The Secret to Writing Better: Find Your Jimmy

James Dowd
4 min readNov 3, 2022

Welcome! This here is Part 7 of a dumb series of dumb writing tips. In these rants, you’ll discover that whatever you need to write — for work or for fun — you only have to follow these dumb little tips to help you think less and write more. If you haven’t already, catch up on the whole series!

So, here we go, and what a title, huh? Find your Jimmy. It’s the weirdest writing advice you’ll hear all day, but I promise you it works. See…

“I think what you write is weird, James, but I love this rule! It’s an important rule.”
— Designer extraordinaire,
Kellie Pcolar

So, you’re probably wondering what the hell it means. Well, “find your Jimmy” is something I tell people who are looking to become better writers. To find your Jimmy is to find that person who will be there to support you, give you valuable feedback, and, most importantly, give you comfort amidst the anxiety of writing.

Your Jimmy is someone you can be raw with, and who will be raw with you; someone who you know will be honest yet constructive.

Mine is friend and fellow writer Jimmy Burt. He is described by everyone we know as “Savage” and that’s in a good way.

The reason I needed to find my Jimmy is because everything I write is bad, until Jimmy reads it. With his approval, I can move forward. I can stop writing, rewriting, and worrying. I am momentarily free from anxiety and fear. I can share with the world! But only because Jimmy said I could.

I know he will take the time, he will be honest, and he will have a good eye. He will encourage me but he will be honest. And while all that is valuable, it’s also a moment to step away from it, to take the weight of writing off my shoulders. It’s on him now, the reader, editor, and judge, so I can finally breathe.

Wait, no, that’s not true. When I give him the writing, I freak. I pace, and wonder what he’s thinking. Does he like it? Did he just lose whatever respect for me he might have had all because of this one thing I wrote? I made a mistake letting him read it, didn’t I? Well where were you before to stop me!?!?!

Still, you need to find your Jimmy.

That’s because writing is painful. It can be embarrassing and revealing. Everything you are, think, and feel can be put on display through a series of dumb squiggly shapes. Those squiggles shouldn’t have that kind of weight and power and magic, but they do! Dammit, they do.

So, to write better at work, school, or wherever, simply find that person in your life who you can trust with your words, and they will make you a better writer.

Keeping in mind, being happy with all your words is one thing, but you’re ultimately going to need someone else to be happy with them as well, or what’s the point? If you intend to do this for work, for a brand, or to communicate with another human being, you have to let another human being see it. Then, you will know if you’ve used the words to express what you intended, or if you need to go back and continue writing.

If you’ve written and shared anything, and I’m sure you have, then you know how uncomfortable it can be. But, remember, writing is a contact sport, whether you want to admit it or not. To get better at writing, you have to let someone beat it up a bit with feedback.

But to get better at accepting feedback, you also have to find your Jimmy.

If your family is anything like mine, then finding your Jimmy is like your mom and dad combined. You get the sweet nurturing nature of your mom and the direct determination from dad to see you better yourself, but for you, your Jimmy could be anyone — mom, dad, friend, neighbor, barista, anyone. Whomever it is, when you’re stuck with your writing, you have to give it to them to read.

You know what? No, not even when you’re stuck…

By even telling your Jimmy about it, you’re then bound to writing it. They’re waiting. You can’t let them down. They’re your Jimmy! Let them even being aware of your writing be an encouragement and driving force in your work.

Write, and share, and listen to them. They’re your Jimmy for a reason, so they’re probably not wrong. They’re not in this for themselves. They’re in this for you — to help you, to be there for you, to make your writing better — so trust in your Jimmy.

But, don’t forget this: your Jimmy has to be a positive person. It’s not enough to get an okay response. Even a kind “good job, way to go, sport” is going to feel terrible, like they’re holding back, or subtly mocking you. No, your Jimmy needs to celebrate you like you just learned to use the potty, because when they’re excited, you’re excited, and a life of writing is good. And there’s no better feeling than that feeling you get when something you wrote is well-received. Especially by your Jimmy.

So, who’s your Jimmy? They’re probably someone you already know. If not, they’re out there. Try coworkers. Try writing groups. Try Tinder even! Find your Jimmy. That’s a great secret to being a better writer.

When you find your Jimmy, you’ll find comfort and relief, a momentary escape from the terror of writing, and a confidence to go further with it — to share, to write more, and more, and more!

So, if you want to write more, better, faster, it’s easy — go find your Jimmy.

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James Dowd

Writer and VP/Creative Director at Rebel. Founder at TheCreativeWild.com — a paid talent accelerator for creatives. Writer of the book WriteDumb.com