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!


Decluttering: The Hard Stuff – CDs

If you haven’t been following along, I’m in the middle of a decluttering project.

This week I tackled my CD collection.


I’ve had to overcome a few mental barriers in defeating this foe.

First: my car stereo was built before iPhones were common. It has a CD changer and tape deck.

I used the 6 hats method to figure out what to do. TL;DR: when trying to think through a problem, imagine wearing 6 hats which encourage you to explore the facts, your emotions, creative solutions, best case scenarios, doubts, and meta thoughts about the decision.

I’ve been struggling with this issue for a while, because the only solution I could think of was to either keep my CDs (which are taking over my house) or switch my radio (I can’t stand the after-market options).

Wearing the green hat, I realized I already had a new tape deck convertor (which I had dismissed as too distorted), and decided to give it another try. Good news: the sound is perfect – I can’t even tell it’s not a CD.

The second barrier to getting rid of my CDs was my mental model of the cost of my collection. Of the 650 CDs I have, roughly 350 are music CDs I purchased. At $12 a CD, this is about $4,200 I’ve spent on my collection! How can I justify getting rid of such a huge investment?

$4200 seems like a big number – but think of it this way: over 19 years I’ve been buying CDs, that’s about $220 per year, or $18.50 per month.

How much is Spotify? $10 per month.

But what if I missed ripping a CD? Big deal – I can buy another for $10. What if there’s something in there I’ll really miss? Again – I can buy it again for $10! What if my tape deck in my car breaks? I can always replace my stereo for $100.

I thought briefly about keeping just my favorites – gather 10% of my CDs, and keep them for the car. Then I realized there is literally no reason to keep them! If my tape player is good enough for all of my other music, why wouldn’t it be good enough for my favorites?

There’s no reason to keep any of my CDs.

I suppose there’s an argument for higher quality music (like a FLAC conversion), but I can’t hear the difference.

So I started to categorize my CDs for Ebay, removing any that are burned copies.

One thing you learn when you’re decluttering is how little your previous efforts can mean in the long term. I remember spending so much time pulling CD books out of the jacket and putting them into my CD case; now, it doesn’t matter at all. Any of these I find are going straight into the garbage.

Listing them on eBay caused me a lot of anxiety. Here are the listings (they’ll be active for another 5-6 days):

Jazz CDs
Christian CDs
Indie Rock/Alternative CDs
Rock/Metal/Grunge CDs

But that’s done! I should have plenty of time to get rid of these (if they don’t sell on eBay, I’ll take them down to Goodwill) before my October 11th deadline!

Remaining things to deal with on my bookshelf: knick-knacks, musical instrument tablature/song notation, and special items (boxed sets, etc). Onward!

Roundup: Gene Therapy, Radical Decluttering, and the Calories In/Calories Out Debate

‘Weekly’ Media Roundup (Sep 9th – Sep 25th)

Well, that ‘week’ got away from me. I’ve been busy decluttering, but I have consumed lots of great information. I especially like some of the nutrition podcasts I list below.






  • dev-human – Things I was unprepared for as a lead developer
    • Interesting list of things to expect when (if) you get promoted into management
  • Matthias Felleisen – Growing a Programmer
    • Traditional university curriculums focus on teaching languages and algorithms and data structures, with little emphasis on how to design and maintain large programs. Let’s flip that script.
  • Jeff Knupp – How ‘DevOps’ is Killing the Developer
    • Stop trying to make software developers into general purpose tech workers. This might work for startups, but developers like to, you know, develop.
  • Sam Altman – Stupid Apps and Changing the World
    • Sometimes world changing apps look like toys at first. Keep on doing what you think is important.

Personal Improvement






  • Healthy Food House – They Said That Drinking Lemon Water In The Morning Is Good For You. Here Is What They Didn’t Tell You
    • TL;DR: Start drinking a glass of lemon water every morning
  • Danny Lennon – Is Your Low-Carb, My Low-Carb?
    • No one seems to agree on what low carb actually means. What should it mean?
  • Dr. Jason Fung – Why Can’t I Lose Weight?
    • This is one article from an extremely informative series on fasting. According to Dr. Fung, fasting (in any of several forms – Leangains, Eat Stop Eat, two weeks, etc) is important if you have built up insulin resistance over time, and can help your body reset itself and drop excess fat. Read this again!
  • Flowing Data – Years You Have Left to Live, Probably
    • Over 95% chance that I’ll live another 20 years? Sweet. Of course, this is totally wrong if you believe in the Singularity.

