The best owners are often quietly drowning.
Not because they’re bad at what they do, but because they’re extraordinary at the work. If the business has grown faster than the structure around it, they’re likely holding it together through sheer force of will. That’s not sustainable and burnout is just around the corner.
Creative businesses underprice because they lack confidence and knowledge.
I charged $14,000 for a full website build in 2009. It took months and it was worth 5x times that. But the number felt big to me, so I assumed it felt big to the client. But that isn’t pricing, it’s guessing.
Hourly billing is one of the most self-defeating things you can build on.
You get faster as you develop your expertise. But somehow that means you earn less? The math doesn’t math, and it punishes growth. What’s the reward for all that hard work?
Contracts aren’t red tape, they are kind.
A contract is what you point to when the conversation gets hard. At Clover Partners we had a client threaten to sue us after we’d already handed over the files, canceled the remaining balance, and walked away cleanly. Our contract was so solid our attorney offered to counter-sue! We did not do that, btw. Kindness backed by clarity isn’t cold, it’s just professional.
You shouldn’t hold on to a client out of loyalty.
My first client was with me for more than thirteen years. As the years wore on, he’d question price, wouldn’t approve design, etc. We ceased to be the right fit for each other, but I kept him out of sentiment (and fear). Letting go felt ungrateful, but in practice, it was long overdue.
Presenting design matters as much as the design itself.
I once watched good work get killed in thirty seconds because the owner (who hadn’t been part of the project) walked into the room and loudly declared that one of the logo options looked like “something out of Star Wars.” The room never recovered. The work didn’t change, but the presentation did.
Outside perspective is a competitive advantage.
The studios I’ve seen grow the fastest — the ones that navigate hard seasons without falling apart — almost all have someone outside the business they trust to give them an honest read. Not because they’re incapable. Because being inside a thing makes it hard to see clearly.
Imposter syndrome is a sign you’re doing something real.
When I launched CW Strategic Advisory, the voice in my head was loud. Who’s going to care what you think? Why would anyone pay you for this? That voice doesn’t show up for things that don’t matter. It shows up because the thing you’re doing is worth doing.
It’s never too late.
I started over at 47. Two layoffs in one year, no severance, two kids at home, a business idea I couldn’t fully see yet. If you’re sitting on something – a service, a pivot, an ask you haven’t made – it’s only too late if you’re dead.
Fear tells you it’s not ready. Fear can just fuck off.
What do you believe? I’d genuinely like to know.
👋 I’m Clint. I help your right-hand person step into confident decision-making, freeing up space for you to focus on your agency.👋 I’m Clint. I help your right-hand person step into confident decision-making, freeing up space for you to focus on your agency.
Work with me!