Meet O Mag Insider – Amy Whitley!

Age: 43

Occupation: travel and fiction writer, hospitality reputation consultant

What did you want to be when you were a little girl?

A veterinarian. I love animals, and don’t fear blood and gore, so this may actually have worked out.

What are some different jobs you’ve had in your life?

Oddly enough, my first paying job was as a public speaker from age 9-15, after winning a writing contest and publishing a children’s book. I was hired through my publisher by public schools, where I’d talk in libraries and gymnasiums to groups of elementary-aged kids about creative writing. My introverted self hated this job, and though it did give me a crash course in how to speak in front of large audiences, I still only speak publicly under duress. In my teens, I worked in hotel housekeeping (a job everyone who likes to travel should be required to do at least once), then later as a kindergarten reading specialist before my writing and hospitality industry careers took hold.

What do you work toward in your spare time?

For the past decade I’ve been working toward a novel-writing career. I’ve completed three manuscripts and have several more in the works, and landed a literary agent in late 2018. I am laser focused on selling one of my manuscripts in 2020.

Are you a morning person or a night owl?

Morning all the way. By 10 pm, stick a fork in me, because I’m done.

What are you most proud of?

I’m very proud of my three kids, but in the interest of not deflecting to my offspring: I’d have to say I’m most proud of the career I’ve built around two things I’m passionate about (travel and writing). I built my family travel website ( from the ground up, beginning modestly as a road trip and camping blog and eventually working with Disney, Hyatt, Expedia, and resorts and tour companies around the world.

What are you known for? 

Friends and family come to me for travel advice, but I’d like to think I’m also known for my determination to succeed and my work ethic. No matter the goal, I try to always put my head down and get things done. I’m a big believer in the power of hard work.

What inspires you?

Anyone who is unapologetically and bravely living their authentically best life. If said life requires extra gumption, rejects the mainstream, or both, all the better.

Tell me something about you that most people don’t know.

This is a weird phenomenon for me, but despite a very transparent and outspoken online life, I still regularly encounter people in my personal life who don’t know that I’m gay. Many acquaintances who know me from what I consider the first chapter of my adult life—raising three kids with the man I was honored to be married to for 22 years—are slow to catch up. Gossip actually doesn’t travel as fast as one might think! Luckily, this just gives me more excuses to introduce them to the wonderful woman I’m now dating (https://www.amywcom/blog/a-full-years-work).

Why did you apply to be an O Mag Insider?

2018-2019 was a period of tremendous growth, unabashed honesty, and painful change for me, which took just about all the daring I could muster. I felt authentic for the first time in decades, which also left me feeling wildly free and strong. The O Magazine Insider concept resonated deeply with me: Oprah is an example of exactly the brand of unapologetic bravery I was (and still am) working hard to achieve in my life, and I wanted to mirror that in whatever ways I could.

How do you live your best life?

Every day, I strive to ‘show up’ to my own life, living deliberately and saying yes to opportunities that may intimidate me. I try to live in the moment, leaning into what feels true for me. My best life is the authentic one I’m living today, but I’ve learned that ‘best’ does not always mean ‘easiest’. It’s important not to confuse the two.

What are you reading now? Where the Crawdads Sing by Delia Owens

What’s a day in your life like?

I’m an early riser, which is a good thing since my travel writing and hospitality reputation work is primarily on East Coast time, while I live in Oregon. I am up and caffeinated before 6 am, and ready for a work break by 9 am, at which time I go to CrossFit, then walk the dogs. I focus on freelance writing gigs, social media, and email correspondence until after lunch, and the afternoon is usually reserved for fiction writing and editing. I’ll either retreat to my tiny house office in the backyard, or sit in the sunshine…I love being outside. I try to close my laptop for the day by 4 pm, when the ‘second shift’ of after-school transportation, sports practices, and theater rehearsals start. My youngest son just got his learner’s permit, however, so my schedule will be opening up soon! Most evenings, I am at my girlfriend’s house for dinner or she’s cooking for us at mine, and I definitely like to end my day streaming favorite shows on Netflix or Prime.

Check out Amy’s links below!


Personal landing page/site:

Recent op-ed piece I’m proud of:

This is part of an ongoing series, introducing you to the dynamic individuals who make up O, The Oprah Magazine’s Brand Ambassadors known as the O Mag Insiders. For more information on the program or to apply, click HERE.

Read the last O Mag Insider feature HERE!

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