Where Do I Even Start? (When Every Room Feels Overwhelming)

This might be the question I get asked more than any other: when the whole house feels like too much, where do you actually begin?

There’s a moment in Alice’s Adventures in Wonderland that captures this perfectly. Alice reaches a fork in the road and asks the Cheshire Cat which way she ought to go. He asks where she’s trying to get to. She admits she doesn’t much care. So, he tells her, it doesn’t much matter which way she walks.

It’s a little absurd and a little brilliant at the same time, and it maps almost exactly onto the ADHD brain trying to figure out where to start organizing.

Two Ways to Get Stuck

On one side of this, you’ve got all the advice about needing a clear vision before you start — know your “why,” picture the end result, keep your ultimate goal in mind while you work. That’s not wrong advice. But for a lot of us, it turns into hours lost on Pinterest, pinning inspiration boards for every room in the house, feeling productive while absolutely nothing in the actual house changes. Overplanning becomes its own kind of paralysis.

On the other side, if you genuinely don’t care where you end up, any direction works — and there’s something freeing about that. Action, any action, beats staying frozen. But pure undirected motion has its own risk: you start organizing a drawer, get distracted by something in it, follow that thread somewhere else entirely, and an hour later you’re deep in a completely different project with nothing finished anywhere.

Both approaches have real pros and real cons. So here’s the simpler fix.

Make the Destination Dead Simple: Less

If your ultimate goal is just less — less stuff, less time needed to keep a space looking decent, less to worry about, less to feel overwhelmed by — then it genuinely doesn’t matter which direction you start in. Every path leads there.

Twenty minutes of straight maintenance in a room makes it feel less scattered. Twenty minutes of putting things away that already have a home makes things feel less chaotic. Twenty minutes of pulling 20 items out to donate is, quite literally, less stuff in the house. Every single one of those actions moves you toward the same center point, the way every entrance into a maze eventually leads to the same middle.

So stop overthinking where to start. Stop worrying you’ve picked the “wrong” task. If everything you do is aimed at less, every direction is the right direction.

Pair This With the Double Down Dig Out Challenge

This mindset is exactly why the Double Down Dig Out Challenge works so well: the goal is simply 20 rounds, across the month, of setting a 20-minute timer twice a day — once for straight maintenance (kitchen, laundry, bathroom, whatever’s calling your name), and once for pulling 20 items out of the house to throw away, put away, or donate.

If you haven’t started yet, or you’re worried you’re already behind because the month’s underway, don’t be. There’s a built-in loophole: this isn’t 20 days in a row, or a strict schedule of one-of-each per day. It’s just 20 unmarked, undated boxes on a printable, and you check one off however it happens. Took out the trash and it genuinely included 20 things? That counts. Cleared 20 random items off the living room floor in one go? That counts too.

I’ll be honest — my own week has been the most chaotic one since I launched this challenge, and I’m sitting at five maintenance check-ins and two item check-ins out of 20 each. That’s fine. The structure is built to flex around real life, not demand perfection.

If you want the full breakdown of the challenge, it’s covered in the previous episode. For extra accountability, I go live for 20 minutes most Mondays in the free community at bit.ly/joylovinghomecommunity, with a printable tracker available there too. If you want more structured support, the $10/month membership includes live Tuesday Zoom work sessions where we’re actually working side by side — details at joylovinghome.com/membership. And if you’re ever stuck trying to join either group, just email me at joy@joylovinghome.com.

Every direction leads to less, as long as you’re moving. Set the timer, and go.

Until next time, continue to choose joy.