Cure Your Insecurity, Part Four: The Question You Need To Ask



If you have followed along so far, we have identified what you feel insecure about and, more importantly, why you feel insecure about it. 

A lot of people think that that is good enough and that they are in the clear now and can go live their lives. 

Maybe for a select few that is the case, but it is rare. 


Knowing what you are insecure about and why is crucial but it is not enough. You have a lot of new awareness but you do not know what to do with it. 

At this point, people often break up into two groups:

  1. They do not know what to do with the knowledge and so they puff their chest up and think that the knowledge is enough and brace themselves for whatever life throws at them.

  2. They think that the next step involves some huge change in order to make new confidence permanent, they hype themselves up way too high, and then whatever change they choose to make is short-lived. It burns brightly in the beginning and then peters out, New Years Resolution style.

POP QUIZ: What do you think happens to both groups?

No, really, take a guess. 

Do not say that they fail, because trying is not failing. 

The answer: both groups end up insecure again! Maybe even about something new!

Why? Because they created a new expectation for themselves about what to do with the new awareness but realized they have a skill gap around what to do next, which can make them feel incompetent.

And the cycle keeps spinning. Over and over. 


Group #1 has it a little worse because they are basically saying "Okay, I got this. Whatever comes my way, I can take it and push through. I will not let it affect me." 

Though honorable, this mindset relies on two huge factors: your adaptability to life things that randomly occur and a level of serious reactivity

What I mean by reactivity is the fact that you are literally opening yourself by saying "Bring it on, World" and so you will always only be reacting to everything.

Remember when we talked about the caveman a month ago? If he did not learn how to learn how to survive, he would be stuck in a cycle of endless reactivity learning how to fight a Sabertooth tiger for the first time every time he faced one. 

Insecurity cycles are the new version of that learning experience. It is about your survival. 

If you set yourself to be in reaction mode at all times, you will be in a constant state of hypervigilance and a low level stress response...which is not healthy. 


Neither is blowing up the next step to be this huge unsustainable life change that you do not really have a chance at accomplishing. 

So what do you do?

Ask a question.

It is that simple. 

Here is what I mean: Last week I asked you to think about the connections for which you are grateful. Before that, you learned what you are insecure about and why.

Beneath insecurity is a desire for something, otherwise you would not care very much about the task or goal and then not have to worry about feeling competent about it. 

So here is what you do:

  1. Choose one of your human connections for whom you are grateful.

  2. Reword your aforementioned desire into a question (I'll give an example in a second).

  3. Ask your connection their advice about the desire. 

This is a matter of classic networking, but with the increased focus on breaking you out of insecurity.

Here is an example: You are insecure about changing jobs.

Desire: to get a new job / gain new experience

Group 1: "I will quit and see what happens. Bring it on."

Group 2: "I have to have a new job and everything all perfectly set up before I quit this job."

What you should do: Ask someone you appreciate: "Hey, I am trying to change jobs. Do you have any advice for me about a first step?"

Other versions of the question: "Have you ever changed jobs before?"  "Do you know anyone who has changed jobs in the past? I'm curious what to do first."


Questions are the most powerful force in the universe, in my opinion.

Questions are the only way we learn anything, and learning things is how we survive. 

In the coaching industry, the sole responsibility of the coach is to ask questions in such a way that guides clients to new understanding without ever forcing a suggestion. Sometimes a coach's questions lead clients to ask new questions of themselves and opens the door to deeper self-exploration. 

When I worked with suicidal youth in the past, suicide was contemplated because they did not know how to ask a question to someone who could support them.

They gave up.

They thought that no one would be able to help them with their core desire and that they certainly could not help themselves. 

That is where I came in. I asked them questions they had never thought of and opened up thoughts they had never had, which led to opportunities they did not think were possible. 

Questions have the power to change your life.

No matter what you are insecure about, there is always another question that can be asked and another person out there who can answer it. 

Keep it simple.