Month / February 2025

by Sam

Inbox Spring Cleaning

I happened to walk up on my charming & delightful roommate while she was mindlessly poking at her computer; I could see she was in her email, releasing a periodic heavy sigh.

“What are you doing?”

“Cleaning my inbox – there’s so much garbage in it that I can’t find anything.”

I looked – she’s right. It’s a mess.

How does it get that way?

“Sign up to become a member of our community”.

“Request a free catalog”.

“Get notified of the latest sales and online coupons”.

“Like us on Facebook”.

Any one of these may plop your mail address in many a mailing list, including lists for which you never signed up.

You might be wondering if it’s too late to stem the tide (or tidal wave). Admitting the problem is the first step – here are a few suggestions get yourself on a better path.

Declare Email Inbox Bankruptcy

Step 1: Select All in the Inbox (Ctrl-A)

Step 2: Delete All. 

Step 3: Confirm deletion.

It’s a harsh step, but sometimes that’s the only way to do it. Here’s a secret: I’ve done it. The theory is that if it’s really important and requires action, senders will often resend it to you (at least in the work world, anyway). It’s surprisingly effective (if you’re comfortable doing it). Once you do it, though, you need to take measures to help keep it clean. So keep reading.

Unsubscribe

Sometimes this is helpful, but it really depends on the credibility of the source. Reputable companies and list managers will truly unsubscribe you, others simply just move you to different lists because you’ve now verified that your address is valid so it’s gets “repurposed” (looking at you, Klaviyo, you bastards). In those cases, it’s like playing Whack-A-Mole.

Use your Junk Mail folder

Most mail systems now have some intelligence behind them, along with a junk mail or spam folder. If you move a message to junk, it teaches the mailbox what junk is for you, and it will start automatically moving things there. Sometimes it misfires, so check it every now and then to make sure there are no false positives. Mark them as “not junk” to keep future messages from a sender out of the junk mail folder.

Use a mailbox rule or two (but not 12)

This is actually the method I use. It’s considered heresy around Pug Hollow to receive a coupon and just completely disregard a savings opportunity while at an establishment I frequent. The answer to that dilemma is to add a rule (Gmail calls them filters) to the mailbox that identifies the frequent-fliers and simply move them to a different folder in my mailbox (for me, that folder is fittingly called Sales Crap). If I’m out and think I have a coupon I can use, I can look in there. Every few weeks or so, I empty the folder with two clicks (instead of wading through my inbox). Incredible time, noise, and stress saver.

Pro Tip 1: Some rules engines (like the one in Outlook) allow you to run your rule on demand on already received items. It’s like taking a firehose to clean your inbox (and helps avoid the bankruptcy path).

If we’re talking about your work inbox, coupons and sales messages may not be the problem; the dreaded CC: on messages might be burying you instead. For that, I’ll refer you to this item from Scott Hanselman about the one email rule that everyone should have. The short version is move those CC: items out of your inbox and into a different folder. CC: can (and should) be translated to FYI. Things that require immediate action should have me in the TO: line. For people that get a crazy amount of mail, this can be life changing.

Be careful not to get nutty and start creating sets of exotic rules or filters that help manage some crazy folder/filing system in your mailbox. You will end up spending more time managing the system than you should. 

Pro Tip 2: Other than my Sales Crap folder, I don’t use folders and there are absolutely no folders nested in other folders. Search is powerful – if I need to find something, it’s proven to be very effective without the headache of maintaining a filing system. If you combine it with using things like Categories or tags, searching on tags is a lot easier than a folder structure.

These tips should help you even the fight with the onslaught of incoming mail.

How you reply matters

If you answer a lot of questions (like I do), it’s really easy to get buried in responses to those questions. They take a lot of time to answer. The bad part about that is (at least in my case) answering the repeat questions – because it’s really rare when I get a true “one-off” request. 

So we have to ask ourselves this question: do they deserve the gift of my/your keystrokes in the form of an answer? It depends on how you bundle and distribute those keystrokes. Going back to Scott Hanselman, take a peek at three and a half minutes of this keynote he delivered. I’ve adopted this approach and can attest to its value. I recommend the whole keynote, but this will jump you to the 18:05 mark.

Spoiler alert: don’t answer in email, unless that email has a URL to the answer.

For my work, I really don’t like using email for collaborating; it’s harder to do, and there are much better tools for group work. I speak to people about better collaboration a lot, because it really does make a difference if you’re willing to change the way you work a little bit. If you’re interested in more on these ideas, drop a note or leave a comment and I’ll share some thoughts.

by Sam

Digital Estate Planning

My charming & delightful roommate and I spent a good bit of time this past summer doing adult stuff. No, not that – the boring adult stuff that’s really easy to kick down the road for another day: estate planning.

