The 1000 Day Rule : What Living the Dream Really Looks Like

The 1000 Day Rule : What Living the Dream Really Looks Like post image

Every so often I’ll stumble upon a blogger who is lamenting the impact of the lifestyle design trend. “Tim Ferriss makes it sound like it’s so easy to get started with your muse business and mini-retirements…”

Cry me a river.

One thing the 4HWW doesn’t do is give a clear idea of how the ideas have been implemented by entrepreneurs, and what their experience looks like when they do.

There are some huge misconceptions out there about muse businesses.

Less than 1%* of lifestyle designers make their money by selling eBooks and courses on how to be lifestyle designers, travelers, mobile business owners, or similar.

I only know a small handful of muse business owners who make their money this way. Contrast that with the 100s of mobile entrepreneurs I’ve met in the past few years and interact with daily. Most lifestyle designers are too busy with their business to blog about it. Be sure to thank the ones who do! Off the top of my head, I’d say less than 1% of 4HWW inspired businesses are in the business of “selling the lifestyle.”

So How Do You Pay for Your Rockstar Lifestyle?

So how are 4HWWers making money? Here are the 5 most popular ways I’ve seen:

  1. Software developers. They own a web app, a popular forum, do freelance database management, or similar. Developers are highly represented in the muse business world, and there is no question they are the most successful freelancers.
  2. Old school marketers. Long form sales letters? Yes. Affiliate marketing? Yes! Porn? Sheebang! These folks have been on the trail way before 4HWW. These were some of the few sources of online income available before Skype changed the game and made mobility a possibility for freelancers and people with virtual teams.
  3. Classic entrepreneurs. These are the deal cutters, the folks who have built something scalable. They have teams, they have processes, they have crazy ambition. They cut deals and make hay. They own valuable stuff. They rarely blog about it.
  4. Online gambling and trading. I suppose you wouldn’t be surprised if I told you tons of people living the lifestyle are making money grinding at online poker tables, day trading, or something similar. A lot of the guys who got involved building muse businesses got their feet wet in poker or trading first. Me included… another story for another day.
  5. ‘New’ marketing. The emerging crowd of social media oriented freelancers, often focused on PPC, SEO, copywriting, niche blogs, you name it. This crowd is newish and generally operating at lower levels of income, but this income can come fast since these markets are developing and scattered.

The 1000 Day Rule

I was chatting with my friend David from Greenback Tax Services the other day about these misconceptions. He said: “people don’t understand they need to be poor for 1000 days.”

Our basic hypothesis: you’ll be doing worse than you were at your job for 1000 days after you start your muse business.

I’ve seen it happen a bunch of times. For many of us it’s been almost exactly those 1000 days it took for us to get back to the level of income we enjoyed in our corporate days.

In my experience, here is what those 1000 days often looks like…

Before Your 1000 Days (the yearning**)

  • You are writing a blog about YOU. The reason you do it is “networking.”
  • You are hating your job.
  • You quit your job and travel on savings.
  • You are buying products from blogs that make a little money on how to make a little money with your blog.
  • You talk about this stuff with your family and friends.
  • You are failing at affiliate marketing.
  • You try to partner up with your best friend or girlfriend/boyfriend.
  • You are buying a bunch of domains, starting a bunch of projects, and stopping when competition shows up.
  • You love Zen Habits. You think you could probably do something similar.
  • You write bitter blog posts about 4HWW.

Day 1 to Day 333 (the great hope)

  • You stop playing around with your GoDaddy account and get to work on putting a buy now button on a website.
  • You start calling potential clients and customers.
  • You regularly use expressions like “margin pressure” and “QC.”
  • You stop talking to friends and family and start hanging with entrepreneurs and people who share your journey.
  • You work out some funky deal for cash runway. You start working during your lunch breaks.
  • You take on freelance work.
  • You negotiate a severance package.
  • You ask friends for money (like an idiot!)
  • You wonder what the FUCK you are doing.
  • Everyone thinks you should take a vacation and get back to your old self ASAP.
  • Most people quit here. You do not. You have the eye of the tiger.

Day 334 to Day 666 (the grind)

  • You have customers. You have clients.
  • You have too much work.
  • Your friends and family think you have gone mental.
  • You don’t visit your family even though you are “location independent.”
  • Your old friends think it’s a fraud. You are chasing a dream. “Get a real job!”
  • You have no money.
  • Your business gets written up in that thing you wanted to be mentioned in– no clients come from it.
  • Constant paranoia. What if my shit is hacked? My competition just made an update!? What did he say?!!?!
  • You get by with a lot of help and hustle. Stuff you could have never planned for starts working out.
  • Clothing and dinners on the town used to be your indulgences. Now you’d take an extra virtual assistant.
  • Your developers are totally fucking you over (you think, but you just don’t know about development yet).
  • You wasted a bunch of money on that one thing that you don’t want to talk about.
  • You are trying to cut some big deals. They’ll “think about your proposal.”

