Cleaning clutter in Simran's house
Photo: Jessica Sain-Baird
Given the choice between a root canal and clearing the clutter from my life, I'd choose the surgery. The dental procedure is finite...and comes with anesthesia. This process of ridding myself of obstacles, on the other hand, seems endless and is stirring up all kinds of emotions about what I thought my life would be (very different—and not necessarily anywhere near as fabulous as what I have).

It's hard—and I don't like it.

I'm being supported through this process by professional organizer Amy Thomas, a spitfire of a woman who set a steady but gentle pace for moving through piles of papers and decades of memories.

Listen to Simran's interview with Amy Thomas.

Amy comes to this work with a graduate degree in project management and a penchant for solving puzzles. She approaches each situation with a compassionate curiosity. Rather than imposing a set of design systems upon me, she remains committed to understanding what works within the context of my life. I won't give up my shoes or bags, and I'm not the kind of person who will file and label each bill. Amy's cool with that and has other ways to keep those items organized. That flexibility gives me the permission to be cool with it too and—in some magical way—helps me let go.