How to design a 365 day project

From the trenches: I’m on day 300 of 365 days of learning how to draw

Eleven months ago, I did a retrospective of my first 66 days of learning how to draw. I am now on 300—baffled at how far I’ve come, slightly impressed that I am still doing it, and curious to see what day 365 will bring.

Along the way, I learned some things about undertaking a 365 day project that I thought I would share. These are the rules and parameters that have helped me to stay consistent, accountable, and committed to an endeavor that—unsurprisingly ;)—seemed much shorter before I started.

For a catalogue of all drawings: Drawing In A Year.

To dive deeper and start your own project, check out my Skillshare class on the same topic: “How To Start (And Finish!) Your Very Own 365 Day Project


1—Establish a daily deliverable…

It should be discrete enough to not make you want to kill yourself, but substantial enough to ensure that you progress. Mine was to make one full drawing a day.

Day 10: Tennis Balls — Day 11: Pyramid of Spheres — Day 20: Playground of Boxes
Day 22: Koala Family
Day 27: Cityscape — Day 39: Whoosh Cloud

2—… But give yourself some breathing room…

Committing to seven days a week might be a bit overwhelming. Instead, I established a minimum weekly threshold. A successful week consists of 5 days of drawing, which means I will finish in a few months over a year. But mentally and temporally, I needed breathing room for the rest of my life.

On the go drawing:

Day 74: On a road trip from the Bay Area to San Diego
Day 87: At the office — Day 98: The morning after a housewarming sleepover at a friend’s new place

3—… And modify as you go along.

Since you will get better as you go, you might need a different (less ambitious) daily deliverable later on. As I approached day 100, I found myself looking for reference photos that were too simple to be challenging. Since my ultimate goal was to be able to draw incredibly detailed pencil portraits, simple wasn’t going to cut it. So I modified my daily deliverable to be either a complete drawing or at least 10 minutes a day of drawing.

Ten minutes a day of anything can—perhaps unsurprisingly—add up to a lot.

Days 227 to 240: Operation Father’s Day

4—Establish an ambitious goal for day 365…

So you have something to look forward to. Mine is to exhibit my drawings—somehow, somewhere (taking offers ;-)).


5 — …But then figure out how you can see progress right away

Otherwise, it’s easy to get discouraged. Mark Kistler’s book, “You Can Draw in 30 Days,” made me feel like I was making an incredible amount of progress in the first 30 days:

“You Can Draw In 30 Days” by Mark Kistler — Left: Lesson 1 of 30 — Right: Lesson 30 of 30

I’ve noticed a lot of the other instructional drawing books spend a lot of time explaining theory upfront. But diving headfirst into theory can widen the perceived gap between where you are as a beginner and where you might want to be. Personally, I need to see progress pretty much immediately. I need to know that I can get good in order to commit to learning at all.

The bigger lesson being: figure out how you learn the best, and design your curriculum to match.


6—Decide on a curriculum ahead of time

To that end, deciding on a curriculum (even if it’s one day out) has the benefit of removing the mental burden of deciding what you will be doing every day. Eliminate choices. Don’t spend 10 minutes looking for the next thing to draw (or cook or knit or learn) every time you sit down to do it.

Following instructional books is a great option. Keeping a repository of all the things you want to get around to also helps.

My Pinterest board of “to draw” items

7— Document your progress

There will be days you will just not want to do it. But don’t break the chain.

Document your progress, so that when you get discouraged and tired and realize 365 days is a long freaking time, you can see how far you’ve come.

Day 286: In Memoriam of Robin Williams

Though, if that doesn’t work…


8—Put some skin in the game

Find an accountability buddy to commit to a 365 day project as well. And then put some money on the line. Five dollars per missed day is a latte in the grand scheme of things, but the mental resistance to ponying up any sort of money will be enough to carry you through most days.

Money I’ve paid thus far: $15
Day I last paid: January 7 (8 months ago)

That’s 3 out of 300 days, which is a 1% failure rate. Not bad.


9—And finally, it’s okay to regress

365 days is a long time. Don’t be too hard on yourself.

Day 274: Attempt at a portrait of Emma Watson—Day 282: Attempt at a portrait of a little girl ☹

Check out my Skillshare class on “How To Start (And Finish!) Your Very Own 365 Day Project” to learn what it takes to do your own.

As a part of my endeavor to rediscover my love of writing, I’m writing one post every week for a year, about design, life, love, traveling. If you enjoyed this, please click “Recommend” below, say hi on Twitter, or come find me on Instagram. I’d love to hear from you. ☺

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