What to do if your digital life is a freaking disaster

It's OK to not be one of Those Organized People

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One of the great joys of podcasting is welcoming guests who are smarter and more knowledgeable than I am about all manner of things. And after recording an episode on digital decluttering with Amanda Jefferson—which aired last week and is replete with smart tactics—I couldn’t decide if life was imitating art, or if life was just life’ing.

In the episode, I make clear that after 18 years of working on the internet as a multimedia creative across multiple business lines—and also as someone who loves photography and is the chief family photo taker—my files are a freaking disaster. I believe I mentioned at least twice in my conversation with Amanda that I wished I could push a red button and go nuclear on my digital footprint so I could just start over and become one of Those Organized People.

And here’s one of the many great things about this conversation: Amanda isn’t interested in forcing people to get their digital lives totally zipped up. It’s all about making progress from wherever you are.

Amanda had many astute insights into my apocalyptic digital desires, and not long after we exited the virtual recording studio, I started to come to terms with the reality that both my laptop and phone were close to 7 years old. I’m pretty sure that the majority of the population replaces their devices more frequently than I do—likely well before death is imminent—and it is a bit shocking that my devices were even functional at this mark given that I use them, let’s say aggressively, both for work and play.

(According to the internet, the average lifespan of a laptop is 3 to 5 years and the average lifespan of a smartphone is 2.5 years. There is variability due to usage and care but I think it is clear that I am not big on the digital upkeep side—see earlier red apocalypse button commentary—so I guess I was just lucky with my Samsung Galaxy S9 and Dell XPS 15 9560.)

As I eyed my aging devices, this comment from Amanda kept running through my head:

I think every single client I've talked to has a Dropbox and a Google Drive and some files on their desktop that they're not quite sure where they live and the external drives and everything. Typically where I always like to start is I joke with my clients that I want you to be able to throw your laptop in the river. Like, I want everything to be on the cloud so that if I threw your laptop in the river, you'd be mad and you'd be upset but five minutes later, you would be able to access every single thing that you need from files to passwords to photos to everything.

I realized that I would definitely be upset for more than 5 minutes if she threw my laptop in the river. Though a lot of my work is done on the cloud, I do have a number of important files that I access regularly on my hard drive, and they are not regularly backed up.

It was time to take action.

And the timing was impeccable. Perhaps my geriatric phone and laptop got wind of the fact that they would finally be relieved of their daily burdens because literally, just as I finished my planned steps to get my digital life in a better place and new technology landed on my doorstep, the screens of death and weird malfunctions started occurring both on my phone and laptop.

Yikes.

You should definitely listen to the whole conversation with Amanda if your digital life is a freaking disaster—or even if you are not a total disaster but could use some improvements. Meanwhile, here are four things I put into action that ended up saving me countless hours of frustration when I switched over my phone and laptop.

1. Create a Dropbox dump folder

When I expressed my woe over the state of my cloud files and the overwhelming prospect of organizing the files, Amanda gave me permission to not organize everything. She recommended that I simply create a folder labeled “ARCHIVE” and move everything I couldn’t deal with organizing in there, and that perhaps one day I would get around to organizing the files…or not. Because I already had a couple of “archive” folders for active projects (the two projects I am actually good at organizing), I created a folder called, “MAYBE I’LL ORGANIZE THIS SOMEDAY (Nov 2024 ARCHIVE DUMP).” It was so satisfying to dump everything in there and have a nice tidy Dropbox main directory.

2. Get all of my desktop files onto the cloud

The tech goddesses were on my side; I happened to finish the crucial task of getting all of my desktop files onto the cloud right before my old laptop started issuing a periodic screen of death and refusing to connect to the internet. I moved inactive desktop files into my Dropbox dump folder. And then I set up a “LIVE WORKING FILES” folder on Dropbox for my active files that I need to shuttle between desktop usage (e.g., actual Word files, PDFs, etc.) and the cloud. This system is working beautifully.

3. Sign up for a password management service

I have been thinking about signing up for a password management site for a long time, but could not get myself there because it just felt like another thing, including another freaking password to remember. I signed up for the service Amanda recommended and this tactic ended up being a lifesaver. Since I had already imported passwords from my laptop, it was easy to access my passwords on my new phone, new laptop, and iPad (which I use for travel). I still need to dig into all of the security tools, but I’m so relieved to now have this service rolling and to be upgrading my weak passwords.

4. Sign up for specialty software that makes my life easier and more efficient

When we were talking about different cloud services, Amanda noted:

“Because I’m an efficiency seeker you might think I’m looking to have one tool that can do many things, but in the tech world, a lot of times it is about finding the tool that’s doing one thing really, really well and going all in on that.”

Before my laptop died, I made note of all the software I would need to install on my new laptop. I realized that I was using an old version of the Adobe Acrobat PDF editor that offers all the bells and whistles, and that I no longer had access to the registration information. For one of my client projects markup tools are essential to the work. I tried to be cheap and find free PDF markup software. The three different options I tried all fell short of what I needed and were also clunky. So while on the one hand, Curmudgeonly Christine thinks $20/month is a ridiculous fee to pay to markup PDFs, Adobe Acrobat Pro helps me do what I need to do efficiently and effectively. Also, Get-Over-Your-Cheap-Self Christine reminded me that my expenses as an independent business owner are absurdly low—at present, less than $9K for the entirety of 2024. I can freaking afford the $240 annual business expense.

I’m so grateful that this conversation with Amanda spurred me to take actions that ended up saving me many hours and tears of frustration on the other side of my tech death spirals. I hope this post gives you a nudge to do some maintenance if you are in need!

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P.S. As a counterpart to digital life, if you’re looking to roll your sleeves up and get buttery, here’s a new quick episode about holiday cookies. The show notes include links to the recipes I am using/considering. Enjoy!

Though I was very sad to say goodbye to my beloved Samsung Galaxy S9 workhorse, my new Samsung Galaxy S24 does work a lot better; for example, it actually can hold a charge for an entire day LOL. Here is the very first picture I took on the S24; Laurel sent me this puzzle.