1. 2020-2025: The Results

2. 2020: The Failure

3. 2023: The Beginning

4. 2024: The Search for Purpose

5. 2025 and Beyond

Intro

This is a story of how a single doodle transpired into 2 years of doodling, with many lessons learned along the way!

The Results

Here are a few of my favorite drawings done during this drawing challenge!

Feel free to join me and others over on: Streakclub/Daily Art Club

To view all of my submissions: Streakclub/u/jasontomlee

2020: The Failure

It all began on January 1st of 2020.

I was scrolling through Instagram and stumbled upon a Calvin and Hobbes doodle. It inspired me to replicate the doodle & practice my digital art skills, so I did. Once it was complete, I had to decide on which platform to post it on.

I stumbled on a site called Streakclub because Leaf (the creator of Itchio) shared about it at the start of the year. I was a fan of his work, so I figured I may as well give the site a try.

After fiddling around with the site, I’ve come to realize that Streakclub was my cup of tea- it was created to encourage users to form daily habits by tracking their posts as daily streaks.

I’ve done writing challenges in the past on a site called 750words.com and hand-drawn challenges a few years prior. But I’ve barely gone beyond the 100-150 day point on all those challenges. So I had very little commitment going into this, but as many ameteurs do, had delusions of becoming insanely skilled.

I had no game plan on becoming a great artist but I knew I needed to at least give it a try. And so, my naive, yet brave, younger self began the journey.

As days and weeks passed, my motivation to maintain the daily streak dried up. I went from posting every day to once every few days. And then just like that, in the blink of an eye, posting every few days turned to NOTHING for the next 3 years.

Did I want it enough? Was I not capable enough? Will I ever do it again?

After the streak had ended, I continued drawing here and there for fun and work. But in the back of my mind, I KNEW that I needed to attempt this challenge again with a new mindset.

I had to prove to myself that I could do it…so I gave it another go.

On January 22, 2023, I began the daily drawing challenge with the intention of drawing for 1 year straight.

2023: The Beginning

The daily challenge was supposed to begin on January 1, 2023, but my first drawing was posted on January 22, 2023.

Why did the challenge begin on a later date? The anxiety of failing again.

Thankfully, I mustered enough courage to start again from Day 1.

I began this challenge by drawing things that inspired me, so I naturally veered towards VFX. At the time, I began a passion project called HackNSlash FX, so I decided to doodle things related to that project.

But as the days passed, my will to draw began to dwindle. I knew something drastic had to change, or I faced the possibility of giving up AGAIN, just like I did in 2020.

I concluded that the solution was to draw solely for the fun of it. This helped reduce the friction of starting a drawing, and in turn, kept the streak alive.

And this is how I began doing dedicated, thematic drawings for weeks at a time. (My favorite being, of course, Calvin and Hobbes!) Drawing things within the same theme for weeks at a time improved my eye for iteration and technical art skills. Having the freedom to start a new theme at any moment inspired me to keep the streak going.

Day by day, I could feel myself improving.

My lines went from thin and sketchy to confident, smooth strokes. Drawing the same thing allowed my mind to search for ways to improve future drawings.

And just like that, a year of drawing passed by.

I had achieved what I set out to do!

Now what? Was I going to quit?

No. But the worst was yet to come.

2024: The search for purpose

After successfully drawing for 365 days, I was faced with a new dilemma. Purpose.

Why did I want to draw every day? Why did I want to improve? Is drawing every day necessary? When should I stop drawing?

As these questions flooded my mind, my drawings devolved to lazy drawings done on my phone and mouse.

Fast forward to 2025, and the purpose of all of this has FINALLY been found.

Discipline.

Yup, that’s seriously it.

Doing something that you may or may not want to do over an extended period is a powerful idea. Regardless of how my life and priorities change, the importance of discipline remains a constant.

2025 And Beyond..

Moving forward, there is no doubt in my mind that this streak will continue for years to come.

My main focus now is to create pixel-art assets, content, and learn 3d to bring my passion project, LearnIndie, to life! Whether or not my endeavors work out, I hope these drawings and blogs inspire you to FIGHT for what others YOU want in life!

Thanks for reading!

-jlee