The Real Female Entrepreneur

TRFE 215 // How to go from Corporate Job to Digital Nomad with Anna Grymes

Season 5Lauren FrontieraComment


”Do it now because one day you’re going to wake up and the only thing you’re going to think about is what you didn’t do, not the mistakes that you made.”


with Anna Grymes



If you’ve ever had the desire to travel the world while working and live the digital nomad life, I’m so excited to share this episode with you! After building her business for eight months, Anna Grymes left her Wall Street job, sold everything in her New York City apartment, and spent the next year traveling the world while continuing to run a thriving business. And I ask her ALL the questions! Starting with the really big one we’re all wondering: how did you find the courage to leave behind this career and cozy six-figure salary life you’d spent over a decade building? Her answer had me praise hands’ing all alone in my office and wanting to scream her answer from the freaking mountains.

So, make sure you listen all the way through for that golden life nugget. I also asked her all of the other questions we’re all wondering (especially those of us who dream of doing this one day): how did you plan so that you’d always have internet? How did you balance work while not having a consistent routine and traveling to see all of these amazing spots? How’d you make friends and meet other people while traveling alone?

We talk about…

  • when you wake up and realize that the life you’ve been consciously working so hard towards isn’t the life you want anymore

  • what it’s like to travel the world solo

  • how to build a business that supports your digital nomad life

  • how to find, meet, and connect with other digital nomads while traveling

  • what the not-so-glamorous and unexpected parts are of the digital nomad life




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Anna Grymes started her entrepreneurial journey in 2016 by creating a marketing services company focused on the real estate industry. Her life’s passion is travel and she built her business around doing just that. While working in the demanding finance industry on Wall Street in NYC she realized she was going to need a lot more than three weeks of vacation to see the world. So, Anna built her business around location-independent living, quit her corporate job, and can be found running her company anywhere from a hammock in Thailand to a pub in Dublin. She has recently launched a business strategy and coaching business to help other aspiring entrepreneurs find that freedom in their lives, too. Anna is a Jacksonville, Florida native and graduated with an MBA from the University of Florida.


Anna on Instagram and Facebook


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