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Some of the most interesting people I know are the ones who’ve had a winding, twisting, irregular career path — starting out doing one thing, then dabbling in something else, and then taking a massive left turn into a whole new arena.

These people have unique perspectives and loads of fascinating stories that never seem to run out. They also tend to have very few regrets because they’ve played out many of their “what if” daydreams in real life.

And yet, most people are also terrified to take an unconventional career path that doesn’t follow on the linear “perfect resume” format we’ve all been taught is correct.

So what gives? Why are we so attracted to people with the most interesting (read: nonlinear) paths in life, and yet we feel so resistant to becoming one of them?

It all comes down to fear: fear of failure, fear of what people will think, fear of rejection, fear of the unknown, fear of disappointment, and on and on.

That’s why I’m excited to have Emily Florence on the podcast today. She felt all of those fears at every twist in her unconventional career path, but she followed her intuition and acted anyway.

Listen in as Kristen asks Emily about…

After you’ve listened, leave us a comment to share how Emily’s story resonated with you!


Emily Florence is the founder of Savvy Miss, which is honored to be named a Forbes Top 100 Website for Women. She’s also the host of the EveryDay Happy Show podcast, a certified life, life purpose and business coach, a writer, and a former entertainment publicist and journalist.

Emily’s a puppy mama to a silly lab named Harper, a lover of green tea, a travel enthusiast and a grateful optimist.

She has a Master of Arts in Broadcast Journalism from Emerson College in Boston, a BA in Cultural Anthropology from the University of California at Santa Barbara and a Life Coaching Certificate from the Life Purpose Institute. Prior to becoming an entrepreneur, she was an entertainment publicist representing award-winning clients including American Idol, Gilmore Girls, So You Think You Can Dance, Malcolm in the Middle, Bernie Mac and more.

Emily loves inspiring and supporting people to create happier, more fulfilled, easygoing lives – and to be kinder to the amazing person staring back at them in the mirror. Find her on Instagram @savvymiss.


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The secret to mastering informational interviews with Elise Austen (July 2020)

Burn This: 8 career beliefs to leave in the 2010s (January 2020)

When life screws up your plans with MaryBeth Bailar-Heath (January 2020)

There’s no such thing as a career soulmate (May 2019)


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  1. Can I say how much I loved this? It was just what I needed right now as I stand on the precipice of making another decision that could completely change my life. I loved her law school story- that’s exactly how I became a teacher. I was staring out the window from my office in New York thinking “this cannot be my life. There has to be more for me.” And a month later I had packed up and moved to go back to school. But now, 10 years later, I’m zooming out having the same conversation and wondering what’s next for me. Unconventional has been my life- it was nice to hear another voice put value to the experience and also point out how much more important it is to just be happy. That’s always the goal right? This was great. Thank you!

    1. I love when our episodes show up at just the perfect time! Really glad you enjoyed this one so much Natalie. 🙂

      I don’t feel like we hear enough stories of people taking unconventional career (and life) paths, so I was really grateful that Emily was willing to be so open about her story. Even though it’s really scary to contemplate making another big change, like you’re considering right now, I hope it also feels a bit freeing. And I hope Emily’s journal validates that there’s nothing wrong with wanting to choose something new, even after years of being on a certain path.

      Thanks for sharing how this resonated for you, Natalie!

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