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How to declutter, organize, and name your digital files

Holding on to files that you think you may use later makes sense. But when you haven't touched some of these files in over three years, why keep them? 

If you can't articulate a reason with a date in mind to continue to keep a file, hit delete. Otherwise, you'll end up on a fast track to digital hoarding. 

The problem with digital clutter

Too many folders and files later, the original purpose of keeping these in your digital library diminishes over time. You may have saved them for one reason, but when it was time to use them, you didn't even remember you had them. Not even searching for them could have helped you in this case. On top of that, the search feature is only as good as how you named your files in the first place.

Getting started decluttering your digital files

Schedule a time to go through all your files and folders and delete what’s no longer relevant. Consider removing everything you haven't opened in over three years and don't have a set date to use them again. So for example those scanned tax documents are OK to keep until they're no longer subject to an IRS audit. Finally if you have an empty folder or folders with less than two files, hit delete. The purpose of folders is to organize groups of files—not to make it more difficult to access a file.

Dealing with a massive digital library?

If your digital library is gigantic, you may have to take a different and faster approach to cleaning up your digital space. After all, the intention here is to increase your productivity.

Consider putting everything in one folder. Then start moving files out of that folder as you use them. Then whatever is still in the folder after let's say a year or two, delete.

Yes, it's a riskier approach. But it'll free you from being attached to a digital monster that does nothing but slows you down. Or even worse, hiding from doing real work behind a never-ending digital decluttering project.

Now it's time to organize

Folders are the drawers of the digital world. They help you find files by grouping them into categories that make the most sense to you. The rule of thumb is to keep folder names short and simple. E.g., family and work; marketing, sales, operations; or whatever your use case is.

Then use subfolders (folders inside other folders) as needed. But don't get carried away, where you have to click through too many folders to access a file—that doesn't seem more productive. 

There is no magic number of how many subfolders you should have. But no more than three layers deep will keep you from going to infinity and beyond. 

Finally, after organizing your digital library, re-organize it as you use it. Match what you had top of mind—when you were looking for a file and couldn't find it—so that's easier to find next time!

Don't let digital clutter happen again

Now that you have a clear and organized digital space don't let it go back to a mess. Schedule a time, like a "spring cleaning," to go through your files and folders and delete what you no longer need. This regular practice will help you preserve a useful digital library.

Best practice for file naming

Search is as good as how you name your files. And there are many ways to approach naming your files. But here's one approach you can use and why.

Put a date at the beginning of each file. It'll give you a new reference date than the file's created or last modified date stamps. This manual date is specially useful when working with documents associated with a future date. E.g., A sales page copy for an upcoming product launch.

Use a hyphen between words. Even though most digital files support spaces, some others don't. E.g., some online libraries will populate %20 per space in the file's URL.

The underscore is another victim. Some systems will process underscores as non-existent—no spaces. So hyphens are your safest bet to preserve the spaces in your file names in most systems.

Finally, use a consistent naming convention for your whole library, or by folder. When using a different naming convention by folder , create an empty subfolder starting with "_". Then use the description of your naming convention as a reference to stay consistent. For example "_date-category-author." The purpose on the underscore here it's to bring the reference folder to the top of the list when sorting by name. 

Special thanks to productivity consultant Debbie Rosemont for advising me on this topic. I included many of her ideas in this post. You can listen to our conversation on digital decluttering and organizing here.

How to do walking meditation

Walking meditation is a great way to step out when feeling overwhelmed or unfocused at work. I learned this practice while at a meditation retreat at a Buddhist temple. The monks do walking meditation in the morning and after lunch to help with digestion.

Here's a quick guide on how to do it.

First, start standing still. Say “standing” three times. Then repeat “I want to walk” three times.

As you make the first step with your right foot, say “right go through,” then as you make the second step, say “left go through.”

As you go through the steps, the balance is on the standing leg. The standing leg controls the landing of the stepping leg.

The pronunciation of “through” should be synced with the landing of each step. “Left go...” as you lightly land the left foot in the floor, say “...through.”

The walking meditation happens in a straight line going back and forth. When you’re ready to turn around, after the last step, stand still again and say “standing” three times.

