Clean Up Your Shit! (Note #1)


self storage overflowing with boxes viewed from outside the unit through an open door
Bing image from the prompt: "self storage overflowing with boxes viewed from outside the unit through an open door"

It’s no surprise: in the Knowledge Economy, the key asset is… knowledge.

When someone leaves a job, their accumulated wisdom goes with them – even if their physical stuff stays behind. (Sorry, but NO ONE wants your 3-ring binders!)

What also stays behind are their electronic files. The question is: are they a useful repository of knowledge or just the digital equivalent of a 3-ring binder?

I’m reflecting on this because I’m leaving my job soon and I’m organizing the files I’ve generated over 10 years with the City. (If I left a mess, I’d be a massive hypocrite!)

I’ve already written guidance on file structures for work (, but this post goes deeper into your close-out process to help your coworkers and the future people who will inherit your electronic detritus.


All of the ideas expressed in this article are my personal statements and opinions, and do not reflect the opinions/statements of the City of Urbana.


Leaving a job happens in many ways: happy or sad, stressor or relief. (In my case: “all of the above.”) In this discussion, I’m focusing on the situation where someone knows they’re leaving and wants to do the right thing on the way out. Let’s not dwell on the unexpected departure, but here’s one lesson: more than one person needs Administrator rights for any technology.

The key message: before you depart, you can help your team and coworkers by culling your files and organizing what’s left.

We’ll get motivated first then proceed to practical suggestions… before I dissolve into philosophical ramblings on Artificial Intelligence and the futility of my whole premise.

Why You Should Care About File Organization

YOU are the one who can best organize your stuff. Only you know what’s there – or at least you know it better than anyone else.

Why bother, though?

Your motivation might differ, but my inspiration comes from organizational loyalty. I like my coworkers and I want the City to succeed, plus there’s some guilt about not finishing things and living up to what I preach to others.

Here are three motivators to prompt some thought for you (Note #2):

Be helpful.

When other people go looking for files, keeping everything is less useful than paring it down to what’s needed.

It’s like a relative gave you the keys to their self-storage unit and told you that a few family heirlooms were inside for you to take. You open the door and see wall-to-wall overflowing boxes. How long will you spend searching before you get demoralized and give up?

I’m serious: it’s better to save too little than too much. Yes, it’s possible you will delete something that someone looks for later. Don’t worry – you’ll be long gone. At the City, many times we searched for a document among past files… and couldn’t find it. You know what? Life went on.

Be thrifty.

Storing files for one person isn’t a big cost but consider the storage costs for all employees (present and past) – and the redundant backups.

If you don’t get rid of your stuff, other people won’t get rid of your stuff either. This is how organizations accumulate a burden of storage that never shrinks. Other people won’t feel comfortable getting rid of your left-behind stuff.  They think “maybe they saved it on purpose” or they simply don’t know what it contains because it’s a cluttered mess.

Leave No Trace

This is an outdoor ethics principle that I learned through Scouting (see Note #2) that applies to digital information, too.

The outdoor principle is that you should minimize your personal impact so that others can enjoy nature without seeing your effects, like your litter or admiring the beautiful shell that you did NOT take home. In other words: don’t be selfish, maximize the experience for others.

Applying the principle to digital files: the goal is to minimize your personal storage and instead improve shared file organization. Read on for specific guidance…

How To Clean Up Your Files Before You Leave

Once you’re motivated to organize, what should you do?

At work, some digital storage is shared, but you probably also have personal files like your Desktop, your Documents, and cloud drives. That’s what we’re focused on here – your file folders. (Email is separate and covered below.) If you created a folder on the shared storage that HAS YOUR NAME on it, then you need to go through that, too! (I’m deeply against this practice: see Note #6 here:

Notice I recommend sticking to the file folder level. Look in a folder only to understand its contents. It’s often not worth your time to sort through the detailed files. (Except for video! Please see Note #3.) But you could apply all of these rules to the file level if you wish.

Here’s the core process:

STEP ZERO: Before you start: make sure you have the ability to recover from a backup. Talk to your IT folks to find out how far back they can recover files if needed. If you have no other option, make a copy of everything to an external drive. (Don’t store it back in the same place – this risks accidental deletion catastrophes!)

