Improving Your Writing

Tips and techniques from an accomplished creative writer to inspire your thinking and hone your skills.


At 5 by 5 Design we believe it’s possible to change the world by posing the right questions, listening to the honest answers, and following the path that emerges from the dialogue. Today’s discussion digs into ways to inspire and push you to be a better writer.

With 10+ years in advertising, Sam Landman has written for every industry. In fact, if he wasn’t in advertising, he’d still be in advertising. Because he believes in “the big idea.” Whether it’s making you want to buy a new snowmobile, persuading you to donate stem cells, or convincing you that, yes, there is a prequel to “White Christmas” called “Slay Belles” (and he’s writing it), he’s all about selling ideas across.

We’ve asked him a series of questions to help us learn how to use inspiration and process to improve the content that gets created. Here’s what he had to say.  

1. How does your personal life inspire your work life?

On average, I’ve got about three to four writing projects happening at the same time. (Even more so during the quarantine.) That includes things I’m literally writing, research I’m doing for future projects, or half-baked ideas I’m outlining.

Those usually drift into my professional life in subtle ways. Like how a brand might approach its social presence with a more conversational tone. Or how an email might need to be restructured in order to stay on topic. Or saying more with less.

2. If you are pulling from your personal life, pop culture, or historical references, how do you judge what will resonate? 

This is obviously a case-by-case thing, but I believe that the unique experiences we bring into our work environments inform the creative we come up with: personal biases, geeky turn-ons, whatever. These things matter.

From a brainstorming perspective, I take the “Adventure Time” route: the word “no” shouldn’t exist in the creative process. Stifling creativity at the beginning can cause the best ideas to keep from surfacing. The important thing is filtering those ideas once you “read the client room.” Because one client’s perception of “weird” or “fun” is completely different from the next.

3. What advice would you give to anyone looking to improve their writing skills? 

Write. Every. Day.
It can be journaling, list making, diary entries, whatever. Don’t feel like you have to be writing the next great American novel in order to create.

Write what you know.
Sounds obvious, but this basic idea is still lost on most writers. Got an encyclopedic knowledge of 80s hair bands? You need to write about it.

Don’t get bogged down in the medium.
Should this be a video script, a novel, a screenplay, or what? Doesn’t matter. If you don’t push that supposedly great idea out of your head, it doesn’t exist yet.

It’s not good (and that’s actually great).
Let yourself off the hook by allowing your first draft to be awful. What counts is that your idea’s down on paper. Now give it a critical eye and make it better.

Give yourself a deadline.
If you work in the industry, you should be used to this anyway. Be your own project manager. Creativity is about results. Hold yourself accountable.

4. How do you get unstuck when you hit a creative roadblock?

I see writer’s block as just another excuse I give myself for not writing. Getting stuck on a project probably means I need to work through it in other ways.

Here’s something I was taught a long time ago: even when you’re not writing, you’re still writing. In other words, if it’s not being physically written out, your brain is still processing it. And that’s okay.

If that means sleeping on it, moving onto another project, or taking a six-month break from it, allow yourself that time. The page will always be there when you get back.

5. Are there any rituals, systems, or other things you do to support your writing?

I never delete anything. Not a single word. If it’s not right on the first pass (which is about 80% of the time), it goes in a pile at the bottom of my doc labeled “Detritus.”

Later on, if I feel like the first draft is missing something, I scroll down and dig through my initial thoughts. Generally, my first swipe at a project will still have something I can use in the “Detritus.” That “aha moment” can be anywhere.

And personally, I’d rather have 10 pages of something I’m not totally happy with than a blank page I’m afraid of.

Because I’m primarily a digital copywriter, I’ve come to hate paragraphs. Unconventional breaks in a chain of thought have become commonplace within all of my writing.

Also, teaming up with a designer will sell an idea across better than simply sending a copy doc to a client. This also forces me to trim content down, getting it to its bare essence.

Other than that, I’m big on set-up. When I’m presenting to a client, I pretend they have amnesia. I remind them the problem I’ve been brought in to solve and why I’m crucial to that process. 

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