Recently I was poking around in my previous posts and discovered a bit of a shocker. Although I talk about a lot of life order stuff, and I’ve had one somewhat forgettable post about planners, it seems I’ve never written about planning. Planning-adjacent, perhaps, but not the actual thing itself.

How could this be?

Perhaps because, as the fish has no idea it’s wet, I don’t really know what it’s like not to plan, not have planned, or not be in a plan. It’s on my mind now because this week, I have a plan to devote the majority of my time this week to strategic planning.

But also, planning can be overrated—overhyped. I’m even questioning right now if it’s worth it to have a whole post devoted to it, but absent something better (and given that it’s been weeks since I’ve posted), here goes.

What I’m getting to here is that we can work on a plan until the recalcitrant cows come home, but it will never play out exactly as we thought it would. I mean this point in the most literal sense.

Any parent who’s thrown a birthday party knows exactly what I’m talking about. You can choose a date, location, activities, guest list, send out invites, order the cake, and book your Young Sir’s favorite ventriloquist – but something you carefully listed out or counted on will change or shift. In my case, it was usually my Young Sir waking up with a fever on the day of. Good times.

“It does not do to leave a live dragon out of your calculations, if you live near one.” – J.R.R. Tolkien

You know how in cartoons or movies the villain will clasp their hands and say something like, “Ah-ah-ah, it’s all going according to my evil plan!”? And, of course, it doesn’t. They inevitably get caught (or escape) without much of anything they were counting on trending in their direction. Batman, or a runaway with a bucket of water, or those meddlin’ kids always manage to barge in and screw everything up.

In a bigger picture, real-life sense, how many times do we say something along the lines of, “It was never in my plan to  _____ [get married at 50, go to grad school, switch careers, have kids, start a business, become a monk, whatever].” Once upon a time, I planned to be a clarinetist in a major orchestra (ideally, the Metropolitan Opera). If someone had walked up to me when I was 19 and told me I’d be doing what I am now – holy cow. 

So many of us (especially those who try to control our fates with excessive strategizing) work all the angles, consider all the factors, get everything lined up down to the finest detail, and beat ourselves up when something throws it off. Like the beautiful, perfect morning routine wrecked by waking up to a kitchen flooded by the dishwasher. The dishwasher cares naught for your routine, silly human. We can’t hold ourselves responsible for every variable – and some of us really chafe against that truth. Thus, planning becomes stressful and disappointing.

On the other side of this spectrum is the person who bumps along, reacting to whatever appears before them in their life journey. Eternally oblivious (perhaps happily so), and continually taken off guard, the bandwidth or know-how it might take to create a plan seems out of reach – or even, ironically, a sign of incompetence. As if thinking through and writing stuff down must mean they have some sort of weakness. They “should” know how it’s all supposed to go, automatically. A plan seems like something other people do, maybe even a waste of time.

And then…there’s the curious situation where people become so taken with the planning of a thing, they burn out before they ever take the first action step. That’s likely another post.

There are many quotes about how failing to plan is planning to fail, most of which I am purposely avoiding. Most leave out a major consideration: the importance of flexibility, acceptance, and the hard truth (although Robert Burns’ “To a Mouse” is worth a revisit). Of course, a plan maps you in the direction of a goal, but something, even if very small, is not going to run as expected. Is it still worth it? Absolutely. 

Say you want to set up your next travel adventure. While there is something to be said for throwing a toothbrush in a backpack and just heading out on the open road, if you’re looking to experience another country or plan around a major attraction, you need a little something to go by – touchpoints to keep you in the vicinity of what you want. When I visited Kenya last summer – oh the planning! Absent our group’s extensive (and well-conceived) itinerary, I’m estimating that 85-90% of what I experienced wouldn’t have happened. The other 10-15%? Nothing that was within our control – and that had to be ok. A sudden thunderstorm meant our Gilligan’s Island-esque 3-hour boat tour was cut short (complete with us belting out the theme song, much to the disgust of the captain). Acceptance was never in question, and we made the best of it.


View of the horizon from a boat off the coast of Lamu, Kenya.
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The calm before…


Consider the resilience of skyscrapers in Japan, specially constructed to handle earthquakes. The structure of the building is required to even have the building at all, but flexibility is engineered in, from the foundation through the many floors. From this BBC article:

“Japan is home to some of the most resilient buildings in the world – and their secret lies in their capacity to dance as the ground moves beneath them.”

Dance, as the ground moves beneath…

Wow. It’s kind of cool to think about plans as dances, isn’t it?

So I’m wondering – what kinds of plans have you made that went awry? How did you shift, or move with the unexpected? 

p.s. Even my plans to write this post went a little sideways. I opened my Grammarly editor only to discover it’s no longer available on my desktop 😩 (and for some reason, the password not saved in my Lastpass 😩 😩). It also tried to correct Tolkien 🙄.