Agonizing about Drawing: 4 Lessons from a Year of Illustrating

….including why it’s not always a bad idea to marry your collaborator.

photo credit: Alice Achterhof

Five years ago, my husband and I began an epic quest to create a game that combined our two great loves: Game of Thrones and Munchkin.

A match made in heaven!

While he did the writing, game balancing, and card composition, I illustrated. There were 168 cards in the initial deck, of which I drew approximately 150 unique illustrations.

While it may seem silly to put a ton of time into a game that is in no way marketable (or possibly even shareable in public spaces), we found that this project accomplished a number of goals for us:

  • We tested our capacity to finish a big project together (and succeeded)!
  • We learned how to give each other constructive feedback.
  • We gained a basis for future gaming/writing/drawing projects.

I’m about to embark on a new epic project (details forthcoming), and this time I’ll be making some adjustments to my strategy. If you’ve ever considered diving into a big hairy project with your significant other, I hope you’ll find these lessons helpful, too!

1. Deadlines will work, but a schedule is better.

Working full time while also trying to draw 150 illustrations as quickly as possible made time management challenging, and so I set weekly deadlines to keep myself moving. My goal was always to spread out five drawings over the course of a week, but since the only thing I had was an endpoint, I would end up jamming five drawings in a weekend. This was a generally painful experience that would put me off track for the following week (continuing my boom-and-bust drawing cycle), and didn’t help me produce quality work. It also stressed out my project partner, who was counting on me to meet my commitments.

The solution I’ve found is to abandon deadlines and instead commit to the scheduling method (which I first read about from James Clear, but have since seen numerous times). This time I’ll be juggling full-time work and childcare responsibilities, so scheduling will be imperative to keep me working (and keep my partner/husband aware of my plans).

2. Embrace constructive criticism as a growth tool, not a personal attack.

One of the pieces of advice I’ve heard over and over in creative work is to keep producing, because even though the initial work won’t be great, the amount of work you do will lead you to continuously improve.

I think this gets you about 80% of the way there.

The other 20% is seeking improvement through mentors, guides, and constructive criticism. This is tough when you’re already gripped by anxiety over the opinions of others, especially when your creative partner is also your spouse, so it’s crucial that the person giving you feedback is someone who supports your work and is committed to helping you grow.

For example, one area I’ve been trying to improve is my shading, which is one thing I felt very self-conscious about in my Munchkin drawings. Compare a Munchkin card drawing to a recent character profile I made for my friend’s DnD character:

In the early drawing (right), the shading is so subtle that it almost doesn’t exist, and in the latter one (left) it’s possibly a little too harsh and wobbly. In this case, my husband thought they both looked nice (very helpful).

The thing is, I can’t improve on my shading beyond this if I don’t have honest feedback. I may be excited about the newer shading technique, but I can tell that there are some problems with my execution. What I can’t tell is if there are any other issues that I’m missing, and without someone to point them out to me I’m not likely to go back and improve them. That doesn’t make the emotional pain any easier though, so actively soliciting constructive criticism is going to be my biggest challenge in this next project.

3. Dive in to drawing tools to get the basics down, then do the research to level up your skills.

For each Munchkin card drawing, I would begin with a rough pencil sketch on paper, take a photo, and then import it into Sketchbook Pro, where I would layer over the original photo with a new, refined sketch, ink it, and color/shade it. I wasn’t too worried about the pencil and paper bit (I took a couple of drawing classes in school), but I found that I had to tinker with the digital drawing app for a while before I got the hang of it.

While the first few drawings took longer and were lower in quality, I had to dive in and get started in order to learn enough about the program to make sense out of the tutorials and user guides (available for free online). If I hadn’t allowed myself to make some crappy drawings at first, I wouldn’t have been able to cross over into better, more consistent work.

Now that I’ve built that basis using a simple app like Sketchbook Pro, I’m moving forward into more powerful digital art programs like Procreate and Photoshop. For example, here is a contest entry for a fan-made calendar based on the game Kingdom of Loathing, using Procreate:

Calendar Month: July

I figured out how to do a lot of the work for this project by Googling and watching YouTube videos, but I still missed out on some key shortcuts (like alpha lock!) that would have given me better opportunities to play with color. I’m looking forward to more YouTube tutorials in my future!

4. Remember to enjoy the process and celebrate your successes!

It can be easy to lose track of why I’m doing all of this when I’m constantly focused on the product at the end. Yes it’s helpful to have an endgame in mind, but I also have to enjoy the process in order to justify spending so much time and energy on it.

I have the most fun drawing when I think the drawing is going to make someone laugh (usually my husband). This is one of my favorite Munchkin drawings:

I laughed the entire time I drew this — I still laugh when it pops up in my facebook memories (you know I shared it). It’s ridiculous, it’s not a super high quality drawing by any means, but I had so much fun making it that it’s stuck with me all the same.

Don’t forget to enjoy yourself, even if no one else cares about your work (although it helps to marry someone who does)!


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Jessie L. Embrey is an artist and teacher. She lives in San Jose with her husband, two cats, baby girl, and countless imaginary alpaca friends. Say hello on Facebook, or sign up for her weekly email (here there be dragons).