Last Tuesday, I arrived at our executive retreat armed with data, presentations, and what my colleague Jake called “the Mary Poppins bag of corporate survival.” This offhand comment stopped me in my tracks. Was my oversized tote really that telling?

Later that evening, as executives gathered for dinner, I found myself studying everyone’s bags with newfound interest. The sleek minimalists with their tiny designer crossbodies. The tech-forward crowd with backpacks featuring dedicated pockets for every device known to mankind. The classic achievers with their monogrammed leather briefcases.

It got me thinking – maybe our work bags are the most honest expression of our professional selves. After all, they hold what we consider essential, reveal our organizational tendencies, and often showcase our practical vs. aspirational selves.

Take my bag: a spacious leather tote with exactly seventeen pockets (yes, I’ve counted). Inside you’ll find emergency snacks, three types of chargers, backup presentations on a flash drive (despite everything being in the cloud), and at least two lipsticks. What does this say about me? I’m prepared for almost any scenario, slightly anxious about technology failures, and apparently believe that the right shade of lipstick can salvage any professional disaster.

Meanwhile, our CFO carries a slim portfolio that holds precisely one notebook and one pen. No wonder he can make decisive budget cuts – the man has mastered the art of eliminating the unnecessary in all aspects of life.

Our head of innovation? Her bag literally expands to three times its size. I’ve watched her pull out everything from prototype samples to international adapters from what initially appears to be a reasonably sized shoulder bag. Her secret? Compartments within compartments – much like how she structures her thinking.

So here’s my theory: our work bags are physical manifestations of how we approach leadership. The over-prepared? Detail-oriented but potentially micromanagers. The minimalists? Decisive but might miss nuance. Those with adaptable bags? Flexible thinkers who can expand their perspective when needed.

What does your work bag say about you? Are you carrying around just what you need, or are you lugging yesterday’s strategies and outdated assumptions too?

Until next time,
Kay

P.S. Since this revelation, I’ve downsized my tote and feel strangely liberated. Turns out I don’t actually need three different types of mints for a single meeting.

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