We caught up with the brilliant and insightful Todd Kreisman a few weeks ago and have shared our conversation below.

Alright, Todd thanks for taking the time to share your stories and insights with us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

In all honesty, I haven’t quite been able to figure myself out. As a rule, I’m risk-averse. I don’t do thrill rides. I prefer to avoid driving at night. I don’t even particularly like going to baseball games on the off-chance I’ll be hit in the head by a fly ball. And yet, at several moments in my life, I have suddenly taken a massive, life-changing risk, as if there’s a thirst for instability and danger always bubbling just beneath the surface of my overwhelming paranoia.

When I was 20 and living in Chicago, I felt I was falling into too much of a routine, and decided one day that I needed to shake things up. I immediately made plans to bike across the country. (I was never much of a cyclist, and made it as far as central Illinois, nearly dying at least twice.) Years later, after working for a long time in an insurance office, I up and quit with no safety net, only knowing that I couldn’t be there another day. I went home, Googled “humor writing jobs,” and lucked into a gig that would allow me to exercise my creativity and writing skills for the better part of the next decade.

But perhaps the most formative risk I have taken to date was one about five years ago. I no longer had my writing job, and I was forced to make a choice. I had actually worked my way up to Creative Director in the company, and could have made a parallel leap that would have guaranteed me good money and helped provide for my little family (consisting of my wife Erin and son Oliver, who was not even two years old at the time). But I knew I had been denying a creative aspect of myself for a long while, and I needed to silence the voice in my head, or I would never have real peace.

First of all, we made the decision to move from Los Angeles, our home for the past 17 years, to Raleigh, North Carolina. We felt it was the right move for a number of reasons, but that didn’t make it any scarier. At the same time, I decided that I had to take a genuine stab at true artistic freedom. I didn’t want to work for another employer, even in a creative capacity.

In the time since, I’ve been trying to juggle perhaps a bit too much. I co-founded a virtual escape room company, then wrote the scripts and devised the puzzles for a number of escape games. I became a monthly contributor to GAMES: World of Puzzles magazine, with over 100 puzzles, articles, and interviews published over the last five years. Most importantly, I finally reconnected with my inner artist – someone I’d kept more or less quiet since my teen years. I joined an artists’ guild, took online courses, regularly attended the University of YouTube, and practiced like crazy honing my skills. I also bit the bullet and started learning everything I could about the marketing and business side of the art business, a comprehensive understanding of which is a vital element of every contemporary artist’s success story.

I still find myself taking occasional risks within the world of art; not content with a single medium, I’ve experimented with acrylic and oil paint, graphite, charcoal, pastel, and colored pencils. I’ve taken on large murals (where I had to climb to the top of a ladder, against my better judgment) and hand-painted my own car per my son’s request. I continue to experience a love-hate relationship with risk, but I’m also astute enough to recognize that everything good I have in my life today is due directly to some venture outside my comfort zone.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I was deeply into art, writing, and creating word puzzles from a young age. I was fortunate to make a living writing for a number of years in my adulthood, but I always considered both the art and puzzles hobbies until half a decade ago.

In 2022 I began taking my art seriously, making a genuine effort to sustain myself financially. I’m still growing, as both an artist and a business owner, but I feel as if I’m on the path to lasting independence. The majority of my work is either acrylic on canvas or pencil on paper. I do a ton of commissions (usually pet or family portraits), but whenever I’m sans deadline, I’m working on my own personal projects.

What I’m most proud of may also be the thing holding me back. I think I have a lot of versatility as an artist. Because I get bored doing too much of the same thing, my work often varies stylistically or subject-wise from others I’ve done in the past. That’s freeing, but also difficult to brand.

One thing I can confidently say sets me apart is my sense of humor. I performed stand-up and sketch comedy in Chicago, and have been a professional humor writer; that frequently shows up in my art as well. While there are certainly other artists who employ humor in their work, there aren’t many who place an emphasis on the ability to entertain and amuse as much as to provoke more somber emotions on the part of an observer.

While I will always be happy to accommodate a collector with a portrait, I am at my most excited when I’m asked to do something outside the box, or when I am given a tad more creative control.

Looking back, are there any resources you wish you knew about earlier in your creative journey?

It may sound like a rather dry answer to the question, but… sales funnels.

Since my art business is still in its fledgling stage, I don’t have the funds I’d ideally like to be able to pour into advertising, but a couple of years ago, when it would have been more feasible, I hadn’t yet heard of sales funnels. As of today, I still haven’t given them a go myself, so I can’t even say for sure that they’re the solution, but I have read quite a bit about them by now, and have heard from countless artists who feel it made all the difference in getting their work seen and purchased.

So that’s where much of my focus is at present, when not exercising my creative muscles. I’m working toward creating a solid, attractive sales funnel that (once I also assemble an adequate ad budget) will get more eyeballs on what I do, and result in more consistent sales.

What do you think is the goal or mission that drives your creative journey?

It used to be quite different. When I was young, no matter what I was pursuing – whether it was writing, acting, comedy, etc. – I had my eyes on fame and fortune. The idea of being recognized as one of the world’s best in some pursuit was massively appealing to me. But I matured (in some ways), got married, had a kid, and moved away from a major city. My priorities have changed. My life goals have changed. More than anything, I want to do my part to provide for a rich, fulfilling life for me and my family, and I want to do it by relying on my talents, rather than by grinding for a paycheck.

Contact Info:

• Website: https://www.toddkreismanart.com/
• Instagram: https://www.instagram.com/toddkreismanart/
• Facebook: https://www.facebook.com/toddkreisman78
• Linkedin: https://www.linkedin.com/in/todd-kreisman-b84b85a/