Digital Decluttering: Mistakes Made, Lessons Learned (Premium)

Flush with my decluttering success, I ended up trying to do too much at once and made too many mistakes, causing me to run up against multiple blockers across each project, halting my progress. And so I am scaling back my unrealistic expectations, rethinking my goals, reversing the mistakes, and returning to a more deliberate, single-tasking schedule.

What can I say? I flew too close to the sun.

And you know what? It’s OK. I did a great job expanding the scope of this work with each passing success and I got more done than I ever imagined was possible. By learning from the mistakes I did end up making, I can get back on track and arrive at a better place. Which is, of course, its own form of progress and success.

So maybe I should explain what that all means first. After all, there are good reasons for what I’ve done so far, reasons that I think justify the work. And as this decluttering project expanded greatly, I came to see that what I was really doing, broadly, was setting myself up for a future that is more manageable and organized. This is a system, a sustainable way of doing things that should prove effective for the rest of my life. It’s just a matter of putting it in place.

The system

Fundamentally, my life is no different than that of anyone else, it’s a mix of personal and professional (or, work). There isn’t always a clear divide between the two, in part because I’ve worked from home for almost 30 years now, but whether it’s the physical items we possess or the digital data that we store, that breakdown is simple and works well conceptually. Personal and work.

As you may know, my wife and I have deliberately spent a lot of time thinking about and implementing ways to downsize and declutter our lives by removing unnecessary things. This isn’t a one-time, set-it-and-forget-it kind of thing. It’s something you have to be mindful of at all times, and because life happens, it’s something you have to return to again and again as things inevitably pile up. Clutter, like life in Jurassic Park, always finds a way.

For a long time, downsizing was a far-off goal, an aspirational ideal. And for all the right reasons: We have two kids and they lived at home until they went off to college, and we purposefully stayed put in the same house for over 15 years to give their lives—friends, school, activities, whatever—continuity and stability. But during that time, we also put our ideas to work through annual decluttering pushes ahead of the summer home swaps we did each year. After all, some other family was coming to stay in our home for three weeks and we needed it to be as clean as possible. Not “straightened up because guests are coming to dinner” clean, but actually clean, the entire thing, top to bottom.

Separately, I would also go through regular purges of things, via “Everything Must Go” events and similar, and by methodically reducing the number of items I had on hand, whether it was for work (electronics and the like) or my personal use. During these years, we moved from physical media to digital, eliminating music CDs, movie DVDs and Blu-rays, and paper-based books. Via my 2019 bulk scanning experience, I digitized virtually all of our organized, paper-based photos and then threw away those photo albums too. After our son went to college, we financially downsized by moving to Pennsylvania. And after our daughter went to college, we literally downsized by selling that home and moving into a much, much smaller apartment.

And as I wrote at the start of this series, I was at that point confronted by the hard reality that all of this work we did over so many years, while not completely in vain, had not set us up for the clean transition we had dreamt of all those years ago. Despite the annual deep cleanings and the regular decluttering, we still landed in this small apartment with too much stuff. And in an interesting coincidence, I also discovered while trying to correct that mistake that much of what I had been doing all along was not really decluttering but rather creating doom piles. I was hiding and organizing many things. All those years, I thought I was doing a great job, but I did not get rid of enough.

The solution there is simple enough: Just get rid of the crap. But the reality is a bit more nuanced. We can’t just throw everything away. Some items are valuable enough to be sold. Some are usable enough that they should be given to people who would appreciate them. A lot of the remainder should be properly recycled. And of course some of it can be digitized in some way and we can then get rid of the physical originals. My wife does most of the work on the physical side of this clutter equation. Where I come in is on the digital side.

And from an organizational perspective, our digital stuff—the documents, photos, music, videos, and other data that I want to keep and protect—suffered from different issues. Some stemmed from the many technological advances that occurred over those years and some was self-inflicted as I evolved how I did things. Music is a good example: As we moved into the digital music era, I ripped my CD collection multiple times, each time to a higher quality and/or superior format, and then as we moved into the streaming era, I let my ripped collection languish more and more as I moved from service to service. And by the time I got to organizing that old collection as part of this recent decluttering push, it was in OK shape but needed some work.

My documents archives (work and personal) and my photos archive (personal) were sadly in much worse shape. The documents were entirely my fault, while the photos were a combination of the same tech evolution that shaped our I listened to music over time (from paper-based photos to digital cameras to smartphones with the addition of high-capacity cloud storage, in this case) and my own mismanagement. Not that it matters: Both were organized to some degree, but there were also hundreds and hundreds of gigabytes of data in “To file” and similar folders that needed to be sorted, deduplicated, and then organized back into master collections that could be replicated to multiple locations (cloud services, a NAS) for resiliency.

