Happy last Sunday of September {{first_name|dear reader}}!
Thank you to those of you who shared feedback last week. Thank you also to person who said what I imagine most people on this list think: “I like it but I don’t really read the whole thing because it is too long.”
So toward that - trying something new this week. Here’s a two-sentence AI-generated summary of this week’s post - if that’s all you want to read from me this week, great, no hard feelings. If you’re intrigued then you know what to expect when you keep reading.
Cheers!
If We Can Save Time, Why Don’t We?
A billionaire is making an app that claims to free kids’ time, but his wealth came from squeezing time out of adults through relentless hours and monitoring tools. This paradox highlights how society consistently reinvests productivity gains into more work instead of genuine leisure.
Last week I mentioned this article as one of the best profiles I’ve read this year:
The main subject of the article is Joe Liemandt, who is spending $1bil of his own money on developing an app called Timeback which delivers a personalized AI tutor, ostensibly enabling children to spend two hours a day on an iPad learning and then the rest of the day doing fun projects (hence the “Timeback” name). The app is coming out later this year so has not yet really been tested but Liemandt is fired up about the potential.
How did he get his money? Liemandt founded and ran a software company that was huge in the late 90s and early 00s. The culture was centered around a grueling hustle: “Recruits and employees alike worked from 8am–12am, often seven days a week and almost always on holidays (‘competitive advantage days’).”
Liemandt then started a private equity firm named ESW that bought software companies, stripped them down, and outsourced all development overseas.
On every contractor’s device, Liemandt implemented a system called WorkSmart, described as a “Fitbit for how you work.” …In essence, it’s a webcam tracking feature that takes screenshots every few minutes, and spyware that tracks mouse clicks and keyboard strokes, allowing [Liemandt] to collect workflow data and track the productivity of each worker. While every contractor agrees in advance to have WorkSmart installed on their device, Liemandt’s innovation in employee monitoring and measurement, combined with his preference for a high turnover workforce of easily hirable and fireable contractors in predominately developing countries, led Forbes to accuse him in 2018 of running a “global software sweatshop.”
That core technology in “WorkSmart” became the core structure in TimeBack: closely monitoring each student’s progress in order to form a highly accurate profile of that person.
On the face of it, the mission to “give kids their childhood back” by enabling them to spend less time in school sounds nice. But after I finished the article and digested it a bit, I kept getting stuck on this contradiction:
The person who is spending $1bil to give kids more hours in their day got that money by asking adults for as many hours as he could possibly get from them.
I wonder: in his worldview, when are humans no longer eligible for Time Back and instead must be asked to Work Smart?
Further: if new productivity and AI tools enabled his employees to only have to work two hours a day to get their jobs done, would he encourage them to do other fun projects and play fun games outside with each other? Or would he just expect them to do MORE work?
Here’s the thing. This isn’t just Liemandt’s paradox - it’s humanity’s paradox. As a species we are not actually very good at giving ourselves “time back” as adults.
This idea has never been as visible as it is today: we have extraordinary productivity tools at our fingertips, including and especially AI tools that can shorten so many workflows into a couple of clicks - and yet we are working as hard and as much as ever. The work day blurs far outside of 9-5 because we are “always on.”
ClickUp (awesome project management software that we use at OpenTent) has this slogan as their core product promise: Save one day every week.
Do I also save one day per week on those 52 days I get back every year?
Even if this marketing was true, that ClickUp customers save 20% of their time every week by using this product, I would bet all of the money I have that those customers do not say “cool, now I can spend one day a week reading fiction and going on long walks with my friends.” They are just going to turn around and do MORE work.
This illusion - that humans would actually be able to embrace leisure when productivity gains allow them to work less - is not new. John Maynard Keynes wrote in 1930 that within 100 years “the economic problem may be solved”:
For the first time since his creation man will be faced with his real, his permanent problem—how to use his freedom from pressing economic cares, how to occupy the leisure, which science and compound interest will have won for him, to live wisely and agreeably and well.
…The economic problem may be solved, or be at least within sight of solution, within a hundred years…we shall be able to perform all the operations of agriculture, mining, and manufacture with a quarter of the human effort to which we have been accustomed. To put the point in another way: the standard of life in progressive countries one hundred years hence will be between four and eight times as high as it is today.
For three hours a day is quite enough to satisfy the old Adam1 in most of us!
Here we are five years from checking in on Keynes’ vision. Is the economic problem about to be solved? Are we only a few years away from not having to work at all - or just working three hours a day to satisfy the old Adam?
Technologically, that timeline seems eerily accurate:
With the extraordinary pace of robot development lately we might imagine physical labor could hit these kinds of milestones in 2030 too.
But it is damn near impossible to imagine humanity reacting to all that by sitting back and “occupying the leisure” or living “wisely and agreeably and well.” A safer prediction is that we will all just egg each other on to work harder and output more or risk falling behind and losing out.
If I had a billion dollars I would use it try to figure out how to give adults their time back.
I’m on vacation and celebrating Yom Kippur in Los Angeles this week - I’ll take the week off from this newsletter too, so see you again in two weeks!
1 Had to look this one up - it’s a reference to Genesis 3:19 after Adam eats the forbidden fruit: “By the sweat of your brow you will eat your food until you return to the ground.”