We recently connected with Jenny Chasteen and have shared our conversation below.

Jenny, appreciate you joining us today. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

I never meant to start a business. I just wanted to tell stories about adventure and magic and treehouses.

But, as I began to learn from the Author Conservatory (an online college-alternative writing program that helps aspiring writers craft sustainable careers)–and as I had already learned from a couple of less-than-bestselling self-published books–achieving my dream of becoming a fantasy author would take more than writing skills.

It would take business skills.

Valuing what I have to offer, identifying my target reader, learning how best to serve him, figuring out where to find him and how to communicate with him, persuading him to choose my book over other books, handling money, interacting with people *shivers*…all of these are business skills that are essential to an author career.

In 2021, as an introverted 19-year-old girl, I faced the most daunting school assignment of my life: starting a small business.

To say the risks felt overwhelming would be an understatement.

What if I accidentally did something illegal?

What if I messed up a project and a client sued me?

What if I hired employees and they didn’t do their jobs well?

What if I poured countless hours into this business only to never earn a single dollar?

What if this business started working, but I hated it?

As a diabetic, I had all the chronic illness “what ifs,” too. What if my blood sugar spiked or crashed during an interview with a client? What if the stress of running a business was more than I could handle?

But the worst risk for me wasn’t any of the practical ones. It was the risk of feeling like a failure who wasn’t responsible enough to admit she should be working a normal job instead of attempting something out of her range.

All the potential disasters raced through my mind, leaving me feeling exposed and helpless.

I almost backed out. My parents even asked the Conservatory if I could have an exception from the business assignment.

But my instructors encouraged me to give business at least a try. They were confident it had enough value for my future that it was worth the risks.

I don’t think any individual factor convinced me to accept the challenge. It was more that starting a business was simply the next thing to do.

For as long as I could remember, I’d felt like I was on an inevitable path toward becoming an author. Storytelling is how I process the world. I’ve always believed it’s my calling, my purpose, the work I was created for.

When you’ve got a conviction like that, risks just have to be dealt with.

So I bit the bullet. I started the business.

Really, very few of my fears ever materialized.

I had a few rough situations with technical difficulties and bad organization, but all my clients were gracious. Nobody sued me.

And no, I didn’t get in trouble with the law. Running a sole proprietorship legally (including taxes) is easier than most people think.

I hit rough stretches without much income, but I also enjoyed fertile seasons of more clients and income than I knew what to do with.

And instead of feeling like a failure as an adult, I feel like a huge success as a student.

Instead of leaving me ashamed, my business has left me more confident than I imagined I could be–not that everything will go well or that I’ll do everything well, but that God will be with me no matter what, and that, with him, I can always take the next step forward.

Now, I get to encourage others by sharing my story of how I served 13 clients and earned over $25,000 as a 19-21-year-old. My generation doesn’t like risks (does anyone?), but I hope to inspire them that the right risks are worth the cost.

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’m Jenny Chasteen, and I constantly find myself on real-life adventures, whether that looks like traveling around the world or walking the long road of Type 1 Diabetes. Through Bible Quizzing, I’ve memorized the entire New Testament (it’s not as hard as it sounds!). I enjoy good books and bad movies way too much, but when I leave my room, I’m usually exploring the restaurants, small businesses, and parks (the more trees, the better) of Kansas City.

I’ve been obsessed with stories for as long as I can remember. As a toddler, I made my older siblings write down the bizarre little tales I’d concocted. At age 6, I officially decided to become a published author one day.

Pursuing that dream led me to the Author Conservatory, an online college-alternative writing program where we learn from industry experts how to craft sustainable storytelling careers. (My classmates and I will graduate this June!)

With the Conservatory’s advice and instruction, I started my business, Life Story Book Services, primarily to develop the skills and experience I’ll need to succeed as a fantasy author.

So, what is Life Story Book Services?

Well, you know how your family always says you’ll write down your grandparents’ stories one of these days, but you never have the time, energy, or resources to finish the project in a high-quality way?

As time goes on, more and more relatives’ stories are lost forever. Dementia sets in, a hospital stay leaves them unable to hold long conversations, or–sooner than you expected–your family member passes away.

Life Story Book Services keeps those stories from being forgotten.

We interview elderly people to find out their life stories, then turn those stories into books with their pictures so they can pass them down to their kids and grandkids.

One thing that sets us apart from others…is simply that we exist! Not many businesses address this need even though virtually every family has it.

Among the few companies that operate in this space, we stand out by crafting our whole process so that a busy family can FINISH it in a reasonable amount of time.

We provide interviews with our clients (typically for 1-4 hours) rather than questionnaires that would take them months to finish.

We implement Draft Review Deadlines to help families make any desired changes to their life story books without letting their projects drag on interminably. (But we offer plentiful extensions so it doesn’t feel like a stressful homework assignment!)

