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

Ryan, thanks for joining us, excited to have you contributing your stories and insights. Are you happier as a creative? Do you sometimes think about what it would be like to just have a regular job? Can you talk to us about how you think through these emotions?

I looked at job listings this morning. Not because I was seriously looking, but just to get a take on what is available in the world. I was pretty good at my “regular” jobs. I spent a lot of time in various levels of management and consulting, as well as more creative positions in marketing and design. I still keep a few regular side hustles going because I struggle to find a work/life balance.

I’ve been working since my early teens. I’m 41 years old and am pursuing a solely creative career–as a writer, artist, podcaster—for the first time. I’ve always been doing creative things, but they were always regulated to the moments between work, sleep, and experiencing life.

This morning, I was thinking about how much more money my past careers are paying. I was thinking about how, sometimes, I miss being part of a team. I miss leading a team and teaching the skills I’ve learned to those on the come up. When I look at job postings now, it is mainly to cause a spike in the levels of anxiety and guilt that will get me past whatever procrastination has seeped into my day.

I’m married to an incredible woman who inspired me by finding a fulfilling career. She is an Occupational Therapist who works in the school system with special needs students. Seeing her success and the joy she gets out of her work—which is incredibly challenging—has pushed me to take this chance.

We’ve taken turns supporting each other’s career efforts, but I still feel self-imposed angst over not being sure how this will all work out. I worry about the stress it might cause her that I’ve given up a regular paycheck, and I fear that she’ll be forced to sacrifice some luxuries because I want to pursue these paths. These are my anxieties. When they overwhelm me, I try to remember we’re a team and talk to her about it.

As for happiness…The moments I’m writing a new story, interviewing someone for the podcast, or just drinking whiskey and painting aliens being sucked out of a coffee mug are always filled with joy. When things are clicking I have these brief realizations that I’m in the moment I’ve been seeking. The rest of the time, I live in a constant state of anxiety about the value of my creative output and wonder which direction I’m supposed to step next to continue down this path.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers

I often refer to myself as a creative raccoon. I see something shiny, and I have to try it. The shiny things being new creative opportunities. I struggle to give a title to what I do or am. In the past few years, I’ve written three novels, a movie script, and launched a blog about entrepreneurship. I started (and lost) a mobile creative office and adventure company. I have a few weekly newspaper columns writing about coffee and the beverage industry. I produced and directed two film shorts. I started selling paintings and launched several podcasts, which have turned into the focused Roast! West Coast coffee podcast and newsletter. The connecting line between all of these projects is sharing stories. In particular, I enjoy learning what motivates other entrepreneurs.

In college, I decided I wanted to be a writer and photographer. At least, I wanted to live the way I thought a writer lived, but after graduation, there was the small problem of paying rent. So I went in another direction. I worked in sales, restaurant management, and commercial real estate, but I always found ways to be creative at my job. Sometimes I would design menus or flyers. Other times I’d be writing the marketing copy. I started a photography company as a side hustle to appease that creative itch and help subsidize my desire to be more than just my job.

Both my wife, Trina, and I went back to school. We were part of the elder millennial group that came out of college when jobs were drying up and then got hit by the recession in 2008. In retrospect, I think that experience created a lot of entrepreneurs. No one told me in school that being a writer or creative requires so many business skills, but it does.

From there, our path got weird. Over the next few years, we lived in Brooklyn, Pittsburgh, Los Angeles, and Chicago while I pursued a career in graphic design and Trina was in grad school. After graduating, she was offered a job in San Diego, where we’ve been for almost ten years.

Through it all, I’ve been writing. After a particularly stressful job ended, I decided I needed to complete my goal of writing a novel. I gave myself a 30-day deadline. I wrote most of it at the coffee shop down the street. It was terrible, but I finished—at least, I finished that draft. It took six months of editing to get it to the point where I’d let anyone read it. It wasn’t The Great American Novel, but it was a creative project that I started and finished. That gave me the confidence to do it again and again. That led to my current fiction efforts with the Eli & Jane series.

Eli and Jane began as a creative writing project and has evolved into a novel trilogy following the titular characters as they take three formative road trips in which they find each other, find themselves, and then decide if they can face the future together or not. In the first book, Eli & Jane, the characters travel from California to the Midwest. The second, Future Eli & Future Jane, is set along the California coast. I’m writing the third and final book now, which takes place in the southwest. While Eli and Jane aren’t real people, the places they explore and the roads they travel are.

My other focused effort is the Roast! West Coast coffee podcast and newsletter. Several years ago, I had the opportunity to open a restaurant. The concept was craft coffee and beer, but I backed out of the deal at the last moment. Primarily, because I didn’t know anything about coffee and I wasn’t confident I could succeed without that knowledge, I didn’t take the risk. It really peeved me off that my ignorance was the main reason I didn’t take the opportunity.

