15 prompts for jogging those "What is my WHY?" juices

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Written by Alison Gilbert


“Each of us has only one WHY. It’s not a statement about who we aspire to be; it expresses who we are when we are at our natural best.” -Simon Sinek

The essence of who we are and why we do what we do already exists inside us, it always has. As we go down “Remember when…” memory lane and look back at moments throughout our life, we uncover stories that make us say, “that was SO me.”

We’ve always been ourselves. The discovery of our WHY is more an excavation of what’s already been there, inside us, buried and covered up by ideas of who we thought we were supposed to be. As Emerson writes, “To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment.”

It’s bugged me for some time now when people put intention into soul-searching and I hear them say “I have to find myself.” I would pose, instead, that you need to reconnect with yourself.

I’m guilty of this myself. I’ve had a moderately persistent preoccupation with finding my voice. As if it’s this elusive, fluttering thing, outside of me that I need to capture in a net, like a butterfly, and harness. It was in recounting a story to a friend about a time I got reprimanded in fifth grade by my science teacher that my idea about this shifted.

I was going through a phase where I’d speak out loud, at times to disrupt the class, rudely. I would also unapologetically emphasize my burps, when I needed to do so, allowing them to loudly bellow out.  I got in trouble and my science teacher implored me not to do that by telling me that “the sexiest thing a girl could be is smart.” In retrospect, there’s a lot fraught with his response to me. For starters, why are you talking to a fifth grade, pre-pubescent girl, about being sexy? Nevertheless, I look back at this with my lens of “who have I always been?” and it’s this memory that was the seedling to help me reconnect with the Alison who has always had a strong voice.

It was the memory of my burping-out-loud phase that led me to remember a Hebrew school teacher I butted heads with, and later a high-school math teacher I butted heads with. The common thread amongst me and these people--because it wasn’t that I was an ill-behaved kid, these were isolated incidences--was that these were moments I was exercising my voice. The burping in fifth grade science class was more an act of wanting to be heard over anything else. This and a flutter of more memories, and some gut-checking with some friends, helped me to see, again, I’ve always been a bit out-spoken. My voice has always been there.

Each of us is already living out our essence, whether we realize it consciously or unconsciously, because our reason-to-be is who we already are, along with the culmination of the experiences we’ve had and collected to date. The difference amongst us is that some people have gone through the exercise of discovering the language to spell out their WHY and some have not...yet.

Finding words to explain ourselves is hard enough as it is in day-to-day conversations. Finding the words that describe our life reason-to-be can feel next-level. But when we articulate, first for ourselves, what drives us, aka our WHY, we equip ourselves with a powerful tool to guide our focus, life direction, and the decisions we make, in all aspects of our lives.

To alleviate the pressure that this exercise can potentially create, think of the WHY exploration as that, an exploration, a journey inward to uncover what about your past self has always been dwelling inside you. This is NOT about figuring out YOUR PURPOSE. That’s too big and overwhelming and, I’m not even sure I believe in that. Think of this as your first step in exploring what your WHY is, a micro-movement toward deepening a sense of yourself.

Whether or not you have a perfectly written out statement that encapsulates exactly your reason-to-be and who you are is beside the point. If by doing this exercise you feel, at minimum, moderately more awakened to yourself, then you have succeeded. And getting to a place where you have a clarified statement written is the cherry on the sundae.

As an exercise to get the juices flowing for crafting your “WHY,” choose one or as many of the prompts below and answer them on a blank piece of paper or in a fresh word doc. I recommend paper. Handwriting activates parts of your brain involved in sharpening critical thinking and memory.

This is a FREE write, the main thing is to let your mind go and let your words come out, without judgement and in as much detail as you feel open to going, the more detail, even if it feels unnecessary in the moment, the better. You never know what could be sparked for you when you reflect and review what you’ve written. When you’re ready, after you’ve done a bunch of free writing, step away from the brainstorm, when you’re ready return back to continue the exercise, get out another fresh piece of paper, read through what you wrote and record the themes you see in what you’ve written.

Then sit with your reflections for some time, maybe some hours, days, maybe even weeks. Come back to a fresh piece of paper to draft out some WHY statements.

To take the next step to turn this thought exercise and initial excavations into a draft of your WHY, check out The WHY’s of 5 Inspiring Women and Tips to Draft *Your* WHY, here.

A pivotal moment in my life when I realized nothing would ever be the same was  ____________.

A time I felt really alive was  ____________. What about it made you feel alive?

A time I remember being really inspired was ____________. And what about is what inspiring?

I’ve been the most energized at times in my life when  ____________. What do you think made it so you were so energized by this?

I enjoy teaching or showing people  ____________. I enjoy doing this because  ____________.

A person in my life who has helped make me the person I am today is  ____________ because ____________.

A person who has shown belief in me in me was  ____________. I think what they saw was ____________.

There was this time I tried ____________. It was new for me and scary but  ____________.

A childhood memory that stands out was when  ____________.

One of my favorite books is  ____________ because ____________.

One of my favorite movies is  ____________ because ____________.

Some people who inspire me are ____________. What about them and what they are doing inspires you?

Something I used to love to do in my free time was  ____________ because  ____________.

Recently I was thinking I’d like to try   ____________.

Something I miss about my younger self is  ____________.

Want more prompts for more WHY brainstorming? Check out these 12 questions for to ask yourself as a step toward unearthing your life mission