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Kari Loya On The 5 Things You Need To Be A Successful Author or Writer

… Write, then keep writing. So maybe it’s not 10,000 hours, but it’s definitely in the thousands. The only way to become a great writer is to write. And write. And write. I have been writing in different forms for the last decade and continue learning the craft.

As part of my interview series, I had the pleasure of interviewing Kari Loya. Kari is an educational leader, storyteller, and adventurer. He loves empowering individuals, teams, and organizations to perform at their best. In his first book, My Top 40 at 40: Making the First Half Count, Kari presented an original, meaningful way to celebrate his 40th birthday by sharing his own collection of 40 favorite stories spanning 6 continents and 2 decades.

He has worked for nearly three decades at a range of innovative educational institutions, beginning with Teach For America and serving as headmaster at the Good Hope Country Day School in the U.S. Virgin Islands.

In addition, Kari Loya is a bilingual, Emmy Award-winning voice talent and musical artist. He has worked with clients such as PBS, VH1, NBC Sports, McDonald’s, and many other Fortune 500 companies. Kari holds a B.A. from Dartmouth College and an MBA from Columbia University.

He currently lives with his wife and daughter in Sugar Land, Texas.

In Kari’s newest book, Conversations Across America, Kari chronicles the TransAmerica bike ride he and his dad, Merv, took to discover America, just in the nick of time. They had a long-standing dream to bike the TransAmerica Bike Trail, which is a 4,200 mile path between Yorktown, VA, and Astoria, OR. It wasn’t until Kari’s dad was diagnosed with Alzheimer’s that they finally seized the day and went on the adventure of a lifetime.

Thank you so much for joining us! Can you share a story about what brought you to this particular career path?

My biggest passions are educational leadership, storytelling, and adventure. This book project — Conversations Across America — was an opportunity for me to combine all three.

Can you share the most interesting story that occurred to you in the course of your career?

In 2017 while I was leading a private school in the U.S. Virgin Islands, we were hit by two Cat-5 hurricanes (Irma, then Maria) in the span of two weeks. It was brutal. But nine days later, we managed to re-open the school despite no power, no internet connectivity, no cell phone reception, and limited water. We then began a slow, long, painful march towards recovery… and we bounced back. Nothing really prepares you for something like that, but the 2015 cross-country bike trip (with my 75-year-old dad, who had early-stage Alzheimer’s) chronicled in Conversations Across America certainly honed my patience, perseverance, adaptability, empathy, and sense of humor — and all those were critical after the hurricanes.

What was the biggest challenge you faced in your journey to becoming an author? How did you overcome it? Can you share a story about that that other aspiring writers can learn from?

I think there are two possible paths with distinct challenges. One is when you are focused on another career outside writing, and you squeeze in time to write. The second is when you make writing your full-time gig (or as part of a sabbatical), then you try to stay connected with the outside world. For my first book (My Top 40 at 40, while working full-time at a school), I wrote 75% of the book while commuting on NJ Transit in and out of New York City — I actually looked forward to my daily commute! For Conversations Across America (while on a creative sabbatical), I stole Julia Cameron’s idea of a weekly “Artist Date” to make sure I got out to museums, cool coffee shops, and other places where I’d see people and keep up my energy, idea flow, and inspiration.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I am so grateful to Anne Lamott for writing Bird by Bird, which I read years ago. She introduced the concept of “sh-tty first drafts” and of giving names to the personalities, the critics, the voices of self-doubt who always appear in her head while she’s writing. So, I have learned to get out of my own head and move quickly to write a lot of terrible first drafts! And I frequently talk out loud with myself while writing, too… whatever it takes to keep moving forward. I try not to take myself too seriously, but it’s an on-going struggle, and those two strategies help.

What are some of the most interesting or exciting projects you are working on now?

