Meet Taryn Skipper | Author, Illustrator, Artist

We had the good fortune of connecting with Taryn Skipper and we’ve shared our conversation below.

Hi Taryn, we’d love to hear about how you approach risk and risk-taking.
Risk is the only way to get the most out of not only our work and pursuits, but out of the relatively short span of our lives.

Every new idea, skill, project, anything you don’t already have experience with involves some degree of risk. We risk our time, our money, our reputations, our egos, our comfortable seat in a world of things we understand and grasp and know—sometimes even bodily harm. These risks should all be considered and weighed and mitigated as possible. But when I consider risks, I do it with the intention of moving forward, and not using potentially uncomfortable outcomes as a reason to limit myself.

The only way to avoid risk is to avoid trying new things, developing new skills, and change or growth of any kind, and I would rather be growing than comfortable. But if I were to somehow eliminate risk by remaining stagnant, I’d risk much more—boredom, regret, and a life and potential that feels unmet and unfulfilled.

So, I say yes, even when I’ve never done what the client is requesting. I am honest with them, and might give them a discounted rate for my first attempt, or let them pay only after it’s completed to their satisfaction. But I’m confident that I can push myself. Everything I know now was unknown and untried in the past, so I might as well keep adding skills. If there’s a chance I think I can probably do it, and it’s something I would like to have done, I say yes. “Can you take all of these grainy black and white photos and create one color family portrait?” Oh, that’ll be a challenge! Yes! “Can you paint a 1-inch portrait of me as a playing card? How about a six-foot painting in another medium of iceland?” Well, that’s new. Yes, and Yes! “Can you serve as president of a literary awards program?” Whoa, scary, but I think I can pull it off. Yes! And the next time someone asks, I can point to where I now have experience.

There are moments of success in business, and moments of failure or struggle. We can’t live for these individual moments and tie our happiness to the ups and downs of daily life. But we can find great joy and satisfaction when we look at the risks we’ve taken, the lessons we’ve learned, the skills we’ve developed, and the way we’ve changed and grown, no matter the physical result.

To me, taking a risk isn’t about what I might get in the end. I do love it when a risk pays off the way I want it to and I end up with a great product people want to pay me for. But the real reward is having taken the risk at all, and the life experience I wouldn’t have if I hadn’t taken the leap.

Let’s talk shop? Tell us more about your career, what can you share with our community?
I work in watercolors, oils, and words. I sold my first commissioned graphite portrait in high school, but I didn’t start a business until after I had my first two kids. My son and I would make up stories at bedtime, and we turned an ongoing theme into a cohesive story. I created illustrations and published it for him. I loved that process so much that I did it twice more with other children’s stories, and illustrated for a couple of other people.

My first book signing was at the Lucile Packard Children’s Hospital, and I made illustrated necklaces to sell with the books as gift sets to drum up more fundraising for the hospital, where my very premature sister was born.
From there, I dove into the art side and created an online store for wearable art and mini portraits.

As I kept saying yes to new and different commissions, I expanded into portraits for people, pets, houses, and even planes and boats. As more people saw and shared my art, more recommended me to others as someone who could tackle projects that other artists said no to, like combining photos into one painting, painting from old or blurry photos, creating custom backgrounds, or changing seasons or elements from recent photos to match a memory or a history.

Now, my art is almost all commissioned by previous clients or word-of-mouth referrals. Saying yes to commissions I’d never done before is always somewhat terrifying, but if I never said yes, I would never learn the skills that make my services valueable and unique. I still struggle with imposter syndrome, because I never went to art school and so many other artists out there are so much more skilled than I am. I secretly worry that everyone is just being nice and I’m actually really bad at everything.

I paint a lot of portraits for people who have lost pets or human family and friends, or who want to honor someone or something special. I feel pressure to produce art that will help them feel what they want to feel when they look at it, and it’s a very vulnerable thing to put your heart into something and present it to be judged by others, especially when they’re paying you to get it right. Every single portrait makes me nervous to start, and all portraits look a little bit terrible at different stages.

But the more I do, the more confidence I build that I can trust the process, It’s nerve-wracking, but there is nothing like seeing the happy tears of a person for who I’ve just immortalized a memory they can treasure forever.

My next big challenge is to take my writing futher. I just put out 10th anniversary editions of my childrens books, and my first novel for young adults, Between Tungsten and Gold, will be published in Fall, 2025 through Splinter Press. The lessons I’ve learned through art–thick skin, tackling revisions, trusting the process–have carried over beautifully into writing novels.

One piece of advice I’d want someone to understand, especially in the early stages of a creative persuit, is that nothing is wasted. If you have to make six versions of the same painting before you feel like it’s ready to sell, or if you paint something that never sells, if you try a new medium and hate it, if you write a scene or a character or an entire book that never sees the light of day, none of this is a waste. If it failed, you succeeded, because you gave it a go. Now you can check it off your list and move on with no regrets. If it suceeds, it’s because you put in the work, which includes endless hours of practice and learning that will never be seen by another soul.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I take everyone who visits me to the place they least expect for dinner: the hospital in Castle Rock. The restaurant inside is called Manna, and it’s locally-sourced and gourmet quality at hospital cafeteria prices, and the menu changes occasionaly so I love going back. Weird, I know, but it’s soo good!

For a lunch I would take them to Cuba Cuba for the lechon asado and maduros–I can not get enough of those! I even bought containers of the sauce to try to make it myself.

In nice weather, I would absolutely take a friend hiking and rock climbing in the beautiful mountains. I live south of Denver in Castle Rock, so I would take them to Castlewood Canyon State Park to cool off in the stream and climb in the canyon. Garden of the Gods in Colorado Springs is stunning any time of the year, and while I was down there I’d hit up the Cheyenne Mountain Zoo for its unique mountain layout.

I’d try to convince them to move closer by showing them the best houses in their budget, as I am also a real estate agent by referral and word-of-mouth only, And yes, every real estate client gets a house portrait or other custom painting of their choice.

If they like shopping, I’d spend an afternoon at the 16th street mall and get dinner over there, and then maybe see a band at the Filmore or a show at Comedy Works or one of the community theaters.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I grew up with parents who followed their creative whims. My mother studied art and learned everything from guitar to photography to basket weaving. My father is a well of ideas and can make anything out of wood. He studied communications and writes beautiful and hilarious poetry and longer works. Trying new things was a way of life, and I never even considered that anything would be unlearnable. We were quite a long way from wealthy, but rich in creativity and support for developing whatever talents we showed interest in.

My husband John Skipper deserves a massive amount of credit for the way I’ve been able to carry my creative whims into my adult life. He provides the enormous privilige of having my family’s needs met so that I can follow creative flights of fancy. He not only supports, but encourages my passions, and reins me in when I start to take on too much (because there are times when we all need to say no).

Thank you to them, and to everyone who puts themselves out there and lets their light shine. I can’t help be be inspired when I witness the hard-earned talents of others.

Website: www.skipperbooks.com or www.skipperbay.com

Instagram: @skipperbay

Facebook: @skipperbaycreative

Image Credits
Brooke Hancock