Decluttering: The Easy Stuff

I’ve been hard at work on my decluttering project.

First, I took everything off the shelves and arranged them in rough piles by category:


I tackled the easy things first.

I’m keeping my yearbooks. I have a few maps that I regularly use for backpacking. I have a SCUBA certification reference book. These things are keepers.

I also had a large pile of old exercise magazines, manuals from my Toastmasters days, and assorted old clippings. These went straight to the recycling bin.

Slightly tougher to part with were the 12 (!!) pads of paper that I’ve accumulated, plus the pack of printer paper (for which I have no printer). I have a hard time parting with these, because they are ‘useful’ – but I remembered the 20/20/20 rule. I kept a pad of paper (since I do use one), but the partially used and ragged ones went in the garbage. I brought the newer pads and paper to work, where hopefully they’ll get used.

Next came the books. There are several kinds of books I own:

  • Books I’ve started but haven’t finished. Unless I felt a strong desire to finish the book (i.e. I just haven’t yet), it went into my Goodwill box.
  • Books I haven’t opened yet. For the most part, I accepted that I probably won’t ever read them, and put them in the Goodwill box. These are the hardest, because they represent money I’ve spent. But I realize I’ve already spent that money, and even if I need to replace one, it will be a small expense compared to the mental burden of keeping them around.
  • Computer books. Programming languages, best practices, interview strategies, etc. I got rid of most of these: if I need to learn C++, there are great resources online. I kept the C Programming Language for now (in my outbox) – it’s a classic, and I’d like to read it again soon. Some of these I brought to work, others I gave to Goodwill.
  • Instructional books. Some of these are easy: the harmonica music books I haven’t touched in 15 years. Some of these are difficult to decide about, like the drawing books I worked part of the way through a few years ago. These will go in the outbox for now. Some of these I’m dreading a little bit: the giant stacks of guitar and trumpet books that stand unused, but not unwanted. I’ll have to make some tough choices very soon.
  • Sentimental books. The Bible ended up in my Goodwill box. I’m an athiest now, but I have a strong connection to Christianity in my past. Books by my favorite authors, like Kurt Vonnegut, Bill Bryson, and Ray Kurzweil I decided to get rid of. Books are no longer things that I keep just for the sake of it.

I totaled the amount I spent (roughly) on these books, largely unread and unused. Often I got these books from used bookstores or as gifts, but this seems roughly correct. It’s also ridiculous, an embarrassing waste of money over the years. Total cover price of the books I’ve donated or given away: $1100.

One final point about all of these things: for the most part (aside from a small pile of books in my outbox, to decide about later), I dealt with donating and recycling and gifting these things immediately. I don’t want them in my house! I’ve made the mistake of putting these things in a corner before – this is a way to delay making the tough decision to part with them! I’ve already got a small pile of things to decide fates of – I’ll get rid of the ones I’ve already decided about immediately!

Over the next few days, I’ll be making tackling some more difficult piles: stacks of music, binders of CDs, souveniers and knickknacks, signed or more valuable books, and binders of personal documents. Wish me luck.

Decluttering: Making a Plan

I’ve been stuck for years trying to get rid of stuff. It’s time to observe The. Most. Important. Thing. So I’ve made a plan, and started to Take Action.

First, I consulted an expert. A friend of mine is into lifestyle design and minimalism, and I asked her to tour my apartment and help me figure out what to do with my clutter.

(She lives in an apartment the size of a prison cell. I think she knows what she’s doing.)

The first lessons she imparted:

The 20/20/20 Rule:

For things you’re struggling to get rid of: if something can be replaced for $20, or in less than 20 minutes, or by traveling less than 20 miles, get rid of it.

The Minimalists call this the 20/20 rule for Just In Case items: “Anything we get rid of that we truly need, we can replace for less than $20 in less than 20 minutes from our current location.” It’s slightly different, but the point is the same: don’t hold onto things “Just In Case.”

The Value Rule:

An item is more valuable if you can give it away to someone who will find it useful, than if you hold on to it, even if there’s some tenuous sentimental value to you.

(She didn’t give me a name for this one. Maybe one already exists?)

You can see how this might apply to your stuff. Got an old table you can’t get rid of because it’s been in the family? Maybe it’s more useful to someone who needs a table, than as clutter to you. A book that’s been sitting unread on your bookshelf? A more expensive tool you’ve been hanging onto ‘just in case?’ It’s easier said than done, but look at your valuables through a different lens.

After I gave my friend and consultant a tour, I made a plan.

