208: This is Harder on Me Than It Is On You: Lessons from Parenting and Organizing

“This Is Harder on Me Than It Is on You”: What Wrestling Taught Me About Decluttering

You remember that old line parents used whenever we were facing the consequences of a bad decision, missing out on something we wanted because of our own choices. As a kid, I never believed it. My parents never looked like they were suffering. But I have a vivid memory of finally understanding it myself, and it ties directly into what I now watch happen with organizing clients.

The wrestling season

My oldest son, early middle school at the time, decided with a friend to try wrestling, a sport he’d never done before. Wrestling, if you’ve never experienced it, is brutally demanding, especially the conditioning. After the initial newness wore off, there came a stretch where dropping him off at practice meant real tears, every single time. I’d remind him, calmly as I could manage, that he’d made a commitment, that teams count on each other, that we finish what we start. It wasn’t dangerous, just genuinely hard.

He lost every match that season except one, which was a forfeit. Coaches, even opposing coaches, were remarkably encouraging about how normal that is for a first-year wrestler starting late compared to kids who’d been at it since age eight. At the end-of-season banquet, he and one other kid, the only two from that year’s new group who stuck it out to the end, received something called the Determination trophy, not a participation trophy, an actual recognition for choosing not to quit through something genuinely difficult.

Years later, when he was packing to move out for good, he sorted through a mountain of participation trophies without a second thought and kept exactly three: the real ones, the ones tied to actually sticking with something hard. That wrestling season became a real, lived proof to him that he could do hard things, something he leaned on again when we moved during his junior year of high school and he had to start over knowing no one.

The parent’s side of it

What I remember most is sitting in the parking lot after dropping him off, crying a little before I could pull myself together enough to go back to being calm and encouraging. It was excruciating to make my kid do something hard, knowing I had the power to simply let him quit and take the pain away. Earlier in life, before I had kids, I used to judge what I called “bulldozer parents,” the ones who swoop in and smooth every hard thing away for their kids. I wasn’t entirely wrong that kids need to face difficulty to discover they can handle it. I just hadn’t understood yet how hard it actually is, as the parent, to resist smoothing the road instead of preparing your kid for it.

Where this connects to decluttering

I see this same dynamic constantly with organizing clients. The guilt over an item, because it was a gift, because it cost money, because it was handed down, because keeping it or getting rid of it feels loaded with meaning, is real and heavy in the moment. I can see clearly what’s on the other side: a home with breathing room, less stress, the freedom to invite a friend over without worrying, the ability to be spontaneous instead of constantly managing too much stuff. And it is genuinely harder for me, watching someone struggle through that decision, than it is for them in that exact moment, because I already know how good the other side feels and I can’t just reach through and do it for them.

This is especially true in my group Zoom sessions, where someone’s working through what they call their “doom room,” frustrated and stuck, and I can’t physically reach through the screen to help. All I can do is remind them: there is a light on the other side of this hard part. Getting through the discomfort of having less doesn’t fix every problem in your life, but it opens up real breathing space to deal with everything else that’s still hard, without the extra weight of clutter and stress piled on top.

The Minimal Mom’s mission

I think of Dawn, who runs The Minimal Mom on YouTube, whenever I think about this. She lived through genuine overwhelm with too much stuff, found her way to minimalism as the actual solution, and now pours her energy into pulling other people toward that same lightness. Her message, that life is simply better with less inventory, lands because it’s real. She knows what’s on the other side, and she wants it for everyone else just as badly as she wanted it for herself.

Your practical, actionable step

Pick one item that’s been sitting in decision-limbo because of guilt, a gift, a cost, a memory attached to it. Remind yourself that the discomfort of deciding is temporary, and the breathing room on the other side is real. Then make the call.

Until next time, continue to choose joy.