In preparing for battle I have always found that plans are useless, but planning is indispensable.

— Dwight D. Eisenhower

My career in software revolved around deadlines. Ship dates. Milestone plans. Large, multi-colored Excel workbooks filled with dates orchestrating the activity of dozens to thousands of people. The tracking of work items, bugs. Status Reports. Sometimes we even had the super-impressive looking Gantt charts.

My new life has many fewer deadlines, most of which I get to chose. Despite this, it has come as a bit of a shock that I now deal directly with harder deadlines. Deadlines from the clock and not the calendar.

If I’ve rented my place out and the guest is arriving at 4:00, they really are arriving. I really have to have cleaned it up and cleared out my stuff. There’s no going home to finish it up overnight or in the morning — there is no home to go to. There’s no postponing the work until the next milestone. If a bus departs at 1:00pm, it’ll really leave then, and I need to be on it or make some other arrangements. If my flight-date arrives and I haven’t booked accommodation, my future jet-lagged-zombie-self will curse me from the taxi stand outside the airport. I no longer have the luxury of sprawling all my belongings over a large home, I need to carefully plan what to pack.

A Detour — What Are you Good At?

It’s a truism that often our greatest talents can cause our greatest challenges. The skills we’ve honed are the ones which cast us into seeing the world primarily through the application of those skills. Hammers find nails. The better your hammer, the more the world seems full of nails. These talents can be hard to turn off when they’re no longer appropriate.

Growing up, I always considered cleverness to be my special skill. It seemed to be the most remarkable thing about me. It let me succeed at school. My precociousness was praised by the adults in my life. Now I’ve come to think that my true talent is deeper: it’s the ability to work doggedly at tasks and delay gratification. Working to a goal without intermediate reward is the sine qua non of many intellectual pursuits: School. Playing with computers as a hobby. Professional software engineering. These are full of little tasks which can take unpredictable and often enormous amounts of time (days spent debugging certain issues come to mind) and great concentration. Not only does the focus get you to the answer, but all the effort builds your knowledge for the next problem, which is all the easier for your effort.

And so a virtuous cycle is created. All that knowledge accumulates and the outward appearance is of someone who’s really sharp. Someone who doesn’t have to work that hard. But for me the root of my talents is my ability to grind away at a problem without reward for long periods of time. This makes me great at the kind of tasks which demand hours of staring into a screen. It makes me good at diets and working out. I build habits easily, much more easily than most people I know.

Aside: This skill has been researched and noted: in the famous Marshmallow Experiment, the books “How Children Succeed” and “Mindset”. It gets called ‘grit‘ or ‘sticktoitiveness‘. Merlin Mann‘s various writings and podcasts turned me on to the subject; it’s really fascinating reading.

Now, recall that truism. If I have this skill, what’s its downside? Well, I build habits too easily. I get stuck in ruts. I push each day to look like the last. I feel it happen even on vacation: the first day is entirely random and unstructured, then patterns start creeping in. Workouts get scheduled. Meals converge on the same things at the same time. Eventually, as in my working life, everything becomes optimized and regimented. After all, a habit is essentially a plan you repeat. A plan with its own deadlines. Up at 5:30. Gym at 6:00. Breakfast at 8:00. Shower. Shuttle at 8:35, etc.. No unplanned going out. No space.

Floating Free

So one of my major goals for this travel is to thank my habits profusely for their help, but let them rest. They’ve earned it! As have I. It’s time to be freer. But there are still those pesky deadlines I mentioned up above. Those tasks which even in this carefree life must get planned. And so my big struggle is to plan what needs to be planned, and to keep my habits from creeping in and regimenting all the rest.

So if my schedule look sparse and undefined, great! That’s what I’m going for; fumbling to find the edge of ‘not enough planning’. Not knowing exactly how tomorrow will look.

With that said, here’s what my itineraries look like:

First Notion

My first plan was this:

  1. Depart sometime in November
  2. Spend about 1 week in Japan
  3. Travel to Thailand. Travel around Thailand, Vietnam, Cambodia, Laos for 3–4 months. Perhaps Indonesia
  4. Maybe make it down to Oz to visit family
  5. Probably head back via Europe to meet my sister and her family in Germany
  6. Maybe spend some time in Montreal on the way back to visit family

As we used to do back in the work world, let’s conduct a short post-mortem of this plan.

First, I’m booked out on December 2nd. Lots of local trips and such, plus the uncertainly of renting my place — and frankly the time it took to purge and pack and prepare for renting — pushed this deadline out. No biggy. It’s one of the more discretionary deadlines. Discretionary before it’s booked. Now that it is booked, it feels very very much like a hard deadline.

Second, Japan is nixed. The idea of packing for two climates, and the costliness of Japan in general have made me postpone that dream. Not entirely: I’ll spend almost 3 hours in Narita airport. I’ve been assured that this is worth one belt rank in Karate, so I’ve got that going for me, which is nice.

Third, Indonesia is all but certain. M has lined up a vacation rental down there.

The others are still undecided. Un-planned. A lot will depend on how much fun the first month is. Travel like this is beautiful in theory… how will the un-romantic reality hit me?

Plan Complete

And so, just a few days before liftoff, this is the extent of my plan:

  1. One way ticket to Bangkok, leaving December 2nd from Sea-Tac, going through Narita. Arriving at 22:30 local time on the 3rd
  2. 3 nights booked an a guesthouse in Bangkok
  3. Likely spend a total of a week or 10 days in Bangkok
  4. Then up to Chiang Mai to spend the rest of my 30 day Thai visa waiver in the north
  5. Then over to Laos, taking the slow boat down to Luang Prabang
  6. Then down to Siem Reap to spend a few days at least at Angkor Wat
  7. Then, in late January, head over to Bali

That’s it. Not certain about Europe. Not certain about Oz. Have the vaguest bullet list of things to do in each place.

This gives an airy sense of recklessness. But that’s not the whole truth. Most of my planning energy has gone into packing, which I’ll describe in a future post. I’m spending my energies making sure I’ll have the resources I need to deal with problems that arise, rather than the details of what I’ll be doing. The idea is to be prepared to take advantage of opportunities.

Let’s see how that plan works out.