Lydia and I have a bit of downtime between stops, so glance at a Google map to see what’s around. The map has around 50 markers pinned all over the city, from stores and restaurants to scenic views and festivals. I prepped it over a week ago in advance of our road trip to Austin, Texas.

It’s a first for me.

Despite traveling the globe for a decade I’ve always been a fly by the seat of my pants kind’ve guy. That usually translates to someone else handling the itinerary, My planning habit has changed that.

Hovering at 75 on the SRHI, my planning routine is just shy of “super habit” status. While sipping a cup of coffee in the morning I pull out my Bullet Journal and update it. The Bullet Journal Method feels perfectly suited to harness my naturally chaotic M.O. With it I can make random pages of thoughts or jot down project notes irrespective of page location, but still index it without skipping a beat.

It also allows me to organize time much more efficiently.  Some wise management luminary once described life as a jar. Fill the jar with sand - the trivial stuff - and you won’t be able to fill it with rocks, symbolic of what’s really important. A better method is to fill it with rocks, then pebbles, then sand.

THE PLANNING DILEMMA

My central “planning dilemma” is the need to do it all. The jar metaphor isn’t just about space, it’s also about time. Planning has shown me just how powerful carving out small portions of a week can be.

Take my next book proposal - a lot of successful writers have advised that you should always be working on something else. When planning, I’ve tried to designate about 40 minutes per week to wrangling together what in my mind seems like a horrendously large project. For comparison, my first two proposals took 9 months each.

Yet in 5 sessions I’ve done a rough draft of the majority of the proposal. This includes an overview, a marketing and competitive analysis, a table of contents, all of my chapter summaries, and an outline of my first sample chapter. A simple, consistent plan has powerful compounding effects. And it appears as though I’m doing two things at once.

ORDER FROM CHAOS

While planning gets me closer to doing everything, in travel it’s seeing everything that’s my main concern. I’m terrible at planning trips, but if I apply the “jot outline” approach, things go well. 

I randomly list out everything I want to do with fixed events acting as anchor points. I structure the rest (the pebbles or sand) around those important rocks, and tasks - like buying tickets or getting a reservation - are assigned based on that model. With both writing and travel planning, this method grows structure from the chaos. 

Lydia usually does the planning by default because she knows I’m not going to do it. A solid planning habit allows me to pick up my share of the emotional load in this, and in other smaller, pesky things. Paperwork, getting back to people, researching a festival, figuring out what parking is like - these all function like sand in that jar metaphor.

STRUCTURED RELAXATION

My mind tends to tense over details, which is why I often opt out of making decisions. But surprisingly, planning is also of great help in relaxing.

I’ve hinted a bit about my concept of Structured Relaxation - when left to my own devices I’ll end up wasting weekends or any time off and end up feeling less rested than before. I try to plan out “weekend menus” to give me options, and planning gives me a place to do it consistently. While I might not check everything off those menus, I do find I’m surprisingly rejuvenated and content at the end of the weekend. It’s a far different feeling than discovering I’ve done nothing but mindlessly scroll on Reddit or Facebook.

STRATEGY

In my last article on planning I talked about long term strategy through mediocrity. A post I recently saw on Brandon Sanderson suggested that he has writing plans for 5 years in the future (and honestly, it’s probably more than that)! That’s something to aspire to, but I’m nowhere near mastering that type of strategy with writing. My problem lies in not knowing how long any give task will take, which is a rather huge issue (though it is something I’m working on). But with other projects  - like knowing how long a habit will take or what vice I intend on quitting next - I’m showing marked improvement on the strategy front.

I still have a lot to learn. The temporal subcategory of the planning dilemma is one of hierarchy across time. You need to work on long-term projects, but the urgency of goals around the corner prevents you. And multitasking can be detrimental when it comes to energy, concentration, and momentum.

The Planning Dilemma - There is no time to do it all
Temporal Corollary - Work on long-term projects is impeded by short term urgency

I think the key is harnessing the right amount of consistency over time. I have a task that I need to finish in a month from now, but I’m only working on it for about 10 minutes per week. Meanwhile, I’m working on my next proposal 40 minutes per week, a task I don’t need accomplished until a lot further off. Clearly, I need to switch this up, assigning 10 to the proposal and 40 for the task due in a month. Carefully labeling and assigning times in terms of time accrual might just be the best way to fit multiple projects into one small jar.

Meanwhile, I’m also researching advanced techniques for project management. This blogger, for example, has a particularly excellent system which uses a Bullet Journal to define, assign a time estimate, and schedule tasks. That then interfaces neatly with a Kanban board to track progress.

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While driving back from Austin, Lydia remarks on what a great trip she had. We didn’t hit everything on the list, but we met friends and did outdoorsy stuff, tried new restaurants and visited old haunts. We did a lot, and the trip was even better for me because I (for once!) had an active hand in it.

I’m not surprised that I enjoyed my visit, but I am at how much I enjoyed planning it.

Photo credits: jars by callmekato, beach by Cristian Viarisio