Are You Enjoying the Ride?

What happens when you're so focused on reaching your goals that you forget to enjoy what you've accomplished?

This week on Trying to Figure This Out, a text conversation about knowing when to walk away, a documentary about legendary football coach Nick Saban, and a much-needed week off lead to a conversation about commitment, success, and the choices we make with our time.

There's something to be said for loving the journey, but what about enjoying the rewards along the way?

Maybe the question isn't just whether you're getting where you want to go, but whether you're enjoying the ride.

Everybody says they want honesty. But what happens when someone tells you something you weren't expecting—or something you really didn't want to hear?

This week on Trying to Figure This Out, Clifton explores the sometimes uncomfortable relationship between asking for the truth and actually being willing to hear it. From knowing whether someone wants moral support or genuine feedback to recognizing when “I'm just being honest” becomes an excuse to say something carelessly, the conversation takes a few interesting turns.

And with so many people willing to offer an opinion, how do we decide whose honesty deserves our attention?

How much do you really want to know—and who do you trust enough to tell you?

What happens when something you do out of care slowly becomes something people simply expect? This week, Clifton explores the quiet shift from appreciation to expectation—at home, at work, and in the relationships where showing up can become so familiar that people stop noticing it. And when you start feeling unappreciated, is the answer to say something, do less, or first take a closer look at what you were expecting in return?

Trying to Figure This Out asks another question along the way: when you genuinely appreciate someone, do they know it?

Have you ever started something without really knowing what you were getting yourself into?

In this episode of Trying to Figure This Out, I’m keeping things light and talking about those everyday moments when what we thought we signed up for turns into something completely different.

A conversation with my guy Dike about The Wire has me wondering how long you’re supposed to give something before deciding it just isn’t for you. A YouTube project my wife started somehow turns into our project. And a five-minute break from deep cleaning turns into something much longer than five minutes.

Then there’s the sentence I probably should’ve thought about before saying it to one of my colleagues:

“Whatever you need, I got you.”

Apparently, what she needed was a cheer chaperone.

Sometimes you start something on purpose. Sometimes you get dragged into it. And sometimes you volunteer before asking enough questions.

Either way, you might end up with a pretty good story.

What’s something you started without really knowing what you were getting yourself into—and how did it turn out?

How much of our lives do we actually get to determine?

In this episode of Trying to Figure This Out, I'm exploring a belief I've held for a long time: I believe I can determine my destination. But when I look back at my life, I can see the influence of decisions I made alongside circumstances I never could have planned.

If two people make equally thoughtful choices but end up with different outcomes, what does that tell us about control? And when an unexpected experience changes our lives, was it always meant to happen, or do we give it meaning once we see how the story unfolds?

I'm also considering how our beliefs about destiny affect the way we live. Does believing something is meant to be give us peace, or can it keep us from pursuing what we want?

I don't know whether the destination I eventually reach was waiting for me all along. But I do know there's something I enjoy about not knowing exactly how my story ends.

If you could see exactly where your life is going to take you, would you want to know?

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?

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.