How Do You Know When a Chapter Is Ending?

I just watched Dave Chappelle’s new special.

What stayed with me wasn’t a joke. It was the way he talked about where he is in his life right now. He said he feels like he’s in a different place, and because of that, he’s there to say certain things to certain people. Not to everyone. Not forever. Just now.

That idea stuck with me because it made me think about how all of us move through different chapters in our lives. Not based on age or job titles, but on the questions we’re trying to answer and the responsibility we feel to answer them honestly.

Most of us don’t struggle because we’re in the wrong chapter. We struggle because we don’t realize a chapter has ended.

In my own life, my content marketing chapter had a very clear ending. We sold the company, and that made it easy to recognize that something was complete and that it was time to move on. So less than a year and a half later I stopped working at the company. I took a 12-month sabbatical, went on a trip to Sicily with my father, and I started to think about what was next.

Most people don’t get a moment like that. And honestly, I haven’t had a break that clean since. There was no obvious finish line and no external signal saying it was over. Instead, it was a gradual realization that the role I was playing no longer matched the questions I was asking.

That’s what makes these transitions difficult. Your title hasn’t changed. Your work still helps people. The money still comes in. From the outside, nothing looks broken. But internally, something shifts.

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I’m seeing this more now that I’m actually looking for it.

I know someone who’s been a successful salesperson for more than 25 years. They’ve built a strong reputation and make good money. From the outside, it looks like a career anyone would want. But privately, they’re constantly questioning whether this is what they want to do for the rest of their life. Almost every conversation ends the same way. This is what I’ve always done, and walking away feels irresponsible.

I also know a teacher who’s been teaching for over 30 years. Teaching isn’t just their job. It’s their identity. Even though they’re tired and quietly wondering what else might be possible, no one has ever really said to them, “You’re allowed to do something else. You can do anything you want.” So they keep going, not because it still fits, but because stopping feels like betrayal.

These aren’t people who are failing. They’re people who are loyal. Loyal to their role, to their past selves, and to the expectations others have placed on them. Over time, that loyalty can quietly turn what feels like a trap.

How do you know a chapter might be ending?

In my experience, it rarely announces itself loudly. It shows up quietly, often in ways we try to explain away.

You may notice that you’re operating on momentum instead of conviction. The work is still good, but it feels more like repetition than discovery. You feel responsible for continuing, but less curious about where things are headed.

Where you used to have answers, now you have more questions (this is a good thing). Often, the work still serves others, but it no longer challenges you. And deep down, you know growth doesn’t happen without discomfort.

None of this means something is failing. More often, it means something has been fulfilled.

Why changing chapters feels risky

One reason these transitions are so difficult is because, from the outside, they often look irrational.

That’s one reason I’ve always admired Michael Jordan. When he walked away from basketball to play baseball, most people thought he was crazy. He was at the top of his game, yet he felt that chapter was complete.

So he started a new one.

It didn’t unfold the way the storybooks say it should. He wasn’t great at baseball. He took criticism and failed publicly. Then, after that chapter ran its course, he returned to basketball and somehow became even better than he was before.

From the outside, it looked reckless. From the inside, it looked honest.

Maybe that’s the real problem. Not that we don’t sense something has changed, but that we don’t want to look crazy. Changing chapters often breaks the story people have about you, and it disrupts the narrative they’re comfortable with. So instead, we stay. We tell ourselves it’s too late, too risky, or that this is just how it works.

Over time, we trade curiosity for credibility.

Understanding the system you’re in

I’ve come to believe that the most important thing we can do is understand the system we’re currently operating inside, and where we are in our own story.

Chapter two of your life is very different from chapter forty. The incentives are different. The risks are different. The responsibilities are different. Yet many of us try to play the same role, using the same rules, long after they stop making sense.

We don’t need permission to change. But we do need awareness.

If you don’t understand the chapter you’re in, it’s almost impossible to know what comes next. You end up optimizing a role you’ve outgrown or staying loyal to a system that no longer serves you.

A pause is not quitting

One thing I’ve learned is that pausing is not the same as stopping.

A pause isn’t escape or failure. It isn’t opting out. A pause is a container. It’s a decision to step back long enough to see clearly, to understand the system you’re in, and to decide what role actually fits now.

Sometimes the most responsible move you can make is to stop producing long enough to listen to what’s changed.

What this means for me, briefly

All of this is why I’ve been spending time thinking about what I’m calling my third chapter.

I don’t have it figured out, and I’m not rushing to define it. I’m sitting with bigger questions around work, systems, agency, and what it means to live deliberately inside them.

As part of that, I’m going to pause the Content Inc. podcast for now. Not because I’m done creating, and not because the show stopped being meaningful, but because I don’t want to keep publishing out of habit. I want to be intentional about what I say next.

If and when I come back to podcasting, it will likely look different and focus on a different set of questions.

A question worth sitting with

You don’t need a dramatic ending to begin a new chapter. Sometimes the only signal you get is a quiet one.

So here’s the question I’ll leave you with. What part of your story are you in right now, and are you still playing a role that fits?

You don’t have to answer it today. But noticing it might be the beginning of something important.