My objective: reduce the objects in my bookshelf by 90%.
My reason: the bookshelf is a source of stress and anxiety, representing a big pile of things to get done, and I should start there
My deadline: October 11th, 2015 (4 weeks)
My reward: the new iPhone (I’ve been waiting to get one anyway… I’ll put it off until I’ve achieved my objective)

I started tonight. Here’s a photo of my bookcase before:


Here’s my strategy:

  • remove everything from my bookshelf
  • separate the items into different categories
    • partially read books, unread books, knick-knacks, maps, music books, cds, personal documents & photos, magazines
  • Decide which items I would definitely like to keep
  • Decide which items I can part with immediately
  • Use an “Outbox” to help me sift through items I can’t decide about
  • Get outside help for perspective and for accountability!

I’m ready to get started. Let’s go!

Roundup: Giant Viruses, Pooping in Public, and the Real Reason We Get Fat?

‘Weekly’ Media Roundup (Aug 30 – Sep 8th)

Speaking of consistency, here’s the latest roundup, in which we learn about topics from viruses to low carb diets and taking a cash payout when you’re pretty sure you’re dying.



  • RadioLab – Elements
    • Go on a sonic tour of physics – from lithium to carbon-14 to cosmic rays and dark matter and
  • This American Life – Petty Tyrant
    • The amazing story of one small time crooked union boss and his swath of destruction
  • This American Life – Lower 9 + 10
    • How’s life in the Lower 9th Ward 10 years after Katrina?


Personal Improvement


  • Question of the Day – Ten-Minute Advice
    • My new favorite podcast with James Altucher and Steven Dubner, with a very simple premise: ask each other an everyday question, like “What’s something you can teach me in 10 minutes that will change my life?”


  • James Clear – Getting to Simple
    • To find out the essentials, you must master the fundamentals, often through hard work and trial and error
  • Structured Procrastination – Do Less, Deceive Yourself, And Succeed Long-Term
    • Use your tendency to procrastinate for good – by doing other lower priority tasks rather than sitting on the couch
  • The Wall Street Journal – To Stop Procrastinating, Start by Understanding the Emotions Involved
    • If you’re a chronic procrastinator, start by examining the emotions – anxiety, etc – that come up with you’re faced with a big task
  • Jeff Ammons – Hacking the Flow State
    • Flow can be necessary to accomplishment and job satisfaction. How do you get those necessary ingredients, clear goals, clear and immediate feedback, good balance between one’s perceived skills and those perceived as necessary for the task, and uninterrupted concentration time?



  • Gary Taubes – Why We Get Fat
    • In an easy to read way, Taubes lays out how people can be fat and malnourished at the same time (here’s a spoiler: processed carbs), and shares an Atkins-like plan for tipping the scales back towards even. (I’ve decided to try this one as an experiment.)


  • The New York Times – Gary Taubes: Diet Advice That Ignores Hunger
    • “Calories in/calories out” has a major problem: restricting calories in is unsustainable, and weight inevitably bounces back once calories are returned to normalcy.



  • Freakonomics – Are You Read for a Glorious Sunset?
    • Serious question: why don’t insurance companies offer a generous payout instead of a long, drawn out stay in the hospital for terminal patients?

The Other Most Important Thing

As I’ve written about before, taking action is The. Most. Important. Thing.

But there’s another thing that’s also important: Consistency.

Over my life, I’ve wondered why certain things are so hard for me… losing weight, getting in shape for a sport, learning an instrument, finding a job.

The answer comes down to my consistency putting in the reps.

When I am losing weight, I am eating well every single day. When I’m plateauing, I am making cheat days a habit.

When I am getting in better shape, I am exercising 3, 4, 5 days a week consistently, whether or not I ‘feel’ like it. When I’m skipping days, the weights and miles don’t go up.

When I’m learning an instrument, those tricky passages start to seem a lot easier when I’m putting in the time every afternoon. When I’m prioritizing other things, the easy parts get harder.

It’s hard to look at success and not see a pattern of consistency.

Bobby Fischer, according to internet rumor (if you have a reference, please share) was obsessed with chess, and read every book about it.

The Beatles played 262 shows at one club in Liverpool over 2 1/2 years (IMDB).

Michael Phelps went 5 years without missing a workout, 365 days a year (Parenting).

What can you do?

Tell your spouse you love them every day. Show up to work early every day. Schedule your workouts on your calendar. Meditate first thing in the morning, not just when you feel like you need it.

Take action, and do it consistently.