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Posted by on Aug 10, 2014 in Podcasts | 8 comments

DE 011: Breakups and startups. How dating advice can help you set up shop overseas

DE 011: Breakups and startups. How dating advice can help you set up shop overseas

What do dating and starting a business have in common?  Fear and unrealistic expectations.

I keep a diary, and have done for about 7 years now. If you don’t write down your thoughts once in a while, I’d highly recommend it.  You’ll be surprised at how intelligent (or stupid) your younger self can be, and it helps you see the forks in the road that led you to where you are today.

Some of my diary entries from 2009 focus on my first business.  I’d worked long and hard, together with my co-founder, for about 9 months to get the business ready for launch. My thoughts on the night before we went ‘live’ were a mixture of insane expectations and crippling fear.  I was sure the business would be a massive success (it was not), and I was also scared that people would think I was a fake (they didn’t).

My younger self could have benefited from some of the advice Mark Manson gives in this podcast.  Mark is an author, blogger and former dating coach who spends his time traveling around the world writing interesting articles about sex and dating, self improvement, lifestyle and culture. A recent article he wrote on gun violence in the US, received 330,000 Facebook shares and over 1000 comments.  He talked to me from Medellin, Colombia, where he is spending 6 months.


  • What got Mark into the dating advice scene
  • Why dating and starting a business are similar
  • How you can use simple techniques to conquer your inertia, and give yourself a good kick in the bum
  • Why you should start testing your assumptions about living overseas before you leave home
  • How to avoid creating unrealistic expectations that will set you up for disappointment
Mark Manson taking in the view in Rio de Janeiro

Mark Manson taking in the view in Rio de Janeiro


You can find Mark on Facebook, Twitter and email (mark [at]


Mark’s 2011 book which he told me has sold over 15,000 copies


In this podcast, we cover some specific strategies that will help you take that first step towards your destination enterprise aspirations.  Share your own strategy for ending inertia, and what worked for you.

Every comment on this blog post will receive a free copy of Mark’s 2012 book, Escape Plan, which retailed for $27, and is a primer for traveling and life abroad.  The book provides tips from Mark’s own travel experiences on getting cheap airfares, finding good accommodation, learning foreign languages and working overseas.


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Click here to download the transcript for Destination Entrepreneurs Episode 11


  1. interesting.

  2. Haha I am terrible at remembering languages but some good tips! Thanks!

  3. What I found to be most enlightening was Mark’s perspective on why so many people don’t reach their dreams. The idea that someone is just unhappy with their job, rather than committed to starting their own business abroad. That the dreaming is where most people stop, whether it be to have a great business, marriage, etc., because they often only think about the upside without being prepared to do the work of mucking through the challenging parts to keep that business, relationship, body etc.

    I created my own life boot camp, decided to move to a new city, and test myself. See what ways I need to grow–when there is not much support immediately available–to make it going abroad. It seems like these tiny steps really are where it all begins.

  4. To get to your dreams, you have to be prepared to muck through the challenges that come with achieving the fantasy.

    If you missed the interview, that’s the gist of it all.

  5. Wow! This was a really nice interview!

    Came at good time too. I’ve been pushing my business to new levels recently, and while there are lots of good feelings, the dominant one is actually uncomfort. Listening to Mark and Hugh has been a good encouragement with great tips to keep in mind. Thanks!!

  6. Some useful tips and ideas in this podcast. I’m working my way through Hugh’s interviews for ideas and inspiration for my own situation – currently in a well paid job, live in a great place, enjoy a great life but not happy. The challenge has gone and the thoughts of is this it are starting to creep in (I’m 38 so I assume this is what a midlife crisis looks like).
    So on the one side I want to give it all up and find something else that I love doing and on the other side I give up what when many would envy to have.
    Some big choices!

  7. Mark, truly knows how to live life to the fullest and really gets women. I wish I knew about his blog 5 years ago! Keep up the good work.

  8. This podcast made me realise that I have to consider all the negative aspects of my dreams, that it wont just be glory days on the beach, and that there is a good chance I will fail. But understanding that as a possibility allows me to better prepare and less likely to fail!

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