  1. Once you know you can recover files, start working your way through the first folder.
  2. Proceed to the deepest subfolder of the first folder and work your way up.
  3. For each folder, are you going to share it, delete it, or keep it? – See the discussion below on these three terms and Step 6 below.
  4. Once you complete the first subfolder, move to the next subfolder, and repeat the process.
  5. As you empty all of the subfolders, delete the folder. Continue this process all of the way up to the top level, so that the root folders start diminishing. Visible progress!
  6. If you decide to keep folders, some extra steps:

  • Create a new top-level folder called Archive.
  • After you finish sharing/deleting everything out of a folder and you want to keep the rest, move it to the Archive folder. This way it’s removed from the folder structures you’re cleaning up.
  • At the end of the process, you’ll have one Archive folder with items you kept on purpose. Do some organizing of the Archive as you move things there. Make it useful!


If other people want access to the folder’s contents, move the folder to shared storage into a structure that’s logical and time-based. If the structure doesn’t exist, create it. Guidance on structures can be found in guidelines 1 and 2 here:

Some structure decisions write themselves. For example, government entities have a retention schedule by type of record. YOU are the best person to judge whether any of your folders rises to the level of a record, and what record classification applies. Structure your files around the records classification and downstream processes for records requests and disposal will go much faster!


Yes, lots of things should be deleted. It can be scary though, so here are some motivators to prompt thought on deletions (Note #4):

  • Be paranoid: If you have personal files that got mixed into your work files, take them with you or delete them. You don’t want to leave them behind.
  • Be merciless: Not everything is an artifact worth preserving. Posterity (or your coworkers) doesn’t care about the 10 rounds of reviews on a document. Just save the final product.
  • Don’t forget to flush! Possibly pushing the metaphor of this blog’s title too far, remember that deleted items from your desktop, cloud drive, and email go to an intermediary location (Deleted Items, Trash, Recycle Bin, etc.). After you’ve done your cleanup, clear out these intermediary locations! Otherwise, IT will still be storing items that you already decided are not needed.


Keeping some folders in your personal storage is OK. But remember, anything that your coworkers might want to find should be shared, not kept!

The ideal is “Leave No Trace” and have zero files left in personal storage. The reality is you don’t have time to review everything. If you follow the process above, you’ll wind up with one Archive folder that has what you intended to keep. This tells others who look in your files that you purposefully kept these items.

email – A Separate Discussion

My views on email are influenced by my role as an IT Manager, responsible for making sure email is operational and protected.

For IT managers: more email = more problems. Searching, backing up, and restoring email takes longer as the size increases.

The problem is that people are email hoarders. I’m an email hoarder.

My Love/Hate Relationship with email

In 1993, I started work at an IT company before we had internal email! Corporate folks had it, but not field staff like us on the project sites. (They rolled it out soon after….)

Since then, email has been both my nemesis and savior. Pulling out an old email has saved me time, effort, and cost many times. But I’ve spent untold hours of my life organizing emails into folders in case they were needed. (I’ve moved a giant discussion of my email process into a page on my website, here:

So, when you read the next section, just know that I’ve been organizing email as I go. I’m not catching up on this now!

How to Transition email

If you have well-organized email folders that you want to share with others, move them to an email account others can access. (This gives you more privacy instead of granting them full access to your account.)

Our IT division has one generic email address we use to register on websites and collect invoices – and multiple people have access to the generic account. (Generic email addresses are my recommendation to all organizations! People come and go, so it’s best to use emails like for unbroken communication. For more on this, see Note #5.)

To transition my email, I’m moving whole folder structures from my personal email account to the generic one.  For example, I have a folder called “Invoices” with sub-folders by fiscal year. I also have sets of folders with discussions from the contracting and implementation of our existing systems. My structure isn’t fancy; I have a folder called “Internal Systems” and sub-folders with each system’s name. For invoices, it’s a folder called “FY 24”.

More relevant for everyone who doesn’t organize email into fastidious folders:

Don’t worry about it! Searching email has come a long way in the past decade. It’s now much easier for other people to query your email to find useful information than it used to be. (Note #6)

However, here is some clean-up for everyone to consider:

  • If you have any personal items in your work email, get rid of them.
  • Do a search for large email (greater than 50 MB) – and consider deleting the email or at least removing unneeded attachments. Your IT team will thank you.
  • One more time: don’t forget to flush! Empty your Deleted Items as the last step.

Kipple, Zombies, and Thermodynamics

OK, now for the philosophical ramblings.

Ten years as a City IT Director were hard for me because I like organization and I’m bothered by informational chaos. When I arrived, shared electronic storage was a mess. Dealing with that situation led me to write some of my blogs, including this one.

I don’t blame my City coworkers. Keeping electronic files organized is difficult for everyone. Sharing data makes it harder, in direct proportion to the number of people sharing it. (Divided by the number of metadata tagging rules that people always follow… plus one, because you can’t divide by zero. Hah! A math joke ; )

In shared storage, everyone lives with communal messiness, which we use to justify our own data slovenliness. Thermodynamics’ second law applies to information management:

“The level of disorder in the universe is steadily increasing.”

