Episode 011: That Digital Nomad Life, Though: How To Make Your Dream a Reality

Episode 010: Day in the Life of a Learning and Development Professional
July 11, 2017
Episode 012: Seeking: Sane Financial Advice & Perspective
July 25, 2017

Episode 011: That Digital Nomad Life, Though: How To Make Your Dream a Reality

SO…..you wanna be a digital nomad, butttttttt:

  • You don’t know where to start
  • You’ll most definitely relegate yourself to a life of Cup O’ Noodles and overdrawing your checking account
  • Who are you to quit a stable job with a steady paycheck?
  • You’re the most undisciplined person ever and will binge watch “Glow” on Netflix all day

I could keep listing all the things that could possibly come up when you contemplate actually going for something that’s been your dream for awhile now, but I think you’re intimately aware of them all.

INSTEAD, let’s do two things:

  1. Grab our Bust Your Fear Worksheet here, which we talk about on the show
  2. Turn to the Career Passport Podcast this week and talk to Erin Greenawald, who spent about six years as an editor of branded content for the Muse, a hugely popular career website for millennials. Erin quit the Muse and flew off into the sunset to become a digital nomad seamlessly and she lived happily ever after.

Sike. It didn’t happen like that at all, and Erin is giving us the real skinny on how she realized she wanted to do this, how she pushed through resistance to stick to the goal and how she actually is working through structuring her life (hint: it’s a work in progress).

“When it came to where I was professionally, my heart and my gut had different opinions (than my mind) on what I should be doing.” – Erin Greenawald, on how she realized she wanted a change


If you’ve wanted to make a leap like this- or really trying anything new like a new entrepreneurial venture, for example, this show is a MUST. LISTEN.  I’m going to include some of the gems here but to get the full raw beauty of this show, you gotta listen.


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  • When thinking about a big change, ask yourself: “Could you use what you have to give yourself the freedom to clear out what’s not working and open up space to find what is working?”
  • Structuring an unstructured life: It’s trial and error and a lot of reevaluating
  • The notion of patience around an unstructured move like this – a different perspective on career (and the impact of social media on your feelings on your career)
  • What if EASE is a metric to help you define success? (Versus hours logged or ‘working yourself to death”
  • How to use authenticity to attract your tribe and potential digital nomad work
  • Change is ongoing- it’s not like most people wake up one day and say, “I’m making a change!!” and then they go full steam ahead with their plan with no reservations. There are ongoing hurdles and this is NORMAL.

Anyway, I’m going to hand it over to your earbuds now so you can grab the episode on your way into work. Maybe, just maybe, it will plant a further seed in you to take the smallest ittiest bittiest next step in your quest to be a digital nomad of some sort.

And don’t forget- we’re on a lot of other platforms now for the Podcast, in case you don’t have iTunes. You can check ‘em out below.


Show Notes (Timings are approximate)

2:15 How Erin realized she wanted to try the “digital nomad” lifestyle + imposter syndrome

5:20 The moment she realized she had to radically listen to her gut

7:00 Perspectives on change

10:35 “Sending Ships” Tool

12:30 Examples of Ships

16:00 What has clicked into place for Erin and what’s she still working on?

18:00 The positives of ‘moving home’

19:20 Structuring days as a digital nomad

24:50 Patience

28:30 Authenticity as a tool to attract your tribe and opportunities

30:45 Resources Erin consulted to figure this out

35:00 Rapid fire Travel Questions


Agenda for 2017 Hustle Fest– at the New Women’s Space

Angela Jia Kim’s “Sending Ships” Tool Crisis Textline

Sheryl Sandberg’s Career Jungle Gym – in Lean In

Erin’s article on the decision to quit her job: https://grow.acorns.com/having-a-cash-cushion-allowed-me-to-quit-a-job-i-hated/



The Artist’s Way- 12 week program on re-tapping into your creativity

Danielle LaPorte: The FireStarter Sessions

digital nomad