Why We Should Question Everything We Think

Back in June of this year, I had a great conversation with Cal Calahan on my podcast program. As always, when I talk with Cal, I have my eyes opened to new things, and this conversation was no different. I thought that I really questioned many things in life, but Cal says to question everything. So my question is, “why?” And believe it or not, he has the answers.

Do you have a superpower?

One thing I can tell you about Cal is that he has a superpower — and that power is to help other people learn how to unlearn. Yes, unlearn what they know. What does that mean? It means to learn something foreign to most of us, which is the way we process the world — our preconceived ideas and beliefs so that we can build a better, more authentic version of ourselves.

Work toward the goal of a Lifestyle Investor

Cal and I both believe that it’s essential to be a lifestyle investor and work toward that goal. You have to learn that instead of constantly expending energy, you have to learn how to conserve and replenish your energy. We have to learn ways of unlearning even in all of our widespread belief systems.

The Great Unlearn

The Great Unlearn is about being extra curious about where you got all of the ways you think about things? And then have the courage to question that over and over — like be curious about your whole belief system — where did that come from?

You’ll want to decide if what you believe about yourself is real — is it you or not? Everything you’ve known about yourself your whole life — you ask yourself — is that really you or not — and where did that thinking come from?

Unlearn or Unbecoming?

I have a friend, phoebe Mroczek who speaks about the same sort of things that Cal Callahan talks about — only hers is called “Unbecoming.” But kind of in the same ballpark — We’ve become these people but was that by our design, or is it a result of who we hung out with? What have we taken from others? Hopefully, a whole lot — hopefully, we are learning from each other every day.

The world we didn’t create

Cal had an excellent point — “We grew up in a world we didn’t create. And one idea after the next—whether it was culture or society—we were told how to look, how to feel, and who to be.”

Cal gives the example of heading to the family picnic, and mom and dad make you hug the weird uncle that you’d rather not embrace? The rents think they are doing the correct thing — but are they? Maybe — maybe not.

Hey! What’s normal?

Most of the time, when we are children, these people in our lives are just trying to teach us social norms and behaviors — but now that you are an adult — it’s time to take a second look and see if that’s you.

As we ask questions, we need to ask about what we are doing some of our actions for? Are we laying down armor for people? Are we led by our intuition or by what we’ve always been told to do?

Check your motives — and the other guys motives too

As I talked about with Cal, we need to check our motives and the other guys’ motives. We have governments and agencies — companies, businesses, and groups who say they are there for our best good and only trying to be helpful.

Is this the case? It’s vital for us to find out, knowing full well that everything we hear and feel, certainly can’t all be wrong. No! But the concept of, “stop and question” is about deciding if that thought is truly what we think — or have we just been on remote control thinking? But ask, “Where are my blind spots?”

It’s not right or wrong or black and white

One of the most incredible things I learned from Cal is to stop always looking for right or wrong and black or white — because most things are in the middle, and we have never really supposed this in our lives. So is it possible for us just to be curious and feel how we feel without making a firm, definitive conclusion?

And then, learn that you don’t always have to be right — because everything we are thinking about is only an opinion. Cal believes that we can be in the space of the unlearn better if we think about all of the possibilities there are. After that, we hold a space for the curious and just ask questions.

Like, we are not trying to answer the questions; we see what others think and then ask ourselves what we believe? And the two opinions don’t have to match, but we want to be curious that the opinions don’t fit — not wondering which is right or which is wrong.

You won’t make everyone happy

There needs to be a great understanding that we will not make everyone happy, which doesn’t even matter. Especially if someone is in power, having the ability to determine what drives their behavior and special interests. Where does the money come from, and what is their liability?

Everyone is taking care of their interests because they’re human. They take care of themselves, their organization, and their beliefs — and that’s how it should be. The thing to remember is that you need to do the same for yourself. It’s refreshing to understand that it’s okay to be fallible because we are all fallible, which means it’s okay to question everything.

Is curiosity the key to all of the unlearning process?

Is curiosity the key to all of the unlearning process? One of the things that helps me is to begin by being open to different ideas and to keep yourself from being defensive about anything anyone else thinks, feels, says, or does. Being curious and not defensive is a way to keep interactions open and be able to reflect on things that you’re thinking about.


I want to leave this post by saying I have learned a lot from Cal Callahan, and since we first met, I’ve been facing facts about myself and how I think. I have always been curious about everything but hadn’t really thought about why I feel the way I do.

Other people think the way they do, and I’m interested in what they are thinking but hadn’t put it together that they may not even be thinking something — they may merely be parroting back something they learned as a child. I like to hear about thoughts — whatever they are. But I’ll be asking a lot of questions from now on — both from myself and others.

Image Credit: Pixabay; Pexels; Thank you!

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