5 Things I’ve Learned Over The Last 20 Years As A Professional Copywriter

Jack Humphrey
4 min readJan 28, 2020
I do all of my work exactly in this position. Especially long copy.

Copywriting is easy, fun, glamorous, and exciting.

Writing on a private beach in Costa Rica, sipping something that makes you wish you were me, I think back on my 20 year career as a copywriter with nothing but pride.

Honestly, I can’t think of a single thing I would take back. I’d do it all again in a heartbeat without changing a thing. Why would I when this kind of stuff happens all the time in my world?

It was 2004 and I was on safari in Kenya, sipping that beer/wine/colada drink you so envy, when my phone rang. The voice on the other side, which sounded like it was being projected through time and space circa 1950, begged me to write a sales letter for a new product that was going to take the “women belong in the kitchen” world by storm.

The “without sink” version was my idea. Upsells/downsells, you know.

It was my idea to include 3 identical women in the piece above. I wanted to convey the machine’s ability to do the work of three people, while signaling to the reader that it takes 3 people to work the thing. The advertiser was worried about false advertising.

Lesson #1: Use humor to write less while improving conversions for your clients. (Cut 1000+ words from every project with a choice photo!)

(And remember to talk off to the side, like this, so readers think you’re right there with them, helping them with their important decision.)

Okay that last line was like Rule #1.A. Give your readers unexpected bonuses!

Point #2: Be consistent.

If you start a list with Roman numerals, stick with it! Nothing ruins your flow faster than switching chaotically among bullets, numbers, and title styles.

Which brings me to Rule #3: Always write.

Like every single moment of the day. No matter what. And if you can’t think of anything to write, just grab a copy of Time magazine and start transcribing headlines and article titles.

Use Technology To Accomplish Miracles

At the time of this writing, there were 39 dictation apps for Android and iPhone. I use them all. Normally I have no less than 6 different apps recording at once. Because each app picks up different audio, it makes telling a story from everyone’s perspective in the room super easy.

Example #4: Never edit your work.

Everyone knows by now that your first run is from the gut. Where most of life’s important decisions are made. Your best copy comes right out of there. It’s no wonder, then, why so many writers do their best work in the bathroom.

Edit: “…why so many writers do their best work in the restroom.”

And finally,

E: Always fact-check.

You don’t want your readers cocking their heads, like puppies quizzically questioning grandpa’s hearing aid feedback.

Like confused hearing aid puppies, people sense you coming off a 3-day Hemingway writing bender on that crime novel (your way out of this freakin’ boom-bust cycle of writing for idiot clients!). It’s easy to spot a writer who’s just riffing to make some of that sweet, easy copywriting coin. (As clearly detailed in Rule #1 through E above.)

Seriously though, everything you’ve read about copywriting for a living is pretty much true. It’s hard work. Have you noticed that everything is if you want to be great?

Every profession has that one article that‘s written over and over about how hard work and dedication will see you through. Let this one be the exception.

Extra Credit

  • There’s no way to ride camels and sit on beaches all day and be a successful writer. (Even if they have a picture to prove it.)
  • Sand, salt, and spilled sugary alcoholic drinks make for a shitty writing environment.
  • Find a place to work where it’s quiet. Unless you do your best work in noisy environments, then screw that last advice.

Jack Humphrey (me, talking in the third person) finds that humor can be an even more impactful way of teaching copywriting than salad-shooting facts and “thou-shalts” at readers. Pattern interruptions are a great proxy for actually picking people up by their shoulders and shaking them. I’ll be here all week. Enjoy the veal and remember to tip your writers!

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Jack Humphrey

Producer & Host of the Rewilding Earth Podcast. I publish articles on environment, conservation, spirituality, ecosophy, biocentrism, motivation, and marketing.