Why doing your own messaging and marketing is so damned hard
(even when you help other people do this for a living)
Adapted from photo by Brett Jordan on Unsplash
Here’s something I know for sure, both professionally and personally: doing your own brand messaging is one of the hardest pieces of work you’ll do as a founder or leader.
Not because you’re not good at it.
Not because you don’t know your business.
And definitely not because you don’t care enough.
It’s hard because everything — including millions of possible messages you might share about yourself and your brand — lives in your head.
Every version of what you could say.
Every audience you might serve.
Every way your work has evolved, shifted, and occasionally gotten sidetracked over time.
Every skill you’ve earned, every result you’ve delivered, every idea you haven’t even fully articulated yet.
And then you’re supposed to somehow distill all of that into one clear, grounded thing you can say with confidence?
Good frickin’ gravy.
Five real reasons your own messaging might feel bloody impossible
When I talk with founders and marketing leaders about why they’re stuck, overwhelmed, or quietly avoiding their own messaging, marketing, or communications, a few themes tend to come up again and again.
You’re too close to the work.
Great leaders can’t always see the forest for the trees because they planted, watered, pruned, and worried about every single one of those little suckers.You know way, way too much.
Expertise is a blessing and a curse. In your head lives nuance, context, exceptions, edge cases, trials, erros, successes, and “yes, but also…” — which makes clarity feel reductive instead of helpful.Your business has evolved, but your language may not (yet) have caught up.
Most purpose-led businesses pivot quietly over time. Multiple times. The work deepens. The clients change. Partnerships shift. The value sharpens. And that can all add up to messaging lagging behind reality (been there).You’re trying to say everything to avoid saying the wrong thing.
Oh boy. For any leader who cares about integrity, inclusion, and impact (that would be all good leaders), the fear of being misunderstood or saying the wrong thing can lead to vagueness, evasiveness, and a whole lot of beige-ness … so it can sound like nothing at all.It feels deeply personal. Because it is.
This is the one that stumped me for about a decade. Talking about your business can truly feel like you’re exposing something about yourself … because you are. It isn’t just positioning. Or marketing. It’s your values, your credibility, your hard-earned experience, and all the blood, sweat and tears. So of course it’s tender territory.
Photo by Nathan Dumlao on Unsplash
And here’s the big one I don’t think we talk about enough:
When you’re working alone on your messaging, there’s no friction — no curious interruption, no one saying “Wait, say that again,” no one reflecting back what actually landed.
You’re stuck inside your own head, trying to edit your thoughts … while you’re still thinking them.
That’s a mighty tricky way to work.
Figuring it out on your own is wildly overrated
I’ll tell you something weird. I find messaging work for other people easy and genuinely fun. (But not when I’m doing it for myself.)
I studied journalism in university (go Raiders!) and worked as a newspaper and magazine journalist early in my career. So being curious, asking nosy—er probing—questions, listening for what someone is really saying (and sometimes what they’re avoiding saying) sometimes feels like second nature to me.
And what I’ve learned from doing messaging work with clients is that good messaging doesn’t come from clever phrasing. It’s not copywriting.
Instead, it comes from attention. From having someone sit across from you and say:
“That part is intriguing — tell me more.”
“It feels like you just glossed over something that might be important.”
“Wow, you just lit up when you said that. Let’s follow that thread.”
“I don’t get that term. Can you unpack that a little more for me and tell me what you really mean?”
That’s not a writing problem. It’s a clarity one. And sometimes, it takes two.
Photo by Christian Harb on Unsplash
How to get to your own best messaging
When I developed my approach to messaging, as outlined in Content With Purpose (and as used in my agency’s Brand Messaging Sprint), I read about and tested so many different things. I tried templates. I tried formulas. I tried hiring messaging experts.
What works for me: I work together with my clients.
I don’t hand you a template and wish you luck.
I don’t disappear for weeks and come back with a “big reveal.”
And I definitely don’t treat messaging like a purely intellectual exercise.
It’s a ‘done with you’ kinda thing.
I ask thoughtful, sometimes nosy questions.
I slow things down when there’s something tricky (or juicy).
I do my best to surface what’s already true — and then shape it into language that’s clear, usable, and honest, the way you’d frame it.
I look at:
what you do now (not five years ago)
who you serve best (and who you don’t)
why your work matters to the people you want to reach
and what needs to be said so that your dream audiences have all they need to take action: to learn from, engage with, or buy from you.
Clarity before content. Always.
The upshot
If you’re still struggling with messaging — that is…
if your brand story mostly lives in your head
If your team keeps asking for “the messaging doc”
If writing posts, pages, or pitches feels weirdly exhausting
If you’re doing good work but not quite attracting the right people yet
… please know this: you’re not behind, broken, or doing it wrong. You’re just trying to do relational, reflective work in isolation. And that’s one of the hardest things to do.
If you’re curious about what it might feel like to work through your messaging with someone — collaboratively, thoughtfully, without hype or pressure — just reach out.
Let me know if this resonates. I’d love to hear exactly how many messages you have in your head. (Me: 4,956,756.)