Planning then executing OR planning and executing?

There’s a subtle difference here that I’d like to explore.

In working with a professional coach this past year – one of the top 5 investments I’ve ever made in my myself – I realized that I’m a pragmatist. This is one of my key strengths. My coach also helped me realize that when we overdo our strengths, that strength can become our weakness – something Ray Dalio emphasizes in ‘Principles’. He encourages that learning to balance your strengths ensures they don’t become your weakness.

As a pragmatist, I love planning. Planning has helped me in a lot of ways, especially professionally. Though I sometimes overdo it.

I once planned a trip to drive across Canada – complete with a spreadsheet containing a packing list, approximated driving times and most embarrassingly, places to sleep every night. Some of those nights were stays with friends – I like to give as much notice as I can to build my plan ensuring we can spend time connecting.

The other nights were…. a reminder that yes, you can most certainly overplan. Sometimes there was rain and I had planned camping. There was the drive home that routed through the US with hailstorms and the ‘nice’ hotel in a rather dodgy small town in North Dakota. The first thing I noticed about this place after checking in was that the key card had extended safety instructions.

“Is this normal?”

I racked my memory to see if I could recall any other hotel where this was the case, and I couldn’t think of any (!). Once I got to the room, the binder that usually has menus and welcome ads had a full page of safety instructions – including not to open the door if someone knocked on it in the middle of the night (!). I pulled out the bear spray from camping in Jasper the week prior. Was I going to use it? I sure hoped not. I woke up to the dogs barking at the door at 3AM. Ugh.

Confirmed – there is such a thing as overplanning.

I definitely get some dopamine hits from planning and then executing. I love both of these steps, though this experience along with some others had me thinking there might be a better way.

I’m currently doing some extended travel for a couple of months through Southeast Asia. I had to fight myself on more than one occasion to not plan a full month at a time. And I’m glad I did. I planned the flight in, booked somewhere to sleep for a few nights to get our bearings, and then had a general outline for the rest that was flexible to things as they came up.

It led us to Northern Thailand – where I got recommendations for an awesome cooking school. We decided to stay a little longer in Chiang Rai than planned. I got in to the top-rated elephant sanctuary because my dates were flexible.

We then flew to southern Thailand where the rainy season has been hanging on a little longer than usual. We decided to head out to Cambodia in the morning where the weather looks amazing. I’ve been watching the flight prices, but I only booked less than 24 hours before it left. That’s a first for me.

I realized the difference is that I’m now planning and executing at the same time. They’re no longer separate phases. This slight difference lets me adapt to changing circumstances rather than being hostage to the plans I hatched for ideal conditions.

A slight, though critical difference.

That slight difference led me to reading and swimming on this beautiful beach all day today.

And that’s okay with me.

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