Organization – Day One

I’m heading into the eleventh month of my year-long Foundations project. This month’s focus is organization—getting a handle on your physical stuff to maximize the benefits those things provide while minimizing their ongoing costs in terms of tidying, storage and money spent. Those interested can check out my previous ten months here: fitness, productivity, money, food, reading, outreach, sleep, reflection, connection and focus.

My Weakest Foundation

I have been nervously anticipating this foundation since I announced the project last year.

While I’m far from expert in many of the previous foundations covered, my baseline in most of them wasn’t terrible. For instance, I’ve made incredible strides in my fitness over the course of this project, but the measurements I took before I began were still somewhat above average for my age.

In contrast, I’m a disaster when it comes to being tidy and organized. 

It’s not entirely from lack of trying. A few years ago, I grew frustrated with how frequently I was searching for books on my bookshelf, so I decided to organize them alphabetically, by author. This worked well. But then, as the books kept coming, I eventually ran out of shelf space.


Many of my books for this project are in a loose pile on the bottom shelf. Frustratingly, I even lost one of the textbooks on relationships I read—I had to resort to probing ChatGPT for the the original research references when I was preparing lessons for the course since I couldn’t locate the book!

Books are the tip of the iceberg of stuff I can’t seem to keep organized. My nightstand at home typically has stacks of books, notebooks and sketchpads. The crawlspace under our house has some neatly organized boxes of documents and old books (again, more books!), but next to that is piles of old baby stuff, unused decorations and random attachments to devices I no longer own.

My paper documents are another case in point. While I have gone through occasional purges and reorganizations, the default state is a pile of mixed documents, most of which should probably be shredded. When I actually need one of them, my first instinct is to try to find the document online again, so I don’t need to go through the pile.

Why Can’t I Tidy Up?

Reflecting on this manifest weakness of mine, I can think of a few key causes:

1. I keep too much stuff. While I don’t have a problem throwing things out, in the past when I’ve gone to declutter, I’ve defaulted to “keep” when I’m not sure what to do with things. The result is that most of my tidying attempts shuffle the mess rather than get rid of it.
2. I don’t have dedicated spots to put things. As a result, many objects that live in my house are vagrant, wandering from desk to shelf as the question of where to put them while tidying doesn’t have an obvious answer.
3. I’m generally bad at prioritizing low-urgency household tasks. As discussed in my productivity foundation, keeping things tidy is only one of the minor chores I struggle to stay on top of. I also let minor household repair chores linger for months, and I delay doing home errands that aren’t urgent.

One explanation I’ve considered is that it’s hard to keep tidy because I share my space with my wife and kids now. Many of the items in our house are shared, and I feel reluctant to throw out shared household items or old kids’ toys. I may have different priorities for shared spaces, so sometimes I’m eager to get rid of things that my wife values and vice versa.

Upon reflection, I have to reject this as the cause of of my disorganization. While it’s true that I need better policies for tidying up items that aren’t exclusively my own, I’m still messy with stuff and spaces entirely under my control. My office, for instance, is full of clutter even though I’m the only person working there most of the time.

If anything, my wife is better at tidying than I am, so it’s doubly unfair to push blame away from myself. When we have done partial reorganizations, she has almost always been the one spearheading the effort. Were it all up to me, I’m sure the mess would be even worse!

Some Cautious Optimism

I don’t want to prematurely declare victory over my messiness. But I also suspect that the problem is far from unfixable. Instead, I suspect my own disorganization stems from a set of bad habits, plus not giving this area of my life the concerted attention it needs.

My initial plan, when I started thinking of this project a year ago, was to spend the entire month tidying up bit-by-bit. However, as I started reading Marie Kondo’s book The Life-Changing Magic of Tidying Up a few days before the month began, I was struck by her strong prescription against this. She argues that tidying needs to be done completely in one shot, or it won’t last.

In keeping with this advice, I’ve decided to devote at least a few consecutive days to doing a complete reorganization and declutter.¹





Fortunately, this month also happens to overlap with when I planned to move offices, so the need to pack everything and move provides a natural motivation and opportunity to completely reorganize my space and ensures a fresh start.²

Can I Become a Tidy Person?

As mentioned above, the foundation where I’ve seen the biggest transformation was with fitness. While I wasn’t terribly out of shape before beginning, the idea of being someone who is in great shape was not a key part of my identity. It wasn’t that I thought exercising was unimportant, but it seemed peripheral to what I felt my life was about.

I think the biggest changes for me have occurred not simply from exercising more regularly, but from a shift in this identity. While I don’t ever expect to be a serious athlete, the gains I’ve experienced this past year have shifted something that was previously on the periphery into a more central part of how I see myself.

If this month is to work, it can’t just be a one-time declutter. Instead, I need to shift some of my beliefs about myself. I need to see myself as a fundamentally tidy person who doesn’t keep junk and clutter.

Staking out an identity that feels so far from where I am currently is a little alien. Indeed, until I actually succeed in doing the initial declutter, I don’t know whether it will even be achievable. But I do think the end result has to include the idea of becoming consistently tidy, rather than doing a one-time challenge or reorganization effort.

Will it work? I’m not sure, but as always, I’ll let you know how it goes!

1. I think the reluctance to scheduling a full weekend (and maybe even some workdays) to do this was also symptomatic of my lower prioritization of this area of my life. One of the greatest benefits of this Foundations project has been that each month creates an “excuse” to make something that never *feels* like the top priority into the top priority for that month. I didn’t improve my sleep habits prior to this project, for instance, because there was always something else I put first.
2. One drawback of this month is that I’m going to be traveling to Europe for two weeks for a family gathering. Normally I don’t like to alter my original project schedule for public projects like these, but I’ve decided that this month is important enough that if I’m not able to finish the complete reorganization by the end of the calendar month, I’ll push back the final focus by a week or two to make it fit. Since I’m already publishing this content with a three-month delay, I’ll stick to the original posting schedule, but I thought it was only fair to mention this modification of the plan.