Wicked Problems of Modernity ft. Garrett Dailey

Bradley Werrell
4 min readFeb 12, 2021



Today’s guest, Garrett Dailey, is quite an impressive fellow to an old guy like myself. In his short life he’s already authored 2 books on philosophy, helped start and operate numerous businesses, fasted for 40 days, and piled more skills into his stack than some people do in a lifetime.

You can learn more about his work at Aion.Media/masterself

Garrett’s concern in his work as a writer and thinker is to solve “wicked problems.” A Wicked Problem is, indeed, quite wicked.

Let’s define our terms, wicked problems are

  • Complex / multiple variables
  • Compounding / each variable plays off the other variables
  • Plain ole hard / requiring lots of effort and energy to fix
  • High-risk / In searching for a solution you will likely mess up
  • Evolving / With each failed attempt to solve the problem, new levels of complexity/compounding difficulty emerge — i.e. the problem gets worse
  • Memetic / With each unsolved instance of the problem, it can cause other people to enter the problem
  • Catastrophic / If enough people enter the loop of the wicked problem, it can cause a cascading failure of systems, which can create other wicked problems.

Essentially, Wicked Problems are the worst kind of problem to have.

Garrett believes that the job of philosophers is to first understand the world and then use that understanding to solve wicked problems (pre-emptively spotting them when possible).

Garrett believes HIS job as a philosopher is to answer the question: What if the source of a Wicked Problem is the very structure of beliefs and systems that allow civilization to exist?

Or, in short, are humans at the mercy of entropy? Or can we transcend the doomsday clock written into our social DNA to create something new?


At BEST MEDICINE I’m intrigued in testing out all ideas, even those that I don’t necessarily agree with. This is one of those times. I think it’s good for the public health to entertain these ideas.

In one view, agriculture itself may be a wicked problem. Yes, as in farming.

Garrett points out numerous reasons for this, including:

  • Before farming there was no property
  • Before farming the limits of a “ruling class” would be over a group of near-equally strong human males at a maximum amount of 150 (Dunbar’s Number). This ability to rule was based on ability to collaborate in the hunt, and nothing else.
  • Before farming, people ate mostly meat. After farming they began eating carbs.
  • Before farming, humans would be in harmony with the Earth. After farming entire supply chains and natural resource extraction operations had to be put in place to support global agriculture. This is exacerbated today where an unfathomable amount of pollution is emitted simply to make sure each McDonnalds has enough pickles.
  • Before farming humans were nomadic. After farming they became more territorial, and thus more war-like
  • Before farming children were not expected to labor in unnatural ways for long hours, after farming they have been (even in today’s age, school could be seen as a form of this, with minimal effectiveness at the public level).
  • Before farming people did not believe they were the masters of time and death.

Garrett’s main argument stems from a fundamental ineffectiveness of farming compared to effort. He would say humans traded an ability to get food for the marginally more effective method of saving food (i.e. preventing one cause of death — starving). However, farming is more common than ever now — and we still have millions of people starving. We also have more pollution, obesity, and conflict over control of resources.

Garrett is playing with the idea that it might not be a good trade.

I’m not so sure what I think of the issue. I enjoy a nice batch of Florida Oranges in the winter. And I quite love northern made cheese on my omelettes. I also tend to think human nature has a violent streak in it that shouldnt be laid at the feet of the “original sin” of farming.

What do you think? Listen to the episode and consider how farming as well as our other fundamental “axioms” that we’ve built civilization off of might not be as amazing as we assume.



Bradley Werrell

I'm on a mission to give patients a more affordable way to receive healthcare, and to give practicioners more ethical ways to provide it.