And this is where the notion of a system comes up. Even in their previous states, there was at least some system in place for these document and photo archives. What I wanted to do was adopt a formal system for both, and where needed for all of my digital collections, one that makes sense now, will make sense forever going forward, and is sustainable. Meaning, I will never need to change this system again. I will just need to do occasional check-ups or maintenance on various schedules. Something simple and fast.

And to be fair, I had the germ of this system in place already, so adopting it everywhere made sense. This system works like my breakdown of life into personal and work, except in this case, it’s about things that are archived and things that are not, or things that are current. Archives are important enough to store and keep, but they are infrequently accessed or updated. Current things are transient and temporary, those things that are accessed only right now, in the present. And when you’re done with a current thing, you archive it or toss it away.

Consider documents. In my OneDrive, I now have two top-level folders in the Documents folder, Archive and Work. This is purposeful because the documents I store are either current work—books, articles, series, podcasts, or whatever else I am working on now or in the process of working on—or they’re archived. The folder names are so obvious that no explanation is needed.

My documents also span both work and personal. And so if I navigate into Archive, I will again find two folders, Personal and Work. And you guessed it, Personal contains my archived personal documents, while Work contains my archived work documents.

From here, the organizational approach I took is just something I prefer because it’s logical and makes sense to me. And it’s mostly date-based. The Personal folder contains folders for each year (1993, 1994, and so on), plus a few topic-based folders (Travel, Future, Eternal Spring) that may or may not be later integrated elsewhere, deleted, or just ignored. (Who cares? It’s an archive.)

The Work folder is organized identically: There are date-based folders (in this case from 2011 onward), plus the folders Books, Penton, and Websites. The Penton folder is basically my pre-2011 organizational system, and there’s no reason to try and re-organize this huge thing into my newer system. (Because, again, it’s an archive.)

The date-based folders in there represent my current organizational system. For the most part, each year contains sub-folders that represent months, and they are named like 2022-01, 2022-02, and so on. (Some year folders contain random topic-based subfolders too for whatever reasons, and I’m not going to bother trying to organize them because, again, it’s an archive. This is organized well enough.)

So that’s the documents archive in a nutshell. Personal and Work folders. Date-based sub-folders. Simple.

But the key to this system, really, is the other half of it—the current items—and how I will integrate these documents when I’m done with them. In other words, how I will archive them. And here, again, I have made things as simple as possible for myself. As noted, there is a Work folder in my Documents folder in OneDrive (next to that Archive folder). And that folder contains just 7 sub-folders, 6 date-based folders, and a Work folder. That Work folder is organized with folders like To-do (everything I’m working on right now) and Book (the books), while those date-based folders are recent archives with names like 2023-07, 2023-08, and so on.

The idea here is that I will at some point move these folders from Work into Archive/Work which, you will recall, contains year folders, each of which contains month folders. When it’s time to archive the 2023-07 folder, for example, I will move it into Archive/Work/2023. This, too, is another key aspect of the system: There’s a schedule. And thanks to me recently fully organizing my document archives for the last time and then replicating it in multiple locations (it’s also available in the cloud storage associated with my Google Workspace and Microsoft 365 Business Basic accounts, plus on my NAS), I will soon need to start archiving documents to those other locations too, and on a schedule.

The schedule isn’t automated, but it’s simple. I create a batch of 6 month-based folders in Work twice each year, once at the end of December and once at the end of June, each time for the next six months. And once each quarter, I move the three oldest date-based folders in Work to the archive. And it’s almost time for me to tackle that latter task as it’s almost October. The nice thing is, I don’t need to create reminders for any of this. I perform these tasks on time all the time because of the way I work.

As you may recall, I pin my Book, To-do, and current month archive folder (2023-09 as I write this) to the Quick access list in File Explorer’s navigation pane.

I organize the files I’m working on as noted before, and when I’m finished with a document—a news article maybe, a Premium editorial, it doesn’t matter—I drag it into the current month archive folder (again, 2023-09 right now) that’s right there in Quick access. And on the first of every month, I unpin the previous month’s archive folder and pin the new current month’s archive folder in its place. If it’s the start of a quarter (the 1st of January, April, July, or October) I will go into Work\Archive, grab the three oldest date-based folders, and move that into the document archives (in Archive\Work\[this year]). (Remember, I create six more month-based folders, for the next six months, twice each year too.)

And here we go: It’s almost October 1. Let’s see what’s about to happen.

