Feeling! Magazine

Feeling! Magazine

How to Start Illustrating

My first illustrated book comes out this year, and I'm sharing all the tips and tools I've used that made me fall in love with the practice of illustration.

Jenna O'Brien's avatar
Jenna O'Brien
Aug 08, 2026
∙ Paid

This article is a part of the summer camp series on creativity! We covered overcoming perfectionism through journaling and tablescaping like a designer. Today, I am sharing an extra cozy read about illustrating and how to fall in love with the practice.

The summer between high school and college did not arrive with ease. Some people can wear life transitions as if they are a breezy summer dress, and I am not one of those people. Things as simple as rearranging furniture, a growing distance from a once-close friend, or ending a job on my own accord make me contemplate writing a memoir. The feeling-everything-deeply trait, which serves me well in creative endeavors, is the same trait that makes me want to throw up on the sidewalk about inevitable life changes. I’ve come to deeply value and admire resiliency in others because I’m strengthening that muscle in myself. I’m getting much better at the resilient bit, I think.

But, if we could flashback momentarily, you can imagine that for a sensitive, nervous, seventeen-year-old, moving out felt like a life or death situation. We put inordinate amounts of pressure on the senior year of high school, asking kids to choose a career, often make a highly expensive decision, and say goodbye to everything familiar and start something new. I was in a tizzy, to say the least. I wasn’t sleeping, wasn’t myself, and the anticipation of changing everything made ruminations and emotional weepiness escalate.

Once I got to school, some things settled somewhat quickly. Normalcy, rhythm, routine. But, alas, some of those anxious roots that sprouted had grown quite strong. And try as I might, fear had a strong grip on my days and especially my evenings.

I had journaled every thought and feeling diligently since I was fourteen. But journaling was not cutting it. One day, tired after classes and feeling poorly, I climbed into my bunk bed, and I drew flowers rather than writing. My mind and body unwound themselves as I mulled over the shapes of the petals. Then I started painting at my desk nightly. Then I got ink pens and started drawing during classes. Then I got a notebook and drew every morning, every evening, and every other chance I got.

And since my first encounter with illustration, the relationship has solidified into one of my greatest loves. Illustrating, to me, feels like this magical potion for times of stress, sadness, or hardship. Drawing has been a balm for pain. Drawing kept me buoyant in hard circumstances.

It is my favorite way to spend an afternoon, start a day, or end a night — pen in hand. I love how I can express and capture things with no limit. And so I believe it may also be a balm, a friend, and an outlet of expression for you.

If you are writing online or off, I implore you to explore illustrating your own pieces to accompany your writing. Sure, it will give you a design edge and make you stand out amongst repeated graphics and stock images, but more so, I think the process of drawing itself is really significant for the creative person.

I believe that illustration can make you feel lighter. And I’d love to share what I know so you can participate in that free-flowing, joyful drawing feeling.

You could use illustrations for: your Substak graphics, making your own wall art, sending better snail mail, gifting art to friends, beautifying your neighborhood, practicing a hobby that relieves stress, making menus for your house, taking more interesting notes, starting a business, etc.

I’ve taken everything I’ve learned from becoming a self-taught illustrator (with my first published illustration book coming out this year!!!) and compiled my best and most helpful tips for learning, loving, and working with illustration below.

If you are looking to enhance your Substack visuals, junk journals & craft projects, or even explore giving away drawings to family and friends just to make them smile — here are my secrets for legitimizing your drawing process:

(P.S. After reading these tips, please share any further questions, thoughts, or feelings in the comments, and I will be sure to respond. I hope I can be a resource to you. Materials, sources, anything! Ask away!)

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