TMBA 255: How People Fail at Sustaining the Digital Nomad Lifestyle

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Will you succeed or fail as a digital nomad? Becoming a successful location-independent entrepreneur isn’t guaranteed. Some of the skills it takes to become a successful digital nomad take years to develop. This week, we are talking about the four major differences we have seen between successful digital nomads and those who have failed.

Listen to this week’s show and learn:

  • Why digital nomads need to be at least somewhat entrepreneurial.
  • How to determine if an office is right for you.
  • Why you need to be a fanatic about systems and processes.
  • What it means to “re-wire your prestige triggers” and why you should be doing it.
  • Why you have to be willing to throw out everything you know and “flip the paradigm”.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian

Published on 07.31.14
  • IvanKrachanov

    Great episode. Turns out that you have started the podcast on my birthday :)

  • John

    Hey guys, I thought you might be re-opening membership in July, but there’s only a few hours left? Any idea when spots will next be available?

  • There is nothing to it but to do it. Just as pimping ain’t easy, neither is launching your Startup if your mental game isn’t on point. Sometimes we have to change who we are to become who we aspire to be. I like how this episode was simple but if you really listen you can see the naked truth. A lot of wantrepreneurs never make it because they don’t do what is required to move forward, they become stuck in some repetitive loop.

    Good Ep!

  • nicolamr

    Hey, does anyone know of any computer science masters living the location-independent life? What I’m getting at specifically is doing really complex things one couldn’t do (easily) without a MSc, but while living this lifestyle. Is any of you doing this? I’d be thrilled to hear from you, since I’m about to finish with my studies and considering this crazy possibility. I’ll be glad to pay it forward. Thanks

  • omouse

    take a page from software consultants like Brennan Dunn:

    there’s a previous podcast on TropicalMBA about productized services. you’re going to have to figure out what specialized tasks you can do and sell them as products to businesses:

    most CS masters seem to find a home at a company or go consulting or go academia which is all 40+hrs dictated to you by someone else.

  • nicolamr

    Thanks a lot for the answer, I appreciate that!

  • nice answer!! dig it.

  • also check out !!! for somebody with a similar background and age range, also David H at

  • appreciate that sir beach house, glad you dug it!

  • membership is open now by application, you must have an established business

  • :D excellent timing!

  • nicolamr

    Yay, thank you! *feels the power of reaching out

  • Seth Overly

    Being willing to dedicate the time and loving the process > outcome – shit’s gold.
    You’re right on in that for many starting out, the “lack of results” after a couple months is the main source of frustration and why a lot of people give up. But if you love the process, and you’re going all in for the long term, realizing that it takes time to make money, you’re much more likely to be successful as a digital nomad.

    Since listening to the Productized Services episode I have completely changed my mindset to focusing on the process and loving what I’m doing, knowing that every day I’m moving in the right direction rather than worrying about the result.



  • hells yeah Seth thank you for that, it’s great to hear! wish you the best in your venture, keep crackin’ :D

  • Casey Ames

    Great post. Just got to it tonight, and it really hit home, as I am 2 months into my first travels as a digital nomad. Especially the part of having a community to work with.

    Being in Rio de Janeiro, it isn’t the most conducive for this lifestyle, and I haven’t noticed much of community down here. It’s gets a bit lonely when my apartment is the only place I’m working (no free wifi + bootstrapping and not wanting to pay for co-working space).

  • This episode is what I needed as I am making another run at working for myself. Always great to listen to you guys.

  • thanks Matt! best of luck

  • hey Casey thanks for that! Rio is an expensive one yeah it doesn’t seem to attract too many of the laptop crowd yet, perhaps you can do a work trade for co-working… might be worth the investment to get out there with others even if it costs ya

  • Casey Ames

    That’s true. Probably a good investment, but I’ll be back in Seattle in a couple weeks.

    I’ll definitely look into some co-working places in Madrid though when I’m there this winter. Especially since from this blog it seems to be one of the go-to places currently.

  • love Madrid!!!! :D

  • brilliant post, exactly what I needed to reiterate that this lifestyle is something I can make a go at. I am currently in the process of setting up my own process so i can work for myself. always great to listen to you guys thanks for all the inspiration.

  • thanks Nayar appreciate that best of luck with the transition!

  • Taylor

    Hey guys, do you have scripts of your podcasts for somebody who is hard of hearing?

  • working on that right now Taylor hopefully will roll them out in the coming weeks

  • Taylor

    Update? Missing out on all the great insights TMBA has! :(

  • The guy flaked, underestimated the cost per episode. Sorry about that!

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