Organizing My Life as a New Widower and Single Dad

Photo by Ilya Pavlov on Unsplash

For the last 15 months, I have spent A LOT of time working on organizing my life. There’s one simple reason for this: On November 6, 2020, my wife Melissa passed away unexpectedly. Suddenly, I was a widower and a single dad to our 13-year-old son. I was overwhelmed with grief and burdened by all of this new responsibility that fell on me alone.

Melissa and I had always worked together, and she was definitely my partner — providing a boost in areas where I was weak, covering for areas where I didn’t have the skills, encouraging me, motivating me, teaching me, loving me.

And then there were all of the things that she had done for our son — providing him with a schedule, helping him organize his life, literally teaching him in school (we had enrolled him in a virtual academy for the 2020/2021 school year), loving him, encouraging him, accommodating him, and just generally mothering him.

Now, I was suddenly alone in this. I knew the areas where I missed her, but what about the areas where our son needed more support than I had been providing him? How would I help him? How would I know what to do? How would I help him finish the school year, and then choose a different school for the following year? How would we have fun during the summer? How would we have food to eat and clean clothes to wear?

It’s not like I had been completely uninvolved in any of these areas before her passing. If anything, it might have been the opposite, as she had been medically retired from teaching due to a chronic condition that qualified her as permanently disabled. So I had spent years doing many things for our family — shopping, cooking, cleaning, laundering, etc. But that had always been with some measure of support from my wife, whether it was reminding me what things needed to be on the shopping list, or informing me of what areas of the house needed to be cleaned, or what clothes needed to be laundered.

I knew one thing that was required of me now: If my son and I were going to be successful in this new stage of life we found ourselves in, I needed to be a lot more organized. Sure, I had been organized previously, but in many areas, I was strictly relying on “brainpower” to keep myself moving. Now, my brainpower was significantly reduced due to trauma and grief. And the number of things I needed to keep track of had grown exponentially, including some things I was unprepared for — funeral planning and arrangements, death certificates, birth certificates, our marriage license, letters from the IRS, Social Security statements, insurance company EOBs, estate planning as a single parent, and more.

Physical Organization

There are a few things that have helped me stay organized with things such as documents.

The Sunday Basket 🗃️

I don’t really like paper (or people handing me things). I’ve always struggled to know what to do with paper. 📝 🤷‍♂️

Digital files make complete sense to me — I know where I want digital files to go. Not so with paper.

The Sunday Basket is a great resource I found in late 2020 to help me organize incoming mail and documents — stuff that I would normally just stack or pile somewhere until it got to be too much. Now I have a way to quickly sort any papers that come my way, and then review them on a regular basis (such as a Sunday afternoon, as the product name suggests) to make sure that bills get paid, correspondence gets a response, etc.

Waterproof 💧 Zipper File Bags

Someone recommended these waterproof zipper file bags to me in late 2020, and they’ve been great for being able to separate different types of documents (one bag for the copies of my wife’s death certificates, one bag for our birth certificates and marriage license, one bag for school-related documents) while also making sure that they’re protected in case I got caught in the rain or something liquid gets spilled.

Fireproof 🔥 Document Bag

Each of the above-mentioned waterproof zipper file bags goes into a single fireproof document bag, making it easy for me to know that I have all of the files I need, that they’re organized within one unit, and that the documents are further protected from both water and fire.

My “go bag” 🎒

I’m not a prepper nor an EMT, but I found I had to develop a “go bag” that routinely had in it the things that I would need once I went out the door from my house. I generally need the bag ready to go immediately, not 10–15 minutes later. I use a backpack that can store a lot of items, is easy to carry, and works with just about any outfit (and also continues looking clean).

So my waterproof zipper file bags go inside my fireproof document bag, and that then goes inside my backpack. My laptop and iPad easily go into the backpack, too.

Here are some other things I keep in or near my backpack for when it’s time to go:

• Writing utensils: 🖊 ✏️ I always need some kind of writing utensil handy, and especially now during the pandemic, if I’m out someplace and need to sign a receipt or fill out a document, I greatly prefer to use my own pen. For handiness, I like the Fisher Space Pen (I almost always have one in my pants pocket), but for writing comfort, I really like the Bastion Bolt Action pens.
• OTC medicines: 💊 🩹 It’s maybe not a full First Aid kit, but getting close. You never know when you’ll need a Band-Aid, some pain reliever, some allergy medicine, etc.
• Water bottle: 🚰 🥤 I like to make sure I have drinking water available, and in a container that can easily be refilled later in the day. My personal favorite is Camelbak’s Chute Mag 20 oz bottle.
• Electronics accessories case: It’s a reality of using electronics, especially of the dongles and chargers that are part of using Apple products. It’s nice to have these accessories organized and easy to find.
• Portable power strip: An additional reality of using electronics is that we’re always needing to charge one or more devices, but I don’t want to take up every plug 🔌 that’s nearby (nor rely on there being more than one available plug nearby). So I keep either Anker’s PowerPort Strip 3 or Anker’s PowerExtend USB-C 3 Cube, which give me additional regular plugs, plus USB plugs.
• Noise-canceling headphones: 🎧 Admittedly, these are “nice to have” items, but I’ll be honest, they’re really nice to have. One of the issues I’ve found in my grief is being overwhelmed by noise, so being able to zen out in the middle of a noisy place is worth it for me. Silence truly is golden, I usually keep a set of AirPods Pro, AirPods 3 (they don’t have Active Noise Cancelation [ANC], but with enough volume, they do the trick, and I think they’re Apple’s most comfortable earbuds yet), or Bose QuietComfort 45's in my backpack for those times when I really need noise cancelation. Granted, these are not inexpensive headphones, but Amazon and Best Buy offer more affordable alternatives.

