Digital Decluttering: Mistakes Made, Lessons Learned (Premium)

Flush with my decluttering success, I ended up trying to do too much at once and made too many mistakes, causing me to run up against multiple blockers across each project, halting my progress. And so I am scaling back my unrealistic expectations, rethinking my goals, reversing the mistakes, and returning to a more deliberate, single-tasking schedule.

What can I say? I flew too close to the sun.

And you know what? It's OK. I did a great job expanding the scope of this work with each passing success and I got more done than I ever imagined was possible. By learning from the mistakes I did end up making, I can get back on track and arrive at a better place. Which is, of course, its own form of progress and success.

So maybe I should explain what that all means first. After all, there are good reasons for what I've done so far, reasons that I think justify the work. And as this decluttering project expanded greatly, I came to see that what I was really doing, broadly, was setting myself up for a future that is more manageable and organized. This is a system, a sustainable way of doing things that should prove effective for the rest of my life. It's just a matter of putting it in place.
The system
Fundamentally, my life is no different than that of anyone else, it's a mix of personal and professional (or, work). There isn't always a clear divide between the two, in part because I've worked from home for almost 30 years now, but whether it's the physical items we possess or the digital data that we store, that breakdown is simple and works well conceptually. Personal and work.

As you may know, my wife and I have deliberately spent a lot of time thinking about and implementing ways to downsize and declutter our lives by removing unnecessary things. This isn't a one-time, set-it-and-forget-it kind of thing. It's something you have to be mindful of at all times, and because life happens, it's something you have to return to again and again as things inevitably pile up. Clutter, like life in Jurassic Park, always finds a way.

For a long time, downsizing was a far-off goal, an aspirational ideal. And for all the right reasons: We have two kids and they lived at home until they went off to college, and we purposefully stayed put in the same house for over 15 years to give their lives---friends, school, activities, whatever---continuity and stability. But during that time, we also put our ideas to work through annual decluttering pushes ahead of the summer home swaps we did each year. After all, some other family was coming to stay in our home for three weeks and we needed it to be as clean as possible. Not "straightened up because guests are coming to dinner" clean, but actually clean, the entire thing, top to bottom.

Separately, I would also go through regular purges of things, via "Everything Must Go" events and similar, and by methodically reducing the number of items I had on hand, whether it was for work (electronics and the ...