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First Things First

Ever since I declared my Big Goal — complete self-employment by my 31st birthday — I’ve been flip-flopping about where specifically to start. Because I’m working with such a long timeline, it doesn’t make sense to chart out every action along the way, because I just don’t know how it’s all going to play out. It’s almost all new territory for me so I’ll need to be making constant adjustments the whole way.

So the “middle game” and “end game” of this goal are going to stay undefined until I get closer to them, but the opening sequence is to be decided now.

I am still abroad at the moment, so my workspace is constantly changing and never predictable. I have no desk and no filing cabinet, not much privacy, and often internet access is expensive or unavailable. There is also an uncomfortable internal conflict between my desire to make the most of my time abroad by sightseeing and socializing, and my desire to get this project underway.

Most of the sub-projects involved in my goal will have to wait until I return home, where I’ll have the stability and privacy to work, with fewer distractions. But I can still make one or two big strides between now and then.

I’ll be living out of my backpack for another six weeks yet. I’ve left New Zealand to explore Australia until I go home. Not that six weeks is a long time — I can’t believe I’m so close to the end of my trip — but I do want to get closer to my goal during this time, rather than defer it all until I get home. Enjoying my trip is the number one priority, but I don’t need sixteen waking hours a day to enjoy myself.

My goal’s general plan is clear to me, and I know that the first stage is going to surround establishing certain fundamental habits: writing habits, workflow habits, networking habits, and blog marketing habits. These habits will put me in a better position to complete everything between now and D-Day (October 8, 2011.) Any good habit established now will pay great dividends over the next eighteen months, and will facilitate the development of other habits.

In my research on habit change, one point keeps coming up again and again: the likelihood of your habit sticking decreases dramatically for every additional habit you’re attempting to change at the same time. If you only focus on one habit, a successful take is almost guaranteed, but trying to change five habits concurrently almost guarantees failure for all of them.

The fact that habits can’t be changed en masse was always a difficult pill for me to swallow. I always tried to change everything at once, and it never worked.

Multitasking is imaginary

Possibly the most useful thing I learned in my time-tracking experiment is that switching tasks is costly and usually unnecessary. Stopping one thing to work on another means the mind has to reorganize itself and get into the flow all over again.

Much is made of “multitasking,” but suddenly it’s very clear to me that a human being can really only do one non-mindless task at a time. Sure you can chew gum while you do your taxes, but you can’t do your taxes while you make dinner, because you’re always interrupting one task to tend to the other.

That’s one thing I discovered during my time-logging experiment last month:

Once you’re on a roll it is almost always much more efficient to keep going until you’re done, or until there is a real reason to stop — such as when you need someone else to act on it, or the building is on fire. I found that many of my projects can be done in one go, instead of just moving it forward a bit and jumping to something else.

I like this new strategy of locking onto one thing and following it through, then moving onto the next, rather than trying to prune down ten or twelve projects at the same time. I used to think that picking one and running with it would mean the other projects would sneak up behind me when I wasn’t looking and eat me. So I was constantly spinning on my heels hacking at each of them in turn, as if my goals are enemies who have surrounded me and are closing in.

Luckily, I’ve let so many huge lists of “imperative” projects completely crash and burn over the years, so now I know that missed deadlines and botched projects don’t actually destroy you. They just make you older.

I’ve learned that the quickest way to get a lot done is to keep your efforts undivided until you’re either done, or can’t do any more until something else happens first. You don’t save any time by dividing your attention — you lose time.

This means wrangling a massive project like my goal of self-employment is actually simpler than it might initially look. Even if I have to do 385 different smaller projects to get there, I never need to direct my efforts any further than the one that I deem most important now.

It doesn’t even have to be the most important, if it must be done anyway. It still brings me closer. As long as I don’t end up doing nothing, which is what I’d end up doing if I felt I needed to do twelve things at once. All of the sub-projects in this big project will happen sooner or later, so I could just pick one out of a hat, tackle it like Michael Strahan, and then line up another.

But having certain habits in place can definitely make it easier to establish others, so it makes sense to pay some attention to the order in which one tackles them. For example, if you wanted the habit of waking at 5:00am (instead of right before you leave for work), as well as the habit of running every day, it might make sense to get the early-riser habit down first. That way you’d have the option of getting your running done in the morning, rather than after work.