Digital Organization

I admit that I’m generally a digital-first, or digital-preferred person. I’ve loved technology ever since my dad brought home that Tandy TRS-80 in 1985.

File and Folder Organization

To organize my digital files, I use Tiago Forte’s PARA method:

• Projects
• Areas
• Resources
• Archives

You can read more about Tiago’s structure in his blog post linked above, but I set up that folder structure in pretty much any app or storage system I use. The one twist I’ve added is putting a two-digit number in front of each so that they always sort in the order that I want them to (and not just alphabetically). So in my file systems, the folders look like this:

• 01 — PROJECTS
• 02 — AREAS
• 03 — RESOURCES
• 04 — ARCHIVES

Each of those folders then has subfolders as needed.

The other “hack” I use for digital organization is a method that I recently picked up from Ellane W, and is displayed just above. From Ellane:

“…I always name files in Sentence Case and folders in ALL CAPS. It helps me to keep track of what I’m looking at…”

Apple Devices

I’ve preferred Apple devices for many years now, so every day I’m using my iPhone (12 Max Pro), iPad (12.9" Pro with Apple Pencil 2), and MacBook (16" Pro) to organize my digital life.

Everything mentioned below will be running on an Apple device (although almost everything will work on devices by other manufacturers).

Password App

If you’re not using a password app to keep track of your logins (and more), you need to be using one. 🙏

Why should you be using a password app?

• You have so many websites that now require a login — your bank, your email, any online store where you make purchases, or any website where you have a membership/account.
• You should always use a different, unique password for each website. Don’t reuse passwords! If someone were to find out that “Fluffy17” is your email password, not only would they have access to your email, but they’d also end up having access to any other website where you’ve used “Fluffy17” as your password. 😬
• When it comes to passwords, the more complex you can make them, the safer you’ll be. I prefer passwords that are at least 16 characters long, with a mix of UPPERCASE and lowercase letters + numbers + special characters.

The password app I use and recommend is 1Password. I’ve also used and can recommend LastPass. If you’re using Apple devices, you’re also secure with using Apple’s Keychain for password generation and storage.

Google Workspace — Gmail, Calendar, Docs, Sheets

If we are going to make it to an appointment or remember an event or birthday, it has to be on my digital calendar with appropriate notifications or reminders. My primary email account is a Gmail account, so I use Google Calendar to keep track of everything, and it’s worked well for me.

For notifications or reminders, someone introduced me to a question last year that has been a good prompt for me: “When will I need to see this again?”

• If it’s picking up my son from school, I generally need a 30-minute reminder — 15 minutes to finish up whatever I’m doing and get out the door, and then 15 minutes to allow for driving time.
• If it’s dinner with family and friends, I generally need at least a 60-minute reminder — time to make sure that we’re all clean and clothed to go out in public, and then time for driving to our destination.
• If it’s someone’s birthday or anniversary, I generally need a reminder several days in advance — time to pick up an appropriate card or gift and get it sent off with a delivery system (postal system, etc.).

On Sundays, I’ll carve out time in the afternoon or evening to look at the coming week, and even a few weeks out in advance, to figure out, “What else do I need to consider?” A recent example was school pictures. When I noticed this was coming up on the school calendar, I asked myself, “What else do I need to consider for school pictures?” Or, as I often ask myself, “What would Melissa consider for school pictures?” And then I can write down the things that come to mind and act on them accordingly — in this case, scheduling a hair cut for the day before pictures, making sure that he has a decent polo shirt for his pictures, and ordering a package of pictures from the school photographer.

If I have correspondence that I’m going to be sending to someone, I draft the letter in Google Docs. I’ve even set up a simple “letterhead” for myself so I can use the same format consistently.

And while I use Microsoft Excel A LOT in my daily work for business purposes, for personal spreadsheet use (budgeting, trip planning, basic math, etc.), I find Google Sheets meets the need.

Apple Notes

If you use an Apple device — iPhone, iPad, MacBook — don’t overlook this handy app.

Features I like about Apple Notes:

• It’s free to use.
• It syncs across all of my devices via my iCloud account.
• It’s easy to create a note and format the text.
• I can create to-do lists or shopping lists that can then be checked off.
• I can organize notes into folders.
• It’s easy to share notes with other Apple/iCloud users — I have a folder that contains notes that I share with my son, such as to-do lists, his school schedule, who to contact in case of emergency (ICE), etc.
• I can use the camera from my iPhone or iPad to quickly scan a document or insert a photo into a note.
• The Search function works really well.

OK, I’ve covered a lot here, but these are my current tools of personal organization and productivity. Let me know what comments or questions you have, and I may break out some specific use cases in future posts.

Thanks for reading!