(Don’t) Be Careful


As I sat across from the nice young man in his sterile, windowless office, his eyes widened and he began to nod.

We sat together in a bank, his workplace, and he was helping me to create money out of thin air.

During his due diligence, he asked me what my Very Cool Life business was all about.

In my roundabout way, I told him about my book and my belief in living a freedom-based life. Going deeper, I told him that I train people to think more expansive thoughts than the ones taught to them by well-meaning (but fearful) people like their parents and teachers.

That’s when his eyes grew bigger and the nodding began. He could hear me; he understood.

Then he shared some of himself with me…

“I know what you mean… My parents wanted me to be an accountant, but I just couldn’t do that all day. I still stare at a screen, but at least here I get to talk to people like you,” he said.

As he shared about some of his life decisions, I could tell he wanted more. I could feel it. When it’s there, I can always feel it.

But no, this was not the time or place to nudge him.

Instead the conversation moved around, each of us sharing more about our personal lives and the things we liked.

I found myself telling him of my desire to have a professional grade zip-line created on my property, just because it would be super-awesome to fly through the trees.

“Oh, wow! That’s so cool! Be careful!” he said.

His last two words struck me like ice water to the face.

Be. Careful.

Really? I wanted to say. Why are you choosing to say that? (I said nothing. Not the time, nor the place.)

I thought about this young man and those two words on my drive home.

The words were not his, of course. No, those words were imprinted within his brain long ago, before he knew he had a choice in listening to them. The old message within his mind was meant to serve as a thin shield to protect him from the dangers in the world. During our conversation, he just hit the PLAY button once more out of reflex, the words tumbling out of his mouth beyond his awareness.

Well-intentioned people have directed those words at me many times over the years. And they still do. (This particular incident stood out because I do not recall hearing the words from someone younger than me.)

You’re majoring in psychology? Be careful.

You’re leaving academia to start a business? Be careful.

You’re not going to have a real job to fall back on? Be careful.

You’re giving up your health insurance? Be careful.

You’re going to climb that mountain? Be careful.

You’re spending all that money on that? Be careful.

You’re going to do what? Be careful.

Again, I understand where these people are coming from. I know they want good things for me, but I also know their advice is less about my welfare and more about a compulsion to share their own fearful beliefs about the world.

When people tell me to be careful, what I really hear them saying is…

I have been taught that the world is a dangerous place where bad things can happen if you’re not “playing it safe” and doing things “the right way.” What you’re doing diverges from what I was taught to believe long ago. Thinking about the world as dangerous does not feel good to me and makes me uncomfortable. Instead of looking inward — and noticing that this discomfort is signaling me how far I’ve moved away from my inner guidance system — I’ll project my fearful thoughts back onto you. I‘m not willing to open up to who I really am just yet. Be careful.

The perception is that on the other end of the continuum from “careful” is “careless.” I don’t think that’s really true.

The entire notion of “being careful” is rooted in the fear of what could go wrong. It’s fearful thinking. So, what’s the opposite of fear-based thoughts, decisions, and actions?


When you are moving through life paying attention to your personal sense of alignment, you are going inward first, noticing how you feel, and following what feels better.

When operating from alignment, very often the choices that feel right to you will not match up with what looks right to the rest of society (the “be careful” crowd). Just know that and move on.

Living from alignment does not mean you will never fail. I have failed, fallen, and jumped in in over my head (both literally and figuratively) every now and again. But of course, that’s how we learn and grow.

Careful people are so afraid to bump into something, to make a mistake, to fail, that they never allow themselves to venture off onto the road of possibility for themselves.  And their fear – cleverly disguised as prudence – keeps them living smaller lives.

Maybe being careful might keep you from experiencing something you don’t want to experience.

But being careful never got anyone what they really wanted.


Be careful, you say?

Thanks for thinking of me… and in the same spirit, I’d like to offer you some words as well.

Stop being so damn careful for a while.

Get to know who YOU are.

Get to know how YOU would really like to live.

Stop protecting yourself from your desires.

And see what happens.


You just might surprise yourself.



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  1. says

    Xcellent and so true, Drew!!
    We are all so programmed to be “afraid”, that’s why we stop living!!
    Thanx for sharing your wisdom, Drew!
    Be alive!!!

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