Structure Creates Freedom
Building frameworks to define "good enough" before I start creating
I launched two new products this month. Started a third.
But I also held back a dozen pieces of content because they didn’t feel “ready.”
The products felt great to ship. The content I held back? I’m still not sure that was the right call.
We’re in the middle of December now. Holiday push. Everyone’s trying to wrap things up before the break. And I’m still stuck on this same problem.
The biggest friction I felt this month wasn’t external. It wasn’t tariffs or pricing or market conditions. It was me. Refusing to accept “okay quality” and ship anyway.
Social media output has been my Achilles heel. With all the AI tools evolving at a rapid pace, it’s really hard to keep up. But more than that, it’s hard to lower my quality bar.
I tend not to ship if it doesn’t meet my expectations. And here’s the kicker: that’s not always good for business.
Sometimes being present is more important than being perfect.
I know this intellectually. I preach it to other people. But when it’s my own work? I freeze.
The Toyota Paradox
There’s this paradox Toyota taught me years ago. People used to say, “High quality costs more money.” Toyota flipped that on its head.
They said: Great quality costs less.
Why? Because quality is about consistency. And consistency means fewer rejects, fewer mistakes, fewer returns. You’re not constantly fixing things or redoing work. You build it right the first time, and it scales. You’re optimizing the “whole” not just the “first part”.
But here’s where I get stuck: that philosophy works great for manufacturing. It works when you’re building physical products with repeatable processes.
It doesn’t always work as well for creative output.
Creative work doesn’t scale the same way. Every post, every video, every piece of content is a one-off. There’s no assembly line for storytelling … yet.
And that’s where my brain short-circuits. I’m trying to apply manufacturing logic to creative work, and it doesn’t fit cleanly.
Present vs. Perfect
I’m a fractional CXO, and one of the companies had a lot of unplanned activity. When that happens, your decision-making around priorities gets really important.
Burnout is easy if everything feels like the same priority.
I’m a productivity enthusiast. I know how important recovery is after a mental sprint. You’ve got to sharpen the saw. Take breaks. Let your brain reset.
And yeah, I’m taking that advice this month. The holidays are forcing it. But I also know that shipping is part of the productivity equation. You can’t just build in private forever. At some point, you have to put it out there.
The tension I feel is this: if I ship something that’s “okay” instead of “excellent,” am I building bad habits? Am I training my audience to expect mediocrity?
Or am I just overthinking it?
“If I ship something that’s just ‘okay,’ am I training my audience to expect mediocrity?”
Structure Creates Freedom
Here’s something that helps when I’m stuck in this loop: structure creates freedom.
It sounds paradoxical, but it’s true. I learned this at Toyota.
I’m a daily planner. Even on weekends. I get up and sketch out what needs to happen. What’s most important, what’s nice-to-have. I sharpen the saw throughout the day. I slow down to speed up.
When you understand your day, the flexibility is off the charts.
If someone hits me up and says “want to go surfing?” I can look at my plan and know immediately if I can say yes. I’m not sitting there thinking “well, I don’t know if I can, t I’m not sure what’s urgent or due today, and maybe I’ll feel guilty later.”
I know what’s on fire. I know what can wait. That clarity gives me permission to say hell yeah, let’s go. Guilt free.
But when I don’t have that structure? I spiral. Everything feels equally important. I can’t make decisions without second-guessing them.
That’s where I need to get better with content. Building the same kind of structure I use for my day into how I approach creative work.
Define what matters before I start. Know when it’s done. Give myself permission to stop editing and ship.
What I’m Learning
I launched two new products this month. Started a third. That felt good.
But I also held back a dozen pieces of content because they didn’t feel “ready.” And I’m not sure that was the right call.
Here’s what I’m working on:
Define “good enough” upfront. Before I start creating, decide what the minimum bar is. If it hits that bar, it ships. No second-guessing.
Separate craft from cadence. Some work deserves perfection. Most work deserves consistency. Know which bucket you’re in.
Trust the process. If I stick to a framework and ship regularly, the quality will compound over time. Perfectionism in the moment doesn’t compound. It just delays.
I don’t have this figured out yet. But I’m working on it.
Because the longer I wait to ship, the less I learn. And learning only happens when you put something out there and see how people react.
If you want more breakdowns like this, I share weekly on LinkedIn: https://www.linkedin.com/in/steveskillings/