This one-thing-at-a-time idea is a powerful piece of insight, provided I take it to heart and act accordingly. Pick a habit change, and focus on it to the exclusion of all other habits until it’s yours. Then do it again.

The inaugural sub-project of my Mega-Project is certainly going to be a pointed habit change, and it makes sense to pick one that will do the most to make subsequent projects and habit changes easier.

After tossing a few ideas around, I’ve settled on the one that I think will aid just about everything I do afterward.

It’s time to return to daily sitting meditation. I can’t think of any habit change that would be more helpful right now.

When people ask me for advice about dealing with sticky emotions or reactivity, I tell them that meditation has helped me to that end more than anything else. It has, and I do believe that’s the best advice I can give, but after all this time I do not have a daily practice habit of my own.

Those of you who have been reading since the beginning will remember my first ever Raptitude Experiment. It was a thirty-day tryout of daily sitting meditation. I wasn’t overly ambitious: I aimed for one twenty-minute session a day. I did learn quite a bit, but for the most part I found it really awful. As much as I tried to give it a positive spin in my progress log, I dreaded my sessions and soon cut them into two ten-minute sessions, most of which I spent thinking about the session being over.

I wasn’t ready.

Six months later, I signed up for an educational retreat about Buddhism in Hollyhock, B.C. Upon my arrival I was surprised to learn that the five-day retreat was almost entirely formal meditation. The first day was horrible. Long, long sitting sessions, 45 to 90 minutes, repeating throughout the 15-hour daily schedule.

But I soon got used to the sessions, and by the end of it I had achieved a clarity of mind I can’t remember ever having before, and I left certain insecurities and fears behind for good.

I was sold on meditation. On the final day of the retreat, our instructor said, “If you want to make this into a daily practice, don’t miss tomorrow.”

I didn’t, but I missed the next three days, then I was on a sleepless 17-hour flight to Bangkok. By the time I recovered I was preoccupied with my trip, and I have been ever since. I’ve only had a few sessions since then.

I am, though, over the hump that made my initial experiment so difficult. I’ve learned to sit back and observe those thoughts like “I hate this and want it to be over” — which at first seemed to be total roadblocks to getting anywhere.

It’s absurd that I’ve put it off it so long. I’ve been something of a meditation hypocrite — I know how valuable it is, but I guess I don’t really know yet. There always seemed to be something more important than focusing on a daily meditation habit — writing, planning, errands, other stuff — even though I’ve always known that it doesn’t take much time and would make all those things easier. What could be more important? It helps everything: it improves moods, quiets mental chatter, tempers reactivity, clarifies priorities, lowers self-consciousness, awakens gratitude, kills distracting internal dialogues, defuses destructive patterns of thought, sharpens focus, facilitates communication and understanding with others, and makes beauty easier to see. These are benefits I’ve already had, not just hope for.

So in terms of where to start a challenging 18 months of goal-mongering, meditation seems like a no-brainer.

I had another topic in mind for Experiment No. 7, but this one is more important. I also didn’t like the idea of doing a second meditation experiment, but this one has a different aim than the first, and the public accountability is too important to do without. Besides, in terms of understanding, I feel like I’m worlds ahead of where I was when I did the last one.

Experiment No. 7

The goal this time is not just to see what happens, as with Experiment No. 1, but to establish sitting meditation as a daily habit. For life.

Sessions will be 30 or 45 minutes.

Jumping immediately into 30-day trials hasn’t worked all that well in the past, because there are always unforeseen problems with the chosen method, so I begin to wish I’d made some changes before starting.

To address this, I’ll have a “test week” preceding the proper 30-day stretch. During this week I’ll conduct my daily meditation sessions, but it will still be okay to scrap the method and start from square one during this time. By the end of that week I’ll have a much better idea of the challenges I’ll face during the 30 days, and I can address them. If I need to make big changes and have another test week, I will.

Also, this trial will be 40 days, not the standard 30. Single months have flown by so fast since I’ve been abroad, I could use a bit of extra time.

My main challenge is that I’m still traveling. My physical surroundings change on a regular basis, so I won’t be able to count on having access to a particular spot or a particular time to meditate.