We’d done some of the necessary work, but there were a lot of details we were overdue in addressing. It also got me to thinking about what kind of planning is needed for modern digital times. I tried to consider as many angles as possible, and started to write them down. As long as they’re written down, I thought I’d share them here in case it helps someone else.

The goal is simple: make it easy for whoever is tasked with sorting out your affairs. Leave them a playbook, be clear about your intentions. Here are the things someone will need to have or know about.

Your Phone

Make sure someone can get into your phone – which means writing down the device pin in a safe but accessible place. Too many pin attempts to unlock devices tend to result in turning them into bricks. This is probably the easiest thing in this list to do – and might be the most critical to making the rest of this work:

  • Your phone probably has apps to access financial systems.
  • You might have authenticator apps (like Microsoft Authenticator, Google Authenticator, or another of the many available apps) that you will need to verify identity using a code.
  • Some systems will text a verification code to the phone – someone may need that to access important info.

Your Computer

Do the same things you would with your phone. These days, a lot of people have their own device (even the kids). Make sure the machine that has access to your playbook, along with other important information, is accessible and can be unlocked.

Electronic Billing and Banking

Most of us by now are conducting some part of our affairs online. That could be utilities, banking, online subscriptions, or anything else involving a username and password. If you’re really doing the right things, you’ve got some multifactor authentication schemes set up. Here’s what you’re going to need to document:

  • It might be challenging, but try to inventory the sites on which you do business. Collect the site URL, and the username/password used on the site. Here’s a starter list:
    • Your email
    • Banks and Investments
    • Credit card companies (including the department store cards if you still have them)
    • Health records (things like MyChart or CVS), for health history or medications
    • Utilities
    • Pensions, Insurance
    • Social Security Administration
    • Streaming services and other subscriptions
    • Amazon
  • Consider using a password manager – something that can act as a vault for your information. Using solutions like 1Password, LastPass and others, you can store (and in a lot of cases, share) your login information in a location that can sync across your devices. They also have built-in tools to support emergency access, should the need arise.
  • I would suggest collecting Account Numbers as well. You may not need them for gaining electronic access, but having account numbers handy and in one place will eliminate confusion.
  • Don’t forget the mobile apps  – most of them have credentials as well (and it’s likely that face recognition won’t be an option).

How and where to store it

It’s perfectly fine to collect and store everything in an electronic format, as long as you’re able to do two things with it: print it (so you can include it with your other important documents), and be able to open it up later (choosing a file format that you expect to be supported down the road is important). Some options:

  • A text file – a universal format that can be opened in a variety of editors.
  • A Word document – it’s a popular format, and the tools are familiar to many.
  • A spreadsheet – Excel, Apple Numbers, or something like it will work well for organizing columns of information.
  • A PDF – while you may not be able to edit it, most everything will open a PDF for viewing.

You’ll certainly want to keep a paper copy of everything with your other estate planning materials. In addition, I’d suggest having a PDF version of all documents someplace you can access quickly. Sometimes circumstances are urgent (I know this from experience), and knowing right where to look helps.

Keeping some electronic version (PDF or the native files themselves) in a secure online location will also help on the accessibility front (while also providing a means to back things up). This can be iCloud storage, OneDrive, or some other online storage solution that can be appropriately secured.

Another option is to use your password manager – services like 1Password and LastPass support secure notes that can receive and store attachments in a highly encrypted manner.

The Major Online Services

Let’s face it, a lot of our lives are in those mobile computers that we carry around. Not just the phone numbers, it’s also got our notes, reminders, files, photos and videos. The good news is that a lot of those things are synced to cloud locations for recovery later (should something happen to the phone). That is, as long as you’ve prepared for it.

Apple, Google, Facebook, and other big services have features that allow you to designate a “legacy contact” for your information. Some of these things are a little difficult to find, so I’ll offer some links here.

  • For Apple, everything is attached to your iCloud Account. You can set up a Legacy Contact by going to Settings > Apple ID > Legacy Contact (here’s a link to documentation).  
  • For Google, it’s your Google ID. Set up your Legacy Plan from your profile and going to Data & privacy > Make a plan for your digital legacy (or go to this link once you are logged in with your Google ID).
  • For Facebook, define a Legacy Contact that can manage your memorialized account (yes, they actually planned for and support such things). Your contact can write and pin a post, see your past posts, download your content, and a few other operations that are appropriate. Check out these two URLs from the Facebook Help Center for more information.

Pro Tip for Facebook/Instagram – take a few minutes to write what you would like your last post to say, and make sure your legacy contact knows where to find it. Nothing like signing off on your own terms with your own words – you can bet I’m going to make you laugh.

The Secret Sauce

The key to making all of this work is making the time and effort to get it done – and keeping it updated. Be sure to have a discussion with or hand over an envelope to those that will need to know where you “buried the treasure” so to speak. If someone is looking for this information in a time of crisis or grief, you’re not going to be of much help.

Make it easy for them, give them a playbook to run. It makes all the difference in the world.