Decluttering: The Really Hard Stuff – Personal Documents, Hobby Supplies, & Mementos

If you’ve been following along, my deadline for decluttering my bookshelf was October 11th. I made it!

Last week, I sold my CDs. It was a challenge, because I was attached to the idea of having a physical CD. Ultimately, I prevailed, because I realized there was no reason to keep them around.

This week I dealt with something much harder: personal documents, hobby supplies, and mementos.

Why are these so hard?

One reason is that they are largely irreplaceable. I can go buy another CD if I didn’t mean to get rid of one. But I can’t replace my high school report card. I can’t replace my souvenir from Thailand. I can replace my trumpet and collection of music, but it will take a lot of effort.

Personal Documents

These are simultaneously the easiest and the hardest. Why are they the easiest? Because you can scan them and upload them to Evernote for safe keeping. But they are also the hardest because they are physical reminders of things you have done. Will a scanned copy of my drawings from over the years be a good enough substitute for the paper itself? Will my college acceptance letter have as much meaning if it’s a scanned copy sitting with a bunch of other scanned copies of things? How about my childhood photos – will an uploaded image substitute for a polaroid kept for 30 years?

I compromised with this one. I scanned all the documents, got rid of the ones I didn’t really have an emotional attachment to, and put the rest, along with my photos, in a box under my bed. Anything I put into the box in the future must be scanned first, and I’ll figure out whether some of these things can be made into gifts for my family.

Hobby Supplies

How the heck do you get rid of your unused hobbies? There’s always this feeling in your brain that if only you had time, you would go back and revisit them again. They were fun to do!

A couple of things helped me get through this process. I had the toughest time giving up my trumpet – it gave me a lot of joy while I was playing it, and if not for personal injury, I would still be playing it today. But I had a hard look at it, and realized that it’s unrealistic that I’ll ever return. First, it’s not an instrument that you pick up once a week and play – you have to maintain the strength in your lips to play it. Second, it’s loud! You can’t just casually play it like you might a guitar. Third, to get any skill back, I’ll have to practice every day. Do I really want to practice every day? When I look at my future, I see exercise, working on my career, and pursuing a family as the primary uses of my time. To be honest with myself, I don’t see an hour of trumpet practice every day.

The second thing that helped me: The Outbox

There are some rules for the Outbox, but the gist of it is this:

  • put anything you’re unsure of in the Outbox
  • take anything you want to keep out of the Outbox, but only after a week
  • at some point, your attachment to items will fade, and it will get easier to get rid of them

The nice thing about the Outbox is that it breaks apart the tasks of sorting and disposing. So you can easily put things in the Outbox without having to make a decision as to whether it should go immediately – you’ve only decided that this is a thing that you’re undecided about for now. You can organize your space first, and decide what to do with things later.

(Later, you’ll revisit the Outbox and wonder why you didn’t get rid of things years ago!)

Here’s where I stand with my hobbies: all of them (my drawing supplies, my trumpet, my guitars, my harmonicas, etc) go into the outbox. I’ve set a reminder for myself: in 1 month, if I haven’t done a particular hobby, I’ll get rid of it. Done.


Some mementos are easy. That souvenir that your relative gave you from their trip 10 years ago? That can go. Some are a little harder: the boxed set from your favorite band, your friends’ wedding invitations, race bibs and medals – what do you do with these?

First, I took pictures of all of it and put them on a Tumblr blog. This is a blog I set up specifically for mementos. I don’t want to forget about these things, and I don’t want to file them in some giant pile of pictures along with everything else.

Having these things in a blog gives me a little bit of a mental freedom: I can get rid of things that I’m not particularly attached to anymore, while not being handcuffed to keeping these things around forever. Now I can post the valuable things on eBay and toss the rest!


I learned a ton – I’ll try to summarize my experience and share my next goals in a future post!


4 thoughts on “Decluttering: The Really Hard Stuff – Personal Documents, Hobby Supplies, & Mementos

    • It was really hard. These are the things I procrastinated about the most.

      One thing that helped was scanning/taking pictures of mementos first. Nothing is destroyed when you scan something, but you’ve saved it to your archive. Then you (often) realize that you don’t need the physical thing anymore.

      For my hobbies, they were really tough because I have great memories of doing them. But a tool for figuring out if you should keep that stuff around is to visualize your future. Do you see yourself in the future actually doing these things again? This works for video games or movies or anything – if you don’t actually want to do it anymore or invest the time, and you are able to visualize that and admit it to yourself, it makes it easier to put it in the past.

      Good luck!

      Liked by 1 person

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