Unobstructed

Fighting The Format

Written by Derek MacDonald | May 9, 2026

I feel smoke rising from my ears.

I'm sitting in a coffee shop, hunched over my laptop, and every time I go to take a sip from my mug, it only makes it about half-way to my lips before I set it back down.

My laptop screen is either goading me or encouraging me, but I can't tell which. I can almost picture the cogs of my cognition working through this puzzle. 15+ years of building resilient marketing operations and enablement teams had, ironically, left me feeling like I’d completely and utterly lost my voice. So when I started my newsletter just over two years ago, I’d hoped it would help me find it again by forcing me to write regularly.

And it did—that’s exactly what I’ve been doing.

Sitting back in frustration, I finally do take a sip of coffee but it turns into more of a gulp. I'm facing a problem with brand consistency; specifically, with publishing through Substack. But, I notice I'm not dismayed in the slightest... I'm fully engrossed in finding a way to make it work. 

The issue is with the email header/banner image. It's the thing that shows up above everything else in the email—title, subtitle, name, any featured image(s) in the body etc. I’ve been using a wordmark with just “Unobstructed” in black text on a white background, which I like, because it kind of gives newspaper vibes.

There's a slight hiccup, though.

Initially, I'm stuck because you can’t set different email headers for different sections of a Substack publication (aka each of the columns within Unobstructed). Having recently introduced a new monthly column, “Breaking Trail,” written by a new contributor, Caleb Walker, I want to differentiate it (slightly), but without confusing people. Even though I announced and promoted it, some folks only skim and/or don’t fully comprehend updates until they’re directly face-to-face with them.

Especially since it’s still new, I don't want the column name + Caleb’s name to catch people by surprise, you know like, “what is this? I never subscribed to something called “Breaking Trail”? And who’s Caleb?”

And I think I finally figured out what to do about it.

But first, some context:

I send the email version of this daily column, “Kickturn,” via an automated trigger on my own website, which is hosted through HubSpot. I also make it available on Substack, but it doesn’t get sent via email through Substack, therefore it doesn’t inherit Substack's email header settings (that can't be customized by column within a publication, which is dumb). So, instead I use a wordmark as an image in the body text that reads “Kickturn” so it shows up at the top of the page like a column header.

And, I use the same typeface as the newspaper-vibed wordmark of the whole Unobstructed publication. Like this—here’s an example of my daily column, Kickturn, sent via email, from my website/HubSpot:

 

And here’s that same example, but from the desktop view via Substack:

See the difference?

I do.

It actually bugs the hell out of me that I can't get them even more congruent... But I've put countless hours into coding and tweaking the template files of the site itself to get it  to where it is now, and I feel good enough about it to point my energy elsewhere.

My coffee's cold, but I'm still tinkering with how best to format this new column, “Breaking Trail” in the text editor itself. This gets published both via email through Substack—where the publication’s universal header settings are in effect—and online through Substack, where those header settings don’t apply.

Wanting to maintain consistency with the other columns of the publication, I'm thinking it's best to try for something that incorporates visual hierarchy, while following the naming conventions and guidelines I already use everywhere else. So I opt for keeping the universal email header, and then add a column-specific wordmark below a brief block of introduction text. That way, it acts as the preview text displayed in readers' email inbox, its branding is recognizable once opened, and the transition into the new column is distinct, without feeling disruptive.

Doing that makes it look like this via email sent from Substack:

And like this online, where it's web-hosted via Substack:

As always, this is a work-in-progress. But small steps stack up, and tiny tweaks become big accomplishments... Like, starting a newsletter two years ago to find my voice, and growing it into a publication with five different columns.

Placing my coffee mug in the bus tub, I head to the door while trying to process how this writing thing led me to compete in The Moth’s StorySLAM competitions and get featured on GBH’s Stories From The Stage, too.

Our Daily MAP Year Prompt
250/365

What's something you've been working on where, eventually, the hurdles feel fun?

onward.

For more on this daily column and The MAP Year Project, read the backstory here. And if you know someone who'd appreciate this, pass it along.