When I look around a cluttered room, I can see it as a physical manifestation of hope. Seriously. Each item that I’m unwilling to part with – it’s there because of hope. I hope I’m going to use it someday. If unconstrained hope can lead to a bloody mess, what’s the lesson? Must we kill our hope if we want to free ourselves from unnecessary stuff?

I don’t want to kill my hope, so I’ll frame the situation a bit differently, and see if a different lesson emerges: Each item that’s cluttering my room – it’s there because I’m avoiding risk. I’m avoiding the risk of regret. I’m avoiding a scenario where I throw the damn thing out and then wish I had it back, only to find it can never be retrieved.

The hat that doesn’t go with any of my clothes? It’s there because of risk avoidance. The folder of old notes? The camera lens I never use? Risk avoidance.

It can help to think of decluttering like investing. You’re investing time and effort in creating a cleaner environment that will serve your future.

What’s the best way to not succeed as an investor? Avoid risk. Be unwilling to lose money, unwilling even to accept the temporary appearance that you’ve lost money.

The same is true of decluttering. Want to fail at decluttering and keep all your unused stuff? Simply refuse to make any decision that exposes you to the risk of regret.

Of course, if you find yourself in tears after a decluttering project, missing everything you gave away, then you were probably too aggressive.  

Moderation works. At the beginning of your decluttering project, aim to miss maybe one or two things when it’s all done. When you experience this moderate dose of regret, take it as a prize, because it shows that you were willing to accept the risk that created the possibility of reward.

If you had taken less risk, you’d still have that old hat – maybe it’s something you loved – but you’d have a pile of other stuff preventing you from finding it.