Day 664 to 1000 (the sunrise)

  • Your friends ask “so what does your business do again?”
  • Family is thankful for your extended vacation time.
  • Your VAs are doing good work, but still pulling the disappearing act.
  • You love to travel, but won’t spend 1 day away from your inbox. You don’t understand people who’d want to.
  • Meeting other entrepreneurs and learning from them becomes a huge priority.
  • You could make money, but instead you think you’ll hire somebody.
  • You have too many business ideas to act on.
  • You are thinking… this just might fucking work!
  • You are thankful.
  • You want more.
  • You’ve got a list of high quality problems.
  • Despite your intensity, you can still do all the Zen Habits stuff, if you so chose.

What day are you on?

*made it up.
**yes, that is a Coheed reference. LISTEN UP!


PS, If you liked this article and want to hear directly from me, put your email address in to the form below.

Published on 09.08.11
  • Dan

    Rockin’ tossed it in my Google Reader. Thanks for the shout.

  • I’m in agreement with you that The 4-Hour Workweek glossed over many of the nitty gritty details about what it takes to build a business that supports a location independent lifestyle. It also left out the long-term mindset requirements of the entrepreneurial process of try, fail, try again, fail, try again, fail, until you eventually succeed.

    As my wife and I transitioned into living what we call a Location Liberated Lifestyle, my wife Heather went from full-time employee to part-time contractor for the company she had worked at for 10 years prior. She is a technical writer and e-learning developer.

    I was trading stocks full-time, but now I’m transitioning into running our travel blog, training and publishing company,, part-time and have also recently accepted a copywriting apprenticeship part-time to support our business mission.

    I think what aspiring digital nomads need to realize is that they need to develop real business building skills that can be applied to any venture such that they begin to leverage the inputs of others. And the focus has to be on discovering their own mission…not some mission-in-a-box given to them by an Internet marketer. This, as I have found in my 10 years of entrepreneurial ups and downs, is paramount to creating real breakthroughs.

    The entrepreneurs I have personally worked with and been mentored by (six millionaires among them) share a single thing in common: They all had a focused mission and vision and kept hammering away at it for years. Enduring all the ups and downs, curveballs, and fires to eventually come out the other side victorious and very, very rich.

    If you really want to change your life, you need to focus on creating a business vehicle born of an inspiring mission that gives you the energy to endure the entrepreneurial process. Anything less will yield poor to mediocre results, frustration, and possibly permanent failure. On the bright side, however, permanent failure can only occur when you stop trying.

  • Dan

    Agreed Adam! Especially the ‘focus on one’ thing part. A lot of being a successful entrepreneur seems to be enduring more pain than others. That’s part of the reason just following your ‘passion’ can be difficult– for a lot of beginners, holding their feet to the fire could be the furthest thing from a passion.

  • Thanks for the reply, Dan!

    Seems like a common enemy here is the “sugar coated” truth that aspiring entrepreneurs encounter.I fell for it plenty of times when I was first starting out and it isn’t easy to find out (and accept!) that you might have to fail a dozen times to be right once.But therein lies the beauty of entrepreneurship. You only have to be right once to potentially set yourself up for life.

    I’ve been at this for 10 years. Been through crazy ups and downs. Broke and bankrupt twice. And did well once. Other entrepreneurs have similar stories and it’s a reality for some of us.I’m a fan of any entrepreneur that tells it like it is, the whole story, whether the audience wants to hear it or not.P.S. Congrats on the mention in the Forbes article. That is awesome and I hope it gave you a big boost!

  • Dan

    Cheers Adam. Sounds like a hell of a story would love to read it if you wrote it up.

  • Great post, I have been sorting through all this info as a newbie to the blogging world. I grew up through the tech bubble and I feel like Im still years behind on blogging its pathetic! Thanks again though for the eye opening post!

  • Dan

    Cheers Andrew. Thanks for reading :)

  • Great. I do have it written but it’s in bits and pieces. So when I assemble it, you’ll be the first to know.

  • Danny Michlewicz

    Dan this ‘focus on one thing’ made me think of the rise to profitability of your nemesis, PayPal!  Employees attribute a lot of the success of PayPal to its employees hyperfocus on one attainable thing at a time.

