Trying To Figure This Out

We spend a lot of time trying to figure things out. But what happens when we actually do? In this episode of Trying to Figure This Out, I’m thinking about what happens after the answer shows up—especially when I don’t particularly like what it requires of me. There’s a difference between needing more clarity and already knowing but not being ready to act on it. Even when the answer is clear, there may still be consequences to consider, people affected by the decision, or a cost I have to decide whether I’m willing to pay. And sometimes, there’s only so much I can learn by thinking about something. Eventually, I may have to do something with the answer and see what the decision teaches me. Maybe figuring something out isn’t the end of the process. Maybe it just gives me a new question. Now what?

What If Nobody Cared? How much attention are people really paying to what we do? In this episode of Trying to Figure This Out, I start with a question that sounds a little worse than I mean it: What if nobody cared? Not what if nobody cared about me. What if people simply weren't paying as much attention to my decisions, accomplishments, mistakes, and everyday life as I sometimes imagine? That question leads somewhere I didn't expect. I think about the difference between wanting something to be shared and needing it to be validated, why being seen isn't the same as being cared for, and what happens when caring about someone starts to feel like responsibility for the choices they make. Maybe the people who love us don't have to carry our lives with them to prove they care. And maybe we don't have to carry theirs either. I don't want to live like nobody cares. I just don't want to live like everybody's watching.

We talk a lot about growth. We encourage people to learn, try new things, and become better versions of themselves. Then somebody actually does it, and they hear: “You’ve changed.” In this episode of Trying to Figure This Out, I explore what it means to give ourselves permission to evolve without rejecting the people we used to be. I talk about changing my mind, choosing new directions, the joy of being a beginner again, and why knowing who I am doesn’t mean I have to know exactly who I’ll become. But that freedom can’t only belong to me. The people in my life are changing too, and part of loving them may be continuing to get to know who they are now—not holding them to who they used to be. I’m comfortable with who I am. I just don’t want to mistake that for being finished.

What does happiness actually look like—and why does it seem like the definition keeps changing? In this episode of Trying to Figure This Out, I explore our tendency to attach happiness to what comes next: the next accomplishment, the next opportunity, the next version of ourselves. The goalpost moves, and before we know it, we're already chasing something else. I also take a closer look at what genuinely makes me happy—freedom, time, good conversations, new experiences, and having nowhere I have to be—and what it means to actually make room for those things. Choosing happiness isn't about pretending everything is good or giving up on ambition. I'm going to keep moving the goalpost. I just don't want happiness to have to move with it.

How often do the things we once hoped for become so familiar that we stop noticing them? In this episode of Trying to Figure This Out, I reflect on what gratitude has started to mean in my life—not as a reason to stop dreaming or growing, but as a way to recognize what’s already here while I continue building what’s next. From leading a basketball program, to taking new leaps of faith, to listening to my daughter talk endlessly on our rides to school, I’m learning that some of the things that frustrate us, challenge us, or simply feel ordinary can also be the things we’re most grateful to have. Maybe gratitude isn’t about wanting less. Maybe it’s about making sure we don’t become so focused on where we’re going that we walk past the life we’re already living. :::

What if one of the greatest gifts you can give someone isn't your advice... or your time... but your full attention? In this episode of Trying to Figure This Out, I reflect on what it means to be truly present in a world that constantly competes for our attention. From missing small moments with the people I love to becoming more intentional about how I show up in everyday conversations, I've been learning that attention shapes far more than I ever realized. This isn't an episode about productivity or eliminating distractions. It's an invitation to consider what our attention reveals, what life might be trying to teach us, and how becoming a student of life begins with simply paying attention. Maybe the question isn't, "What has my attention?" Maybe it's... "What deserves it?

We all have voices that shape us. Some belong to people we love. Some come from mentors, friends, coworkers, or complete strangers. And sometimes, without even realizing it, we give those voices more influence than they were ever meant to have. In this episode of Trying to Figure This Out, I reflect on how experience has changed the way I listen, how life has taught me to pay attention, and why not every opinion deserves a seat at the table. This isn't about shutting people out. It's about learning the difference between being open to wisdom and living at the mercy of everyone else's expectations. Because in the end, the question isn't just who gets a vote...  

How many of the limits in your life are real... and how many are stories you've stopped questioning? In this episode of Trying to Figure This Out, Clifton explores how experiences become identities, why we often mistake familiar stories for truth, and how a single question can change the way we see ourselves. This isn't about having all the answers—it's about becoming curious enough to question the stories that have quietly shaped our lives.

Why did I start a podcast? In this check-in, I share the story behind Trying to Figure This Out—why I've wanted to do this for years, what finally pushed me to begin, and the kind of community I hope we build together. This isn't a place for perfect answers. It's a place for honest conversations with people who are trying to grow, learn, and make sense of life one conversation at a time. If you've been wondering where this podcast is headed, this episode is for you.

Where do our beliefs come from? More importantly, have we ever stopped to question them? In this episode, I reflect on the ideas we inherit from family, teachers, coaches, and life itself—and how some of those beliefs continue to shape us long after we've outgrown them. This isn't a conversation about changing careers; it's about examining the stories we've been telling ourselves and asking whether they still fit the person we're becoming. Sometimes, one honest question can change the direction of your life.

A trip to New York and music from 25 years ago became a reminder that looking back isn't about living in the past—it's about appreciating how far we've come. What if nostalgia isn't holding us back, but helping us move forward?

The biggest lies aren't always the ones we're told—they're often the beliefs we never stop questioning. In this episode, we explore loyalty, identity, and the courage to examine the blueprint we've been living by. What if honoring your past doesn't mean staying there forever?

Between the longer conversations, I'm sharing what's been on my mind this week. In this first check-in, I explore the fear that keeps us from taking the next step and the simple question that has changed the way I think about growth, purpose, and new beginnings. What if it does work?

Episode 1: Maybe It's Finally My Turn What happens when you've spent most of your life doing everything you were supposed to do...and suddenly realize it's time to ask a different question? In the first episode of Trying to Figure This Out, we explore the moments that shape us, the stories we tell ourselves, and why the questions we ask can change the direction of our lives. Through personal reflections on family, purpose, work, and life's transitions, this conversation is an invitation to pause, reflect, and consider what your next chapter might look like. Because maybe the most important thing we can do isn't find all the answers... It's start asking better questions.