Then say “I want to go back” three times. After that, lift and pivot your right foot to the right, as you say “going back.” Then lift your left foot and land it next to your right foot as you say “going back” for the second time. Now, lift and pivot your right leg to the right as you say “going back” for the last time. Then lift your left foot again and land it next to your right foot.

Now that you’ve turned around start again by saying “standing” three times. Then say ”I want to go back” three times, and start walking as you say “right go through, ” “left go through.”

Do it out loud for a couple of rounds to help with concentration, then silently.

Strategy vs. Tactics: the difference and why you need both

Strategy and tactics often get confused. In some cases, strategy gets omitted completely from the plan.

So what's the difference between strategy and tactics?

Identifying a tactic is simple. Any type of specific action item that you can do or assign, and add a deadline to it—it's a tactic.

The simplest way to design a plan to achieve a goal is to set up a goal, then start outlining a list of to-dos to get there.

Then why is strategy important?

Because with a tactic-driven approach you can't intelligently change directions. Then when a tactic isn't working, it becomes a tactical roulette in hopes that something else will work.

The strategy is an element of planning that groups tactics under a common path. So that if a tactic doesn't work, is not game over, and your strategy will help you understand which tactic you should do next.

Examples of strategies and tactics

Marketing

Strategy: Engage industry thought-leaders to become advocates for our product.

Tactic: Create a list of top 10 industry thought-leaders and send them a free product sample.

Other options: If the free product samples don't work, what are other tactics we can try to engage them? E.g. Invite them to a product launch party, partner with them for content creation, etc.

Sales

Strategy: Close more deals by targeting our ideal client profile.

Tactic: Build a list of 30 accounts that meet our ideal client profile, and send them a tailored sales email.

Other options: If tailored emails are not working, how else can we engage them? In what other ways can we reach out to get their attention? E.g. Get introduced through mutual connections, send them a printed industry research report via direct mail, etc.

Personal development

Strategy: Take care of my body by achieving a weight within my Body Mass Index (BMI).

Tactic: Exercise 30 minutes per day.

Other options: If exercising 30 minutes per day doesn't work, what else can I do to achieve a weight within my BMI? E.g. Set a calorie goal and track calories burned and consumed, meal prep on the weekends to avoid eating junk food during the week, etc.

Special thanks to Seth Godin and Scott Perry who helped me clarify this topic in the The Marketing Seminar program.

A cheat sheet to achieve inbox zero and save time

Here are three simple tactics to improve your email productivity.

Reduce input

The more email you get, the longer it'll take you to clear your inbox. So the first thing you can do to improve your email productivity is to unsubscribe.

Free yourself from those ongoing emails you signed up for who knows when. Keep only the ones that matter to you today. Don't overthink it, if you change your mind later, you can always re-subscribe. To streamline this task, you can use unenroll.me to audit and update all your subscriptions in one page.

Auto-organize

Some ongoing emails may be critical to keep for reference, e.g., system notifications. For these type of emails that don't have a call to action, auto-organize them in folders.

You can do these with most email clients with either their filters or rules feature.

Set rules or filters to auto organize these emails in folders that make the most sense to you. So that if you need to see these for reference later, you can do that without letting them clutter your inbox.

Don't check, process

If there's one thing I want you to leave with after reading this post, is "stop checking your email." Opening your email to see what's new is a waste of time—procrastination. It also clutters your mind with other people's agendas over your priorities for the day.

If part of your job is to be available 24/7, then this advice would not apply to you. But if others are counting on you "to execute" more than "to be instantly available," then keep reading.

Here's how to process your email effectively:

  • Consider scheduling two to three small blocks of time a day to process your email. In my experience 11am and 3pm work best.

  • Start from top to bottom, so that if you're looking at an email with a running list of replies, you can see the full thread.

  • Process each email by taking one of the following actions. Delete if the message doesn't need a call to action or is spam. Reply if is something that will take you two minutes or less. Move it to folder for future reference and add it to your to-do list.

Using social media for your business (without the addiction)

An interesting podcast interview by lifestyle entrepreneur Lewis Howes with author Cal Newport on his new book Digital Minimalism [1]. My favorite part of their conversation was Cal's advice for those who use social media for business.

On the one hand, Cal preaches that we're better off without social media. On the other, Lewis teaches people how to use social media to build and grow their business as he has done for himself. So it was natural that Lewis would ask for Cal’s advice for those who use social media for their business.