October 1 is, of course, the start of a new month. On that day, I will unpin 2023-09 from Quick access and then pin 2023-10 there instead. But October 1 is also the start of the quarter, so it’s time to do some archiving. Looking in Work\Archives, there are six date-based folders, 2023-07, 2023-08, 2023-09, 2023-10, 2023-11, and 2023-12, representing the last six months of this year. So I will move the first three of those folders (2023-07 through 2023-09) to the documents archives. In the past, this was literally one destination, in OneDrive. But now I will put a copy in my Google Workspace and Microsoft 365 Business Basic accounts, plus on my NAS, as noted, too.

This may seem ponderous to you, and it’s certainly ponderous writing about it. But in practice, this is simple and quick. And as important, it’s sustainable. And I know that to be true because I’ve literally used this exact system (with documents) since 2011. It has never not worked.

At a high level, this is what I’m looking for with all of the “stuff” that I store digitally. A simple system that works, makes sense, and is sustainable. The wrinkle—it’s not really an “issue”—is that the other archives and collections are each a bit unique. Fortunately, they’re also easy enough to describe quickly, unlike the documents system described above. And each requires little or no ongoing work.

The photos collection is perhaps the most similar to documents in that I have archives—in this case, scans of older photos plus older digital photos—and more current photos, which were mostly taken with smartphones. But the nice thing about photos is that the system is now semi-automatic: our phones back up automatically to Google Photos, OneDrive, and now Amazon Photos too. And when we decommission a smartphone because we’ve upgraded to a new one, I copy all of the photos off of it first and copy that to the NAS. That’s the only thing I have to do manually.

The music collection requires no further work. It’s organized and archived in multiple places and there is no “current” anything. I can just leave it alone. It’s an archive.

Ditto with our home movies and video collections. We don’t take home movies per se anymore, but any videos we do take with our smartphones are backed up and archived along with the photos. Home movies and videos are archives as well.

Simple.

And when you consider all this, you can see the sustainability component. My work documents require some manual monthly, quarterly, and biannual “work,” but it’s simple and fast. And our photos require me to perform a backup to the NAS whenever we upgrade a phone. That’s literally all of it.

That said…

I still have work to do

With all that out of the way, it’s time to look at where I’m at with decluttering, the mistakes I’ve made, and the changes I’m making to both the process and the schedule so that I can move forward with this work in a more efficient and sustainable manner. Then, I wanted to discuss some of the lessons I’ve learned during this process though, spoiler alert, me being me, I did write up some of these as I went. So this will be a summary plus a few new or overreaching thoughts.

In Digital Declutter: Finish Work, Final Scans, and a Peek at the Future (Premium), I wrote about how I was expanding my declutter work in the wake of my document archive success. There was a  massive paper scanning task that I then thought would put an end to that kind of work, but the thought of all that scanning was daunting so I decided to declutter my music collection and then re-digitize the home movies for which I still had the camera first. And God help me, both of those went great: The music collection was reasonably clean to begin with, and I found some cheap cables and made short work of the DV tapes.

But, as noted, I made mistakes.

First, I announced that I was moving my video archive to YouTube, and I did so pretty early in the process, and before I completed the document archive. This was always a good idea, on so many levels, as I could stop archiving what amounted to many, many GBs of video files, store them in YouTube for free (thanks, Google!), and share them with the world too.

But maybe I got a little too excited. Looking at my various Google accounts, [email protected] (the Google Workspace account associated with this site) and a personal Gmail account, I (understandably?) chose [email protected] and started uploading. And then I realized that I should “rebrand” the YouTube account associated with [email protected]. And that it should be the official YouTube channel for Thurrott.com, this was very exciting, and boy did I have so many videos to share. Within a short time, I had uploaded about 300 of them.

It was at this point that I realized the downside of this change. I had been using [email protected] for years for everything, work and personal. It’s my primary email account and where I consolidate all of the emails I get at my other accounts. It’s my primary online identity. It’s … me. And because I use this account to sign in to many other online accounts, it’s messy. I have my music associated with this account in YouTube Music, for example. And so when I played music, I now saw the Thurrott “T” logo instead of my face in the profile picture.

I responded to this by deciding to finally do something I had wanted to do for a very long time and “declutter” my online accounts too. I would switch to my personal Gmail account for personal things (YouTube, YouTube Music, etc.) and I would stick to work-related things with [email protected]. It was so obvious, and the push I needed to make this happen. (I had big plans for my Microsoft accounts too.)

There were just two problems.

The first was the many blockers that I then ran into when I started this online account decluttering process, something I only glossed over when I wrote Digital Decluttering: Online Accounts (Premium) because I had run into so many roadblocks and still believed that moving my main digital photo collection in Google Photos from Google Workspace to Gmail was manageable despite its mammoth 558 GB size.

