Olivia MacDonald on Life, Lessons & Legacy

We recently had the chance to connect with Olivia MacDonald and have shared our conversation below.

Good morning Olivia , it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? What is a normal day like for you right now?
On an ideal day when I’m not vending at an art market, I start my morning around 9ish with a matcha, then head to a heated pilates or sculpt class in South Boston. It helps get my energy flowing and my mind clear before diving into art mode. After that, I’ll usually swing by the post office to drop off orders, and sometimes restock a few local cafés that carry my prints and stickers (one of my favorite parts of the day! I love seeing my work out in the wild).

Once I’m back home, it’s time to catch up on commission requests, messages, and emails. Then I settle in and start drawing, working on custom pieces, prepping new designs, or putting together my monthly Ink Club envelopes, which are little surprise snail mail art envelopes with exclusive hand-drawn art and goodies. Somewhere in between, I’ll handle the behind-the-scenes stuff like cutting prints, packing orders, or ordering more inventory. It’s a mix of creative flow and small business hustle and I love every part of it.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Olivia MacDonald, the Boston-based pen and ink artist behind Ink by Olivia. Since 2018, I’ve created over 1,800 monochromatic pieces, fine-line drawings that blend emotion, reflection, and whimsy into one. My work began as a way to support a loved one through a tough time, and it’s grown into a brand that shares thoughtful, expressive art through prints, stickers, tattoos, apparel, and my monthly Ink Club subscription.

At the core of what I do is the belief that art doesn’t need color to be powerful, just honesty, intention, and a good pen. Alongside commissions for everything from tattoos to album art, I’ve collaborated with brands like Brahmin, Hilko Guitars, and Strathmore, and I’m always working on new ways to make meaningful, accessible art.

Okay, so here’s a deep one: What part of you has served its purpose and must now be released?
For over five years, I committed to drawing every single day on Instagram @inkbyolivia, which was an incredibly valuable practice. It helped me grow my skills, build my audience, process a lot of personal emotions through art, and connect with people around the world. But eventually, that rhythm became more of a pressure than a passion. It didn’t leave much room for reflection, rest, or simply existing outside of productivity.

I’ve realized that constant output isn’t always the same as creative fulfillment. So I’ve let go of the need to create daily in order to give myself space to slow down, be more intentional, and actually live the moments I want to capture in my work. Releasing that expectation has been a big step toward not just protecting my creativity, but also taking care of myself.

Was there ever a time you almost gave up?
There were so many days I didn’t know if I was going to pull it off, just sitting at my desk for hours, staring at a blank page, trying to come up with an idea for that day’s drawing. I started my daily drawing practice while still in college, so most nights it came after hours of homework, design projects, and everything else on my plate. Sometimes I’d have to wake up early and just scrounge an idea from my brain, hoping something—anything—would come together in time to post.

But somehow, it always did. There were drawings born out of exhaustion that ended up meaning a lot to people. Like the one of a mermaid curled in a teacup, which I drew when I felt like I had nothing left to give, or the one where the curve of a crashing wave mimics the back of a human skull. I was so mentally overloaded, I just wanted to wash my brain clean and that image poured out of me.

There were countless moments I almost gave up, not on art itself, but on showing up daily. I’m glad I didn’t. That season taught me how much I’m capable of, even on days when I feel empty. And now, I know how to create from a place of intention, not just discipline.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What truths are so foundational in your life that you rarely articulate them?
There are a few quiet truths that have shaped everything I do, even if I don’t often say them out loud. One is that consistency matters more than inspiration. Creativity is a muscle and some of my most meaningful pieces came from showing up even when I had nothing in me. Another is that quiet things are powerful. I work in black and white because I believe softness, subtlety, and stillness can speak just as loudly as color. And maybe the biggest truth is that vulnerability creates connection. When I share honest, emotional work, people respond in ways that remind me we’re all trying to make sense of similar things. These beliefs are at the root of everything I make.

Okay, so let’s keep going with one more question that means a lot to us: Are you doing what you were born to do—or what you were told to do?
I’m definitely doing what I was born to do. No one told me to become an artist. In fact, the world often says art isn’t a “real” job. But instead of letting that stop me, I let it fuel me.

I actually majored in creative writing with an illustration minor in college because I loved writing too. But somewhere inside, I always knew art was my first true passion and I was drawing long before I even started writing as a kid.

I started my daily drawing journey as a way to process emotions and bring some joy, and it grew into something much bigger than I expected—so big that I was able to become a full-time artist right out of college. It’s not the safest or most traditional path, but it feels like the truest one for me. Art’s not something I was told to do, it’s something I can’t NOT do.

Contact Info:

• Website: https://inkbyolivia.com
• Instagram: https://www.instagram.com/inkbyolivia/
• Facebook: https://www.facebook.com/inkbyolivia
• Other: TikTok: https://www.tiktok.com/@inkbyolivia