The Art of the Messy “I” in Business
Box Cutter Co. Free Issue No. 81
I just spent eight days in a fevered haze.
Hallucinations. Bizarre dreams. Thought loops circling like vultures.
One morning, I stared out the window, in a cold chill, watching shapes dance past my eyeballs. (image above)
For over a week, I was not very functional.
In my past employment days?
Sick days would have covered me.
As a business of one?
Nothing to lean on. No fallback. No safety net.
This is the reality of running a business — especially a creative one.
It’s unpredictable. Messy. Full of contradictions.
Some days, you have momentum. Some days, you barely function.
And yet—this mess?
It’s not the exception. It is the work.
The Business of “I” is often a little messy.
Be Wary of the Frameworks and Systems
I read quite a few posts from digital business gurus.
Many talk of “systems,” “frameworks,” and “structures.”
Clean. Precise. Like a nicely arranged set of Lego bricks.
A straight line. A clear path. A satisfying “click” as things fit beautifully and grander structures take shape.
Except… businesses—especially creative ones—are rarely that neat and tidy.
The “I” in business—you—isn’t a straight line.
It’s a tangle. A mix of contradictions and experiences. A tangle of inner child and wise adult.
A shifting set of strengths, doubts, and decisions.
You think, you build, you pivot, you second-guess.
Some days, it feels seamless. Other days, it’s a bloody mess.
And that mess is the work.
The Problem with Clean Narratives
Many loud voices online tell stories of clarity. They always “knew” what they were building (yea, probably BS)
The path was inevitable, and the vision was obvious. But this is where murky hindsight turns mess into method.
These stories edit out the detours, the dead ends, the doubtful mornings staring at a blank screen.
Businesses—especially businesses of one—are living things.
They grow like forests and grasslands — Not spreadsheets.
Some things flourish. Others fall away. And the falling away is critical. Things must die for other things to live. That’s the natural cycle.
I find a lot of what’s shared online erases this truth. Glosses it.
The messes. The sticky processes. The long stretches before things click.
A Sustainable Business Must Hold the Messy “I”
Building something long-term generally means leaning into the mess, the contradictions, the unknowns, and so on.
It means designing for both momentum and uncertainty. For growth and shrinking.
It means knowing “I” is never a fixed thing. Not static.
If your business is an ecosystem, you are its keystone species. Keystone species evolve. You adapt, shift, experiment, and reframe.
Your business is not just a plan.
It’s a set of relationships between you and your ideas, energy, readers (or audiences), and evolving and shifting goals.
Sometimes these might be ‘growth’ focussed, and sometimes they might be simply ‘enough’-focussed.
I find it takes constant balancing of:
Structure and Fluidity. A creative ecosystem needs both.
I ‘plan’ some of my writing and creative projects but leave a lot of space for ideas to emerge unexpectedly.
Ambition and Enough-ness. Not all growth is good growth.
I’ve turned down well-paying ghostwriting and consulting projects that didn’t align as I believe strongly more isn’t always better.
Public presence and Private reflection. The work behind the work matters (often the most).
I often spend hours thinking, not-thinking, researching, walking, and experimenting before posts go public.
Momentum and Patience. Some seasons are for building, others for waiting. Trust the timing. (Often easier said than done.)
Patience is probably one of the most critical skills for the messy “I” in creative business (I’ve been at this for almost 3 years now).
I’ve found the real work isn’t in choosing one over the other—it’s learning to live in Both/And… adjusting as needed or felt.
I’m finding a sustainable creative business is built in cycles (sometimes messy), not straight, planned lines.
The Beauty of the Messy “I” in Business
This is what makes one-person businesses different. Unique.
They are not just a smaller version of a company. But something much more personal.
Fluid. Flexible. Intentional.
A shape-shifting entity.
The messy “I” isn’t a flaw. It’s a feature.
It’s the reason your creative business isn’t just another company.
It’s why you can shape, shift, and build something that fits you—not the other way around.
A ‘living in the making’ rather than ‘making a living’.
How about you?
Do you have approaches to maneuver the Art of the Messy “I” in Business?