Today we’d like to introduce you to Penny Wasmund.
Hi Penny, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
Penny’s Playful Portraits has been many decades in the making. As far back as I can remember, I have always been a “creative”, whether it was sketching people for fun, learning to knit or crochet, sewing clothes for my children, or creating and painting sets for community theater productions.
A few years ago, I was working as a respiratory therapist in a Charlotte Hospital when I had to undergo chemotherapy. While my cancer was put into remission, the chemo rather severely compromised my immune system, which caused me to get sick frequently while working with patients in the hospital. I knew I had to find something different to do.
I was looking for a job that would incorporate my creativity and would allow me control over my schedule so that I could pace myself and not get too run down, which could contribute to more frequent respiratory exacerbations. I now take weekly immunotherapy infusions that have helped boost my immune system.
I got into Caricatures because my daughter, who worked for a large corporation in Raleigh (Celonis), and arranged many employee events throughout the year, told me about hiring Caricatures artists to draw at these events.
Soon after, I searched YouTube for various Caricatures artists and practiced many different ways of drawing faces and facial features, eventually landing on my own style that was in line with my idea of wanting to draw people in a positive and complementary way.
I then began my business and called it Penny’s Playful Portraits, with my motto being “I draw caricatures that won’t have you running to your therapist the next day!” I began booking 2-3 per month and it just steadily picked up over the ensuing months.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I think learning to face my fears to even get started drawing people LIVE, while onlookers watched my process, was perhaps my first struggle, and quite frankly one that I am surprised that I overcame as quickly as I did.
Another obstacle I have had to overcome is learning new things, especially where technology is concerned. It seemed that everything I wanted to do for my business, was requiring technology that I was unfamiliar with. So I would have to give myself a pep talk, reminding myself that I could be a grandmother who was born before computer technology, and still be able to put in the effort to learn new things. And while it has paid off for me, there’s always more to learn!
Can you tell our readers more about what you do and what you think sets you apart from others?
I specialize in positive drawings of people in a slightly cartoonish way, but never in a way to make them feel badly about themselves. I have had so many guests sit in front of me, fearful that I would draw them in an unflattering way, some still traumatized from a previous caricature. I am so proud and happy when I see genuine smiles on their faces and delight with my drawing of them.
After 2 1/2 years of drawing thousands of Caricatures at events from corporate to weddings to every type of party one can imagine, I began to offer a new option called Penny’s Doodle Booth. This booth has been a huge hit since its inception in late 2025. It is a cardboard booth created to be reminiscent of old Photo Booths, where I draw quick “doodle” portraits on 5×7 cards, and deliver them through a drop tray in the booth, which always elicits smiles and gleeful chuckles from the guests.
Is there anyone you’d like to thank or give credit to?
On one of my early gigs, I met Jordan White (Cartoon Jordan), and we became fast friends and shared a positive drawing style and business model, built on an abundance mindset, which included sharing with each other things that have worked and not worked, new supplies we love and ways of streamlining our businesses. Jordan’s friendship and her younger and more tech-savvy abilities has been such a wonderful help and encouragement to me.
We meshed so well, that we started a venture together called Party Portraits, NC, after seeing a need for a business that would supply larger events with multiple artists. We make it more streamlined for the event coordinator to communicate with and pay just one entity.
Jordan and I are the only two female LIVE gig artists in NC, that we’re aware of. That has created a bond, and we truly enjoy drawing together. We also get together frequently for “Art Play Dates”, gathering at a coffee shop and trying new supplies, styles of drawing and just chatting about our lives, outside of art.
Contact Info:
- Website: https://pennyscolorfullife.com/
- Instagram: @pennysplayfulportraits
- Facebook: @pennysplayfulportraits
- LinkedIn: @PennysPlayfulPortraitsandDoodleBooth
- Youtube: @pennysplayfulportraits
