How to be an Intermediate


Six mistakes intermediates make that keep them from becoming experts.


In the three areas of my life that are most important to me—my career, girls, and friendships—I’m only an intermediate. So if there’s one area of my life in which I’m an expert, it’s being an intermediate^1.

In my experience with being an intermediate, here are the pitfalls I’ve found—errors in thought and action that not only mark the intermediate, but keep the intermediate from becoming an expert.

Reflecting on your craft in the wrong way

It’s natural to look back at where you were five or ten years ago and think about how far you’ve come. The intermediate looks back on how far he’s come to feel good about himself, so he fails to see the next level. The expert looks back on how far he’s come as a way to contemplate how much further he can go.

Example: I spent most of my 20s being a jackass in social interactions. When I met a new person, my dominant thought wasn’t, “oh, here’s a nice person to talk to and find out more about,” it was, “let’s size up this person so I can say the most offensive thing asap.” Now, my social interactions are driven by genuine interest in other people, humor, and to sublimate my former jackassery. It feels good to know I’m no longer a raging jackass, but I’d be a raging intermediate if I thought there was no more room for improvement. For instance, I probably need to make more of an effort to keep in touch with people after I meet them.

Criticizing others instead of learning from them

Once you begin to get better at your craft, you’ll notice where other people are messing up. The intermediate criticizes these people to feel better about himself in an “at least I’m not as stupid as that guy” kind of way. When you move beyond intermediacy, you’ll look at where other people mess up as a point of learning.

Example: Once I got better with girls, I would see another guy out with a girl, observe the interaction, and notice how badly the guy was messing it up (which is usually the case). He was smiling too much, nodding too much, and in general, looking like a dork. Of course, I still did all these things too; maybe not as much, but I still did them. Though as an intermediate, I only felt better by feeling better than others, rather than thinking, “oh yeah, that interaction reminds me of last weekend when acted like a dork as well.”

Example 2: Both Jon Stewart and Bill O’Reilly will remain intermediate thinkers because their job is to point out the holes in each other’s thinking, never their own. Bill O’Reilly never looks at Jon Stewart and thinks, “where am I making a similar mistake?” If O’Reilly did, then he wouldn’t be such a Catholic. And if Stewart did the same, he wouldn’t have such a savior complex.

Feelings of entitlement

As you pass through intermediacy, you’ll have some success. This makes you feel entitled to more success, or at least a consistent amount of the same success.

Example: When I was in college, I wrote my first article that was—dare I say—good. A few people even cut the article out of the paper and hung it on their walls. So I figured, because my mind and fingers were capable of such a feat, every article I wrote from then on was worthy of the wall-hanging treatment. That turned out to be all kinds of false.

Example 2: Years ago, when I had my first one-night stand, I thought my life was going to be a girl avalanche from then on. Mega falsies on that one. An expert never rests on laurels, and when he does expect something from his environment, it’s no more than what he contributes.

The sharing of successes

Intermediates feel the need to share their successes, even exaggerate them. When you feel competent in something, you sooner talk about your mistakes than your successes.

Example: Healthy people rarely talk about how healthy they are. They rarely talk about their diets, or the weight they lost, or how good they feel. For them, being thin and healthy is a natural part of life. In my experience, high-achieving individuals are that way because, in part, they think the high achievement is natural. For you, abstaining from a few breakfast beers is natural, but to an alcoholic, that’s an achievement.

Example 2: The guy who doesn’t shut up about the three girls he had sex with last month, though it was probably only one girl.

You “have to” do your craft

Intermediates complain about doing the craft they’re an intermediate at. Then they come up with reasons why it’s okay for them to complain about it.

Example: When I first started writing for a college newspaper, it was new and fun and exciting, and so I would always find time to do it. Then, throughout my 20s, as I realized writing is miserable sometimes, I only did it begrudgingly. This was a difficult mindset to get out of because I had awesome reasons for why writing is miserable: it’s an indoor activity and I like being outdoors; the chance of success is slim; I didn’t begin early enough; I don’t know the right people, which is all that matters anyway, etc. Eventually, I had to learn that writing is this thing that, while extremely miserable at times, is also a privilege. Not only am I thankful I have something to write about, but I wouldn’t trade the freedom of writing for anything in the world.

Example 2: Healthy people know broccoli tastes like crap, but they’re in touch with the benefits of broccoli, so they associate the taste with the good feeling of being healthy. Thus broccoli tastes good.

Validation vs improvement

Once you become an intermediate at something, you become good enough to receive validation, whether from your peers or from within. When this happens, it’s easy to fall into the trap of only doing your craft in the same way, over and over again, to get that hit of validation. This keeps you from trying new things, and so impedes progress.

Example: You see this at open mics all the time. Guys will find jokes that get the laughs, and they’ll just do those jokes for months. If a joke works, then it works. Move on and try new material.

Example 2: This is why guys get caught in habit patterns with the girls they date. Girls, being extremely scary, tend to keep you in those patterns of behavior that validate you rather than improve you. Players will keep girls at arms length, and relationship guys will latch on to girls. So if you are a player, try a committed relationship. And if you are a relationship guy, then try being a player. No matter what happens, you will learn something and be less of an intermediate.


Colin Cowherd, an unofficial mentor of mine, says that if you want to be excellent at your job, then never join a union. After becoming an expert at being an intermediate, this makes sense. Unions construct rigid rules about how a job is to be done. It’s like taking too many precautions to protect a plant from the elements, and in doing so, you stunt its growth.

To be an expert, however, the relationship between you and your craft is never static. There’s always a new way for you to grow, and there’s always a new way for your craft to grow right along with you.