  • Dan

    Speaking of focus– for the time being– paypal has made good with me. They fixed their international BS and so I’m happy. I think. :)

  • Danny Michlewicz

    Excellent news!!  Some of their fees are still ABSURDLY high.  Especially with countries like China I believe.

  • Stacey

    what day am I on…well you tell me brother…you tell me.xx

  • Dan

    day ‘get back to bali’ 

  • GREAT article, Dan!!! I shared this with our 4HWW Success Stories community by linking to the article on our facebook page.

    I don’t really know which day I am on, as I still have my 9-5 job and at the same time try to come up with ‘something of my own’. But much of the aspects you write in ‘before the 1000 days’ so rings a bell. Want proof? See my short blog post ‘Entrepreneur or Wantrepreneur…??’:

    As you said: ‘Cry me a river…’

    Regards from Greece,

  • Dan

    Hey David thanks for that man! Checkin’ out your blog now.. 

  • I think master minding is a great way to deal with that getting over cry-me-a-river, by the way. What’s your opinion about / experience with that??

  • Dan

    I think the power of masterminds is profound… I spend a lot of my time and energy building and cultivating masterminds.

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  • I should be around day 700 or summin’ but since I’ve taken detours and time off (6-12 months) it feels like day 300 but with the experience of day 800! What’s that – day 1800? Haha.The math might not make sense but the roller coaster … hoo boy. I can see clearly now and in the midst of my 4th rebrand in 2 years, 2012 is starting to look a lot like day HELL YEAH IT WAS ALL WORTH IT.  ;) Tia. 

  • Dan

    Day 1800? That’s good news. I think cocktails on the beach in Mexico come at 2200. :)

  • Been through all that, The really hard part is the first 1 through 333 because there so many ways it can fail and you are not that confident yet! Also noone i that i know of talks about the fact that your first business DOES NOT have to make a million dollars 

  • Dan

    just enough for rent and beer :)

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  • I hoped on over here from the most recent post, now I remember. I’ts more like a game of snakes and ladders for me, I was in the 800s and nor I’m squarely back at day 365 I’m pretty sure I will be getting a few more ladders this time around though.

  • Dan

    yoy! not the first time. once you can get to day 300 you can pretty much get there at will, anytime. 

  • I’m a little late to this game, but it’s because I just read the ENTIRE post for the first time. Somehow, I only got the 1,000 days part and missed the different phases! 

    I’m on day 396 and have just compiled my biggest life lessons until this point – sort of a year one memoir. That’s why I returned to this post, to link to the 1,000 rule!

    Honestly, it was hard to read this knowing I’ve made some of the mistakes (or am making them) on the way to success. But then again, I know success could often not come without them. 

    So I’m keeping my tiger eyes blazing! ;-)

    I am also making a point to follow TMBA more closely starting today because the real business smarts – cutting deals + process + scalability – those are the tools I need to get MacGuyver-like creative skills and that’s my goal for year two!

    Thanks for this post!

  • Dan

    Hey Terrisa appreciate the kind words!!! 396 in my case was a lot of agony!!! :) 

  • Yup, sounds spot on!

  • Nice to see courage wolf here. I made some decent money from software. Now I build niche websites. I think the software was easier!

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  • Shit I’m everywhere!

    Still yearning, in great hope and grinding but definitely not sunrising (yet).

    PS. I really couldn’t stop laughing at this one: “You wonder what the FUCK you are doing.”

    That’s something I still ask myself every single day but oddily enough… I also think “this just might fucking work!” as well.

  • Dan

    haha :)

  • Dan

    Now that’s worthy of a courage wolf!

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  • Cameron

    Thank god I found this!!!! I was starting to think I lost my mind or had some sort of demon in my way. Apparently, the “demon” was named Sugar Coating. Made it to day 333 and then ended up back at square one and went back to a job. I sort of like what I do but the pay and the schedule suck and I can feel the creeping dread approaching about a year out. Thanks for this post! I greatly needed it!

  • Dan

    Cheers Cameron! Hope it helps.

  • Tom Krawiec

    I wish I read this article a year ago. I now understand all those earlier steps ;)

    I’m moving from ‘The Great Hope’ into ‘The Grind’

  • Dan

    Cheers Tom!

  • Oh wow! I’m totally in the “Before Your 1000 Days” phase and working on The Challenge as we speak! lol

  • Great Article Dan – Your 4HWW emo pic made my day.

  • Dan


  • Dan

    Thanks Dan !

  • Adam Finan

    I am still in the great hope working towards the grind!

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