Why? Seriously, why?

What you should ask yourself to stop the world from walking all over you.

Hey everyone,

If you comment on these Substack posts or reply to the emails, I’m going to start sharing my favorite one each week. Last week, Brett left a great comment!

Quote of the week

“Cultivate a reputation for being dependable. Good reputations are valuable because they’re rare (easily destroyed and hard to rebuild). You don’t have to brew the most amazing coffee if your customers know the coffee will always be hot.”
— Conor Barnes


How often do we make sure that we actually understand something?

Much of my college experience involved as much cramming as humanly possible. I would work all day, have night-classes, party after, and memorize as much as I could in-between. A framework that many students before me had success with.

Unlike college, the real world doesn’t really care how much you memorize. Being able to recite things and fill in bubbles can ultimately only get you so far. My bosses never really seem to care how fast I can deliver on an answer. Instead, whether I can reliably deliver an answer that won’t send them up a creek.

And so how do you become someone that can reliably deliver an answer? How do you ensure that you actually understand something? Why should you even care at all?

It’s easy, and it’s by nature of one simple question: “Why?”

There was one college class that didn’t reward me when I memorized. It rewarded me by thinking a lot and being actively engaged in the class. That philosophy class was productive discomfort at its finest. The professor would drill into our beliefs by asking us extremely thought-provoking questions. The professor had no vested interest in being right in any debate, his point was to prove that we generally had an insufficient amount of information to support ourselves.

If you’re at all familiar with philosophy, you have heard of the Socratic Method. The Socratic method is especially effective in teaching as it encourages students to draw their own conclusions through questions as opposed to answers. By definition, it’s a cooperative argumentative dialogue between individuals.

It’s asking “why?” a shit ton.

If you don’t ask yourself why, the world will walk all over you. Someone with malicious intent can very easily get what they want when you don’t understand what’s going on. Someone that is ignorant could accidentally mislead you. Especially if you are in management, this can really happen a lot.

More often than not, most people do not ask why.

The issue is that getting complete information is challenging. By simply intervening any discussion with a ‘why’ can run the risk of coming off as a burden. I would wager this is why most do not ask “why” as it’s far easier to accept what you’re being told. But the tail-end of incomplete information is almost always problematic.

I think this is a pretty discernible distinction between someone who does well in the world and someone who ultimately does not. Someone that is continuously curious and isn’t too proud to ask “why” can make better decisions. They often understand the complete picture - for better or for worse. They’re more effective individuals.

I can’t emphasize enough: never accept things at face value. This extends outside of career and into our daily life as well. When Warren Buffet studies, he reads every single footnote. His version of ‘why’ is being relentlessly thorough.

It’s important that this is actionable for you. Try and remind yourself of this often:

→ When someone says anything, ask yourself why. Why do they claim or ask this? What information are they operating with?

→ When you’re reading something ask yourself why the text says so. You might end up deep into some rabbit holes but you will know for certain.

→ Most important: When you don’t understand something, ask yourself why? When you lose in chess - why? When you miss a deadline - why? When someone claims something you don’t understand - why?

Ultimately, I suggest you seek depth with everything you do. And the fast track to doing so is by continuously asking why. Exhaust your curiosity until the bitter end.

I just know that anyone I’ve ever encountered that is impressive has an insatiable curiosity. Or, at minimum, they just understand the world around them really well. You will have to trust me on this because I don’t have the data to prove it.

Or you might start looking around and asking why.


100 Tips For A Better Life

I recently read this post from Conor Barnes and it was one of the most agreeable lists I’ve seen in some time. You should check out the full thing, but here’s a few of my favorite tips from him:

48. Keep your identity small. “I’m not the kind of person who does things like that” is not an explanation, it’s a trap. It prevents nerds from working out and men from dancing.

66. Being in groups is important. If you don’t want to join a sports team, consider starting a shitty band. It’s the closest you’ll get to being in an RPG. Train with 2-4 other characters, learn new moves, travel from pub to pub, and get quests from NPCs.

79. When dating, de-emphasizing your quirks will lead to 90% of people thinking you’re kind of alright. Emphasizing your quirks will lead to 10% of people thinking you’re fascinating and fun. Those are the people interested in dating you. Aim for them.

95. Some types of sophistication won’t make you enjoy the object more, they’ll make you enjoy it less. For example, wine snobs don’t enjoy wine twice as much as you, they’re more keenly aware of how most wine isn’t good enough. Avoid sophistication that diminishes your enjoyment.


The last week

This past week, I moved into a new place downtown Denver. It’s an absolute dream here and I’m excited to be living somewhere I’m actually proud of.

Wishing you and yours the best,

Cullin