Trying something outside your professional comfort zone is a little bit like running down the street wearing a new pair of running shorts, suspecting the whole time that the shorts may not be covering your bum well enough. But since you can’t see behind you, all you can do is keep moving forward.I happen to be in the middle of trying something new (writing fiction) and I also bought a new pair of running shorts last week. So I have had this exact experience.
It’s unnerving when you’re not quite sure if you’re “good” at this new thing you’re trying. Is it the right fit? Are you going to wind up shamed and embarrassed (the professional equivalent of your cheeks hanging out)? There’s no one there to tell you (and honestly, you’re probably afraid to ask). So what are you gonna do? Tug at your shorts every five seconds until it’s all you can think about? Go home?
It is HARD to leave the comfort of core competencies. Hard to step away (even just for an hour each day) from those things you get praise for. The stuff you have in the bag. I didn’t realize how hard until I started doing it. I didn’t realize how much I relied on outside validation until there wasn’t any. I didn’t realize how much I liked the feeling of my peers respecting me for quality work in content marketing writing and magazine writing until I had no idea if what I was doing was quality. Cue Tom Waits’ song here (“I never saw the East coast ‚Äòtil I moved to the West . . .”)
This is the point at which I would like to say the Absolute Perfect Thing—to myself and to any person or organization struggling with this issue of trying to get good at something they’re probably not good at yet. Steven Pressfield is the one who says the perfect stuff about that though.
What I do have are three little hacks I’ve carried with me—one for a long time, one for a few years, and one that I added just a few weeks ago.
#1  Stay focused on your work.
I had this professor in graduate school for a literary theory seminar (reading literary theory is best described as an urgency of confusion: imagine reading hieroglyphics on a cave wall with a dim flashlight, and there’s a baby crying, and you have to pee really bad). Anyway, this professor’s name was Laura Mandell, and though she looked a whole lot like a young and blonde Diane Wiest, her personality was more akin to a lion (in all the best ways). One day, she stood at the end of the seminar table, fierce in her petiteness, and said something like: “I need to tell you all something, and it’s very important. In this field, no matter what you do, always stay focused on your work. Your work. Respect what you are doing, even as you’re taking in what your colleagues are doing. Focus on what YOU are doing.”
I was 22 and wholly focused on me and on my ideas about the books and theories I was reading. I had no context yet for what she was talking about—but it stuck with me nonetheless, because I had a sense that someday I might. I think back now and realize that she was probably about the age I am now (maybe a few years younger). She was mid-career. She was smart. She was motivated. But she was probably looking around, wondering if she was measuring up, wondering if the new ideas she was putting out there were actually any good. She was talking to herself as much as to us.
I’ve thought of that moment SO many times during my career—not just in the “trying something new” phases, but also the “in the bag” phases, when I would look around and wonder if there should be more.
Last week, I finally took a thin Sharpie, wrote carefully on a sticky note, “Stay focused on your work,” and stuck it to the wall above my desk.
Thank you, Laura. Eighteen years later, I get it.
#2  Close the gap with volume.
Ira Glass has a fantastic little spoken treatise on what happens you start new creative work. You’re not very good yet, he says. But you have self-awareness and killer taste—so you know that you’re not very good. You recognize what remarkable is, and your work isn’t it. It sucks and hurts and makes you want to quit.
The only way to close the gap, he says, is by volume.
Do more of the work.
Me recapping this is not that inspiring-sounding . . . you really need to hear him saying it, because he is Ira Glass and his voice is, well, he’s Ira Glass. Here’s what I recommend. Go to this brilliant video that Daniel Sax made. Close your eyes and just listen the first time (I know, it takes restraint!). Then, open your eyes, play again—and this time watch the video. It’s so lovely and fantastic, but I think if you’re not familiar with this Ira Glass piece, it might distract you the first time around.
#3  Mastery is boring.
For the past few weeks, I've been listening to Elizabeth Gilbert’s “Magic Lessons” podcast, which she created to support her new book, Big Magic. There is an episode featuring a woman who is a successful portrait photographer, but wants to try her hand at podcasting. She and Liz talk about the desire to try new things, especially after achieving a certain level of mastery with something. “Mastery is boring!” Liz jokes. She’s right though. But, for me, that knowledge comes with a sneaky little fear that says that if I don’t milk what I’m good at for everything it’s worth, then the success I’ve built might disappear, melted by the sheer audacity of my ungratefulness. My fear asks me, why in the world would you try something else? You might be really bad at it. And then, that’s the end! The jig is up! You will become distraught, ashamed, shunned . . . and then die alone and penniless!
If you’re like me, it’s actually not just fear talking. It’s a chorus of fear AND guilt. It’s guilt over the idea that your current success and mastery of something isn’t “good enough.” The chorus sings loudly, pelting you with questions: Why in the world do you need to try something new, when you already have success in one area AND you enjoy it? There are people who never even find ONE thing they enjoy doing, and you can’t be content with this successful career? You think you’re destined for something more? Seriously? Why, oh why, would you want to try something else?
I love that the answer is allowed to be: just because.
Just because.
Are you trying something new? It doesn’t have to be fiction writing—that just happens to be my thing. Maybe you’re trying to add a new capability, launch a product that’s a complete departure from what you’ve done in the past, or work in a medium that’s foreign to you. I’m not going to stroke your ego and tell you that you’re great at it right now. You’re probably not. Your bum might even be hanging out.
That’s not a reason to go home though. Just keep running.