I will be keeping a daily journal, to record my thoughts about the how it’s going. I’ll write down how I’m feeling about my progress, as well as any difficulties I’m encountering.

I will only publish excerpts from this journal in my experiment log, not the whole thing. This is so I don’t spend much time editing my journal and preparing it for mass consumption. I just want to take a few minutes and get my thoughts down, that’s all.

Another hindrance that became apparent last time was that I was always trying to find an ideal time and place to meditate. I figured it wasn’t worthwhile if I was a little too tired, or if there was a background noise I thought might be distracting, or if I still had some caffeine in my system, or it was too hot or something. It’s more important that I just do it, regardless of the quality of the session. So my motto is: Put in the time, good, bad or ugly.

Finding an appropriate place has been a huge pain in the past, so my first order of business upon arrival in a new city is to find at least one place I can sit for 30 minutes and meditate, and preferably a backup spot. Nothing else is necessary really, except the intention to do it.

Forgetting to meditate won’t be nearly as much of a problem as unconscious excuse-making, but just in case, I’ve loaded Google Calendar with reminders to write in my journal. Journaling every day will be even more important than meditating every day, because as long as I journal I will have a chance to explore any excuses or hindrances that “prevented” me from meditating. In any case, reminding myself to journal about meditation will also remind me to meditate.

Test week will start officially on Friday, May 21, but I will experiment with meditation times and places between today and then. I am tackling another Life List item Monday through Thursday, taking a four-day surfing camp, and I’d rather not have those two goals compete. The formal 40-day trial starts Friday, May 28, and the last day is July 7. By then, daily meditation should be a habit, and if it’s not, I’ll have a pretty damn good idea of why.


Photo by David Cain

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Tim May 19, 2010 at 12:12 am


Halfway through the article I was thinking, “It’s a good sign that I’ve heard all of this before. The repetition means that I actually am ingesting all of this and still coming back for more.”

But the whole “order is a must” thing caught me in a bit of surprise.

What I got out of this:

I don’t really know. Something about habits. I’m hoping my mind will make something out of the stew of thoughts in my head. One ingredient is most definitely this article.
.-= Tim´s last blog ..Mini Movementalism =-.

David May 19, 2010 at 7:01 pm

I think the “One thing at a time” part is much more important than doing things in the optimal order, but I can’t think of a better place to start than with daily meditation. In the past it has improved my performance at just about everything. It keeps my thoughts from overwhelming me, and helps me do one thing at a time a lot better.

Vincent Nguyen May 19, 2010 at 12:12 am

It is great to see that you are enjoying your Australian trip.
I agree with you about the difficulty of making a habit “stick” because trying to develop too many habits all at once, but my argument is that I have so much energy.
What I found worked for me so far is prioritizing my habit into a habit hierarchy; from most important to least important.
I have been quite successful by picking my two most important habits to develop and work on both at the same time but just at different times of the day.
This is quite challenging but it can be done with lots of focus and you have a clear understanding of what needs to be done for each habit and why.
Once I felt I have one or both of the habits developed, then I remove them from my habit hierarchy and focus on my next two habits.
Therefore, my habit hierarchy is always reconfigured once two high priority habits have been developed.
Let me know if you ever give this method a shot?
.-= Vincent Nguyen´s last blog ..212 Degrees: The Extra Degrees: Do you have what it takes? =-.

David May 19, 2010 at 7:02 pm

I’ve been trying to figure out a way to work on at least one other habits without endangering the first one. Your idea makes a lot of sense to me. One clearly has priority over the rest, and you can drop it if the first one starts lagging. I will do that once I get a bit of momentum behind meditation.

Brenda (betaphi) May 19, 2010 at 12:19 am

So many bloggers are throwing in the towel. I’m glad you’re not. You seem to have found a path that involves sharing your path on Raptitude. I find that interesting. I like reality TV too. Reality blogging, is that what you’re doing here? No, that’s not it. Maybe evolutionary blogging. No, that’s not it either. Habits is an interesting topic. I haven’t read much about how habits run (or ruin) our lives. Good luck with the 40 days and 40 nights. Are you going to the outback?
.-= Brenda (betaphi)´s last blog ..Hay! =-.

