I had a wonderful phone conversation yesterday with a fellow Beatles fan whom I’ll call “Rich,” because that’s his name. As is generally the case when Beatles fans (or, in this case, fanatics) talk, the conversation soon turned to Beatles trivia. Rich asked me some great questions, and then he wanted me to ask him some. I asked a few, but he kept saying, “C’mon—make them harder!” I asked some tougher ones, but he kept at me: “Make them harder!” Even though he was getting them all correct, he wasn’t satisfied until I finally started coming up with questions that really challenged him. By the way, Rich is also enormously successful in his field, and I don’t think the two traits are unrelated. See, Rich isn’t content to simply achieve easy success with no challenge. After all, most of us could beat a 5-year-old in tic-tac-toe, but where’s the fun in that? (I mean, after the first ten or so games.) But I find that too many so-called “leaders” are perfectly happy to keep winning at tic-tac-toe. So my question to you is this: are you a real leader, or a tic-tac-toe leader?

The problem is that it’s actually pretty easy to achieve moderate success. And that’s where most people stop. Most people are content to go through their lives racking up one easy victory after another. And that pattern will bring you to a very comfortable place called “average.”  You’re doing okay. You may not be living the life of your dreams, but you’re not starving. To put it another way, you’re not dissatisfied enough to make a change. And that’s what makes people like Rich different. Rich isn’t satisfied with “average;” he isn’t satisfied with easy answers. He knows that the real fun is in the challenge.

Jay Leno once said to me, “Sometimes the worst thing that can happen to a guy is to make $35,000 a year.” What he meant is that for most people, $35,000 is enough to get by on. You can pay your bills. It’s not enough money that you’re truly satisfied, but it’s enough money that you’re not unsatisfied to the point of aiming higher. It’s that “middle ground” that doesn’t exactly light your fire, but it doesn’t kick you in the pants either.

Now, if you’re truly happy at that level, then good for you. You’ve made it. For that matter, there are a lot of bar bands that are perfectly happy playing a weekend gig for a couple hundred bucks and free beer. And then there are the Beatles.

So what’s the difference between the Beatles of the world and the bar bands, between the Riches of the world and the tic-tac-toe leaders? Simply this: the ones who achieve enormous success don’t fear a challenge; they relish it. They don’t want to stay in the wading pool all their lives; they want to dive into the deep end. They get to that level of moderate success where most others stop, and they say, “C’mon—make it harder!” The challenges don’t upset them, they drive them.

So how about you? Do you want to spend your life beating 5-year-olds at tic-tac-toe (and then taking their candy, because that’s easy too—trust me)? Or do you want to dive into the deep end and swim with the big fish? And yes, I know I’m mixing my metaphors, and I don’t care. So stop nitpicking and go find a real challenge.