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  • Jason R. Waller

My Journey with Insecurity

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



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 Iraq a year later, the first time I’d really been outside my home and comfort zone.

I was good at my job and I was good at being a soldier. I wasn’t the smartest or the most physical, but could balance both better than most. I earned more qualifications than my peers, had more badges than my superiors, and was named honor graduate at most courses I went to. In the military, I could aim for “perfect” and usually get pretty close. And people looked up to me for it, for the first time in my life.

This was the high I was looking for. Success. Achievement. And I didn’t just want more of it, I wanted all of it. I wanted all the A’s and all the trophies. In the military, I enlisted as an infantryman, then got promoted to noncommissioned officer, and finally commissioned as an intelligence officer. In parallel, I went to a local state school, then transferred out-of-state to a top-tier public university, and finally made it to an Ivy League school for my graduate program. For work, I volunteered as a consulting intern for a local hospital, then joined a respected public sector consulting company, and finally landed a role at one of the top-three consulting firms in the world. I got married, had two kids, lived in a half-dozen countries, and sought out a fun, new experience every few weeks. Happiness was a checklist and life was a ladder. Until one day, it wasn’t.


The death of my identity

After two decades of chasing a high of achievement, I finally made it to the top of my ladder. Eventually, I didn’t see any more rungs to climb. I couldn’t figure out what to add to my checklist and I didn’t know where to go next. To add to the confusion, I also wasn’t happy where I was.

Like I said: in the military, I could aim for “perfect” and usually get pretty close. Working with Fortune 500 executives at the world’s preeminent consulting firm, though, I never once felt like I was good enough. This is something I only realized in hindsight. At the time, I just felt anxious and overwhelmed, filled with dread on Sunday evenings as I headed to the airport to fly out again. The insecurity — this need for perfection — that had always pushed me forward started to push me over.

A more self-aware man would have realized what was happening. A stronger man would have leaned in, tried to understand, and asked for help. But, despite fighting every day and in every conversation to be seen as a strong man, I was not a strong man. I started drinking most days, and then every day. I would flirt with the bartenders and flight attendants. Anything to escape the feeling of not being special, of not being good enough. I threw myself even more into work, looking for validation and connection. I let my wife focus on being the parent and I set to work being the provider. I accepted my role as the “hunter” and my purpose as leaving on the hunt. My greatest value became being gone.

Along the way, I was so invested in being perfect and strong, in playing my role, that I never even understood what I wanted. I did lots of “fun” things, sure, but I never let anybody — myself included — know what I really needed. Anything I did for myself was surface deep, a distraction. And then I would move quickly back to playing my role of strong provider, never complaining and only thinking of others. Only thinking of myself in the context of others. Each week, I would martyr myself on the altar of responsibility and duty. I was “around” as a father, but I never showed up as a parent. I was “around” as a husband, but I never showed up as a partner. I see myself in the quote by Anaïs Nin:

“I was always ashamed to take. So I gave. It was not a virtue. It was a disguise.”

I’d like to tell you that I found myself along the way. That, bruised but not broken, I came to my senses and woke up. But I didn’t find myself then. I was broken. My marriage ended in divorce. My consulting career ended in me quitting before I was fired. And my crusade for perfection ended in the deepest feelings of inadequacy. All of these words, these labels that I had fought tirelessly to earn, started to die.

Husband. Successful. Consultant. Strong. Father. One by one, my identities stopped breathing. Some ended abruptly and violently. Some ended slowly. I tried to resuscitate them, clinging to their survival, but it was like trying to punch waves back into the ocean. And then one day, there was no more fighting, only grieving. I entered a period of mourning. Not for who I was now, but for who I was no longer.


My identity’s rebirth

My divorce was the lowest emotional point in my adult life. It was my decision in the end, but it was still traumatic. Dr. Gabor Maté said that trauma “… is not what happens to you” but rather “what happens inside of you as a result of what happens to you.” I like that idea, because my biggest difficulty with my divorce wasn’t in the process of the divorce, which was thankfully civil and parenting-focused. What felt really painful was the disconnection with myself and my identity that I felt afterward.

The year of my divorce was a forest fire event, and it burned away almost everything that had grown. It scorched the landscape I had become familiar with. But, just like a forest fire, it marked both an end of what was and a beginning of something new.

In slowing down and reflecting, I was confronted with who I had been becoming over the last several years and how I had been living outside of my values. It wasn’t until I was standing in the rubble of my life that I realized I was holding a hammer. I had stopped paying attention to who I was and who I was becoming. I had stopped being kind, especially to myself. Seneca said that “All cruelty springs from weakness,” and in many ways I was weakening.

