Thinking Strategically About My Career

Thinking strategically about my career. Image of a person playing chessEditor’s note: A couple of years ago, I began to contemplate how to create more time to start thinking strategically about my career. I’d read Dorie Clark’s book, The Long Game (see below), and realized that I  was just galloping through my days.

This month, for the first time in ages, work has been quiet and I don’t have any travel planned. So I’ve actually been able to sit down each morning, when I write my morning pages, and start thinking strategically about my career. It’s been amazing. I’ve reorganized the memoir I’ve been writing…I’ve decided to make a platform change for my newsletter…I’ve done some important thinking about this blog. None of that could have happened without what Clark calls “White Space.” If you don’t have enough time in your calendar to stop and think about the big picture, I strongly recommend that you find it. It’s magic.


It’s always gratifying when the book you happen to pick up off the shelf is *exactly* the book you need to be reading. So it was with Dorie Clark’s The Long Game: How to be a Long Term Thinker in a Short-Term World.

Allow me to set the scene. I’d just gotten back from a month off.  After castles in Edinburgh, long walks in Manhattan, and a seemingly endless stream of pale ales, I arrived home to a veritable mountain of work. And within 24 hours, I was in back to waking up at 5, working weekends, and fitting my friends into “windows”.

Enter Dorie ClarkThe Long Game is about how to lay the foundation for long-term, strategic thinking and professional success. I’ve read all of Clark’s books on career change and entrepreneurship. They’re insightful, filled with practical tips and eminently readable. And while some of the ideas in The Long Game were already familiar to me, the concept that really rocked my world was that of “white space.”

White Space

The book begins with an indictment of the “busy culture.” Many of us (raises hand), not only live life at a gallop, we consider that busyness to be a marker of success. And the danger of that way of thinking, according to Clark, is that “if we venerate busyness, even subconsciously,” we will inevitably make decisions that lead us in that direction.

But as she so wisely puts it, “Being so busy may seem like the path to success. But without time to reflect, an ominous possibility looms: What if we’re optimizing for the wrong things?”

So if we want to make smart choices about how we spend our time, we need to set aside time to think,..and plan.

Strategic Thinking at Work

I’ve gotten better about planning my time, and in particular, about setting aside a few hours a week for “admin time.” But that’s just about keeping my head above water. It’s not the sort of thinking strategically about my career Clark has in mind.

She’s talking about the big-picture, blue sky thinking: deciding you’ll become a Master Gardener, or start that social enterprise you’ve been dreaming of, or join that community theater troupe down the road. (If only!)

In my own case, I’ve put so much time into launching my own business over the past three years, that I’ve never really stopped to think about where I want it to go. How big  do I want to get? Do I need to start contracting out work to other freelancers when I have too much to do? Do I want to get certified as a coach?

These are the sorts of big-ticket questions I simply don’t have time—or rather, make time—to ask myself. But I need to. Otherwise, I’ll just keep on living day-to-day, and lose track of where I ultimately want to be.

Strategic Thinking at Home

This lack of strategic thinking is also true in my personal life.

Take our house, which we love. When we moved in seven years ago, we knew it had a huge “damp” problem, as they say in the UK. And we know we need to fix it. But have we? No. Instead, there is literally moss growing *in* our kitchen, and on occasion water pours out of the light fixture. I’m no architect, but this strikes me as something we need to get on top of.

And speaking of houses, as I get older, my friends increasingly ask me if I’ve thought about where I will retire. I have no idea. Part of it is that my husband and I are not “forever house” sorts of people. And that’s fine. But we really need to get started on serious financial planning to make whatever we’re going to do doable as we get older. Instead, we just keep putting that off.


The sad part of all of this is, I know how to fix this. Some of it is practical: learning to say “no”. (Even to good things, as Clark helpfully adds!). It’s also about identifying your priorities and cordoning off time in advance to address them.

But like most things, it’s also about mindset. It’s about ceasing to see view busyness as “I’m in demand,” and re-framing it as “I don’t have control over my own schedule.”

Watch me go…

Image: Photo by JESHOOTS.COM on Unsplash

Note: This blog first appeared on Sixty and Me.

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