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

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

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.

TMBA_Time_700 (1)

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

Published on 11.11.14
  • dylanized

    Can’t underestimate what I call the “Deep Freeze” – an extreme isolation sprint allowing a deep dive on one project. Helps to go to an unfamiliar town where you don’t know anybody – or seclude yourself on an 18-hr airplane ride ala Peter Shankman.

  • oh wow that’s a great one! love the name too :) Yeah I was blown away and impressed by the severity of his plan, but makes a ton of sense.

  • I haven’t completely figured out my travel/home style yet (mostly slow travel though) but as far as working hours go, I like to do ‘self care’ stuff in the morning (meditation, yoga. write 1000 words) and do 4-5 hours of work in the afternoon. At night I’ll meet up with friends, go out, have fun or just watch a movie.

  • Great breakdown. Right now I’m doing the horseshoe because it meshes perfectly with my husband’s schedule (school in the AM, work in the PM). When I need more of the day free I switch to four and done (or just take the day off!)

    For me there’s a big difference between growth phases and maintenance phases, though. Maintenance is so much lighter.

    Whatever structure one uses, I think they key is to be aware of it and adopt it joyfully, since there’s no one right way to do business or live life. Some people thrive on the “chronic/consistent” structure, others would get totally stressed out by it. Some people adore mini-retirements, others either wouldn’t be able or wouldn’t want to be totally disconnected from their biz for that long.

    If the paradigm you’ve adopted (or fallen into) isn’t workin’ for ya, consciously choose to change it and see if a different model suits your needs/desires/personality better. The beauty of a lifestyle business is that YOU can design it the way YOU want.

    As this movement matures, people have to be careful not to exchange one rigid script (the 9-5 cubicle thing) for another (“I have to be constantly traveling! I must hit $X in revenue! I’ve gotta do A, B, or C like that other guy over there, otherwise I’m not a ‘real’ entrepreneur!”)

  • Joel

    Did something like this on a recent LHR – NYC trip and wrote about it here ( Great for quick wins on a mid-sized projects.

  • Nice! your entire blog is a case study in this!

  • this reminds me of an approach Neil Strauss once described as having “units” i think his were: work, physical, social, and relationship… i can’t remember maybe it wasn’t that great! :P I love the self-care unit though, I’ve been adding this in the past year myself, spending 2-3 hours every afternoon sitting in hot rooms and trying to pick up weights :)

  • first, owe you an email! drowning over there!

    the hardest part with awareness for me has been recognizing all the things that i’m not doing, for some reason that’s gotten harder (but also more rewarding). for many years i think I could actually get to the things my flimsy “should” bubble could get around, but nowadays it’s very clearly impossible, so that’s opened up a kind of freedom to focus on what i’m going to do daily and that’s it kinda thing. i still fall into the trap of thinking i can do more and (maybe like chris duckers myth of the golden va) sort of have a myth of myself as capable of these giant productive days, but working hard to focus on patterns.

    re: your last paragraph, a big strain in my thoughts these days has been precisely this, it’s one of the most wonderful things these businesses have brought us but we sorta need to fight a battle to maintain it for ourselves, i am a fan of creating space for all different kinds of paths to be viable and profitable “real” or not! :D

  • On a bigger scale (one year, 10 years, your entire life), I think meaningful events such as DCBKK have a big role to play.

    For my yearly goals, I’ve started to use DCBKK as the deadline rather than December 31st. (I wrote more about this idea here :

    Ancient Romans had a bunch of festivals to structure the year. Now we get to opt-in to the symbolic events we find most meaningful (or even invent them).

  • Hey Stan good point there, I think I toyed around with ‘conference hopping’ but didn’t put it down… that’s a great idea as well and honestly an honor that you consider DCBKK worthy.

    BTW here’s the updated link seems the one you offered has an extra character:

  • You’d surprised how many of us are going to wear the red bracelet for the whole year !

    (I even saw people at the event with two of them)

  • Two that I’ve noticed in myself recently:

    1. Traditional rituals re-emerging – Sunday Brunch and taking a “sabbath” day or siesta/afternoon breaks. When you de-industrialize/cubicalize, there seems to be a tendency to fall back into pre-industrial rhythms which have some inherent intelligence to them.

    2. Intensity cycling/volatility – Do the hardest task first thing in the day, do the hardest day first thing in the week. I usually do my longest days on Mon/Tues then taper through Saturday and take Sunday afternoons off which recharges me for Monday.

  • Very interesting, I’m assuming you’ve listened to this:

    RE: #1 I took a whole chunk out of this article about this stuff. Another time!

    And RE: #2 I’ve taken to calling “routine” “chronic” perhaps for to explore similar ideas.

  • I’ve tried them all and they ALL work… at the appropriate moments.

    Right now I am in “chronic” mode (and no not the Snoop Dog variety) as I have a unique opportunity to build 2 businesses at the same time. Both present financial AND intellectual stimulation, which is the most important to me these days TBH.

  • Yea, John Reineck sent me that one.

