How to know if you’re on a good path

I’m fascinated by the idea of judging whether you are on a good path. Because everyone wants to know if they are doing okay. The problem is that if you look at things out of context, you can’t really see what’s going on.

See the picture up top? You can’t totally tell what they are doing until you see other pictures, pictures of similar but different paths.

These photos are by Lauren Ceking. I think you need to see at least three of them, and look closely, to get a sense of what people are doing.

This is an extreme example, but I’m certain this is true for paths in real life, as well, which is what makes this good art, by the way.

Do you know where you’ll be ten years from now? That’s not a path, that’s a destination. If you can see where you’ll be, you’re already there. If you know for sure where you are going then you are actually living someone else’s version of a path.

I did an experiment where at the end of my writing webinar, I offered to edit peoples’ writing for three months: unlimited editing at a flat price. I thought only a few people would take me up on the offer, but nearly everyone in the webinar signed up for the editing.

At first, I had a lot of work to do. Then, my editing effectively raised the bar on everyone’s writing. They wrote much more slowly. Because, after all, writing well is tortuously difficult for even the most successful writers.

By the third week I found myself telling everyone they will not write well unless they are surprised. If you are not surprised at the end of your writing, then the reader is not surprised, and then the writing is boring both of you. But it’s hard to let yourself be surprised in your writing because it’s not that fun to not know where stuff is going.

I’m near the end of my third month of editing. There are only a few people still writing, because sticking to a path that’s full of surprises is really difficult, but it’s the only path worth taking.

Most of you are not writers, but in fact, we are all editors of our own lives, and we owe it to ourselves to demand surprise at any path we take the time to explore, because that’s the only way to grow.

I wanted to lie and tell you I charged people $800 to edit for three months. In hindsight I think I could have charged that. Actually, not in hindsight. Melissa and I were doing the writing webinar together and she thought the editing should cost $800, but I worried that some people could not afford that price. And I wanted people to sign up. I wanted to edit the people in the webinar because I loved them all and I wanted to continue working with them. And editing is fun.

But not so fun that I want you to think I undercharge because now many of you will send links about how women undervalue themselves. But I’m going to save you the trouble and tell you that I keep my rates low for editing (and coaching, for that matter) because I get lonely. I want to talk to interesting people.

I thought of not writing that because it maybe makes me look pathetic, but you probably would have known anyway. Because people give themselves away in their writing by their quirks. I know because I just read this article about James Pennebaker’s book, The Secret Life of Pronouns.

For example, a guy who wrote notes threatening to kill a woman started many notes with the word fuck. This is not a normal way to start a note. Or a sentence. It’s a quirk. And the quirk was consistent with notes in his email history as well. The jury was convinced.

In another case it was a stupid misspelling: “kan” for can. The forensic linguist knew that no one would really make that mistake. It’s an educated person trying to look uneducated. From that information and a few other clues, they were able to narrow down the suspect list and find a killer.

Pennebaker also writes about the language of secrets. And how trauma is not as accurate an indicator of future emotional mess as much as secrets about trauma is. Secrets are what give long-term emotional bite to the trauma.

So I try very hard to not keep secrets. This blog is what keeps me in line. I can tell I am keeping a secret when it starts to nag me. When I start to tell myself, “Oh! Don’t go there, don’t write about that, you’ll get into trouble.”

But one of the most true things I know is that the more you talk about secrets, the more you are able to talk about secrets. It’s like forming a habit for anything. And an article in the Atlantic, about forming habits, has a great quotation from Aristotle: “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”

So fine, I only charged $400 for editing. But I learned a lot about being surprised. Which is that we don’t like it. Do you want to know what’s happening when I don’t post for ten days? I could tell you that I’m busy, but that’s total BS. The truth is that I don’t have the emotional space to cope with being surprised. Good writing surprises us. And surprises are exhausting.

So do you want to know if you’re on a good career path? Are you scared? Are you a person who makes emotional space in your life to be routinely surprised? If not, you probably need coaching, just like the writers of boring stories needed coaching to get to a path that matters to them.

This post would be a great ad for coaching. Honestly, I’m surprised to have gotten here because I’m not a person who is good at advertising myself. It’s embarrassing. I hate that I get embarrassed to ask you for anything. Well, I mean, I ask you to read to the end of the post. It’s so important to me. And I feel like I can’t ask you for anything else that would mean nearly as much.

So here’s my career growth. I’m not going to cut this part about how you should get coaching. Because it makes my stomach hurt just to type it. I hate promoting myself. But you know what? I want to be on a career path where I get to talk to interesting people. And how else will I get there if I don’t seek to surprise myself?