How Do You Organize Your Time When You Don’t Have a 9 to 5?

In 2007, in a beige cubicle in California, I used a spreadsheet to determine that I controlled about 20% of my waking hours. The other 80% were determined by my job and related activities–  from commuting, to mending clothes, to checking emails in the evenings.

I didn’t have too many options with the 20% that I did control. My location, and thus my home, was also determined by that job. I spent little energy thinking about what to do with the time I did control (although I did fantasize about traveling a lot). I  mostly just stayed at work longer– a case of the (time) poor getting poorer.

Many entrepreneurs continue on with the “9-5” way of organizing time long after they’ve left their day jobs. We trade 40 hour work weeks for 80. We structure our businesses and working days like the jobs we once knew, and serve clients who expect as much.

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A 9 to 5 hangover.

For 9 to 5 knowledge workers, the question of “what should I do with all my time” asserts itself with urgency only at a few critical moments in adulthood– when one graduates from school, when one retires, and if lucky, when one achieves FU money.

The answer in all three cases is often (at least initially): take time off to travel! The same is true for a large percentage of new location independent entrepreneurs. When many of us first hit the road, we borrow structure from our days as travelers. We book the trips we dreamed of in cubicles.

And while we are bouncing from hotel to hostel, we are feeling vaguely anxious about our clients and cash flows. They might even start to disappear. Many of us end up declaring that a life of travel is unsustainable.

We tap back into the routines that made us productive during our corporate lives— dual monitors, gym memberships, regular basketball games, etc.

But once you’ve separated your earning from your location, the concept of home changes, at least a bit. For me at least, home was always the place I needed to be in order to earn, cultivate, and stow my (limited) wealth. The place where you make the harvest. For location independent entrepreneurs, perhaps it’s more apt to say “home base” (“home base” = home + mobility freedom).

I suspect that the location independent lifestyle will inspire us to come up with new concepts of “home base” as well as “work week” (I list some possibilities below and would love to hear yours).

Managing success means managing time.

Many of us, by design or luck, have successfully seized control of the large majority of our waking hours. We are sitting on a time goldmine!

In a recent interview on Tim Ferriss’ podcast, Rolf Potts pointed out that not much has been written on how to manage success. He spoke of how the press reacted to an already wealthy Dave Chappelle turning down money that he didn’t need– they questioned his sanity. 

Many people think lifestyle entrepreneurs are crazy too! For leaving money on the table when the opportunity to make more, to work harder, to go zero to one is so “obvious.” Often what lies behind these stories is an entrepreneur who understands and cares about time wealth.

If the problem your business works on is compelling, and you can make a good living from it, why not consider working on it over the course of many years in such a way that gives you autonomy to both do interesting work and enjoy your time wealth? Unlike many in the TechCrunch-osphere, lifestyle business owners don’t think that running a business (or even something with “startup” potential) needs to be such a time depraved pursuit.

What do you say instead of “9 to 5” or “home.”

Below I’ve listed concepts I’ve seen replacing things like “home,” “9 to 5,” and “40 hour work week.” They can be seen as tactical approaches to “filling the void” in lifestyle design.

Concepts for work:

  • The horseshoe workday. Working both first thing in the morning (until about lunch), and for another few hours in the early evening. Much like polyphasic sleep, this working schedule seems to catch people in more commonly productive times.
  • Four and done. If you are just getting started, you may want to push yourself to find your 5 hours, but if you want to continue to grow and operate a successful business, I think four hours of creative work a day is a realistic target. It’s probably more than many 9 to 5ers work! This time equation is in my view the fundamental value proposition of the lifestyle, so much less time input and you get to own the asset you create in those 4 hours. See also: find work you love. 
  • 30 day challenges or longer term life quests. I first became aware of 30 day challenges on Steve Pavlina’s legendary personal development blog, Tim Ferriss recently ran one called ‘NOBNOM.’ 30 day challenges aren’t unique to location independence, but entrepreneurs have the potential to go after much more aggressive goals during these challenges.
  • Mini-retirement. Bail out on your life for 3 to 6 months in order to go somewhere new, ideally to engage in a project that is uniquely interesting to you.
  • Take a cruise. If you want to know what run-of-the-mill bloggers like myself will be talking about in 3 years, read Tynan’s blog. I love his concept of jumping on cruise ships to focus on projects. Similar to masterminds, retreats, and “jam” sessions (described in detail in this episode).
  • Chronic and consistent work. Work all the time. Track the amount of time you do it. Work out only to spark your hormones. Take the correct stack of supplements. Eat clean. Try to keep it fun. “Business is the only 24/7 sport.” “Spend 5 years like nobody will so you can live a lifetime like nobody can.”
  • Moving to a cheap foreign place and flaneuring around. Check out “This Essay Took Me 4 Years to Write.” Similar to “1,000 and a Backpack.”  I’ve met many people for whom a lifestyle of constant wandering works. I always considered it to be an entrepreneurial insurance plan for me. I figured, I would prefer to be living “1,000 and a backpack” to “9 to 5,” and relatively speaking, wondering around the world on 1 to 2K a month in earnings is a less stressful way of living than 9 to 5. Also: RTW trips or  Vagabonding.
  • Hyper family orientation. Entreprneurs can choose to spend a great deal more time educating and raising their children, and I’ve seen many parents take this approach to organizing their time around creating experiences and learning opportunities for their children (and then finding ways to pay for it!).
  • Bi-phasic or polyphasic sleeping.

Concepts for home base:

  • Flag theory. 
  • Slow travel. 3+ months in a location, slowly moving from place to place and setting up shop.
  • Digital nomad hub. A place you can land and within 24 hours be hooked up with a serviced apartment, a place to work, and some like-minded entrepreneurs to hang out with (all without paying through the nose). These things change fast, at the time of writing these types of hubs exist in our community in Austin, Berlin, Bangkok, Saigon, Chiang Mai, and perhaps Medellin. More to come there for sure as this is a growing trend. A hub probably requires a critical mass of 20 engaged community members and can have sort of collegiate vibe, so lots of impromptu hanging out, long debates over coffee and beer, fast friendships and easy to strike up new projects.
  • Distributed base or “honeybee” base. Similar to “summer home/winter home,” a collection of locations and relationships that together form a home base. I’ve often used “honeybee” as a metaphor for going back to important places and relationships– a series of places that I continue to go back to in order to maintain those connections and relationships. Imagine that the bee continues to go from flower to flower in the hopes that multiple flowers might bloom. A challenge to the traditional notion of home, something would feel amis if I didn’t visit my accountant in Hong Kong once a year, for example.
  • Hub and spoke. Similar to industrial and corporate workers maintain, “hub” would be an investment in a home or home-space, but with long term stays elsewhere or abroad.
  • Baseline. Find a place to live that reduces your expenses as low as possible to extend your cash runway and extend your free time.

I’m excited to see the structures that emerge in the post 9 to 5 era.  I’d love it if you could share more that you’ve seen! Are there structures that you’ve used to order your post corporate life and business that you’ve found particularly fruitful?




PS, if you are interested in some further reading here’s some applicable stuff: How to Take a Walk, Against Productivity, Sometimes Just Go Home, Why Broken Sleep is the Golden Time for Creativity, Do We Have to Retrain Ourselves to Enjoy Our Free Time?, Anything You Want