Week of May 2, 2021

The week started Monday morning, waking up in a camper somewhere in South Carolina with two gassy dogs. It was unpleasantly early, especially for a Monday, especially considering we had a long way to go before we could even think about getting to work.

Then again, who said Monday morning’s had to be for work?

The week had a feeling to it. It felt like everyone needed a break. The end of April, the looming tax deadlines, the onset of Spring Fever, baseball, warm afternoons inviting cold beer. We have all been in this intense…


Hi, it’s me. Here’s another round of stories and ideas for you to chew on. Nothing to sell, but you can certainly tell your friends about this. Or, you can sign up to get every issue delivered directly.

Photo by Ella de Kross on Unsplash

“You remind me of myself two lifetimes ago,” Larry said to us. The joke being, he’s three times our age because he has no idea how old we are. How could he? We’re under masks and behind sunglasses, and he’s surprised to hear how we are in our mid-thirties.

“Oh, well, the feeling is the same!” he says. Looking at Larry was…


Week of April 25, 2021 — copywriting, freelancing, and the scarcity mindset.

Published a few days late. I was off the grid for a bit; most of what’s below is transcribed from handwritten pages.

When it comes to writing for a living, especially when a lot of what I write is connected to the online space, I get this anxiety whenever I know I’ll be offline for a few days. As though I need to cram even more work into the days leading up to the departure, no matter what the deadlines or schedules say.

I think it’s a defense mechanism, a way to buy time. If I send something before I…


Week of April 18, 2021

A lot happened, more is on the way. Right down to the skinny of it:

On the business front:

I launched OutWord — because a great story is about so much more than copy, isn’t it? My primary goal is to work with owners who want to find new ways to tell better stories. A simple premise, a lifetime of work.

Interested in working with me? Message me directly.

My dance card is already lush, which is exciting, but I’m always pushing for more, newer, and exciting projects to tie myself to. I’ve sold out my deep-dive, story-driven copywriting course…


When I was 19, I was teaching 8-year-olds how to shoot guns. Oops.

Photo by Adam McCoid on Unsplash

I recently published this to my Revue. All the good stuff goes there first.

Perfectly Controlled Chaos

Never a weapon.

Always a firearm. Avod the word “gun” if you can.

Never a bullet. Use “round” instead. Depending on the firearm, “cartridge.”

All of this falls under the umbrella of “shooting sports.”

For over two decades, I was tied into the Boy Scouts of America in some capacity. Shooting sports, especially in Colorado, were a significant part of the Boy Scout program as it had been since the founding of the program. …


The person you’ll never see again versus the one you wake up next to every day.

I shipped this with my new Revue. You can get stuff like this delivered. It’ll be fun.

There’s that weird thing how you can be more honest with a total stranger than with most other people in this forsaken world. That’s how it always seems to go. It’s rounding 11:30 at night, last call is in a bit, and you slide your credit card across the bar and tell the bartender how you’ll buy a round for the rest of the souls who are straddling stools.

“I’ve racked up plenty enough as it is,” you tell the strangers, “I’m sure…


Hi, I’m David, and I’m finally graduating from freelancing.

Today, I’m launching OutWord because I want to bring a little magic back to the world of copywriting.

A little over four years ago, I was not-so-suddenly laid off from my last full-time job. I worked in digital advertising. It was more ones-and-zeros than it was copy-and-concept — and that sort of bothered me.

You know how it goes: it doesn’t matter what the ad says; we can target it precisely to your dreamboat customer. The entire industry danced around the glory of their 2% conversion rate — and that was at its highest.

There is a place for advertising…


Week of April 11, 2021

Well then, dear reader, how do I tell you all about the progress I’ve been making when I have spent the past week totally checked out and on vacation?

Weeknotes #6. Week of April 4, 2021 | by David Pennington | Apr, 2021 | Medium

There are those in my circle who romanticize the “you can travel and work from anywhere” lifestyle. You can see it in the pictures of the laptop, on a beach, drink in hand. It is usually bullshit.

The last place your laptop wants to be is anywhere near a beach. Sand.

Before I left I…


Week of April 4, 2021

It is Easter morning, this week is supposed to be a vacation. I am in a place without wifi.

For the best, I suppose. This Weeknotes is written on a phone, so links will be limited.

After last week’s unexpected travel, I had to double down on clearing the todos before I left yesterday morning. Why is it I feel like I have to work harder leading up to a vacation? And, even with so many invoices shipped, I still feel like I haven’t done enough?

Designing a copywriting workshop right now. Building it as I go. I asked a…


Week of March 28, 2021

I keep telling myself this will hold me accountable. Already, I’m a day late in publishing. Here’s the rest.

A while ago I wrote it into every service agreement I could: no more 24-hour turnarounds on copy. I then extended this idea not to feel obligated to get back to anyone about anything within a week. The reasoning: I needed time and sleep to do my best work. If I have to get something back to you by the next day, I haven’t had enough time to, quite literally, “sleep on it.”

This week was evidence of this. A last-minute…

David Pennington

Been writing for years, now I’m helping others do the same. #copywriting #content #email Never miss an update: http://dtpennington.com/subscribe

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