Self-Awareness through The Why Game

The game isn’t fun, but the end result is usually useful

Raven Jenkins
Nov 8 · 5 min read
Photo by Jon Tyson on Unsplash

Over the past few years, I’ve been obsessed with the idea of ‘why’. I believe that a person’s actions and the impact of said actions are heavily impacted by why they do it. I also believe that when we understand why we do, say, or believe something it impacts our ability to carry out an action.

In job interviews, we’re asked why we want to work for the company. We are asked why we are looking for other opportunities. We are asked why we left (or in the process of leaving) our old job. We are asked why they should hire us in the first place.

When a lover does something to betray our trust, we ask why they would do such a thing. We may ask why we allowed ourselves to happen the way they did. Or we’ll even ask other people why they think things didn’t work out.

When something tragic happens to a beloved friend, we ask why bad things seem to always happen to good people.

Without knowing it, we all understand that finding the ‘why’ behind a situation will better help us process emotionally and thoughtfully.

Finding out ‘why’ sounds great and inspiring until you have to do it in a way that doesn’t give you the warm and fuzzies. There are times when I have to apply ‘finding why’ to my internal struggles. We can all benefit from being more self-aware, but becoming more self-aware isn’t always a feel-good activity. In fact, it can be quite daunting when you gain a level of understanding about your own problematic behavior.

The Why Game

I’m not sure why I ended up calling it a game. Games are supposed to be fun, but The Why Game is something that I dread every time I “play” it.

Photo by Dewang Gupta on Unsplash

It’s not something that I pull out at every given moment, but if I do come to realize that I’m in a slump — be it personal or emotional — I have to get down to the bottom of it. I know that whatever is blocking me from doing what I need to do is typically internal and not external. I’ll just use a brief example of how the Why game works when it comes to my writing. I start off with one simple statement.

I didn’t meet my personal writing goals for today.

After the statement, I role right into the questioning:

Q: Why didn’t I meet my writing goals for today?

A: Because I didn’t have time among my other tasks for the day.

The thing about The Why Game is that it keeps me from having a cop-out answer. Rarely is the initial answer to the ultimate conclusion of what went wrong. So instead, we continue asking:

Q: Why didn’t you have time today?

A: I didn’t do my calendar planning the night before like I usually do.

Q: Why didn’t you do your calendar planning?

A: I was doing my daily read and fell asleep.

Q: Why did you fall asleep?

A: I fell asleep because it was a long day and I made the mistake of doing my planning on my bed instead of at the table.

This is just a simple example, but you get the point. I went from “I didn’t have time” to “I didn’t take the proper steps to ensure I would get everything done today”. It creates a situation where I’m actually in control of what happens and I don’t go blaming ‘lack of time’. It’s something that I hear all the time: Everybody has the same 24 hours in a day, it’s just a matter of what we do with that time.

Digging Deeper

The previous example just shows how The Why Game works in a very simple setting. However, I find The Why Game most effective in times where I am going through some sort of emotional turmoil. This is when The Why Game gets uncomfortable, but discomfort isn’t always a bad thing. Sometimes I just need to be real with myself about what’s going on. When we can be honest with ourselves, we’re far more likely to tackle the root of a problem.

Not too long ago, I was feeling very down about something that seemed very small. I didn’t understand why such a small setback was making me so upset. It got to the point where I couldn’t focus on the work I was doing. It was time for The Why Game.

Q: What’s wrong?

A: I’m just really upset.

Q: Why are you so upset?

A: I got another rejection email

Q: Why does that make you upset?

A: I don’t like the situation I’m in and I want to get out of it

Q: Why do you want to get out of your current situation?

A: I’m really unhappy

Q: Why aren’t you happy there?

A: It’s not relevant to what I like or what I studied. It’s not even a little bit fulfilling.

To make it short, The Why Game helped me figure out that the reason I was set about that particular rejection is because I was so sure I’d get the position I wanted. I had gone through rejection emails before, but because my confidence was so high for that one, it took a blow to my self-esteem. The rejection hit my self-esteem because I was so anxious to get out of my job so I could feel fulfilled again. I didn’t read it as a simple rejection email, I took it personally. I was ultimately tying my self-worth into whether or not someone thought I was “good enough” for the job. The conclusion: I was upset because I was tying my importance to what I do and not who I am.

The Why Game is mainly used in situations where I feel stuck. Sometimes I need a moment to get honest with myself about something, and other times I need to hash out my emotions in a way that’s not self-deprecating. The most important thing about The Why Game is that it’s not meant to kick you while you’re down, but to build you up. It’s just that sometimes building yourself requires some dismantling and reconstruction first.

Raven Jenkins

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Writer | Entrepreneur | Blogger | Dreamer | Pro-Oxford Comma; Feel free to check out my blog at

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