Why is it important to ask hard questions?

The pieces I have enjoyed writing the most are the ones where I don’t have a general outline or sense of direction before I start. Instead, I pick something I’ve been thinking about and find interesting and try to turn that into words that make sense. In that process I often begin to discover what I am seeking, which I find to be both very rewarding and fun.

Asking hard questions

You know those moments in life when you’re talking to someone and they ask you something that you have no answer to, even though you should? Sometimes it happens by chance, but more often there are a subset of people that think about those types of questions and ask them frequently to many people.

I love those moments because they challenge us, our notions and our self concept. In order to feel good about ourselves, I, along with many others, think about how others might perceive us for the choices that we make.

I didn’t understand it when I read As One Is by Krishnamurti, but I do now. That part of us is the ego. Very interesting topic that I’m thinking a lot about, but for the purposes of this article, I bring it up because it makes us answer most questions that people ask before they ask them.

If someone says how fast is your mile? I want to be able to share a number that I’m proud of. If someone asks where I go to school, what my GPA is, what my summer job is, who I got coffee with yesterday (the list continues), I (we) want to have answers that we believe others will be satisfied with.

Due to this, I find myself making a lot of my decisions by including a consideration of “if I do this, what will the impact be from another’s perspective?” Even more detrimental, though, is the notion of using our ego as an answer for why we are doing something. Why am I working really hard in school? If the answer that I give to myself (which nobody ever admits, often not even ourselves) is, “so that others see me as hard working,” then there is a critical mistake being made.

The reason is twofold. One, there are a lot of things that society, as a whole, would respect. We respect an array of different professions, and if I am making decisions purely based on how others will see me, then the choices I make end up becoming relatively arbitrary based on my environment. The second reason is because our time is extremely valuable. Anytime that I am spending doing one thing means that I’m not doing another.

Thinking like that all of the time can drive people crazy, but the thing is that you don’t have to think about it all the time.

A huge portion of our life is spent in the physical act of doing as opposed to thinking. I’ve talked a little about this before, but once you take the time to align to your values and beliefs and come up with a plan of action, then you can move on it with persistence and (hopefully) some sort of obsession.

To get to the values and beliefs, though, you have to ask really difficult questions that primarily start with ‘why?’

What are the questions?

Hard questions force us to think deeply about our beliefs and our actions. To be a high-impact person, or even find what you love to do, I am convinced that you almost certainly have to be very good at asking these questions.

They can come in many different forms, and while asking them to other people can push them, the most important piece is to be able to ask the questions to yourself.

When you do this, you get to the core of why you do certain things. If it’s a problem (either in life or in a company), then getting to the very root is crucial to finding the solution. In businesses we’ve often heard the idea of continuing to ask why until you find the real problem. I believe in that, but it’s talked about a lot.

What I find more interesting is asking hard questions to people (or ourselves) about the life decisions we make.

Now, the super important distinction, and this can make it even harder, is understanding what the goal is. For every person, that is different. I could ask one person why they are working in San Francisco and they might tell me that it’s because they love nature, they love living in a city as vibrant and progressive as SF, they love good food, and those are the things that are most important to them. They make them the happiest, and the work they do is to support their other endeavors. That’s a great answer. I might ask someone else why they are in SF and if their answer is “there are a lot of cool tech companies,” then that’s usually bullshit. That’s our ego talking. Making decisions based on how we want to be perceived by others.

How do we escape it?

I just finished a book called The Fountainhead that I’ll write about, separately, that includes these ideas a lot, but to touch on them:

There are some people that were either raised or born (maybe?) in such a way that they care 0% about what others think. They pursue the thing that makes them the happiest all of the time and they don’t sacrifice. Elon Musk or Steve Jobs are great examples, but there are many people on a more micro scale. Think about the people you see that are 100% sure of themselves and could give two shits what others think. They might be a barista or an amazing parent. They don’t have to be changing the world. The key is that they are doing what they want to be doing.

Part of me wishes that I had that mental, but I don’t. I was conditioned when I was younger to care about how others saw me. I wanted to fit in at school and when I didn’t, I strived to be more like everyone else. While I’d consider myself more of an independent thinker than most, I am still constantly thinking about how others see me, and it’s detrimental.

The reason that this is related to the questions that we ask is because the surface level answer is quite often ego-driven. I might be taking the internship in San Francisco, not because I want to learn and make an impact but because getting an internship is the right thing to do. The surface-level answers are SO easy to come up with and not be challenged by most, which is why we have to challenge ourselves.

“Why do I want to be a consultant? I like to travel and I want to learn to be a better problem solver.” That answer is sufficient for many people.

I’d urge you to continue asking. Does it take you two years of your life to learn how to solve problems? Do you like travel when it’s every week for almost two years straight and sometimes when you don’t get to choose the location? Is there another thing you could do that would help achieve both goals without sacrificing two years of your life?

This can apply on a career scale, but also in how we spend our free time. “Why do I go to a lot of parties? I like meeting people, pushing myself to be better socially and talking with girls.”

Continue asking. Is the party where you drink a lot and then go dance for two hours pushing you socially? How many girls do you go talk with?

These are harder questions to ask, especially when we don’t have good answers to them. The longer that I might go doing something that isn’t aligned with my values, the more I will align my values towards that thing. Eventually the consultant has 10 reasons why they wanted to go into consulting. The partier now loves to dance and they think the only way they can have fun is to be fucked up.

We want our actions to be consistent with our beliefs, and sometimes it’s easier to alter our beliefs (even when they fundamentally aren’t changed) than it is to alter our actions. Especially when our parents want us to be consultants and our peers will praise us, or when all of our friends are going to those parties each week.

There’s something that has begun to give me the strength to escape this type of thinking.

We can do whatever we want

Part of escaping this trap is realizing that the world is limitless. I could not go back to school in a few weeks, take all the money that I have and go live on a Kibbutz in Israel. And, even though we might be judged or scorned for it, we’re going to die in 60 years anyways and who will care then? (sorry a bit morbid).

When you realize that we have complete autonomy of our choices (admittedly, this is speaking from a fortunate point of view where I don’t have to be working to feed my family, and that is an entirely different case), then it helps you ask the right questions. Why am I spending my summer, working 40–50 hours a week in San Francisco for company X when I could be traveling around the world, or going to the beach every day or learning how to code.

The diligence that we are able to use when asking ‘why’ in a business setting should translate the exact same way back to our lives.

Surround yourself with other independent people

The other piece I find to be empowering is being around other people that ask the right questions and are doing what they love. Being around people that are tied up in society’s norms makes it harder for you to do anything different because it means that you have to do the opposite as your friends and peers. If you’re around others that are following their dreams, though, and that aren’t worrying about the pressure around them, it makes it a lot easier. All of the sudden, I’m being encouraged to become a yoga teacher and explore spirituality.

We shouldn’t need the encouragement, but I have realized that taking a big leap is really hard for people. Not to say it can’t be done, but when you’re used to being around people and validation all of the time and you suddenly isolate yourself, it can be a lonely feeling that hits people hard. If you’re around people that can help you make the jump, though, even though the jump has to come entirely, 100%, from within, it makes it easier.

I could go on about this for a really long time and don’t think I’ve tackled any big questions, but I’m slowly wrapping my head around it.

Resonate a little bit with what I’m saying? Reach out, let’s talk about it.

Thanks for reading :)

NBA