David May 19, 2010 at 7:05 pm

Reality blogging, that’s one good way of looking at it. I don’t like talking about myself all the time, but this one was too important not to make into a public experiment. I need the accountability.

I am infatuated with surfing at the moment so I think I will mostly stick near the beach, but I’ll take at least one stab into the outback before I go home.

Angus Stocking May 19, 2010 at 6:50 pm

David, I’ve been self-employed for a while as a freelance writer in infrastructure. Since we have similar backgrounds (I’m a licensed surveyor) you might consider it. Can’t beat it for flexibility, as you can live anywhere so long as you have internet and phone. See my work site, http://www.InfrastructureWriting.com, for more info, and read The Well Fed Writer by Peter Bowerman.


David May 19, 2010 at 7:08 pm

Angus! Good to hear from you. That is my goal: location-independent self-employment. Freelance writing will probably eventually form a part of it, but writing takes me a lot of time and I’m not always so pleased with my writing. Both of these things will improve though. I’ll check out infrastructurewriting.com and the books you mentioned.

Angus Stocking May 19, 2010 at 7:33 pm

You have more than sufficient writing skills for commercial writing – it’s way more about getting the work, than doing the work. And being easy to work with.
.-= Angus Stocking´s last blog ..Fly Eats Lady =-.

Joy May 19, 2010 at 7:59 pm

I don’t know what this says about my intellect at the moment, but what I got out of this post is that you are going to surfing camp, in one of the top ten best places to surf–woo hoo!!!
So, that’s how *I* live life then, and why your writing fascinates me. You plan, you think it all out, you experiment, you document, and you follow through. While I,hmmmm…I *can* do all of those things, but I usually choose to just jump. Even if I’m afraid or don’t have all of the details down–maybe *especially* if I’m afraid or don’t have all of the details down. So, reading your thoughts and how you live teaches me the importance of how it all works for you, and would probably work for me.
However, surfing jumped out at me, because surfing is a way of life in my area and each year I dare myself to learn, each year I do not learn. I watch, my friends are avid surfers, it looks amazing, I understand wave action and am athletic. But, it’s one of the very few areas I haven’t jumped into yet…although I know it’s absolutely fantastic, and you are going to have great fun!!! So, enjoy, as I know you will. Oh, did you read Jaimal Yogi’s “Saltwater Buddha”? He talks about the wisdom he learned from learning then participating in surfing….
.-= Joy´s last blog ..Wisdom Wednesday: Your Wisdom…a video =-.

David May 21, 2010 at 12:05 am

I am not a seasoned planner. “Jumping in” is how I’ve traditionally done things, but over the years I’ve seen too many things slip between my fingers because I insisted it was not necessary to plan. I am really excited about becoming a more organized person, and the doors that it will open up.

Surf camp was awesome, and it wouldn’t have happened if I did not have a Life List. I would have drifted toward the easier and more immediate pleasures rather than consciously tackling something I’ve always wanted to do. I am now a surfer and can’t wait to surf more. But it took a premeditated effort to make it happen.

I’ve received many recommendations for Saltwater Buddha and will definitely read it.

Lisa May 19, 2010 at 10:35 pm

Good advice as always. It’s funny you mentioned waking early/running, I recently attempted this and failed. I never thought of it as 2 separate habits though. The habit I was trying to form was running in the morning, and to do so I would need to wake-up earlier. I’ll try just waking up earlier for awhile though and then add the running in later.
Also, the task switching is whats killing me right now! I have 1 short paper left between me and my Masters degree, and yet i’m constantly switching between paper, tv, and internet, making what should have taken a few hours to write into a 2 day saga. The tv is set to record though, and i’m closing the internet after I type this. I’ll see if I can pull off total focus until the paper is done. Thanks again for your help!

David May 20, 2010 at 11:55 pm

Impulsive task-switching is probably my number one productivity-killer right now. Good luck with your changes Lisa!

Tom K May 19, 2010 at 11:14 pm
David May 20, 2010 at 11:53 pm

Looks like it’s right up my alley. Will check it out. My to-read list is getting ridiculously long.