Cal's advice is very practical. If it's clear to you that social media is essential for your business, treat it as something important. Use social media like a pro.

Social media pros are not on their phones 24/7 checking their company's social media channels. They use professional desktop tools to manage their social channels to fulfill a business strategy.

So don't use the excuse of using social media for your business to continue to justify your addiction to it. There is no need for you to be doing social media for your business while you're in the toilet, at the dinner table, or in bed.

To make it right for yourself set boundaries or in Cal’s words "put some fences around it." Block time in your calendar to maintain your social media channels, schedule your posts, and use social media management tools to avoid ads and other distractions.

Reference:

  1. The power of digital detox with Cal Newport

Your personal values: why they matter and how to honor them

“Personal values” refer to what you consider most important in life. They’re the foundation of how you distinguish between right or wrong, and how you react to the World around you. They also affect how you use your money, energy, and mind.

At first, you pick up your set of core values from your parent’s behavior. Then these core values stay the same unless you go through a significant emotional experience, or make an effort to change them.

Living in alignment with your values gives you peace and joy. Living in the opposite way results in dissatisfaction.

When you live with ignorance of your core values, it’s easy to be misled by harmful emotions or desires. You may also live according to someone else’s values (to fit in); or lose yourself into the values that dominate society like money, power, and sex. It’s an unconscious and unskillful way of living life that can make you unreasonable.

This ignorance is why sometimes you react, behave, and make decisions that you later regret. It’s why you continue to practice bad habits that you can’t seem to quit. It’s what makes relationships difficult. It’s why you rely on others, material things or circumstances to feel happy. It’s why you feel dissatisfied—even though you may be successful in the eyes of others.

In contrast, knowing your values can help you decide what kind of career to pursue or whether to start a business or not, what kind of relationships you should seek, or how to best resolve conflicts with others. When your values are clear, making the right decisions gets easier.

So take the time to acknowledge your values to gain clarity about who you’re before you go after what you want.

You want to grow, so you work hard pursuing goal after goal. But fulfillment doesn’t come from achieving goals. It comes from fulfilling values. So take the time to slow and reflect what’s important to you in life first.

To discover your values, visualize the worst and best moments in your life. The worst times will show you your values based on the value or values that were violated at the time and which had a negative impact on you. The best times will show you your values based on the values you honored and made you feel great.

Another way to discover your values is to think about the attributes of the people you most admire. These attributes will show you your values based on values that you aspire to make part of your character (who you’re). Finally, get an outside perspective from people who love you and know you well. Ask them why they appreciate you. Their answers will show you your values based on the values you’re already living today.

Using these tactics, put a list of 10-20 values. Then rank the importance of your values as if it was a tournament. Put them into a bracket, and start making your picks. Prioritizing matters because it will assist you with difficult decisions. As sometimes you’ll have to pick between choices that may meet different values. This is when you must know which value is more important to you.

Don’t stop at discovering your values. That’s only the first step.

After you narrow down on your core values, don’t just let them get stuck in a sheet of paper or your computer. Set up a time to check-in with your values monthly or quarterly. During this time, score each value from 1-10 based on how well you’re honoring each. Then plan steps you can take where there is room for improvement.

By working on narrowing the gap between your values and how you behave, you’ll feel more satisfied about your life.

Can I trust you?

Trust means someone can count on you. It says that when you make a promise or commitment, you keep it.

People who we trust are responsive, honest, objective, and reliable [1]. Here is how these four behaviors manifest in different roles.

AS AN INDIVIDUAL CONTRIBUTOR

It means you respond to your messages or calls within a day. You always tell the truth. During disputes or comparisons, you treat everyone or everything the same. When someone is counting on you with a task, you "do things right" and on time. Or at least communicate when you can't make a deadline.

AS A LEADER

As a leader you also must be responsive, honest, and objective. But how you’re reliable is different than an individual contributor. Your team is counting on you to assign them with "the right things to do." Everyone should understand how their work fits into helping the organization reach its goals.

Synergy means 2+2=5. Our existence and growth depend on synergy. But without trust, we can't create synergy. You can't break trust, you can only break yourself when you're not trustworthy.

Can I trust you?

Reference:

  1. Four Behaviors to Building Trust