What is a Lifestyle Design Blogger to Do?

What is a Lifestyle Design Blogger to Do? post image

The other day I was on the phone with my mastermind group. These super smart and successful guys were totally cracking up making fun of lifestyle design bloggers. RIGHT IN FRONT OF MY FACE!!!

Admit it… You’ve done it too…


They were all like… “hey the book came out 4 years ago, we aren’t impressed that you managed to move to Southeast Asia… “

Ah… Lifestyle Design. What are you and why do people love/hate you so? My buddy Chris Ducker is even questioning the godfather’s lifestyle design creditials.

Lifestyle design dudes and dudettes get a lot of flak in the blog world.

  • “Lifestyle designers don’t have real businesses.”
  • “Lifestyle design is a scam– you develop a cult of personality then you sell it off in the form of training guides to be like you.”
  • “Lifestyle designers are young stupid dudes who live in Thailand and glorify the whole thing.”

I like to think about this kind of stuff. What ticks people off so much? There are obvious things like the gloat-y nature of it all… hey people!!! I’m makin’ a million bucks in sales this year!…. and so on…

It got me thinking. What’s a useful next step for the lifestyle design blogosphere to head? What should I do?

* * *

Today I was working on an article about why internet business owners should incorporate in Hong Kong instead of places like Delaware, California, or heaven forbid Germany.

Not many people are talking about stuff like that. I’ve got a hunch why: not many small business owners or location independent types inspired by the 4HWW movement are doing it yet.

I believe strongly that “location independent” isn’t “location arbitrary.” If your small global venture isn’t taking advantage of your mobility or the locations you find yourself in, you are leaving it on the table.

Have you seen what Simon Black is up to?

I respect his blog. He is prolific and interesting. He is genuinely helping people in the lifestyle design community reach their aims. In his case– helping readers explore overseas investment opportunities, diversify their assets, and optimize their citizenship status, among other things.

His material isn’t that useful for start-up entrepreneurs or small business owners who are making international decisions about their growing business. I think there is an opportunity there.

If you are starting a location independent internet business, where is the best place to incorporate? How do you take advantage of the labor codes in the Philippines? How do you live and work in Indonesia for 2 years on a tourist visa? How do you legally minimize your taxes as a US citizen running a start-up in Thailand?

This is the direction I’m going to start taking our community here.

The folks in the TMBA community are largely focused on the following geographic locations:

  • United States / Canada
  • China
  • Philippines
  • Thailand
  • Indonesia
  • Vietnam

We are also building an approach to lifestyle businesses that is unique to our community. This will help us to attract similar business owners and people who can help us on our journey. Here are some of the focuses:

  • Understanding and exploiting loopholes and grey areas that arise from internationalization.
  • Concrete advice on lifestyle arbitrage– cash runway and real costs of living abroad.
  • Employing virtual staff and running multiple overseas corporations from home.
  • Living and running start-ups from abroad.
  • Employing people in multiple countries.
  • Structuring deals and investments in multi-national small businesses and start-ups.
  • Optimizing international business structure for start-up and growing enterprises. Where should you incorporate? Where should you live? How can you legally minimize your tax liability?
These are the kinds of things I’d like to work on here at the TMBA in the coming months. If you have any further suggestions, I’d love to hear them.


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Published on 08.17.11
  • Get a job hippie!


  • Tim

    Liked the post, and the direction you are talking about talking. Would love to hear your opinions/talk further about China specifically.

  • I definitely concur on having more info about deal making… I want to know the nitty gritty details of making and structuring deals and getting them down on paper. For example, for web entrepreneurs, if you are going to sell a niche website for 4-5 figures or more (to whomever), can you talk about the step-by-step process from putting up the for sale sign to having your hands clean of it? What are the documents you want to have signed, the non-competes and special clauses, the transfer of funds / escrow services, and any other procedural considerations to make sure the deal is neat and tidy, and at the end of it, you’ve got your cash, they’ve got their website, and you are fun and fancy free?

    I think something like this would be of incredible value as the “lifestyle design” community has a huge steak in developing (creating, building, monetizing, selling, and/or buying) web properties, but might not have the experience with deals worth a significant sum of money and with insuring the complete transfer of the goods.

    There’s my .02!

  • Dan

    Tim thanks for that…. would love to talk about China more. If you’d like specific questions answered about it, feel free to email me Dan@TropicalMBA.com

  • Dan

    Now that’s one possibility I won’t consider :)

  • Dan

    Ryan, good stuff. I think my approach to this probably sucks, but I’ll share it and see what kind of feedback I get from people. 

  • Stuart

    I do think that the lifestyle design crowd overhypes what it is that they actually do. I can never decide if that is because the bloggers are mostly from the US (and in lots of places American’s have a reputation for hype), or because they are bloggers and have to do some hyping to get an audience.