I got a job as a barista at a friend’s new coffee shop. I spent a year working mornings before going to my full-time job. I loved that time. I didn’t know it when I started, but the owner, Chris O’Brien, is truly a world-class coffee person with an infinite well of coffee knowledge that he willingly shared. I kept thinking that other people would love to learn more about coffee too. It is one of the few products that connect people around the world. The complexities of the drink, economic impact, and passion it inspires are really interesting to me.

It wasn’t until the pandemic hit that I had the time and motivation to revisit the idea of sharing coffee education. Podcasts had become a popular d.i.y. medium that made sense. I bought a microphone and started cold calling local coffee roasters to see if they would let me interview them virtually. The show quickly evolved to be just as much about the entrepreneurial journeys my guests have been on as well as coffee education. The show appeals to anyone who likes hearing how businesses are built, what motivates people to pursue a passion, how entrepreneurship inspires creativity, and of course, coffee. Chris even makes regular appearances to teach me—the coffee idiot—how to coffee smarter, as we say on the show. I also write the scripts and edit the content.

The show is in its sixth season. With more than 100 episodes already available, there are plenty of stories to be heard. What I’ve realized is that regardless of the medium—podcast, book, short-form writing, photography, painting—what I love to do is tell stories. I especially appreciate the stories of entrepreneurs and enjoy uplifting anyone in an industry that is so passionate about a craft that they make it their career.

Is there mission driving your creative journey?

My biggest goal is to spend the time that I have trying to make something that I’m proud of and hopefully improves the world, or at least a few people in the world’s lives. That sounds big and somewhat pretentious, but I don’t know another way to say it. What motivates people and how they travel from point A to B in their lives is incredibly interesting. I’ve learned so much about how to be a human from books, art, music, and hearing the stories of others. I’ve been inspired by those stories and encouraged by them to seek alternative paths to wherever my life is going. I hope the work that I put out does that for someone else.

I’m also very driven to make my Wife proud. I’m a better human because I met her, and sometimes I wonder if I’m only a good human because she inspires me to try to be better at everything I do. I am definitely the type of person who can fall down a rabbit hole when seeking answers be it why road trips inspire life changing decisions, are tacos or burritos better, or why someone might prefer serif to sans serif fonts. I’m also someone who can recede into himself while pursuing those questions. Having someone I can share those journeys with is one of the great gifts I’ve had in my life, and it motivates me to put more of myself out into the world…even when I’d much rather stay home and read.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I’ve always believed I had to be able to do everything alone. I think a Midwestern work ethic is tied into that ideal, and I would not do things if it meant I had to depend on others. Then when I finally decided to partner with someone else on a business, it really took off. My business partner and I developed a start-up adventure co-working concept that would enable us and others to tap into the creativity that comes with being outdoors. We had complementary skills, and from the project’s beginning, I felt inspired and more productive than ever. I could see my working future laying out before me. My career was starting to match the vision I always had to be a creative entrepreneur.

Then it crashed and burned in spectacular fashion. My business partner wasn’t seeing the same path laying out before them, and they walked away. I tried to keep the business afloat on my own, but the reasons we were succeeding were the same reasons it ended up failing. Without both of our skill sets working together, it was doomed. I spiraled both mentally and physically. I learned a lot about how stress can impact physical health. It would have been easy to go back to trying to do everything alone, and I’m sure that was the path I was on.

Thankfully, I was offered the opportunity to turn around a struggling restaurant. It was a huge job, and it took 18 months to get it to where I felt comfortable saying I had succeeded. It also forced me to not only work with but lead a team. The job was so big that I couldn’t do it alone, and I was forced to trust the team I had built. I’m not sure why but it was clear to me that the only way up was to try and uplift everyone. I changed my entire management style to be more inclusive and open. I spent more time training and looking for ways to motivate each person based on their needs instead of making them adapt to me. Together we accomplished so much more than I could accomplish alone.

I tend to take on a lot of projects. I can’t help it. My brain never shuts off, even when I want it to. I’m probably better at helping others improve their businesses or pursue their artistic pursuits than I am at my own. My goal for this period in my life is to be more focused on just a few things. Right now, that is writing more books and the Roast! West Coast coffee podcast. Even that is a lot, so I’m trying to apply the lessons I learned from my failures and successes. That means asking for help when I needed—more often than I’m comfortable with—and being willing to uplift others over myself, knowing that my success is more fulfilling when I’m not experiencing it alone.

Contact Info:

• Website: https://www.roastwestcoast.com, https://www.onewildlifeco.com/
• Instagram: @roastwestcoast, @onewildlifeco
• Facebook: https://www.facebook.com/roastwestcoast, https://www.facebook.com/onewildlifeco
• Linkedin: https://www.linkedin.com/in/ryanwoldt/

Image Credits
Trina Woldt