As part of my creative sabbatical, I have done a deep dive into music and songwriting. I love how a three-minute song — another form of writing — combines my passions of educational leadership, storytelling, and adventure. My recent songs have included a Putin protest song (“The World Says Nyet”), a space tourism song (“Roller Coasters on the Moon”) and I’m now working on a quirky, fun song that could be sung by World Cup soccer fans. I was at Luzhniki Stadium in Moscow in 2018 to watch England vs. Croatia in the World Cup semifinals when the song “Three Lions” came on, and the entire stadium started singing it. It was magical. So, I thought I’d try to create something similar… we’ll see what happens!

Can you share the most interesting story that you shared in your book?

One conversation we had in Idaho was with a young veteran who’d completed two tours of Iraq and had received a purple heart. He was dedicated to helping other vets — including many amputees — regain their emotional health, and sense of purpose, by taking them on bear hunts. Later, he’d get calls from their wives saying it was the happiest they’d seen their husbands since returning from duty.

After our trip, I realized that our cross-country cycling adventure was like my dad’s bear hunt. For several years, he’d been navigating through a frustrating, rising sea of “nos” and “can’ts” — internal and external. Our two-wheel bear hunt gave him the chance to feel powerful again.

On our last morning — Day 73 — on the Oregon coast, we hit a stretch of a state park closed to traffic and, unexpectedly, came upon a bear 30 meters ahead. And like with the bear of Alzheimer’s, we stared at it directly, respected it as it crossed the road, then continued our journey.

What is the main empowering lesson you want your readers to take away after finishing your book?

Find someone you love, and instead of worrying about what you can’t do, find something you CAN — and seize the day. Also, we have an amazing country with amazing people. I hope more people will get out of their silos and connect with others different from them.

Based on your experience, what are the “5 Things You Need to Know to Become a Great Author”? Please share a story or example for each.

1. Write, then keep writing. So maybe it’s not 10,000 hours, but it’s definitely in the thousands. The only way to become a great writer is to write. And write. And write. I have been writing in different forms for the last decade and continue learning the craft.

2. Develop a routine. For me, writing early in the morning — often pre-dawn — ensures that I build a distraction-free space for myself where I can play with words and ideas. Consistent structure (time, place, etc.) is essential for building momentum.

3. Outline next steps before you leave. I have found it helpful to jot down a couple ideas for the next chapter, story, song, etc. before I get up from my desk. This helps reduce a little of the daunting “blank sheet/blank canvas” that paralyzes many writers.

4. Study all forms of writing. Novels. Non-fiction. Advertisement copy. Song lyrics. Spoken word. Anything! My daughter and I analyzed in detail Amanda Gorman’s Inaugural Poem “The Hill We Climb”¾what brilliant writing! It’s a masterclass in alliteration, repetition, phrasing, the rule of three, double meaning, and so much more.

5. Deep dive on styles you’d like to emulate. For my first book, I highlighted language in David Sedaris’ books — I love his sense of humor. I enjoyed phrases he used like “It was the sort of sound that…” I had pages of notes of devices like this that I could easily incorporate into my own writing. For Conversations Across America, I did the same using Gary Smith’s stories (Sports Illustrated). Gary is incredible at capturing the hidden meaning and the stories that aren’t being told aloud.

What is the one habit you believe contributed the most to you becoming a great writer? (i.e. perseverance, discipline, play, craft study) Can you share a story or example?

I wish it were as easy as one thing. But probably the most important thing has been perseverance. It’s just like an adventure climbing a mountain. The view will get better the higher up you go. But you gotta take another step. And another. And another…

Which literature do you draw inspiration from? Why?

I love great fiction — A Gentleman in Moscow by Amor Towles — was such a treat for my eyes, brain, and heart. But probably 90% of what I read is non-fiction, and I’m especially drawn to stories by or about entrepreneurs and artists, and I draw inspiration from them taking new paths, creating fearlessly, and persevering.

You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Our world would be a much better place if every day we all spent 30 minutes biking and talking one-on-one with someone else, including people we know and don’t know… and afterwards we each had to share one thing we learned in the conversation. That would be transformative. Walking outside — ideally in nature — would do the same thing. But since my new book is about a bike journey, it makes sense to turn this into a Pedaling Movement J



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