A Cheatsheet for Contextualizing New Technology

5 min readJan 13, 2022

I grew up during one of the biggest technological upheavals in the history of humanity. Within the space of a few years the entire way we as humans interact with our world has shifted dramatically. In middle school I got my first phone: a Nokia brick with Snake 2. By high school, I had an iPhone, and spent much of my social time on group calls with friends while playing Dota 2. And by university I was battling social media addiction and writing about the ways Facebook has fundamentally damaged the world. Nowadays rich tech-workers pay top dollar to send their kids to Silicon Valley private schools that preach a “no-screens” philosophy to early education. Chamath Palihapitiya, a former VP at Facebook who headed User Growth describes an intense feeling of regret for the part he played in productizing the individual mind, saying Facebook and social media like it is “ripping apart the social fabric of how society works”.

The difference between someone like Chamath and I is that I am part of the generation Facebook controlled. There is little glory or praise in that. But I am now fiercely cynical of modern technology and the claims made on its behalf. As I claw out of the hole people like Chamath and Zuckerburg put me into, I am wary of the next trap, the next big thing to make a few people rich and extract capital in all its diverse forms.

It means I do not love Big Tech. We are adversaries, and even as a software engineer in Big Tech, there is no trust or mutual love. Instead, I have a vested interest and strong understanding of how new technology’s unintended or unforeseen negative impacts can and should be nipped in the bud early on. Why? Principally because I want to protect myself. But also because as I’ve learned to skeptically observe and interrogate the claims of modern technology, I have developed insights and a perspective that could benefit others.

That’s why I’m sharing this mental cheatsheet I use when considering new applications of modern technology here. And why I believe you should take this cheatsheet to guide your own critical thinking around new technologies, whether you are a school teacher, CEO, or small business owner. Following this cheatsheet will serve you well, and provide a small antidote to the constant creep of ‘unintended consequences’.

Above all, you’ve got to learn to cut through the bullshit and get to the truth behind any new tech, whether it is web3, NFTs, Social Media, AR/VR, Crypto, IoT, et. al…

It starts by asking the classic questions: Who, What, Where, When, and Why.



Who does this technology benefit? Who does it harm? Who will use it? Who will be used by it? Understand the people affected by it.


What is the technology? What is the cutting edge of the technology’s capabilities? Fully understand the technology beyond a surface level “this is how my new toy works!”


What’s going on in society right now related to this technology? Consider the historical context of its used (the past), how people are using it now, and how people intend to use it moving forward. In particular here, pay attention to ways the intentions of the technology in the past didn’t line up with how it is being used today.


Where is the technology being used? In China? In the US? In Africa? In low-income communities? In wealthy communities? By homeowners? Contextualize the technology within its geographic and social contexts.


Why are we using the new technology? Maybe to fix a problem. But dig deeper. Is the problem a new problem, or an old problem? Is the problem something that people have tried to fix before and failed with other technology? Why now? When you ask why you consider the biases and latent factors driving the decisions. Oftentimes asking “why” opens up clarity into every other facet of the technology’s current application.

From Idealized Abstraction of Grounded Truth

I want to dig deeper into the “why”, because it is very important to understand how a technology’s “why” can often hint at the factors that could lead it away from any idealized intentions. Asking why is an essential part of critical thinking and can often reveal the biases creating seemingly objective or unbiased facts about a technology. For instance, you could know so much about an apple, how it tastes, the texture, if it tastes good in a smoothie, when to tell if it’s ripe, etc. But why does this apple exist? Are you buying this new Cosmo Neutron Apple at the store because you like it more, or because the old strain of apple was killed by a bacteria and this new strain is more resilient? Asking why is complicated and often creates a lot of grey space within your understanding. But it also creates the opportunity for a far deeper understanding, particularly with new technologies.

Take Uber — why were Ubers cheaper than Taxis? Are they still cheaper than Taxis? Why did Uber succeed? Sometimes asking why reveals a core strength in a technology, like “because it is X% more efficient than the best alternative”. Other times it shows a truth that people try to hide — Ubers were so cheap at the beginning because they were subsidized by Uber itself. And they were doing so because they wanted to rapidly build market share while undercutting the incumbent business on the market, and the better functionality of the Uber app and Uber ride experience wasn’t enough.

Example Scenario

Consider a simple application — you want to install a new camera system to livestream a public space. Sounds fun! Sounds simple. What pitfalls? Remember — be critical.

By following the cheatsheet, you dig deeper. Publicly available Turing Processes for enhancing image quality exist. In authoritarian regimes, camera systems are used to track individuals. Computer Vision technology is getting better and better. You can learn that if you do want this camera, it will come at a cost. People do not like to be tracked and observed. Can law enforcement request access to the camera footage and legally take it even if you don’t want to give it to them? And from there, you are better able to weigh the pros and cons before making your decision to install it. Maybe the conclusion is, install the camera, but point it so that it captures the tops of buildings and the sky. Or reduce the image quality. Do not save footage. Or you perform the heuristics and reach the conclusion that this system should not be installed.

Avoid Ignorance. And Don’t Feign It.

It’s ok to mess up. It’s tough when we make bad decisions, and face regret. Chamath has dealt this. But it is inexcusable to feign ignorance as a tool for hiding the truth when you’re productizing people and fundamentally altering lives for the worse. Companies like Facebook continue to do this, and will keep doing this as long as there’s money to be minted. The more you think critically about new technology the better you’ll get at making informed decisions with their applications.





Software Engineer passionate about the future of cities. Currently building libraries for Azure IoT.