This past year, the live portrait portion of my business has grown so much, and I’ve been blown away by all the love and support folks have shown for my work! As 2025 is coming to a close, I’m reflecting on some memorable moments and taking a walk down memory lane of drawing live portraits in previous years.

2017

I’ve always loved drawing people, but the first time I offered live portraits at a market was at Alki Art Fair in 2017. I think this may have also been one of my first multi-day craft markets! was leaning more into a classic “caricature” look with a big cartoony head and small body. I really liked the concept of live caricature drawings, but felt the traditional style was so unflattering. I wanted to make something similar in simplicity and quickness, but hopefully cuter. I think I drew a handful of folks and it was really fun!

At that point, I only did live drawing at Alki Art Fair once a year because it just seemed like a fun extra thing I could do when I knew I would have a booth helper available.

2018

At Alki Art Fair in 2018, I thought it would be cool to try out digital caricatures. In my mind, this would be easier and less pressure because I could erase, undo, resize, and rearrange as I wanted. Plus it would be simpler to pack supplies and materials (aka just my iPad). Turns out, having more options meant it took me longer to finalize a portrait, since I always felt like there was one more tweak I could make or one more part I could redo.

2019

The next summer, I went back to pen and ink portraits! Looking back on these, I really miss the loose and whimsical line quality that I have going on. I wouldn’t mind steering my style a little more back in this direction, but for some reason, intentionally trying to make my drawings look casual always makes it harder to achieve. Does anyone else experience this??

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2020

Covid happened! Everything was on pause.

2021-2022

I had a baby! Everything was further paused. I still drew digital portrait commissions for people here and there, but didn’t give much thought to live portraits.

2023

In December, Kaitlin & Kaitlin from Sairen invited me to draw portraits for their anniversary event! I hadn’t drawn them in a while, but actually kind of missed it so I was excited to give it a try again. I thought I would mostly be drawing people, but there were so many requests for people with pets, or just the pets themselves! At this first pop up, I drew everyone live while they sat across from me for 10 minutes (often unsure of where to look, haha).

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2024

I started doing pet specific pop ups, starting with my first one at Dog Yard, where I learned it’s much easier for both me and the dog if I draw them from a photo. I also drew portraits at a wedding for the first time!! I loved it, and am so happy that I was asked by my friend Kelly, owner of Kemi Dessert Bar. I had a chance to draw at my first corporate event as well, and it was during the 2024 holiday season that I came up with the idea of drawing mini portraits.

I was constantly tweaking and experimenting with my drawing process throughout this time. I think at each event, I adjusted or changed at least one thing and was able to gain a lot of helpful data points in the process! Some things I experimented with were pricing, portrait appointments and time slots, sign up process, pencil sketch first vs straight to ink, line width of pen to use, set ups, signage, wording, etc. It all helped me to figure out what would work best, and how to make my time and effort most worth it.

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2025

I drew for a veterinarians dinner, a 50th wedding anniversary celebration, a first birthday party, and took on some bulk commissions drawing kids and animals, and booked some more weddings!

In July, I tried out a “Doodle Booth” concept for my daughter’s 4th birthday after seeing some people on IG doing something similar, and it looked so fun! Luckily others thought it was fun too, and I was able to do more pop ups and add it to the menu of custom artwork services I offer.

Most of my markets and events this year were for portraits and only a couple were focused on greeting cards and stationery. I think I’m still trying to process what that means, and how to handle or balance the two moving forward!

Concluding thoughts

Looking back, I can see my portrait style evolving over the years, but it somehow doesn’t feel like I have full control over it. It’s very strange, like I’m just watching it all unfold as an interested observer. But I think that’s the beauty of art! Each artist creates out of who they are, and their individual style emerges and evolves as a result of their life and experiences.

It’s been so special to make art for all types of events and celebrations. Each one is a little slice of life, a peek into a community, and a glimpse into another world for me. I love taking it all in and pretending I’m part of it for a few hours.

I’m so grateful for everyone who has supported my portrait work, and am definitely continuing to learn as I go! It means the world when folks come out to my events, purchase my drawings as gifts for friends and family, or share that a portrait I drew for them in the past is still displayed in their home. However long this lasts, I will never take it for granted and consider it such a gift to get to do this for a living for any period of time! I’m excited for what 2026 will bring, how my art will continue to change and grow, and what other joyful collaborations I can be a part of with all of you!