ask now aren’t just about understanding others—they’re also about embracing the complexities of life, recognizing that not all answers will be neat or comforting, but they still hold value in shaping who we are.

I’ve come to realize that my once greatest insecurity—this need to seek understanding in the face of uncertainty—has transformed into my greatest strength. In seeking to understand others, I’ve learned to better understand myself. And perhaps most importantly, I’ve learned to accept what I cannot control, to forgive what I cannot change, and to move forward with a deeper sense of peace and purpose.