The first time I ran a workshop, I wanted to look like I had it all figured out.
I walked in with slides that felt like armor. I overprepared because I didn’t want to get caught off guard. I wanted to be the guy who answered every question smoothly, the one who looked “solid” from start to finish.
The question that exposed the friction
Then something simple happened.
Someone asked a question that should’ve been easy. Not a tricky question. Not a “gotcha” question. Just a real question from a real person trying to apply the lesson. And in that moment, I realized my deck was polished, but my session flow still had friction. People were listening, yes—but they weren’t moving.
That was my first honest lesson: I didn’t need more polish. I needed more iterations.
How I actually got better at workshops and snackable courses
I run workshops and snackable courses, and people sometimes assume I got good because I’m “naturally” good at teaching.
But if I’m being honest, most of what I know came from moments that didn’t look impressive. Awkward pauses. Activities that fell flat. Instructions that sounded clear in my head but confused people in the room.
After every run, I would go home with one question: “What do I change next time?”
Not a dramatic overhaul.
Just one change.
One better question. One cleaner example. One shorter segment. One clearer instruction. One better ending that made people act instead of clap.
That’s the kind of progress that compounds.
The two stories that keep people stuck
Somewhere along the way, I noticed how people carry two old stories about success.
The first story is luck. “Swertehan lang.” The right timing. The right connection. The right break. So we wait. We hesitate. We tell ourselves we’ll start when the stars align.
The second story is mastery. The idea that you must be great before you are allowed to share. The idea that your first version must already look like a final version. So we refine in private and delay in public.
Iteration breaks both.
Because iteration turns luck into logistics. It turns mastery into a trail of small improvements you can actually see.
What iteration looks like when you teach for a living
Here’s what iteration looks like in my world.
In a workshop, it’s when I notice the energy drop at a certain part—so I don’t blame the participants. I don’t blame “attention spans.” I redesign that moment. I cut the explanation, add a story, simplify the instruction, or give them an example they can recognize from Monday morning work.
In a snackable course, it’s when I see people stop at Lesson 3—so I don’t romanticize discipline. I fix the course. I shorten the video, tighten the structure, add a quick prompt, and end with one action that takes two minutes to do. The next batch goes further, not because they suddenly became better humans, but because I made the learning easier to use.
This is what I mean when I say iteration is not a tactic.
It’s respect.
Respect for the learner. Respect for reality. Respect for how people actually change.
Why I don’t worship “10,000 hours”
And yes, this is why I don’t worship the “10,000 hours” idea the way some people do.
Hours don’t automatically create improvement. You can repeat the same workshop 30 times and just get more comfortable. Comfort can look like competence, but it’s not always growth.
What made me better wasn’t time.
It was feedback plus adjustment.
It was treating every run like data, not like a performance review of my identity.
Perfection is a sneaky form of fear
I’ve also learned that perfection is often fear in a nice outfit.
When I want to make something flawless, what I’m really saying is, “I don’t want to be judged while I’m still learning.”
But learning is the whole point.
Iteration is how I stay honest. It’s how I stay grounded. It’s how I keep my work useful.
I don’t need to be “done” to be valuable.
I just need to be one version better than last time.
A challenge you can try within 24 hours
Pick one thing you’re building—an agenda, a module, a lesson, a script, a workshop opening.
Then ask: Where do people get stuck?
Not where they complain. Not where you feel insecure.
Where they actually slow down, get confused, or go silent.
Fix that one moment.
Then run it again.
Because the fastest path to good work isn’t luck.
It’s iteration—with courage.
Jef Menguin