So many aspects of my life were tapping me on the shoulder, asking me to wake up, warning me that I was on autopilot. But even if I had grabbed the wheel, I wouldn’t have known where to steer. Even though I felt malnourished, I never had the vocabulary to say exactly what I was hungry for.

The gift in this painful rebirth was the opportunity to give voice to the hard questions I had been ignoring. What were my core and guiding values? What purpose did I want for my life? What did I define as happiness? Slowly, painstakingly, I pulled apart my armor and looked at the scared boy inside. There’s a great quote by Rumi:

Your task is not to seek for love, but merely to seek and find all the barriers within yourself that you have built against it.

My own barriers were many — the need to be perfect, defensiveness in the face of disagreement, avoiding deep emotions, ruthless destruction of anything that looked like weakness, and many others. But these beliefs were all birthed by a bigger idea, a single belief that governed my whole life to that point: that my value and my worth were conditional. I had to rewrite a lot of assumptions in my life, but this was the hardest by far to undo.

I feel that I didn’t actually become an adult, a man, until I let go of this belief. It’s only recently that I “woke up” and grew into an independent version of myself. I don’t pretend that I’m a Zen master with super awareness — in many ways I have a long way to go. But I do feel now that I’m on the other side of an important mile marker. I feel like I’m past a midpoint, where I’m now walking out of the forest, not into it.

As I write this, I’m living the happiest day of my life. And I expect, but not out of hope or desperation, that tomorrow will be even better. I still source some of my self-worth from others or from what I believe they think about me, but I believe less and less that my value is conditional on what I do or how well I do it. My identity is less and less tied to my accomplishments.

Amazingly and unexpectedly, this has also unlocked new levels of productivity. I’m so much more effective when driven by curiosity and authenticity than by shame and insecurity. This isn’t the only paradox I’ve unearthed or discovery I’ve made along the way. In fact, I’d like to share four of the big ones here, in my writing, to hopefully leave you with something “bigger than me” and my own experiences. A thing or two to take with you on the adventure.

Confidence is just shorthand for safety

So much of my wrestling with insecurity was tied up in the word “insecurity” itself. I fought with it, put it down, ignored it, and shamed it away. But it was just a symptom, a shadow cast by a bigger concept. Insecurity literally meant that I didn’t feel secure or safe. The confidence I was searching for was really just safety. Today, when I work with clients on insecurity, defensiveness, impostor syndrome, you name it, it’s always a core story running on a loop of how they don’t feel safe being themselves or sharing themselves with others. If we want to feel confident, we must first look to where we don’t feel safe and why.

Our core stories are written in childhood

Safety is a basic tenet of survival. Our minds are hardwired to keep us safe and to look out for threats. There’s a saying in evolutionary psychology: life has to win every day, but death only has to win once. At a human level, we are incredibly risk averse. And to maximize chances of survival, we learn our definitions of safety at a very young age. These ideas or beliefs might have other words in them, like love or acceptance or value, but at their core they’re all about survival. To understand our own core stories, we must look back to when they were written.

Our stories must be rewritten in adulthood

Fundamentally, there’s nothing wrong with our safety programming — survival is a good thing. The caveat here is that the world is both more complex and less threatening than our programming would lead us to believe. We don’t need to be as risk averse as our stories might tell us and, in fact, we might lose more than we gain. Failure might be painful, but it’s rarely fatal and might lead to important growth. There comes a time in our lives when we need to rewrite our stories. As a first step, though, we need to acknowledge that they’re here for a reason. We need to look at our stories with compassion, even appreciation for what they gave us. My perfectionism drove me to do great things, but later it held me back and sabotaged my growth.

We rewrite our stories as authors, not the characters

Our closely held beliefs are not easy to reprogram. There’s a technique in horticulture called “espaliering,” where you prune a tree against a frame, training it to grow flat. The tree keeps two-dimensional shape long after the frame is taken away, much like our adolescent stories keep their structure long into adulthood. By recognizing and acknowledging these beliefs, though, we empower ourselves to write new stories. It isn’t easy. It takes time and practice. We’re used to being led by our stories, not the other way around. But to craft new stories, we need to take the first step: pick up the pen.


In closing

I was able to pull a few lessons out of my experience, but this was all in hindsight. My struggle with my identity and the confusion of life being turned upside down was just that — a struggle. I only now have the language to talk about it, and I’m certain that in a year I’ll have an even newer clarity to share. I’ve come to appreciate and rely on this pattern, that every realization is building on the last one. That clarity comes day by day. That awareness compounds.

For anyone who’s struggling with the death of their own identity, take comfort: this too shall pass. For better and for worse, nothing stays the same. But one thing will never change: your labels are not your value or your worth.

You are enough. You have always been enough, even if you didn’t realize it.

Good luck on your journey.

Originally published in Mind Cafe