My Journey with Insecurity

The birth, death, and rebirth of identity — what I learned living in constant fear of not being good enough.

Jason R. Waller
Mind Cafe
Published in
11 min readAug 23, 2021

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Photo by Artem Kovalev on Unsplash

Most articles I write are focused on sharing a skill or specific idea. This one’s a bit different. This is a story. My story. As I write it, I’m not exactly sure what I’m hoping to give you, the reader. I guess this one’s a bit more for me.

The birth of an identity

I was raised in a small wheat farming community about 40 minutes from the nearest stoplight. This is one of the first things I tell people when I introduce myself. I lead with that because I think it’s something a bit interesting, a bit different. It’s a little out of the ordinary, and I like that. Also out of the ordinary: I was an only child to pretty conservative parents and was homeschooled for most of elementary school. Later in life, my parents owned a retirement home, and I actually lived by myself in a studio apartment of that retirement home all through high school. I was very used to being by myself.

I had a lonely but safe childhood. Looking back, there were times when we obviously didn’t have money, but I never felt or noticed it. My mom especially was always making sure I had everything I needed to be a happy child. She was always trying to lift me up. She would tell me I was amazing, smart, special — perfect. Which was such a blessing but also, in some ways, a burden.

Partly out of expectation and partly out of isolation, I started needing to do well in school and in sports. More and more, I needed to get the A’s and the trophies. I needed to stay perfect. And, in the process, I couldn’t look like I cared or like I was trying. Because more than anything I needed to be accepted, and being perfect was just part of that. By now you might realize where this is heading. The lonely boy who grew up hearing he was perfect became an insecure man terrified he wasn’t.

When I was 17, I joined the military. I often say it’s because it’s “what kids from small towns do” or because “my friends were joining” or because I “needed discipline in my life.” These are all true, but what I really craved was community and purpose. I didn’t want to feel lonely and I didn’t want to feel valueless. I left for…

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Jason R. Waller
Mind Cafe

Executive coach to CEOs and leaders. Partner at evolution.team. Speaker, combat veteran, ex-consultant. Top writer in Leadership. www.jasonrwaller.com