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A Good Strategy Incorporates a Dose of Serendipity

While I spend a good deal of my time helping my clients develop and implement a strategy, I realize that rarely (if ever) do things work out exactly as we planned. Opportunities arise that we didn’t consider, some objectives fall short and some exceed our wildest expectations. I’ve been spending a lot of time thinking about how many achieve success and realized that it is a combination of a great strategy, solid execution and serendipity.

Serendipity is defined as “An aptitude for making desirable discoveries by accident.” Pretty straight forward and I’m sure we can all think of many instances in our lives that came about in this very way. It’s part luck, part skill. It’s also not a smart way to rely on to achieve your objectives…or is it?

You need to incorporate into your strategy a process to create and take advantage of serendipitous moments. Sounds like planning for accidents, right? You clearly cannot plan for all of the unexpected opportunities that may come your way, but what you can do is analyze the unplanned opportunities that come your way and search for a pattern of some sort.

These patterns can vary wildly – a senior executive picking up your book at a book store and reaching out to you, meeting someone at a conference or on an airplane, a blog post that goes viral, an introduction to someone by an old friend. The possibilities are endless. What I’ve learned is that although the possibilities are endless at a macro level, at the individual level they can be somewhat predictable. If you can figure out the commonalities you can actually devise a strategy that increases the chances of the random becoming less random, possibly even somewhat predictable.

While this concept may seem counter intuitive, I’d argue that it actually makes a lot of sense. Why not integrate the best of both strategy and chance into your plans? For many of us a plan is comforting, it makes us feel as if we are in control, and for the most part that’s true. However, acknowledging that chance and circumstances beyond our control often do play a part in our success allows us to open our eyes to more opportunities whether we planned for them or not.


Peter Winick has deep expertise in helping those with deep expertise. He is the CEO of Thought Leadership Leverage. Visit Peter on Twitter!

This Post Has 4 Comments

  1. Great point, Peter. Business is broken. The approach you mention is what I like to call Continuous Improvement. We won’t get it right the first time, so we have to allow our business/people to adapt. Taking on the mindset of continuously improving our position while keeping our strategy in mind is key. Happy Tuesday!

  2. Great article, thanks for sharing this with us. Strategic planning doesn’t mean being rigid in our processes to capture new opportunities. This could be the main reason why organizations stoped planning for 10 years and started planning for only 3 years so they would not lose any opportunities.

  3. Peter,

    Recognizing the unplanned, or serendipitous, is the key to being able to take advantage of them. We can become so consumed and so focused that we sometimes miss the really good stuff.

    It pays to pay attention to the little things that are otherwise overlooked.


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