1.
In Back to The Future Part II, Marty McFly travels to the future and gets his hands on a little book called the Grays Sports Almanac (which eventually falls into Biff's hands). The Almanac possesses invaluable data that a time traveler could use for financial gain: it tells the results of every major sports event until the end of the century!
The Almanac represents a classic way of thinking: If only we had the right information, all of our problems would be solved, we would be rich, etc.
Yes, it would be nice to travel back in time and buy a bunch of bitcoin. The only small risk being that we could change things that werenโt supposed to change and create a paradox leading to a tear in the fabric of the space-time continuum leading to the destruction of the entire universe. Who knows, right?ย
But anyways, time travel aside โ access to information is no longer as valuable. Imagine that you, and only you, had access to wikipedia 100 years ago. Youโd be one bad motherf*cker. But since we all have wikipedia today, youโre not so special.
In the past, your success was defined by the information that you had. You knew the right person, learned how to read, went to the best school, and you were set for life. Today, most people can read and Google and YouTube and Harvardโs full curriculum is available online. And yet we are more, not less, confused.ย
School, which is pretty outdated if you ask me, reinforces this traditional view that we just need to find or learn the right information. Occasionally in university a student in my class would find last yearโs answer to the multiple choice test. If the teacher was careless they would use the same test this year, so all you had to do was memorize last yearโs answers and youโd ace the test.ย
Learning to cheat the system like this โ and having multiple choice tests in the first place โ supported this idea that there existed โcorrect answersโ. But it never really prepares you for life after school, where the answers tend to be more sticky, vague, ambiguous, and often donโt have a clear answer (or, there might be many answers). Not to mention, you enter a world where information is exponentially growing and your attention is being pulled in a million and one directions, so itโs not even clear what the question is in the first place.ย
Today, we may not be in school, but when we insist that there is a singular answer to our problems, and itโs out there somewhere online, we still treat life like a multiple choice test. When we ask questions to Google and YouTube and Twitter, we are searching for the most relevant and quick answers and solutions to our problems. We want nothing more than to better understand the world.ย
This is extremely useful when we want the best meatball recipe or trying to find out why your cat is teary-eyed (is it allergies or glaucoma?) or learning how to beatbox, but implicit in the Search Engine is the idea that the answer is out there, and we just have to find it. And this is where it becomes problematic.ย
2.ย
You have an idea for a business and think that your first step is to create a pitch deck and start looking for investors. Not an uncommon thing to do. Your blindspot is that your knowledge of business comes from a hodgepodge of Hacker News articles and watching Shark Tank and The Social Network and the vague recollection of your old roommate Jimmy who sold his company a few years ago.

This could lead you to google โpitch deck templatesโ โhow to make the perfect pitchโ and โhow do I find investors.โ The bigger, more important question could be โdo I even need to raise money?โ and โwhy do startups fail?โ And yet another one could be, โwhere can I talk to entrepreneurs (online or around me)?โ Surely, talking to others before starting your business could be a good idea and save you valuable time (ditto for starting a new job, school, etc.).
Itโs a bit tricky for the algorithms to take into account your assumptions (at least for now), so what ends up happening is that you are searching for answers through your own filter bubble.
The point is that when we ask google a question, it tells us nothing about the quality of the question we are asking. What if we are asking the wrong question? What if we are making the wrong assumption? Unfortunately, the output is only as good as our input.
Asking good questions is difficult. Knowing your own blind-spots and challenging your own assumptions is even harder. You canโt just magically pull the right question out of a hat. You have to find it.ย
One idea is to start with the mindset that your first question is probably not the right one. Instead, itโs an evolving process of asking lots of questions. Before spending time googling answers, spend time brainstorming better questions to ask. Is this really the right question? What other ways can I look at this? How can I reframe the question?
Here are a few prompts you can use to think of other questions:ย
Can I be more specific or more broad?ย
What is the opposite view?
Why am I asking this question?
What are my assumptions in asking these questions? Can I use those assumptions to ask different questions?
Am I priming myself to confirm something I already feel, or am I open and curious to discovering new information?ย ย
Next time youโre looking something up, take a minute to list out more questions and see where it leads you.
3.
You hear about these conspiracy theories that point fingers at certain people or corporations claiming they have single handedly conspired to keep poor people poor or who engineered COVID to control the population via cellphone towers or who actually pull the strings on a global level like Bill Gates or the Koch brothers.
The problem with these theories (and this observation has been made many times), is that the world is too complex for one person to understand, let alone orchestrate something at such a grand scale given the many moving pieces. Conspiracies do happen, for sure, but at a much smaller scale (like Peter Thiel and the Gawker takedown).ย
If they could really fake the moon landing and spray the earth with mind-control substances using chemtrails from airplanes, they should equally be able to drop a few billion dollars and solve world hunger, famine, war and make sure the waiter gets my order right at Dennys. Iโm pretty sure I ordered dressing on the side, but that sure as heck looks like ranch all over my salad.ย
We want simple answers to big questions. Why am I not happy? Why isnโt everyone vegetarian? Why did the school shooting happen? I have a finger and Iโd like to point it at somebody or something, please.
Itโs possible that you come across questions that donโt readily have answers. The more heavy the question, the more variety of answers you are likely to find, and the greater likelihood of bullshit. Especially for the big, meaty questions (relationships, work, finding meaning, etc), you could spend a lifetime searching, and many people do.ย
But there are many ways to live a good life, be a good partner, and be happy at work. There are lots of ways to do lots of things. There isnโt one answer, and yet the empty, white rectangle can make it feel like there is one answer.ย
Itโs easy to create a false dichotomy between good/bad and right/wrong and should/shouldnโt, particularly if you have popular click-bait articles popping up in search results. When I notice myself getting adamant or hard-headed or one-sided, I search out for contradictory information.
That means becoming comfortable holding contradictory views, and accepting that there arenโt always correct answers but just different perspectives. Perspectives, not ultimate truths.
โThe test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.โ โ F. Scott Fitzgerald
Thinking this way takes a little bit of the edge off trying to be โrightโ when we accept that there is more than one right. With an immeasurable amount of information and opinions, I take some comfort in the uncertainty of not knowing.
Perhaps itโs okay to not immediately have every answer at your fingertips and be simply okay with not having all the answers. And instead, let yourself bask in the mysterious, often incomprehensible world that we live in. That we donโt have to know or have to know right now or cannot know. And even if we did know, would that really make things better?
I hope you enjoyed this weekโs newsletter! Let me know what you think and drop me a message in the comments below. I respond to each and everyone one.
Brilliant!