This morning, as happens all too often, I saw a social media post that argued planning over improvisation or “winging it.” I saw another one that suggested winging it was always better than planning. Both arguments seem sound to me and I came to the realization that to be truly successful you have to do both. The challenge is that they require different talents and different skill sets. That said, if you can plan AND improvise then you all but guarantee yourself success in any endeavor. Let’s think about this a bit and discuss a few particulars about each approach.

Planning is a learned skill but some people seem to have a true talent for it. To formulate your plan you have to know what your objectives are and have a complete list of every task you have to undertake to meet your objectives. Further, you need to know what supplies and resources you need as well. Typical planning involves knowing your starting point, your goal(s), what you have to work with and all of the steps – in proper order – necessary to go from A (beginning) to B (successful completion).

No plan survives contact with the enemy.” – Helmuth von Moltke the Elder

That idiom, whether you’re planning anything even related to conflict or not, is absolute truth and has been proven thousands of times over the years. “The enemy” is reality. Even if all you’re doing is planning a family picnic, the enemy is everything you can’t take into consideration because you have no way of knowing what it will be. It’s the completely unpredictable circumstance that will show up out of the blue and do its best to derail your perfect plan.

Actually, if your plan is perfect then you included options for when the unexpected happens. That’s difficult, at best, to do because you never know what will happen, when or where, or how it will affect your plan. The best military strategists plan in multiple layers so that they have redundant backup plans to activate when the unexpected happens. They understand the need and include it in the planning process.  Even then, no matter how thorough the planning is, plans get derailed. It’s at that point, if the people involved are going to be successful in meeting their goal, they have to improvise; they have to adapt. They have to adjust their actions, planning on the fly as they take unexpected circumstances into consideration, to keep moving forward toward their goal.

For each of us, as we formulate our own plans to pursue our own goals, we have to recognize the need for thorough planning, the gathering of resources, the launch and aggressive pursuit of plan completion. It’s equally imperative that we realize the reality of the unexpected and we have to be capable of not letting it just stop us. We have to commit to reaching our goal, adapting as necessary along the way, and adjusting our plan in the most efficient way we can given the resources we have. Quite often the largest challenge anyone faces is their own self-doubt when a plan doesn’t easily succeed or gets off track due to unexpected circumstance. That lack of confidence in our own abilities to plan and adapt has been cited as one of the largest causes of failure or hesitation in pursuing a goal.

So, going back to the posts this morning, they were both right, but too limited in their thinking. Quite often, that is what holds us back the most: limits in how we think. Lots of people are skilled at linear thinking – going from A to B to C and so forth – as they plan. It helps them make fantastic plans. Other people are good at abstract thinking – going from A to M to D to J and then R – and it helps them when the unexpected happens and they have to improvise.  Most of us lean one way or the other in our talents.

But if you consider all of the most successful people you know, I think you’ll find that they incorporate the best of both: they plan thoroughly using their linear thinking skills and then they execute aggressively depending on their abstract thinking skills to keep them moving forward. Embrace and exercise both sides of your talents.


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