I Had Much To Learn

The Pirate Wanderer
4 min readAug 12, 2021
Created using StoryBlocks under license

Long, long ago I discovered that I was creative. Sadly, it was in an engineering sort of way. Which means I tempered my creativity with to-do lists, over-analysis, and a calendar (or two). And thus the mold was set, the old career launched, and to this very day I am hopelessly addicted to my (virtual) Daytimer. But … and this is a huge but … that paradigm is failing me. For you apparently cannot be both creative and organized. Who knew?

Let’s paint a picture. I am in a constant state of switching organizational tools. I have lists of lists. And so when I decided to tackle YouTube more or less full-time, I decided that checkboxes were needed. I had multiple lists for today, tomorrow, groomed tasks, raw tasks, weekly tasks, and long term stuff. High on my list of daily creativity must-do items was this beauty …

[ ] Be Creative Today

Yes, I actually gave myself the pleasure of reading that, considering something new, and then clicking on “done!” each and every day. How in the hell can one distill that action into three words and consider it a success? Enough so that you feel glee at yet another thing marked off?

The other thing I did (incorrectly) was create a schedule. I was going to make Video X every Tuesday and Blog Y every Thursday. Without fail, for that is the creative flow! Well … no.

Granted it is important to allot time for creativity. Writing the Great American Novel means sitting in front of the typewriter regularly. But isn’t real creativity more than just an assembly line? What if I wanted to make … gasp! … two videos in a week? Or none, because the juices weren’t flowing and I needed something to come out of me that was better?

I also discovered that I allowed myself to be a victim of dogma. As in … “They say you can’t do X because of Y”, so that’s that. Well, isn’t creativity … finding ways around X and Y? Graceful, flowing, unique ways of making something out of the ordinary? That is the very nature of creativity, and I was ignoring it all in the name of process and self-analytics. (Must check those boxes on time!!!)

Creativity appears when we’re living our lives, not when we’re sitting at our desks trying to be creative. Inspiration happens when it happens. You must give it opportunity, but you must also grasp it and run with it when it appears.

But all of this is worthless, because even fixing these creativity mistakes doesn’t fix The Big Thing.

Last night, while discussing all things YouTube with some creator buddies, I got a complement. A big one. I was told that my last few videos were light years more advanced than anything I had ever done. That I was on a track to make an incremental leap forward. And the reason for this? I told a story.

I knew/know that story is important, but somehow I confused creation with education. I thought that doing Edu-Tainment was the way to go, after all my engineering mentality takes to that quite well. But I didn’t consider the importance of story. Using words, images, and thoughts to bring someone into the moment, and not just tell them about it with diagrams and graphics. Story is about connection.

I have this bad habit of trying to be too clever. I actually was trying to use stories to make my videos, but I was using several, all at once. Figuring that if one is good and all that. But that isn’t story. Those are examples. And examples are not stories. People aren’t going to follow the weird pathways in my head. What I had done in two of my recent videos was show a single story. Something personal and somewhat funny. I thought it was too simple, but creativity isn’t complexity. Again, it’s about making a connection with a single person and sharing something special. Whatever learning that takes place happens alongside.

So this morning I went over each and every video idea I had in the hopper and discovered that I didn’t get the memo when I wrote them. “My Love Affair With Barcelona”, which to me was a single tale was actually five separate stories. So I’m going to listen to my buddies. Because my biggest lesson today is that creativity is about moving in unusual directions, looking for beauty and connection. And when they are discovered, to bring them into the light for the world to see.

I discovered that story is everything.

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The Pirate Wanderer

YouTuber, Skoolie Bus Driver, Chaser of Shiny Squirrels, and the Occasional Purveyor Of Fine and Sometimes Uncomfortable Truths