But Google Photos was just the tip of the iceberg. For example, I have, to this day, never successfully transferred even one of my many, many YouTube Music playlists to any service, let alone my Gmail-based YouTube Music account despite trying and paying for multiple services that exist only to do that very thing. This is a surprisingly painful and error-prone process that will require me to manually add missing songs and fix incorrectly identified songs. Like, dozens of them in each playlist. This will take way too much time.

The second, and you just have to laugh it’s so dumb, is that we already have a Thurrott.com YouTube channel. For f#$k’s sake, of course we do. This channel has over 5,500 subscribers and over 1,400 videos, most of them episodes of First Ring Daily, and I cannot afford to just drop that channel and move to something new. Even though I have uploaded 300 videos to that new channel.

I am, in a word, an idiot.

Or, to be fair, a little overwhelmed. In addition to taking on this business this past year—there are so many moving parts, which will make for a Behind Thurrott.com post soon—and still having to do my normal everyday work, I took on more decluttering work in a short period of time than maybe was prudent, and seeing enormous success then expanded that work to more things. And this happened. I mean, f#$k me.

There were two obvious solutions. I could keep both channels, I guess. Or I could do what I am doing by understanding that moving those 300 videos from the new (and soon-to-be abandoned) YouTube channel to the original channel would be both easier and smarter than any alternative. Tedious, yes. But easier and smarter.

And so I am now working to correct that mistake. I used Google Takeout to download all of the videos from that new channel, which was actually pretty quick. And then I began uploading them to the existing channel. As of today, I’m about 25 videos short because YouTube has a daily video upload limit of 150 videos, which I hit both yesterday and the day before. And then I will use the meta-data I also downloaded with Takeout to (re)add the titles and descriptions for each video, publishing each as I go, making them live on the original channel.

Tied to this, I’m cleaning up the branding on that channel and have already added a few playlists—for First Ring Daily, First Ring Daily special episodes, and Live events—and will add more topic-based playlists for these 300+ new videos and whatever else is up there. This task alone is fairly big, obviously, and it will take some time. But I’m doing it.

Very much tied to this, I am scaling back my online account decluttering ambitions. I have to. It’s just too much. That means that I will continue to use [email protected] for YouTube Music and YouTube, among other things. The dream remains just that, a dream. I won’t waste time describing all the work I’ve done setting up my personal Gmail account for any number of things, it’s not worth it. But that is all winding done.

Well, most of it is.

In Digital Decluttering: Online Accounts (Premium), I discussed my surprise that my so-called master photo collection in Google Photos does not, in fact, contain all of my photos. And so this decluttering task, at least remains: I will consolidate that collection with the folder-based version in my OneDrive (that is duplicated on my NAS) and then ensure that the final version is replicated across all of those places (plus Amazon Photos). And that, going forward, the system I described above will ensure that they all stay up-to-date automatically (or, in the case of the NAS, manually).

I also have the loose scans to finish, and that takes two forms.

First, there’s the collection of items I described in Digital Decluttering: Detail Work, Final Paper Scans (Premium), in which I spent a manic weekend, I thought, “finishing” at least the scanning part of that job. That work is still ongoing, and while much of it is organized in place, there are over 1,800 files in there and there are still dozens of unorganized, undated, and meta-data-free photos to figure out. That will take time too.

Second, as I wrote in From the Editor’s Desk: Groundhog Day (Premium), as part of a difficult weekend of “pre-moving” last weekend, my wife and I moved three van loads of stuff from our current apartment to the condo we’ll be moving to soon, I discovered to my horror that my doom piling ways had victimized me yet again: We found even more paper items to scan, hidden in bins that were in a storage container in a closet I never open or look at. The amount of work there is unclear, and while I’m hoping it’s not as much work as what I did over the manic scanning weekend, it could be. It doesn’t matter: I will solve this problem later.

Indeed, all of these events together have conspired to help me formulate a new decluttering strategy and a new schedule. There is the work I hope to finish before we leave for Mexico City in mid-October. The work I will begin after we get home in early November. (And then the work I will do while in Mexico City, which is updating the Windows 11 Field Guide for the Fall 202 Update/23H3; more on that soon.)

Before the trip, I will work on the video uploading and publishing and the associated YouTube channel, plus the loose scan organization and archiving. These are both big tasks, but the good news is that I can continue this work from Mexico if need be.

After the trip, I will get started on all the new (“final”?) paper scanning and see what that looks like, plus find a service to digitize my non-DV home videos (for which I don’t have a camera). My goal by the end of 2023 is to expunge whatever physical clutter I have, and to do so I will leave all out in the office I’ll have in the new place. No more doom piling.

