Guilt, Productivity, and Why I Finally Said Goodbye to “Getting Things Done”
I’ve always had this odd problem with to-do lists. People tell you, “If you’re overwhelmed by your list, just get started. You’ll feel better the more you get done.” Well, I’d do that, and start getting stuff done, and I’d feel worse. And the more I got done, the worse I felt, and the more I felt like I needed to do to feel better. At its worst, I’d finish the entire list — days’ worth of productivity in increasingly edgy, frantic hours — and instead of feeling ridiculously accomplished (I mean, really, who ever gets an entire to-do list done in one sitting?), I’d feel ten times worse. And nothing I’ve ever tried has made it any better.
This was always an occasional problem because, with a full-time job, I rarely had long periods of unstructured time to fill with self-started tasks. However, last year I quit my job and started a year-long period of studying and home-keeping, and the occasional quirky problem turned into a constant monster problem. Every single day was either doing everything and feeling like trash, or avoiding everything and feeling like trash anyway… and I’d run out of ideas for solutions.
Finally, I stopped trying to address the specific problem directly. Instead, I blanked out all the specifics and asked, “what does this framework look like? What do I know where I feel compelled to complete some action, but the more I do it, the worse I feel?”
And I knew immediately.
Somehow, I’d managed to get myself stuck in a years-long obsessive-compulsive pattern out of trying to be productive.¹ And the minute I knew that, the minute I had the key:
So I started, inch by resistant inch, to unravel it and let it all go.
I forbade to-do lists with more than 3–5 items on it, so I couldn’t get caught looping through them anymore. If there’s more than 3–5 things that need to get done, I put them on a different list with enough separation that I can’t just move from one to the other.²
I realized I never took any rest days. Seriously, not one. I had only two categories of days: days where I got a lot of things done, and days where I was feeling guilty about not getting a lot of things done (which obviously aren’t restful). I mandated a minimum quantity of days where I do my best to do neither, and get to feel virtuous about healing and taking care of myself.
I started a long, deep look at my expectations about how much of what things I was considering “baseline minimum standards of productive adult”, where they were coming from, and how they stacked up to other successful, productive people I knew. And wouldn’t you know, they turned out to be wildly unrealistic and shot through with toxicity from start to finish! What a surprise. Dismantling them is going to be a long process, but I’m on my way.
I overhauled or discarded every productivity tool I was using that made me feel guilty, and let go of my guilt about using them “wrong”. And yes, that meant a bittersweet farewell to David Allen’s Getting Things Done, which I’d been evangelizing for nearly a decade. Contrary to what I’d always told myself, it wasn’t my fault for not adhering to the system with the appropriate degree of unattainable scrupulosity. It’s simply, keeping a long list of immediately actionable items (that core “Next Action” list) triggers my guilt and hyper-responsibility problem. I still collect outstanding items to get them out of my head- but deliberately in an unactionable way, so I don’t feel as compelled to do them. Once a week or a maximum of twice, when things get very fast-paced and busy, I transfer the highest-priority ones to my 3–5 item to-do lists, and immediately and ruthlessly shunt anything that isn’t going to cause extreme negative consequences if indefinitely left undone to a “Low Priority” purgatory list.
When I started down this road, I accepted that I’d probably be less productive for awhile, as a cost of being healthier and less paralyzed by guilt. After all, how could I possibly get enough done limiting myself to 3–5 things at any one view? But something unexpected happened along the way. I’ll be sitting around, not feeling bad about getting things done, and I’ll just… feel inspired to get up and do something. Not every time, but enough. Not because I have to, or else something bad will happen. Just because I want to — in positive anticipation of the benefits it’ll bring; out of love for my home, my partner, or myself; or because I want to get up and move in a healthy way. Clearing out all the guilt blocking the way allowed all those things that people tell you “should” be motivational to actually arise naturally and spontaneously. And, corny or not, that has been the sweetest accomplishment of all.
 This is an issue I’ve had with my own cognitive wiring since childhood, which I knew about, but never thought would show up here. It probably isn’t particularly widely applicable to others, but I suspect the guilt realization I got out of it might be useful to some.
 Shoutout here to a friend who created www.randomhopper.com after I asked for a to-do list that would only let you look at one random item at a time. Literally not being allowed to look at the whole list helps avoid feeling compelled to do the next thing, and the next, and the next… and probably would also help anyone who just generally feels overwhelmed looking at their whole to-do list.