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The flattening of the to-do list and the over-quest for optimization

Picked my friend up at the airport yesterday. On the way there, I listened to this April 2019 podcast from Ezra Klein about how “work is identity, and burnout is lifestyle.” The two guests are Anne Helen Petersen, who wrote a BuzzFeed article about millennials becoming the burnout generation — and Derek Thompson, who wrote the “workism” article in The Atlantic.

Fun fact on that “workism” article: I was working at an agency at the time, one of those “Everyone is so slammed!” places, and one dude — Vadim, who was on my podcast — sent that article around. No one seemed to “get” it. It was a Slack conversation that died almost instantly. Ha.

Anyway, the podcast linked above (not mine, the more popular one) has a lot of interesting points, especially if you can’t really detach yourself from work — which wouldn’t make you that unique, since we broadly deify the workaholic. Let’s tackle two points quickly.

The flattening of the to-do list

Years ago, in a galaxy far, far away, I started using Trello because one contract I was on used it a lot. I liked it. So I started using it for work and personal. Eventually, my then-wife tagged onto my board, and we were doing work + work (each of us) + personal + home. Trello was like the base of everything. There was no line between work and home, personal and non-personal. (I guess everything is “personal,” so that’s a stupid sentence.)

Anyway, it became a never-ending to-do list. The to-do list was now flat. It just keeps going to the horizon line, then there’s a new horizon line. It doesn’t end, you see?

Very few people in human history like sitting down and listing out all the shit they have to do in a day or week. You do it because (a) it helps you organize and (b) when you check off an item, you will get an endorphin hit. Now, we know from research that roughly 11% of people can even accomplish a full to-do list, so it’s not really about being efficient. It’s about feeling accomplished when you do the strike-through.

But when the to-do list becomes flat and never-ending, that sense of accomplishment wanes. Because if you get to Friday and you’ve killed it at your M-F work job, awesome. Well, now it’s Saturday and there’s a new list. At some point, crossing stuff out over and over loses value. It’s like what happened to the social media “like.” How valuable is that anymore? It’s almost meaningless, I’d argue.

The joy disappears when the list flattens. You know?

The optimization of everything

We took a bath in this shit because we all over-worship Silicon Valley and their “growth hacks.”

Here’s the example Petersen gives on that podcast: let’s say you need to take your shoes in to be fixed (“cobbled”). The modern mindset is, “Well, I need to do this in an optimized way. I need to hack it. Is there a shoe app? Is there something disruptive?”

It’s like — listen Ashleigh, maybe just grab your shoes, grab your phone, grab some Air Pods, put on an informative podcast, and go walk to the cobbler and think about the issues being discussed in your ears. It might take 35 minutes as opposed to 2 minutes, but it’s OK. Thinking and walking around and contextualizing things … those are OK. It’s very human to do that. Not everything has to be “optimized” or “hacked.”

That leads to a discussion about the grand promise of capitalism. Capitalism itself is a good system (yay) but the end promise of it is a complete lie. The idea at some point was, well, if we keep getting more efficient and productive, eventually we’ll have all this leisure time on the back-end and all become Da Vinci or whatever. Almost the complete opposite has happened. As we’ve “growth hacked” everything, most of us work more, burn out more, and are more stressed. It’s the inverse relationship of the grand promise.

I have a friend who used to live in Texas; her and her husband run a little marketing agency type deal. Everything has to be optimized. Every second of every transaction and interaction. Now, in one way, that’s awesome and hopefully it leads to some significant financial success for them — something I have lacked for much of the past year. But at another level, you know what I did Sunday? Read some stuff, watched a bunch of TV shows, and researched some true crime cases. Does that make me a worthless sack of shit that I wasn’t “growth hacking” my Sunday? Sure, maybe. But it also makes me a person ready to come out and try to hit some targets on a Monday.

It’s OK to not optimize every single thing. There’s not really always an app for that. Sometimes you can just stroll along a riverfront and contemplate the universe. It doesn’t mean you won’t ever be Elon Musk. Well, it probably does, but eh. You know what I mean.

Work should not be identity

It really can’t be, because work is transactional in most contexts. There is no reciprocity. You can be piped at any second; you can also choose to leave at any second. It’s a part of what you do and where you go and how you spend time and what you spend energy and thought on, yes. Is it your entire identity? It shouldn’t be. That’s very dangerous.

Thompson says this on the same podcast: religion, at least, there’s kind of a “no-failure” clause to that belief. God is not coming down and laying you off because of a bad quarter. I’m not saying religion is perfect by any means. But if you want to wrap yourself in a belief that will give you a little more stability and hope, religion is probably a better choice than, say, work. God has an explanation and a place for Ted Bundy. Now ironically, Ted Bundy at a corporation would probably become a SVP … and maybe that’s a topic for a different post … but the point is, work punches you in the mouth all the time. God embraces both good and bad.

Now, let me get off this soapbox for a second and let’s go back to the bigger discussion: how do you feel about to-do lists and the over-focus on optimization?

Ted Bauer

4 Comments

  1. Between pressure from narcissistic executives ,pressure from middle managers fighting for relevance in order to avoid #Terminated, and pressure to make the light bill and insurance on the same check, being a workaholic is damn near inevitable.

    Either we have to in order to earn enough to make the bills, or we have to in order to dodge the annual layoff. When 50 hours of your life is spent in one place, it takes dedicated effort to make sure you don’t over-value it. Some companies , managed by Glengarry Glenross types, culturally mandate workaholism as a requirement to keep your job. If the execs home life is a mess because he’s spending 60 hours at work, he’ll ensure that misery is shared among his lieutenants. Who in turn do the same to theirs, and on and on.

  2. I use a to-do list, almost to an extreme. I start with my vision, carve out my mission, develop goals to achieve that mission, and then start listing tasks that push me toward achieving the defined goals. And it works. For me.
    What I have found ALMOST as helpful is my “stop doing” list. I can procrastinate with the best of them. I consciously make a list of my favorite timewasters. As I find new ways to waste time, I add them to the list. Through the day, if I catch myself doing one of those things. I stop. Just stop. I break myself from the attraction. Then I turn back to my task list and move myself closer to my goals. I confess, I do find that psychologically rewarding.

  3. Funny you write on work optimization. I was just reading an article about a Minnesota tech company that has started microchipping their employees. The justification was that this would reduce time enter and leaving the building, logging on to devices, and the purchasing food from the vending machines (its apparently tied to the employees’ bank accounts).

    Yeah, no thanks.

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