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Strategic Jaywalking is at once a playful, yet sober assessment of how we might live and lead better by judiciously keeping our devices and policies on a leash and exercising a little more conscious thought and decision-making responsibility in our work and lives. It relies on something that nearly all of us were taught at a young age - how to safely cross a street, and yet, by idiot-proofing the experience via rules and technology (think painted crosswalks, beeping timers, and flashing red hands,) we have in many respects made the process both slower and more dangerous. In too many ways, and for too long, we have done the same by allowing leadership to morph into 'supervising' because, well, it's simpler and not as messy. Jay is of the mind that you 'supervise' young children, with a goal of willful compliance. Adults, on the other hand, engage much better via the influence of competent and capable leadership that lets them think for themselves.