    From a European perspective, most people in Europe know lots of other people that have moved abroad and are doing interesting and productive things in their new country. I can think of a couple of hundred people I know in their 20s and 30s that have moved abroad to study, then off to another country for a job and then quite a few that are in another country again for the next job. Some have started their own businesses, some are employed, some are self employed.

    Most major European cities (London, Paris, Brussels, Amsterdam, Barcelona, Dublin and many more I’m sure) are chock full of people from other countries making their way in the world. Its no big deal really. And it has been like this for years. Its nothing new.

    They aren’t blogging about it because it is pretty normal.

    Of course, the lifestyle design crowd will explain how little they work and how much they ‘live’ but I think they are mostly working pretty hard and mostly not living the lifestyle of a Tim Ferriss that sparked all this.

    If they are still legally resident in the US, are they even living abroad? Its just fun until you legally move.

    Dan, if you can use this blog and other spaces to move this ‘community’ in a more productive direction, more power to you. I wish you every piece of luck I can.

  • Ken Standard

    I agree with your thinking, that there is a unmet need of providing information of how best to leverage the location independent business lifestyle – in the form of where and how to incorporate, banking, cost of living in various areas, etc. I have learned some valuable information from your various posts and podcasts on this subject, and a few other sources, but I will admit I am also a bit confused on which advice to take action on. The more you can blog about these topics I think the better all of your readers will be.


  • haha the lifestyle really has become a caricature of itself.. Glad you can laugh about it! 

    I never did read 4HWW. Now I don’t really feel I need to because I’ve heard about it so much, it’s almost like I’ve read it. I moved to SE Asia regardless of the book.. I had made the heart decision way before I made the mind decision! 

  • Dan

    haha yeah ya know would actually say if you’ve got a spare moment or time for a bedroom read its def still worth a read… its a way sharper book than it’s responders on the web would have you believe.

  • Dan

    Ken– thanks for that…. yeah ya know it’s super confusing even for Ian and myself, there is just so much information to consider with this stuff… all the more reason to focus on presenting the best we got as simply and as often as we can. 

  • Dan

    haha Stuart, yeah ya know us Americans we are so gosh darn self-impressed. We are cute that way– you know it’s freakin’ expensive relatively for American’s to leave the center of the world– not only are plan tickets expensive, but there is a gravitational pull due to our central nature on the planet. ;)

    Regarding the overhype– don’t really have a particular opinion on that. Sean Ogle for example is a lifestyle design blogger with absolutely no hype. He just is who he is, so actually don’t fee like people oversell stuff to much I guess…. Chris G is another example of a guy who I feel like is a really straight shooter…

    Anyhow… gonna try to keep things BIZNASS focused over here !!! At the end of the day, any way you slice it, that’s what pays for all the travel and fun.

  • Steven Moody

    Great move Dan.  

    Have you ever bought cage free chickens?  The secret is they don’t open the doors until the chickens have become conditioned to staying in their space.  They have mobility, but no one shows them how to use it.  I feel this way living in the US.

    I’m particularly interested in the hidden costs of starting a business in different countries for a service business.  How much longer does it take to train a native Indonesian versus an American if they are both college educated?  What security measures should you consider?  How do you find the experienced workers for specialized (non internet marketing) positions?

  • Dan

    haha… got it Steve. For sure there are big time challenges running a service business in 3rd world countries, if you play your cards right in places like the Philippines, however, you can see HUGE advantages. If you haven’t yet I”d take a quick look at the OutsourcetothePhilippines.com blog… will continue to address these types of issues here and feel free to email me if you have any really specific questions. 


  • Eugene

    While I agree that lifestyle design blogging has become vastly overpopulated, I really don’t think the community is going anywhere.  As long as humans want to grow in new directions, they’ll want to travel.  And as long as they’ll want to travel, they’ll want to incorporate that travel in a seamless manner with their lives, keeping the door open on people giving such advice.

    To me, lifestyle design is simply valuing your time more than your money.  This is a new and radical concept to the 401(k) IRA crew who value graduate school and certifications, but more and more people are seeing even PhDs struggle to keep a well-paying job.  Sure, the bloggers telling you to learn WordPress and make millions are going to fall off a cliff, but the people giving quality life/business advice and opening up people’s eyes are only going to multiply as the demand multiplies.

  • Dan

    Agreed… I don’t have as much of a problem with the community as many do. In fact, I don’t really have a problem at all. My primary concern right now is doing something thats useful, inspiring, and that I can be proud of. 

    I do value my time more than money, in general, but not absolutely. But that’s exactly the crux of LD for me as well– considering time, cash, and mobility as an ecosystem. To me that’s the most important introduction that Tim Ferriss made in 4HWW.

  • Dennis

    Hey great job guys

  • appreciate that Dennis

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