Generally, having “I’ll do this later” as a mantra will not bring you success. I’ve spent the last few months driving home the idea that taking small steps now is the key to digital organization progress. That’s certainly still true. But it struck me this weekend that postponing specific parts of a big job can help move you closer to your target in multiple ways.

Think of your looming digital data clean-up project as an onion, with each layer representing one of the tasks (or categories of tasks) that you need to get done before the project is complete. Going straight to the core requires a sharp knife, a firm hand, and many tears. But peeling one layer at a time will still get you there without needing to make those deep, irritating cuts along the way. If you encounter a section that’s hard to get through, leave it alone and move on to another section. By the time you get back to it, you may find that it comes off easily.

Postpone to Settle Emotions

Over the weekend, I took on a data organization task that I’d put off for well over a year. Maybe multiple years. I don’t even know for sure, but it was a really long time.

It was a collection of data brimming with nostalgia: art, writing, and other school projects going back to my childhood. I’d already whittled it down twice over the past 15 or so years, and I was subconsciously dreading the task of going back through it again—even though the idea of having it done was simultaneously tantalizing.

I mentally cycled through the process many times:

  1. Think about all the stuff
  2. Dread the process of filtering it again
  3. Postpone the task
  4. Wish the stuff would disappear so I could stop thinking about it

When I finally sat down to make it happen, I found it to be emotionally much easier than I was afraid it would be. Working through those thoughts above repeatedly prepared me to get rid of a lot more than I thought I would, with far less hesitation.

Man freelancer in eyeglasses sitting at table with closed eyes and relieving stress by meditation
(Not actually me, but sorta)

Although it took hours to complete, I didn’t feel stressed, sad, or disappointed about tossing out most of what I started with. I kept only a small fraction of particularly fun or joyful works: things that I’d like to share with friends and family as a single binder of “Jeff’s Formative Years” when I’m older.

I realized afterward that I couldn’t have achieved that result if I’d tried to do it years earlier. I simply wasn’t ready. The extra time to adjust my perspective about what matters allowed me to do the work much more efficiently. That layer of my “organization onion” didn’t want to come off easily, and I only needed to wait a bit.

This approach can’t work for every step, of course; if you take years to let your emotions settle about every little thing, you’ll be dead before you make much progress. But it works for big challenges that are largely driven by fear or nostalgia:

  • A large collection of memorabilia that only matters to you
  • A set of downloaded music files that could be 97% replaced by a Spotify subscription
  • Personal email archives going back to the 1990’s that even you would cringe to re-read
  • Every hilarious cat meme you’ve ever downloaded

Keeping too many digital things just because you can’t see them physically is still just that: keeping too many things. I know first-hand the temptation to hold onto things. But I also know first-hand the wonderful psychological release that comes from letting them go.

Do One Thing

Think about your digital organization tasks (email, photos, old hard drives, etc.). See if you can choose one to intentionally postpone to allow yourself to focus on immediately attainable goals instead.

You don’t have to mercilessly delete everything at the beginning, or even by the end. But with some extra time to think about it, you might decide that you and everyone else would be better off without the extra stuff after all.

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Ready to get your data under control? You can do it!