And we keep our scheduling and packages flexible to each family’s unique needs.

Plus, my team and I apply our fiction training to how we tell these real-life stories.

As an interviewer, it’s intimidating to ask people the kind of deep, personal questions that make for a gripping story.

But we go there. As long as our clients are comfortable with it, we’ll ask hard questions like, “What do you wish you had done differently? What were you most afraid of? What helped you get through that hard time? Why did you make that choice?”

That’s how we help future generations see our clients, not as numbers on a timeline, but as people. As the protagonists of their own stories.

What amazes me about this business is how well it fits my author brand–I didn’t do that on purpose! Both through Life Story Book Services and through my fantasy books, I get to encourage people to go on adventures that are worth the cost.

Now, my team and I are all college students, and several of us have big life changes coming up that will require us to step back from this business for now. Because of that, we’re no longer taking new clients and are closing down Life Story Book Services this spring.

But I still believe capturing parents’ and grandparents’ life stories is a critical project for every family, and most families need help to complete it.

That’s why I’m now partnering with my friend Ruthie Burrell of Rooted Biography. Her resume and team are incredible, and she and I are on the same page (sorry for the groan-worthy book pun) in terms of the values we bring to our businesses.

When you contact Ruthie through her website, ask her about the special packages she’s offering people sent to her by Jenny Chasteen!

What’s been the most effective strategy for growing your clientele?

Local business networking meetings! Hands down.

Because my business is so relationship-based, I’ve never gotten much traction from social media outreach, online collaborations, or even email marketing.

What’s worked for my business is showing up, week after week, and talking to the same people, face-to-face, over and over.

Now, before I got invited to one, I had no idea such a thing as a “business networking meeting” existed.

For anyone who doesn’t know, these are basically what they sound like: meetings of businesspeople from a certain local area who spend an hour or two getting to know each other, making connections, providing referrals, and maybe even becoming each other’s clients.

But these events aren’t nearly as boring, terrifying, and soul-draining as they sound like they’d be.

Many of the businesspeople are, like me, creative entrepreneurs trying to expand their reach. Lots of people come just to invest in the community. Even the people with more stereotypical jobs (bankers, insurance agents, real estate agents) are often really fun to be around.

I showed up to these meetings hoping for connections to senior living communities. As it turned out, the people I hoped would be my referral partners became my clients.

I thought I needed to market to elderly people, but I learned that I really needed to market to their children and grandchildren. Local business networking meetings turned out to be the most effective place to meet them!

I also started kind of…enjoying these meetings? They’ve helped me get to know my community better and…make friends? Who knew–marketing can be good for your personal life!

Is there mission driving your creative journey?

My initial motivation for writing seemed simple: it was fun. I loved it.

But there was always a deeper desire behind that, too.

In stories, everything had meaning, purpose, and order. The characters’ lives were interesting and made progress toward a better state. The world was full of ancient myths and magic that were still alive and active in the present.

Why, I thought, can’t real life be like that?

This led me to a habit of spending as much time as possible escaping from real life into stories where all these wonderful things were true. The stories, in a way, started taking over my real life.

But here’s the thing: since then I’ve come to believe that everything good about those stories IS true of our world.

I grew up in church, but it wasn’t until my teens that I started connecting the stories of the Bible with what I saw around me on the average weekday. I started wondering…

What if I didn’t just say these things were true?

What if I lived like these things–the cosmic war of good vs. evil, resurrection, new creation–were real?

What if I lived like God were really here with me right now?

And if I say those things are true…aren’t I in serious trouble if I don’t live like they’re real?

For the last few years, it’s been my mission to live like the story in the Bible is real. Sometimes I do a horrible job at it, either by choosing fear over adventure or by letting the idea of heroism give me a selfish bravado.

But in spite of those failures, it’s been an amazing journey.

Oddly enough, it was stories that led me to ask questions about adventure in real life, and now it’s these questions that drive the stories I write.

Plus, though I didn’t design it this way originally, Life Story Book Services, my business where I help families capture their elderly relatives’ life stories, dovetails with this mission perfectly.

Through this business, I tell true adventure tales to encourage future generations to live well–following their ancestors’ wisdom, learning from their ancestors’ mistakes.

Believe me, my clients have led more adventurous lives than many fictional characters.

Meanwhile, on the fantasy side, I write stories where you come for the worldbuilding and stay for the characters.

There’s still that draw of simple fun. The joy of an exciting tale.

But what serves my readers on an even deeper level is how the characters choose to live adventurously and grow as a result. It’s how the characters live like what they believe is real.

I hope I encourage my readers to do the same.

Contact Info:

• Website: https://jenny-chasteen.ck.page/d0b8a560df
• Youtube: https://www.youtube.com/channel/UClkRTkU-xkVvs0vYdHmOHig
• Other: Purchase my book: https://authorconservatory.com/anthology-jenny-chasteen/