365 Days of Drawing

A Retrospective

Cynthia Koo
Dec 29, 2014 · 7 min read

To learn how to do your own 365 day project, check out my Skillshare class on “How To Start (And Finish!) Your Very Own 365 Day Project”!


On Black Friday, I finished my 365 day project to learn how to draw.



This was my 10th:

From Mark Kistler’s You Can Draw in 30 Days, Lesson 2 (Bonus)

This was my 30th:

Also from Mark Kistler’s You Can Draw in 30 Days, Lesson 12 (Bonus)

And this was my hundredth:

Based on this reference photo on Pinterest

This was the first drawing I gave away (day 22):

To my cofounder and his family

This was the second—and my absolute cutest (day 98):

Based on this reference drawing from Pinterest, and given to my boyfriend

This was my first “real” (not manga ☺) portrait (day 58):

Lesson 28 of 30 from Mark Kistler’s You Can Learn to Draw in 30 Days

This was the 15th (266 to 273):

Emma Watson

This was the portrait that I was most surprised by (day 74):

Because it was the first time I thought I could actually be any good at this ;)

Finished in a hotel room in LA, mid-road trip from the Bay Area to San Diego, and based off of this reference drawing

This was the portrait that took the longest amount of time—5 attempts in total, over the course of 47 days:

Attempt #1 (301 to 310)


Attempt #2 (311 to 318)


Attempt #2.5 (day 319)

Failed attempt at a scribbly pen drawing ;)


Attempt #3 (320 to 323)


Attempt #4 (324 to 328)


Attempt #5 (329 to 347)


(And the reference drawing)


This is the portrait that took the shortest amount of time—one hour, in one day (day 286):

Rest in Peace Robin Williams

These were the portraits I did of my family:


And of my best friend (361 to 365):


This was the first drawing I abandoned in the middle because I decided to give myself permission to start again (day 170):


And this was the last (356 to 359):

… at least for this year. ☺


Thanks for reading! And for all the words of encouragement. It’s been an eye-opening, instructive, and progress-filled year. When I started this project, I had no idea how long 365 days could feel. ;) And I never would have anticipated that I could go from these:

To these:

So, thanks, 2014! It’s been a good year. ☺


As a part of my endeavor to rediscover my love of writing, I’m writing one post every week for a year, about designing a life I love.


Chasing Magic

My year of writing every week. On design + love + designing a life I love. Written by @cyn_koo

Cynthia Koo

Written by

Designer, entrepreneur, obsessive list maker. Chief Dimsum Eater @wontoninamil

Chasing Magic

My year of writing every week. On design + love + designing a life I love. Written by @cyn_koo

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