On a roll

On a roll

“On a roll” is an expression we use to talk about good luck, good fortune , or success. But not just one success: if you’re on a roll, you’re winning repeatedly , over and over, for a period of time. And those wins can be external or internal .

By “external,” I mean successes in the real world; by “internal,” I mean, you feel energized or motivated . Let’s look more closely at what I mean by each of these. We’ll start with external.

External success: Winning in the real world

I don’t gamble . In fact, I’ve been to Las Vegas twice and if you add up all the money I’ve gambled in Las Vegas, you get one dollar. The first time I went, I put one dollar in a slot machine —and that was it. I just didn’t need to do it again. But some people do like playing the slots. And sometimes people get on a roll. That’s part of the appeal .

What does it mean to be on a roll at a slot machine? You win once, and that’s good luck . But then, you win again. All right now we’ve got something. And then you win yet again. And pretty soon, it feels like you can’t lose. You’re “on a roll” because luck seems to be on your side , and you keep winning. You have multiple wins, multiple successes.

But being on a roll isn’t always about luck. You can be on a roll if you experience a series of professional successes. So let’s say that you’re in sales . And if you’re in sales, you know that sometimes you win, sometimes you lose.

What might “being on a roll” look like if you’re in sales? Maybe you get a new client one day. The next day, an existing client wants to double her business with you. And that same afternoon, a previous client calls and says he wants to come back to your company. I would say you’re on a roll. That’s a series of successes, of wins, right there.

A sports team can be on a roll. I’m recording this in October 2024, and my favorite American football team, the Chicago Bears, have just won three games in a row . They are on a roll. The Bears have not been good in recent years. But they’re looking good now.

In American football, they play once a week. A few weeks ago, the Bears just barely won a game. Then they played better the next week; they won again. And then last week, they had an excellent game and won 35-16, which was a big win in football. So the Bears are on a roll. They’ve won three games in a row, and each game has been better. So they’re experiencing a series of successes, one after another . They’re on a roll.

That’s what I mean by an external success: in the real world . It’s winning at a slot machine. It’s landing some new clients. It’s winning a few games in a row .

Internal success: Building confidence and momentum

But being “on a roll” can also be about how you feel. And this is what I mean by internal success.

Tell me if this sounds familiar. Sometimes you feel like you’re just getting through the day. Sometimes just getting through the day is a struggle . But other times you have a lot of momentum , and you have a lot of internal energy , and it feels like you can continue working easily, or you can continue doing what you’re doing easily. When that happens, you’re on a roll because you have internal energy and momentum. You feel like you can continue for a long time.

Writers can get on a roll. If you’ve ever written anything— a long report , a novel , or, I don’t know, a podcast episode , whatever —if you’ve ever written anything, you know what this feels like. Sometimes, it’s hard to get words on the page. After an hour, you need to take a break . You’re out of ideas. Maybe you don’t even like what you’ve written. That happens to me.

But other times, the words flow freely . An hour passes and you barely notice . You want to keep going. The ideas are coming into your head faster than your fingers can type them . You’re focused . It doesn’t even feel like work. You’re on a roll. Notice, this isn’t about external success . It’s not about anything happening outside of you. It’s about how you feel.

Now imagine you have a regular weightlifting workout . It’s typically 45 minutes and that’s enough to leave you feeling exhausted . But one day, you finish your workout and you feel amazing—full of energy instead of tired. Since you’re feeling great, you decide to keep going and head out for a 30-minute run right afterward. You’re on a roll. You’ve got a burst of energy and confidence . You don’t want to stop! If you’re on a roll, take advantage of it. Go for it. Lean into it.

Okay, so those are your two ways to use “on a roll.” You can use them with external, more concrete , real-world successes. And you can use them for that feeling of having momentum and internal energy. Here’s an example that illustrates the difference.

Sally Rooney is one of JR’s favorite authors. She’s on a roll with her novels. She has just released her fourth novel. Her first three were very successful; two of them were adapted for television. Now her fourth is highly anticipated . So she’s on a roll; she has had those external successes. But creative people have good days and bad. And if you picture Sally Rooney writing for three, four, five hours at a time—that’s what it means to be on a roll on a more internal level.