How to Make Bold Career Pivots: Plan, Embrace Discomfort, and Follow Your Calling

Everyday Better is LinkedIn News’ weekly personal development podcast and weekly newsletter hosted by Leah Smart, a LinkedIn News Editor . You’ll hear from some of the world's brightest minds and bravest hearts who use science and story to share strategies for how we can flourish individually, in relationship to others and to the world around us. We talk about improving emotional, work, physical and relational health.

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When I was in my late 20s, I made a major career pivot. I quit my job in sales—a field I’d been in basically since I graduated from college. I felt a calling to do something that had deeper meaning and purpose, both for me and for others. I didn’t know exactly where that calling would lead, but I knew there had to be more.

Starting over after all the years I’d put into sales felt like a huge risk at the time—and it was! I worried about being an entry-level candidate again for the roles I wanted. There was no guarantee people would want me without the years of experience or advanced degrees that my competition had. Plus, there still aren’t many Black women hosting shows about the science and stories of personal development and well-being.

Today, I feel incredibly lucky to do the work I do, but that doesn’t mean it’s always easy—or even comfortable. In fact, I’m uncomfortable a lot.

My guest today is Carole Hopson . She's a writer, mother of two and a Boeing 737 captain at United Airlines . Carole is all about embracing discomfort in service of what she calls your “one true thing." During our conversation, she declared it's the risk you’d take if you knew you couldn’t fail.?

Carole wanted to be a pilot as a child, but she didn’t begin her second act of flight school and earning her license until she was my age—in her mid-30s. Her first act was spent in corporate America, leading HR and Learning and Development for major brands like Foot Locker and L’Oréal. Despite her success, Carole was drawn back to the calling she’d had as a kid to fly planes. So, she made it her mission to take one of the biggest leaps we’ve ever heard of on this show. All in all, her pivot took nearly 20 years—from earning her license to becoming a captain!

Not only did she completely transform her skill set to become a pilot, but she also became one of fewer than 200 Black women in the country who fly for a living, with even fewer serving as captains. Carole also recently became a published author (another calling) since entering her second act. Her historical fiction novel, A Pair of Wings , which was recently re-released, tells the story of Bessie Coleman, the first Black woman ever to earn a pilot's license in 1921. Carole’s "one true thing" and her drive are a perfect complement to Bessie’s story.

Now clearly in the middle of her second act as a pilot and her third act as an author, Carole has a lot of wisdom to offer about how we can stop holding ourselves back from pursuing our dreams—big and small. When it comes to career pivots that may seem farfetched, she encourages us to embrace our "one true thing" and take action, despite all the discomfort. Take a listen to our conversation here .

Carole's 5 Steps for a Career Pivot

Carole said to make her pivot she first had to realize that the difference between a dream and a goal is a date. So she took these five steps to make her big career pivot dreams a reality:

1. Define point a and point b: Assess where you are today and where you want your pivot to take you.
2. Know the process: Have a clear understanding of the steps to make the pivot. Lay out key details, like how long it will take along with costs you'll incur on your way to your pivot and once you're there.
3. Take an honest look at your skills: Know where you're strong but pay more attention to where you need to upskill.
4. Close the gap: Find books, courses or people who can support you in becoming proficient in your weak spots.
5. Clear your path: Get your finances and support system in order. Ensure you have what you need to make the transition as smooth as possible.

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Read: Carole Hopson's first novel, A Pair of Wings

Get Involved: 100 Pair of Wings Foundation to send 100 black women to flight school by 2035

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Everyday Better is LinkedIn News’ weekly personal development podcast hosted by Leah Smart , a LinkedIn News Editor. You’ll hear from some of the worlds brightest minds and bravest hearts about how to live with more clarity and intention every day, in and out of work. Subscribe to the show's newsletter .

?? This year, Everyday Better was awarded a gold medal for "Best Self-Development/Self-Help" podcast from the Signal Awards , one of the most distinguished honors in podcasting. Thanks to you, our community, for helping our work flourish by listening to, watching, and reading it! If you haven't had the chance, please rate us on Apple or Spotify so we can continue bringing you well-being experts and practical insights.

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