Playful & Taskmaster and Me

I am of two minds. I have two very distinctly different personalities. They’re both very important, but neither one of them can drive my life well without relying on the other. I simply call them ‘Playful’ and ‘Taskmaster.’


When I was a kid I would often sit in my room and just daydream. I had no plans or responsibilities. I would just imagine stuff. Occasionally I would write out, draw or act out what I had imagined. My mom still has boxes full of notebooks I filled when I was a child. I miss those times.


Back then ‘Playful’ was full in control. I’m not even sure ‘Taskmaster’ existed back then. If he did, he mainly only existed to execute orders by others like teachers and parents. As I got older I accrued more and more responsibilities like most everyone else does. But I was never all that great at self motivation. Occasionally I would come up with an idea I wanted to execute and I would make it happen. But the older I got, the less frequently that would occur. I spent so much of my taskmaster energy doing what others told me to do (work, study, chores) that I never matured that side of me very much at all.


I became an adult who didn’t often do what I wanted to do. I worked for people for money in order to survive. I aimed my life toward being creative professionally, but I kept waiting for others to give me permission to do things. For example, I wanted to tour the country doing comedy. So, I auditioned for Second City & Mission Improvable. Neither cast me at first. And so I gave up on that dream. I didn’t search out other touring troupes or try to form my own. I just accepted that if they weren’t going to hire me it wasn’t going to happen.


I spent the vast majority of my time and energy working for other people and not doing much in the way of self motivated projects. When I moved to L.A. I had a great resume for an improviser/sketch performer, but I had very little to show in anything else.


As is the case with most people who move to L.A. to get into the world of HOllywood, I did not hit success right out of the gate. I realized that the only way to really do what I wanted to do (write and act for camera) was to push myself. So, I learned techniques and philosophies from books and interviews about self motivation. I started to do a few things here and there.


And it went pretty well considering. I have a YouTube channel. I got to be part of a truly viral video and I have an IMDB page with ten credits. I’m still not nearly as far along in my career as i want to be, but I am way further ahead than I was. The trouble was that while I was developing ‘Taskmaster’ I was very much ignoring ‘Playful.’


The playful part of me wants to do playful things like hang out with friends, listen to music for hours on end, binge watch TV, hike, go on trips and stuff like that. The taskmaster in my knows that when I’m doing that stuff I’m not accomplishing anything toward my career and therefore sees that as a hindrance.


And I realized that what had happened was I put ‘Taskmaster’ in control of everything. And I locked ‘Playful’ away in a cell demanding that he do things for me such as write and act without allowing him to play.


And I was miserable. I was yelling at myself for wanting to do the things that I love to do the most. And I realized that something had to change.

Now, I understand that both Taskmaster and Playful work for me. I’m the boss. And good bosses reward their staff for a job well done. They give their employees kudos, gifts, vacations and fun outings. A good boss doesn’t yell unless it’s absolutely necessary (which it rarely ever is), but instead encourages, guides and helps.


So, this year I plan on bringing balance to my life way more. I’m going to accomplish a lot while also relaxing and having fun. I need both. I’m fairly certain this will cause me to significantly decrease my worry and anxiety. How am I going to do it?


Aside from all the things I’ve been changing in my life (reading more, meditating regularly, breathing more, etc.) I will recognize that the two sides to my personality are not at all at war with each other. They need each other and balance each other out like Dean Martin & Jerry Lewis, Stan & Kyle or Key & Peele. So, I’ve made a list of strenghts and weaknesses for both:


Creative Side 


Gets scared easily

Knows how to relax

Not great at focusing on one thing

Finds new and creative ways to solve problems

Smiles a lot

Does not respond well to scolding

Likes to free write and be insightful



Taskmaster side

Productive/organized/on time

Gets frustrated easily

Knows how to persevere

Not great at melding ideas

Executes actions that are repetitive or that I’ve done before

Can endure discomfort in order to accomplish a task

Needs structure and order

Likes to schedule and organize

Cracks the whip


My taskmaster side needs to chill a bit. It’s doing a phenomenal job, but it needs to remove the stick up his ass. And to be fair, that stick is there solely because I have placed outrageous productivity demands on him. I need to be the type of manager I love to be managed by. I will genuinely let go of the anger I get when I don’t do something I want to do. I will let go of the absolute need to get pissed off if my plans don’t unfold the way I want them to. Let it go.


My creative side needs to breathe thru the stress just a bit and realize that it’s best if we can restrict play time to happen when I need it to and not just whenever I feel like it. If I’ve got a crazy hectic day, there won’t be  much time for play, but I will recognize that and plan something fun in the very near future to make up for it.


My taskmaster side needs to realize that even though I do desperately want to change my life, that I will lose a lot of happiness if I deprive myself of too many things or yell at myself for not working hard or fast enough. My taskmaster side is a leader, an encourager and a motivator.


My creative side needs to realize that it’s going to be even more fun when my creativity coalesces into something more than just ideas waiting to be developed. We need the taskmaster to help us finish our books, sketches, screenplays, blog posts, etc. My creative side is awesome, but by itself it’s not good enough to make it happen.


So, that’s basically it. No matter the situation, one of the two sides of me is going to be better at it than the other. It is up to me to recognize when I need to play and when I need to work. I will encourage myself rather than yell at myself. I will try to have the most fun I can while still accomplishing what I need to get things done.


Realizing this was a true epiphany. In hindsight it seems quite obvious, but I never realized there were multiple sides to me. I saw myself as simply having flaws. But they’re not flaw, they’re strengths to be used at different times in different situations.


And that excites me for what I’m going to do with my life from now on.
Thanks, y’all!