Put more colloquially:

As we accumulate more shit, it gets harder to find things.

Busy people don’t have the time to organize their files, but without constant effort data chaos will seep in.

Two movie references to illuminate:

  • Fighting against this disorder is a hopeless slog. You feel like one of the characters still alive in a zombie movie; no matter how far you go, the opposition just keeps mounting. I’m on record that zombie movies are the scariest because it’s a mathematical certainty that they’ll soon outnumber you. (This is explored in Note #2 here: In the same way, we will never defeat data chaos.
  • Kipple is a wonderful term for this data chaos. The (much better!) book that was adapted into the film Blade Runner – the book was titled Do Androids Dream of Electric Sheep? -  described Kipple as “the debris that naturally built up around a society when not enough people were willing to participate in maintaining the environment.” (Source - Blade Runner fandom Wiki) If no one takes action, Kipple simply accumulates – like electronic files in shared directories.

Oh Wait, Forget Everything – I just Said

Here’s the futility of everything you just read above. (I’m sorry for wasting your time!)

Let’s acknowledge the AI-liphant in the room.

My whole thesis that “Organization is Important” is undercut by improving search algorithms. Technology can classify documents based on rules. Tools can retroactively recognize text on PDFs that were scanned as images. Even video files can be “watched” for searches by keyword or the whole video can be summarized for you.

So, why not just keep everything? Storage steadily drops in price and years of past files can now fit on a USB stick. People are just going to search it anyway – so why organize at all?

I don’t have a good answer to that, but I’m not taking that excuse myself. Maybe my guidance can be turned into rules for categorization. (If so, please see Note #7) Let’s hope the AI doesn’t learn its rules from the average organization’s shared storage!

Another reason: while AI has capabilities, organizations will need time to leverage these tools – especially in local government. In the meantime, people will still be looking for the “heirlooms” that you leave behind, so Clean Up Your Shit!


Here is an update on a past blog, which also relates to me wrapping up items at the City.

The Internal Website transition finally occurred! I wrote about it here:

That was about two years ago, and we just changed over in March 2024… talk about Tectonic Speed! The delay was my choice: I was holding on to this task for our new Business Analyst position, but the position was posted too late to overlap with me. I wound up like a relay runner with no one to take the baton.

So we went live with a soft “burn the ships” approach We took the most used content and revised it onto the new screens, then simply cut everyone over. Cutover was crisp. The Internal Website is everyone’s browser home page. After a warning, we just flipped the switch on a Tuesday. (Tuesday is always the best day to try new IT things. It’s not Monday, but it gives you the rest of the week to get support for the inevitable problems.)

It was a “soft” burn the ships cutover because I kept an escape path: there’s a link that they can use to go back to the old site. Resolving all of the information on the old site (accumulated over 20 years!) will take some more time. Good tasks for our future Business Analyst…


Note #1: Sorry for the crass title, but I’m completing my trilogy of “Shit” articles here – titles derived from George Carlin’s classic routine on the “Two Minute Warning”. ( - but I added a link to the clip below!)

Note #2: The first two points are borrowed from the Scout Law and the third is a principle adopted by Scouting. My appreciation for Scouts BSA runs deep, as described here:

Note #3: Video files are worth a mention, due to file size. After you decide what folders will be in your Archive or shared storage, do a search there for video files. Can you delete the video, while keeping the rest of the folder’s contents? If so, your IT folks thank you.

Note #4: These motivators in the “Delete” section are NOT from the Scouts BSA. Just making that clear...

Note #5: If your organization doesn’t use shared generic email address like then ask your management/IT folks to create one. It really helps with transitions between people.

A second piece of advice for your team: start using a shared password manager that handles Team accounts. Then each person has their personal passwords and also access to passwords shared among the team. When one person updates the shared password, the change updates centrally for all – and no one has to ask or be told about it.

Note #6: Given email search, are organized email folders still useful? Yes, because searching is more efficient. If you pinpoint a folder to search within, you’ll have fewer results to review. But if I knew 10 years ago how good search would be, then I would have created a lot fewer of them. Now I use consolidated folders (e.g., “project discussions”) instead of folders for every topic.

Note #7: Here’s a rule to automate for those people who create the tools. When a folder (or sub-folders) has multiple files with similar names and an indicator of a version number (v1, v2, …) assume they’re all drafts of the highest version – and recommend that the rest be deleted as “draft copies”.  In many organizations - especially ones with legal staff - this will eliminate thousands of unneeded files in a swift pass.

George Carlin - "Die Big/2 minute warning"