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Writer's pictureKelsey Shields

How to Get Started as a Live Guest Portrait Artist in Three Steps

Updated: Oct 1

I would like to begin with a bit of context. Guest Portraits have taken the event space by storm. Inquiries for this type of service began ramping up in 2023 and gaining immense momentum in 2024. For the 2025 season, the idea of live guest portraits as an elevated, custom party favor is becoming commonplace at weddings and events.


My story with live painting began in 2019 after I left a career as an art teacher. If you find yourself in this boat, I believe many of the skills required to teach art make for a great live painter! For example, demonstrating to a classroom full of students is not so different from painting a ceremony scene or live portraits while engaging with guests. Regardless of where you're coming from, whether you are jumping into being an artist full time, have been an artist for years, or are looking to make extra income on the side, there is space for guest portrait artists in the event and wedding industry.



 


There are THREE THINGS you can do to get started as a Live Guest Portrait Artist.


  1. Up first, you need to find your portrait style. No shockers here, but this means getting out supplies that excite you and begin creating. Use photos from loved ones or even your own personal images. I was lucky enough to have done this back in 2019 when I decided to create a Valentine's Day Portrait offer. I created examples that reflected my personal style and have been tweaking that style for over 5 years now.

I recognize that you probably do not have years to develop your live portrait style, but if you start now, years will inevitably pass and your own story around art portraits is sure to form. This is the beginning; how exciting! When I started making Valentine's, I had no idea that they would lead me to creating portraits live at events around Colorado.


Below: Examples of my Valentine Portraits.

These were simplified when I was finding my style for live portrait events.



2.Next, you should create an offer. This is a necessary step for so many reasons. Creating an offer is going to lead to more opportunities for practice and style development. It will get you to consider pricing, guidelines for each piece like size and materials, and eventually launching the best product you can. See my first portrait offer and product at the Valentine Collection page.


Perhaps most importantly, creating an offer is a perfect way to claim the title of "portrait artist". Your confidence is going to grow around being known as a portrait artist and it is going to warm up your audience to the idea as well. Remember, the end goal is creating portraits live at events, but you need something firm to stand on before you land there.


Below: My first "live guest portrait" examples and the materials I use.



3.Lastly, you will prepare to book your first live guest portrait event. This part of the process isn't so different from the first two steps. As you wait for your first client, continue working on your style, making your product better, and claiming the title of "live portrait artist". Create a landing page on your website to highlight this new title and wait for inquires to come in. View my Guest Portrait landing page.


There is a lot that goes into booking a live event and then executing on the day of. Continue to announce to the world that you are a live portrait artist. Spread the word to friends, family, and other live painters, post about it across social platforms and when that first inquiry comes in, take the big leap!


Below: Guest Portraits from my most recent events. Photo credit to Kari Joy and Afrik Armando.




 


Receive your in-depth guide on how to become a live guest portrait artist. The free download will land directly into your inbox!


Follow the link to receive your guide "Getting Started: Step 1" of the Becoming: Live Portrait Artist series. Get the guide here.


About the Guide:

  • 15 pages taking the three steps above and taking an in-depth look at how to work through them.

  • Contains example images, personal stories, and encouragement.

  • My exact strategy for entering the event industry as a live painter.

  • What to do in a slow season.

  • Ideas for pitching and landing your first live event.



 

Kelsey Shields is a live wedding painter based in Colorado. She specializes in beautiful mountain vistas that highlight the happy couple during their chosen moment. She also creates live guest portraits as an elevated party favor.

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