134 // Failure Is Always an Option with Jonathan Willis

We have a special guest on the podcast today – Jonathan Willis.Β 

Cincinnati Endeavors

A part of the dilemma people face when they delay starting families and getting married is they don’t have any weight that they’re carrying to create traction. The story can be entirely about you. There is no sense of responsibility or heaviness of needing to make it work. If it had been a choice for us to have done the family things that were put upon us very early, we would have just delayed it. But because it was placed in our laps, we just found ways to make it work. There is a problem you can create for yourself if you’re waiting for the right circumstances before you allow yourself to take a risk.

There’s a point where discomfort is actually driving you, and we think that’s something we should live without, but that discomfort is the friction that allows you to move forward. A frictionless life is not all that exciting.

You guys had the photography practice, and you have also launched a restaurant and a nerf arena in Cincinnati?? Tell us the stories of the things you’ve tried and what gave you the confidence to try them.

We make the idea of failure so fear-based, so I decided to live my life as an example. If I were to try something and fail but was able to say I did it, what would it be? I love the idea of cowboy food, and I had been kicking this concept around for a while. We traveled and camped a bunch as a family, and before we left, I would make this big pot of beans with green chili powder. I wanted to open a restaurant in Cincinnati based on cowboy food. I was doing video work up to this point, so I transferred some of those skills into a pop-up event. We’ll be open for one night. It’s strange, but often the most successful night of any restaurant is opening night, so let’s just stick to that! We put these cards on every table that begged the question: if failure was totally an option, what would you try?

Part of the reason why The Snake Bite was one of the most rewarding projects I have ever done is that I decided for myself that it was going to be a zero-profit endeavor. Anything we made, I just spread out among the people who helped us out that night. If I wanted to make it about a profitable outcome, I would have tried to make it bigger and built disappointment into it. So I took money out of the equation.

Failure Only Hurts for a Little Bit

I’m a pretty optimistic, excitable person, and I was skeptical. We got in the car after playing, and nobody went to their phones to check out. It was a 20-minute drive home of engaging with each other. I took that feeling home and could not stop thinking about it. So we opened Dart Rush here in Cincinnati. We had two locations, but we didn’t make it through Covid. But you can see this trend of graduating from smaller ideas to a little bit bigger ones.

I love that it was rooted in inviting people back to play. I think we’ve all lost the ability and the desire to play together. As you tell that story, I feel like that is what you’re doing-you’re just playing. Why is it that you’re able to try these ideas when most people are stuck in their lane and feel like they have to toil their way for the rest of their career until they retire, and then they’ll get to play and try things and take risks? What about the way you set your life up gives you access to try this stuff?

I practice a mini counseling session with 80-year old me. Is this something I would be glad I did, or am I wasting my time? At the risk of wasting my time, I often assume I would be glad for the experience, and I just go for things. I try to put my vision down the road in that respect. On the other hand, I have grown to believe in the theme of family. I established my career as an artist, which is very individualistic, but the heart behind everything I do is to fuel energy and resources into advocating for family. I doubled down on Dart Rush because I hadn’t experienced anything that brought the family together that way. If I find something that evolves the family, I’m more willing to go for it.

A Creative Marathon – Family Photography

That is a great transition into the Simple Portrait project. Tell us about what you’re up to there and why.

The Simple Portrait project is an annual, fast-paced, highly experiential family portrait experience in Cincinnati. It’s a celebration and affirmation of family. One thing I didn’t ever want to be was a family photographer. Ironically, it’s the work I’m the proudest of because it really means something. We’ve seen families that come every year for almost ten years. For some families, it is just another layer of glue that keeps them together. If what we do in those 20 minutes can remind you throughout the year that it’s good to be together, I’m into it.

When people think of family photography, there’s a very forced image that comes to mind. You’re trying to show the opposite of that. These are real-time, no-structure photos. You’re inviting families to put their genuine selves on display.Β 

When we started the portrait project, I said: if I do this, how can I turn it into a creative marathon? I wanted to see if I could do a hundred family portraits in a hundred different ways in the same set. If I can find something new every year, that’s where we get our push creatively.

You’ve tried a bunch of random things. Most have had success, some have had short-lived success, some have failed, all of it feels fun. I know people are listening that are like: gosh, I have those ideas. What would you tell them?

The fear of failing can create more pain than the short-term sting of failure. Being afraid to fail is a long-term diagnosis. Failing only hurts for a little bit. So many times, people think failing is the worst possible outcome, so they never try. But never trying is the worst outcome because you’re missing an opportunity to grow as a person. You learn way more from your mistakes and failures than from your success.

Want to reach out to Jonathan Willis? http://www.jonbob.com/ or learn more about the Simple Portrait Project: http://www.thesimpleportraitproject.com/

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