Feeling Insecure? Here are Two Questions for You

February 22, 2024
Reading time: 4 minutes
Power of Thoughts, Self-Sabotage, Self-Worth



It’s no fun. And even the most empowered and self-assured among us encounter insecurity from time to time. It’s sneaky that way… Insecurity is a subtler form of fear, and we often operate from insecurity without ever realizing we are doing so.

While fear is an uncertainty about what could happen as a result of a perceived threat, insecurity is an uncertainty we have about ourselves—a lack of security about our worthiness, our skills, or our capability to meet certain challenges.

Insecurity can look like any one of the following:

● Anxiety
● Fear of abandonment or rejection
● Imposter syndrome
● Extreme self-sufficiency
● Suppression of emotions
● Inability to express anger
● Harsh self-criticism
● Perfectionism
● Comparison to others

Have you ever “let something go” that you probably shouldn’t have in relationships or the workplace? And if I had to guess, you didn’t bring it up because you felt the risk of a negative outcome was too high. We owe ourselves self-advocacy. We deserve to express our desires, set boundaries, and create a life that supports us. And yet, for many of us, we are far more inclined to advocate on behalf of others.

Does this sound familiar? “I procrastinate with confrontational things and uncomfortable conversations. I’ll give myself a deadline. And then I’ll change that deadline when that deadline shows up.”

Relatable? Maybe you’ve said this to a friend as you’ve tried to sort out just how to approach a stressful situation.

Insecurity is the culprit, and while that statement might feel innocuous enough, that response over time can become incredibly detrimental. What may seem like mild avoidance in one instance can grow into a massive blindspot and long-term stagnation. It’s also important to know that there are many different kinds of insecurity, and understanding how and when it can arise for you will better support you in facing and dismantling it.

Psychologists have identified that insecurities fall into one of six categories:

1. Physical
2. Emotional
3. Social
4. Financial
5. Intellectual
6. Relational

Interestingly, for something that can creep in anywhere, insecurity is made, not born. It certainly has a psychological component, but it typically arises from an outside source early in our lives— a message, a thought pattern, a belief that we took on as the result of a person or event. Understanding this can help us stop it in its tracks the moment we recognize it’s happening.

Before we go on, I’ll say it right here: while the source may seem external, this is a purely inside job. If you consistently think you’ll feel confident once you achieve something or look a certain way, I’m here to burst your bubble.

The kabbalists teach that what we see on the outside, in the material world, is a mere 1% of our entire experience. Not even close to the full picture. The other 99% resides in the unseen realms—our inner experience, our consciousness, beliefs, emotions, and perspectives. Shifts made in the 99% realm are what create shifts out in the 1% world of form. When we are overly focused on the outside, this is when we get stuck, frozen in a loop of insecure thoughts and beliefs. Want an example of how powerful the 99% experience is?

That quote I shared above about putting off uncomfortable conversations comes from none other than Oprah Winfrey in an interview she did with Fast Company in 2015. Arguably one of the most successful women in history, her outer world would be everything most people think they need in order never to feel insecure again! And yet, insecurity does not escape her. She doesn’t allow it to control her, though, and in the interview, she described the two questions she asks herself when those insecure feelings arise. They are not unlike the many tools I offer to eradicate fear from our daily experiences and can be used whenever you’re feeling the chilly grip of insecurity:

1. What’s the worst that’s going to happen here?

When you’re feeling insecure or anxious about a situation, pause for a moment and ask yourself, “What’s the worst that’s going to happen here?” By doing this, you’re stepping outside of the immediate emotional response and encouraging critical thinking about the actual consequences of the situation. Often, you’ll find that the worst-case scenario is either highly unlikely or something you can handle. Even this realization can significantly minimize the intensity of those insecure feelings. Here’s a step-by-step guide to approaching this:

Identify the Fear: Clearly define what you’re insecure about. Is it fear of failure, embarrassment, or fear of losing an important relationship? Get really clear on what you’re fearing will happen.

Imagine the Worst-Case Scenario: Think about the absolute worst outcome that could realistically happen. Be specific in your analysis and really lean into making it as horrible as you can imagine! This one is counterintuitive because one of the tools to stop fear in its tracks is to stop catastrophizing. Here’s the difference, though: if you consciously and mindfully catastrophize, you should realize just how ridiculous and unlikely that outcome is. If this tool doesn’t work for you, try the opposite. Instead, visualize the best possible outcome.

Plan for the Worst: Even if you feel it’s unlikely, you can still plan ahead. What are the things you could do to handle the worst-case scenario?

Remember, You’ll Bounce Back: Things are rarely as awful as we imagine they’ll be. Winston Churchill put it eloquently, “Success is not final, failure is not fatal. It is the courage to continue that counts.”

2. Why do I fear this experience?

This follow-up question serves to get to the root of the insecurity, which is the first step in eradicating it. It is a powerful technique for confronting and understanding why certain people and situations bring up insecurities. Beneath the insecurity is an array of negative thought patterns and limiting beliefs that may need to be examined, and this question is the door to that exploration.

  • Why do I fear having a difficult conversation?
  • Why am I afraid of giving this presentation?
  • Why am I afraid to ask this person on a date?
  • Why am I resisting taking action on this?
  • Why do the photos of that influencer’s perfect house make me feel bad?

This self-reflective approach also helps to build a greater sense of control over your emotional responses—the key to diminishing your insecurities’ powers over time. When you can ask these questions, you’re inviting rational thought into the mix, which also helps you view the situation from a grounded, intellectual place.

Insecurity is something we’ll all face—you, me, Oprah—but training yourself to see it as an opportunity instead of a defect will help you transform it into growth. Coming face-to-face with our insecurities removes their power over us, and when we can rise to difficult occasions, we’re saying yes to our transformation. Our greatest life requires a willingness to be uncomfortable, and being able to confront and manage the voices of insecurities is a part of the process. Can insecurity really hold us back to this degree? It absolutely can. But only when we allow it.


  1. Jonathan Daniel Kruger Erbstein : February 26, 2024 at 6:28 pm

    Amazing, thank you!

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