Char (PSI Tutor:Mentor) May 21, 2010 at 5:31 am

If I had 385 things to do I would likely do nothing either, and I’m a goddess ~:-)

I would of thought that your project is already well in motion. Fewer distractions is an amusing concept.

Brad May 21, 2010 at 10:25 pm

I really like your analogy of being surrounded by goals as if they were enemies poised to strike you down. Spot on. :)
.-= Brad´s last blog ..Entrammel =-.

David May 23, 2010 at 1:03 am

Yeah I’m trying to reframe my goals as “glittering prizes” instead of stuff that might knock me over and run away. Old habits die hard.

Carrie May 24, 2010 at 10:32 pm

“There is also an uncomfortable internal conflict between my desire to make the most of my time abroad by sightseeing and socializing, and my desire to get this project underway.”
“I can’t believe I’m so close to the end of my trip — but I do want to get closer to my goal during this time, rather than defer it all until I get home. Enjoying my trip is the number one priority, but I don’t need sixteen waking hours a day to enjoy myself.”

Very Buddist and existential at the same time. David, 6-weeks is NO TIME at all! I’m so sorry for you that your trip is almost over, and you’re still in a dilemma about enjoying it, socializing, and figuring out your life. You do need 16 waking hours a day to enjoy yourself, if that’s how many hours you’re awake! How about doing everything you want, and allotting one hour for worry- planning, getting the project under way, whatever you want to call it. And enjoy that hour too! Real life looms! Enjoy the trip!

David May 27, 2010 at 6:55 pm

Haha… things are just fine. I’m in Byron now, and I’ve scaled down my trip so that I don’t have to rush anywhere.

Douglas May 26, 2010 at 11:52 pm

I just recently started forming habits again, mostly from the idea being instilled in my head from your blogs. So far, they have all failed miserably! Except one, which is the easiest “The no-shampoo hair wash”. All of the other ones, waking up early, meditating each day, going to bed early, have failed. Maybe that was due to multitasking? Or more likely because I didn’t stick through with them, log them daily, and take the time out of my day to focus on them.

So along with you, if you don’t mind, I plan on trying to form the habits again (excluding an early bed time). The two habits I would like to form along this same time span are meditation (my 3rd try in 2 years) and waking up early. I’m hoping that combining these 2 habits don’t distract me from properly working on each. I plan on using my alarm clock to wake up normally each day. I don’t want a “set” time to wake up, just whenever I set my alarm clock. I will set my alarm clock at more of an early morning time for me, but on days were I need an extra 30 mins of sleep, I don’t want to be forced getting up at that set time. For meditation I will take 50 mins out of each day to practice with meditation. I expect 20-30 for reading a small book on meditation, which helps me get more enthusiastic about meditating, and 20-30 minutes of actual meditation.

How does that sound? Would you suggest anything different?

David May 27, 2010 at 6:54 pm

I’m definitely no expert habit-changer, but I can tell you what I know. I know that it’s crucial to track exactly where the habit breaks down. There is always a moment when we make a decision against maintaining the habit right then. Today is the first day of my meditation regimen. Dutifully, I went down to the beach at 7:30 to meditate, but the sun was already blazing and I couldn’t find a shaded spot that wasn’t soaking from the rain last night. So that’s a sticking point: finding a dependable spot. I will have to make routines to sort that out. I’m going to take a hike now for the sole purpose of finding a dependable meditation spot.

Often these breakdowns can be patched up if we set things up so that we don’t encounter that same sticking point again.

You really have to picture how it is realistically going to go down though. I could solve my sunshine problem by getting down there at 6:30 instead of 7:30, but it’s unlikely I’d be able to keep up the habit of waking at six every morning while I’m in Australia’s party capital. I used to count on willpower to bulldoze through these sticking points, but it doesn’t work. Sometimes the willpower is not there. You have to set it up so that it is as easy as possible to maintain the habit, rather than depend on bringing huge amounts of energy or enthusiasm to it each time.

I’m learning too though. If you like you can track your habit’s progress in the comments on my progress log here:


The only thing I would suggest for your plan is that you make regular, honest assessments of how it’s working out for you. 50 minutes is a sizable chunk to carve out from your day for a new activity. I would maintain a journal or a log so that you can examine, each day, what’s working and what’s not.

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