Are You Playing Chess or Checkers With Your Career?

When I get to know new clients, one of the things we explore is the strategy they’re using in this often chaotic career game.  Is the strategy like checkers – direct, tactical.  Or similar to chess – nuanced, layered and strategic.  Or something else entirely – Battleship, Risk, Hungry Hungry Hippos . . .

For now, let’s stay with chess and checkers.

Early in our careers, we’re usually playing checkers.  Lots of focus on the next moves, checking boxes, building experience, gaining momentum and quickly advancing from one opportunity to the next. Attention is centered on foundational growth, increasing income and stepping from one square to another.

As we move into mid-career and beyond, the game shifts towards chess.  Our personal and professional needs are more layered, and the variables become more complex. Advancement requires greater nuance, as we encounter subtle positioning, unexpected paths and longer view than in the past.

At the same time, our options become less flexible.  Employers tend to prioritize depth over breadth, hiring for expertise and the insight obtained from those earlier experiences.  We still want to advance, gain experience and increase income, but it can get harder as we let go of familiar roles and step into less familiar territory.  And just to make it more interesting, the strategy shifts between chess and checkers – adjusting as the environment demands.  

As you think about the next few years of your career, ask yourself what the field of play requires. Is there a direct path to your next goal?  Will you have to identify a dynamic approach?  What might you need to let go of – or risk – to get there?

If you’d like support thinking that through, I offer a free Discovery Call or a deeper dive Pivot Intensive session.