But as I’ve said so many times recently, there’s always more. So we’ll see.

Lessons learned

Almost two months after I started my 2023 digital decluttering journey, I’m finally slowing down and am ready to put this phase of the work, at least, behind me. For a little while. Reflecting on this time period, and all that work, I see a lot of highs and then the inevitable lows, and I recognize in the latter the impact of those blockers, internal and external, that always seem to prevent success when completing daunting tasks. But overall, I’m happy. I did get a lot done.

The key lesson here, perhaps, is to never get into this kind of mess in the first place. As is the case with so many things in life, including even far-afield topics like health and personal relationships, it’s better to be proactive than reactive. As per the Pournelle quote at the top of the article, try to learn from my mistakes. You’ll save yourself a lot of grief and wasted time.

But there’s more, of course.

Don’t take on too much at once, as I did towards the end of this process. I started out strong, tackling one task after the other, but it all fell apart when I took on too much at once. No matter what you’ve fooled yourself into believing, people can’t multitask. And none of us are exceptions to that rule. Create a plan, stick to it, and finish it … one task at a time.

Don’t doom pile. For the ADHD sufferers like me, this is a common practice that creates the illusion of decluttering and cleanliness. But all we’re really doing is hiding clutter. And in my case, I had to learn this hard way, by moving—twice!—and being forced to confront the ramifications of my inaction. Doom piling is a bit like what I used to call “fake hustle” in basketball in that it gives the appearance of the real thing but doesn’t actually achieve your goals.

Learn to walk away. This is a great example of something I’m working on myself, but I went into this process being positive that I would fail, and I was surprised when I didn’t. This inspired me to keep going, which is good, but it also inspired me to take on too much, which is bad. Instead of continuing the downward spiral, I finally did as described in this article, cut my losses, and hit reset. This isn’t just smart, it’s healthy. And I’ll be ready to take on new decluttering tasks in a few months. And who knows? Maybe I’ll even finish what I started.

Finally, I have to come back to my age-old notion of “the right tool for the job.” I almost got bogged down early in this process when the tools I was using—File Explorer, that horrible HP Smart utility—were so ineffectual and slow that they made an already difficult task all the harder. And as I wrote throughout the series, I was helped along immeasurably by a range of tools, many of which I had only fleeting or no prior experience with. Key tools that help me here include:

DirectoryOpus. This powerful and complex file manager app is so useful in so many ways that I can’t stop gushing about it. It is much, much faster than File Explorer and it offers incredible built-in tools for things like finding duplicate files. It also works with anything that integrates into the Windows shell.

WinMerge is a dedicated file de-duplicator, but the key advantage to this app is its ability to compare duplicate files side-by-side and then sort the display into “left only” and “right only” entries so that you can quickly determine which to delete.

WinDirStat. This one I was very familiar with, and it’s a great tool for finding the biggest files within any drive or folder. That said…

WizTree works exactly like WinDirStat but is much, much faster and it has a prettier UI. It’s also free (donateware).

Pixillion. This solution was so useful for saving tons of disk space by batch-converting image files across my archives into more efficient file formats that I paid for it.

Mp3tag. This useful music file utility helped me batch reorganize my entire music collection into a consistent, logical folder-based format. Delightful.

7-Zip. Windows 11 has built-in file archiving and unarchiving capabilities, but 7-Zip is faster and more efficient, and it works much better when you have many archive files to bulk unarchive, as I did thanks to my Google Takeout downloads.

NAPS2. This is a free and open-source scanning utility that came up too late in the game to help me with my paper scanning in this phase of decluttering, but I intend to lean heavily on it in the next round.

I also use and rely on a number of online services, mostly from the big players like Amazon, Google, and Microsoft, as noted throughout this series. And though I think I’m pretty well versed in most of that, sometimes you can be surprised. And the big surprise in this process came when I went to upload my documents archive to both Google Drive (part of Google Workspace) and OneDrive for Business (part of Microsoft 365 Business Basic).

Given how much I use (consumer) OneDrive, and how well it works, I had expected OneDrive for Business to work identically. But I had so many problems getting that archive to successfully sync to this service that I gave up repeatedly before finally muscling through it. Google Drive, though, worked perfectly: I checked it the morning after I started the sync and was surprised to discover that it was done, with no errors, on the first try. Nice.

So nice, in fact, that I am experimenting with using that full-time in Windows instead of OneDrive. See? I haven’t learned from my own lessons.

Anyway, this is beyond long enough so I’ll end it here. I will check in again when I’ve finished up with the shorter new list of to-do items. It could be a while.