A great strategy is about rearranging dots

I spent a long time in the marketing space. And several years as a strategist. One catchphrase you always hear is, “Great strategy is about connecting dots.” There is some truth to this

Transformational strategy can involve seeing the connection between items before anyone else and seizing that. But more often than not, that is not the trick.

When I left Cape Town on REIMAGINED in November, I aimed to “get as far north as I could” before hurricane season. I did not really define how far north. But the one variable that was not within my control was “hurricane seasons” as defined by the marine insurance industry. Although it is a little variable, it is essential from mid-June to mid-October, and I needed to be south of the Grenadines or north of Savannah.

I devised a plan of ways and places to visit, with rough timing and off-the-beaten-path experiences. I connected dots in what I thought was unique to create a journey “as far north as I could get.”

However, I soon realized there were some flaws in this approach. One, I underestimated the amount of warranty work required on the boat. I also underestimated the complexity of the global shipping and logistics network. And finally, I underestimated how many interesting places I would have missed. So, I needed to break apart my plan and rebuild it with my new information. Undoubtedly, I could have powered onwards with the original plan and made it “way up north,” but in doing so, I would have sub-optimized the experience. Now, I have a better strategy that will result in better returns. First, I connected some dots. Then I received new information. Despite the high effort and cost of refactoring the approach, I refactored the dots.

I saw this all the time in the former industry I worked in. You have people working at organizations who believe they are experts but are not. They are way too far removed. They have an idea, and they become so positional about it that they can not break apart the dots and reconnect them. Ultimately, they, like I was about to sub-optimize outcomes. They believe they are great strategies, but they are not. People see that.

This sailing season, I am going to stay south of Martinique. There are dozens of islands, towns, and places to explore. Once I leave the area, I am not sure I will be back, so if I were to rush through this unique part of the Caribbean (the windward islands), I would be doing it so that I could play out a strategy I made when I did not have all the information.

Connecting dots is essential.

Having the courage to break them apart and reconnecting them is more important.