Throughout my work career, my days were governed by lists. In private law practice, there was always a mountain of tasks waiting to be scaled. Later, at the Justice Department, the stakes grew exponentially. Every single morning, Attorney General Janet Reno, the Deputy, the Solicitor General, and I would gather to go over her personal to-do list, item by item. As the days blurred together, that list grew at an relentless pace.
There is undeniable utility in writing things down. Whether it’s a high-level government agenda, a grocery list, or a bucket list, putting pen to paper organizes the chaos of the mind. In fact, entire fortunes have been made simply by designing “planners” and “organizers” to help us tame our days. Even now, having slowed my pace, I still find that writing things down is a vital anchor for my memory.
But lists can easily become chains if we let them.
We risk becoming compulsive checkers of boxes, prisoners to a self-imposed itinerary. Looking back at my old law practice lists, I realize there was never anything joyful written on those pages. The only fleeting happiness came from the act of crossing something off—the relief of temporary survival. Certainly, Janet’s daily agenda wasn’t designed for lightheartedness; it was a heavy roll call of national crises, from the World Trade Center bombing and Waco to grueling Congressional hearings. (Though, in hindsight, I should have told her to write down a few fun items. Knowing her, she would have approved.)
The trap of the modern checklist is that we treat life as a series of debts to be paid rather than moments to be lived.
If we are going to write down our obligations, we must also write down our items of joy. Whether we weave them into our daily schedules or keep a separate tally entirely, we must actively schedule room for lightheartedness. Otherwise, we risk organizing ourselves right out of our own lives.
A list should be a tool that serves us, not a warden that rules us. After all, the ultimate goal of getting organized isn’t just to clear the desk—it is to clear the space to actually live. When we look back at the pages of our lives, the most important items should be the ones we chose to linger on, not the ones we couldn’t wait to cross out.
I like this! But what about the calendar? Shouldn’t it, to, be flexible?