    Also just read The Paleo Manifesto

    Interesting from the angle of a super popular book that more or less rehashed/repackaged a lot of existing concepts in a popular movement, but to the point about traditional rituals, he has a chapter where he basically relates all traditional Jewish laws to modern scientific discoveries. eg. kosher anticipates germ theory.

    Got me thinking about all the other traditional practices that probably anticipate things we haven’t discovered yet.

    The punishment for working on the sabbath was death! Makes me feel like taking a day off might be smart, though I’m having limited success on implementation.

    Feel the same Re: Meditation/prayer – so universal, there has to be something there.

  • Awesome dissemination in this post Dan! Horseshoe method works for me, but flexibility is key. In the past I have tried rigid work schedules (i.e. write between 9-10:30, 10 minute break, work on ads between 10:30-noon, 45 min lunch, etc) but ultimately these schedules never end up working for me and I much prefer simply “most important/money making tasks first” and sort out the rest later.

    I’d love to see a related post on relationships. Bouncing around for me isn’t as fulfilling as having 1 home base and going other places for anywhere from 2 weeks-3 months at a time. I feel like my connections at home are much more solid, my dating life is better, and I love the “feeling” of having a home base, among other things. Also, there are many places in the world that to me are worth visiting, but not for 3 months. I like the idea of spending more time in the “really cool” spots, say 2-3 months, while taking quick 2-4 week trips to places I find interesting but not as livable.

    Also the idea of traveling solo vs traveling in groups, with significant others, friends, family, etc is an interesting related topic. I think all can be great but you can have a much different experience going solo than if you go with say, your best friend or spouse.

    Lots of tangents here…great blog, looking forward to your next one!

  • Man, I could relate so much to what you’ve said. Nicely put

  • enjoyed this book as well but totally missed that part… probably had some prejudice there… good to keep and eye out for this vein of thinking. seems double edged at times ! the same logic could apply to shitty stuff

  • dat chronic! pumped to hear how it goes for you DT

  • hey Kevin I agree with the rigidity, always ends up breaking down for me to, I need a system that flexes… man I’d love to see one from you on relationships sounds like you have more interested ideas!!! :) It’s a great point though and I do have one thought about relationships, many people seem to be ‘optimizing for location’ when it comes to finding a mate, for example, moving back to a big city with lots of creatives in the USA in order to bump into somebody, but the people I’ve seen have the most success in this community seem to be ‘optimizing for passion.’ this seems to make sense in my experience, like what are the chances, if you can literarily leave your home base half the year (and enjoy doing so), and have specifically built your life for the better part of a decade so you can do so, (and on and on), what are the chances you’ll be ultimately happy with somebody who isn’t at least on a similar path.

    Also re: groups/solo etc yeah man I guess that’s a pretty damn good prompt you got me thinking! :)

  • MaggieAppleton

    Vaguely related – Just finished listening to an episode of BackStory (phenomenal history podcast) about time structures across U.S. history & how radically they’ve changed sleep cycles, influence of tech, work standards, etc.

    Well worth a listen for people thinking about this topic in historical context:

  • Wow thanks Maggie gonna go grab it now.

  • Fantastic post!

    I know you consider Tim Ferriss the Godfather of the whole lifestyle design thing, and he’ll forever be in the history of all people living their life this way.

    But I also want you to know that what you do works – I mean coming up with new terms about stuff from the life of location independent entrepreneurs, analyzing how things are changing over the years, making predictions every now and then, and contributing to this phenomena in general.

    Take me, for example – I’m a 23-year-old girl from Bulgaria, working on her blog (and seeing improvement), hustling, writing (the passion all this is about), having an audience of Americans and basically planning to make money abroad while still living here.
    And can say that many aspects of the location independent lifestyle are made for me, but not exactly traveling all the time. I may spend a month or a few in Thailand, Bali, etc. every year one day while having an 80-hour workweek the rest of the time (not because I have to, but because I want to).

    It’s interesting how I’m developing some qualities of people who already live like that but am not successful yet.
    Lately, I came to the conclusion that you first need to become the person you need to be that will be financially independent, doing what he loves for a living, living at more than one places at the same time, etc.

    And it feels so right.

    Seriously, ‘the horseshoe workday’, the ‘chronic and consistent work’, ‘honeybee’ base – all these, for instance, are something I’ll be glad to be doing.

    And I’m ready now. I’m not really in a hurry, though. I’ve got a lot more to realize and learn, many mistakes and sacrifices to make.

    But I already have the ideal lifestyle in my mind – and am loving the hustle. I know exactly how I want my days to go in the future, and work is a big part of them.

    I’ll stop now as I can go on like that forever. There’s not really anyone around me in real life that even thinks about stuff like that. And I’m not sharing my vision on my blog yet.

    Just wanted to let you know that your content helps me a lot. Each post matters and makes a difference.

    Anyways, we’ll see how things will turn out.

    After all, I’m already living in a cheap country with a need for development and lack of competition. Maybe that will be my asset, who knows. Ha!

    PS, The fact that I confessed all that says a lot about how important your blog is to me. I don’t usually share my goals with anyone in real life – as it only distracts me from the things I need to be doing daily. And – as we all know – a project like that deserves all our attention.

Next post: