Your Loosely Organized Career


Sometimes we underplan our career. We float, wander, take the first offered opportunity, then take the next offered opportunity, etc. We end up feeling lost as if our career has sort of just happened to us.

Sometimes we overplan our career. We say we will take Job A to get us to Job B in X years. We get this degree to get that position for Y years then to leave and start up Z Inc. We try to cover every base that will get us from here to retirement at Millionaire Acres. Overplanning leaves us tired and stressed.

There is value, however, in both approaches. The value of planning is the delightful satisfaction of actually achieving something meaningful to you. The value of not planning is the access to opportunities, connections, and coincidences that stud the life stories of every successful person.

We need, then, a hybrid approach. Let’s call it a Loosely Organized Career.

In a Loosely Organized Career, we set high-level, meaningful goals based on our SweetSpot. For example, instead of saying, “I want to be EVP by the time I’m 48 then get a package at 55 to start my winery,” we would say, “I want to be a senior leader in a field I love, I want to make more than enough money, and I want to engage my passion for viticulture and good food along the way.” We then do just-in-time planning. Maintaining our focus on “there,” we take the next best step to get from here to there, repeating as needed until we get there.

As we go, our loose plan has room for serendipity to guide us to the ways, means, and outcomes we never could have planned for. We end up loving the journey and living that satisfying life well lived.


In your corner,



Today’s photo credit: Un ragazzo chiamato Bi via photopin cc


2 responses to “Your Loosely Organized Career”

  1. Diane Avatar

    I LOVED today’s message. Isn’t the “middle way” frequently the best approach?

  2. Mike Avatar

    Funny, as I was editing this post I deleted a PS that said, “Yes, I do like third-way approaches.”

Leave a Reply