What’s your biggest insecurity?

Jonathan Chew
Sep 11, 2017 · 3 min read

Recently, at a family party, I was asked this question. At first I didn’t know how to answer, but then I reached down deep inside and grabbed some of the first feelings that came up.

The uncertainty of whether I was choosing the right path.

There’s probably a lot more to this and it’s just scraping the surface of a part of me that has always been worried if I was doing the right thing or whether I was making the right decision.

I had recently hung out with another friend who liked to ask people,

What’s your biggest fear?

I think the the two questions are synonymous because they both reach at something that you are most afraid of doing/seeing/being. And yes, you can always answer with a superficial answer, but I think we should always ask ourselves these types of questions because there is always a part of us that we are “resisting”… a part of ourselves that we just simply… don’t like.


It is exactly this aspect of ourselves that we should not turn away from or ignore, but look head-on and maybe straight at ourselves in a mirror and address by asking, “What is it I don’t like about that exactly?” because then you start seeing what the causes are and maybe even start getting to the root of the problem.

“I think that in order to truly experience the light and the bright, you have to see the darkness. I think if you shield yourself from the darkness, you’ll not appreciate — and fully understand — the beauty of life.” ~Jocko Willink, former U.S. Navy SEAL commander

When we turn to face our fears and address our insecurities, sometimes we see that it’s actually not as big as we thought it was and/or the reasons that are causing it no longer fit our view of the world.


We all have rules that we make for our lives. They’re what we define since childhood and they’re what guide our decisions going forward. Subconsciously, you may not realize you have rules in a certain area, but say you have a fear or insecurity, there is a possibility that there may be some underlying rules about life you may have that is causing that insecurity.

For me, I think I have certain rules surrounding success and my expectations for how I should feel, but through mindfulness exercises and self-exploration, I’ve come to see that life is really about the journey, and that it’s the unfolding of that journey that makes life the most exciting!

The Future

So, in order to decrease your insecurity and fear, you have to be more present with yourself and with the world around you. Some worrying about something that hasn’t even happened yet, or mulling over something that has already happened and that you can’t change. The only thing you can really alter is your current situations and your current state of mind. Once you change your paradigm, the entire world will shift.

Focus on Next Steps

“Where your focus goes, energy flows, and results show.” ~T. Harv Eker

Pay attention to what you focus on and ask yourself more positive questions. We all have insecurities and fears but if you focus on those, then you’ll just bring more of it into your life. They should be addressed by seeing what may be causing it and assessing the blueprint rules you have created for yourself about feeling this way or not feeling this way. Instead of worrying about why you aren’t feeling a certain way or doing something you should, perhaps just choose to feel that way and see what comes up. Start creating the life you want to live instead of expecting life to do it for you.

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Jonathan Chew

Written by

Disney Imagineer. Startup enthusiast. Sci-Fi/Self-Help novelist on a mission to build a Positopian world. Follow me @JonathanGChew or go to: www.chewsjoy.com

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