Whose Why Is It Anyway?

Successful leaders start with why. Thriving leaders go even deeper.

Holly McCann
Grail Leadership
4 min readFeb 25, 2024

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Photo by Luke Leung on Unsplash

Simon Sinek’s wildly popular 2010 TED talk How Great Leaders Inspire Action centers around a simple premise: Start with the Why of your organization to get people to buy your product or service.

Connecting to a clear Why is crucial for business success: Why does your organization exist? What impact does your product or service create for people or the planet? What are your values, hopes and dreams for the company or initiative you’re leading?

But let’s go deeper and get up close & personal with your individual Why.

Why? 😉 Because as an individual leader, consciously connecting to your most authentic Why ~ the Why that makes you come fully alive ~ can mean the difference between burnout and thriving.

And… that is easier said than done.

One of the first questions I often ask my clients is “What does success look like for you?” With a puzzled look, most will say they’d never been asked that question and hadn’t actually thought too much about it.

I hadn’t. For decades, I was chasing an amorphous ideal called Success without going deeper into what that really meant for me.

What is my why?

Why am I in business? Why am I working so hard? For many years, the answer seemed obvious to me. Because… success. { shrugs shoulders and murmurs “Duh”}

The Playbook taught me that hard work is the key to success. I didn’t need to question anything further than that. It was obvious ~ everyone was doing it and it worked. Until it didn’t….

Once I started to collapse under the weight of all my hard work, I finally began to ask some tougher questions ~ and to open myself to the confronting answers.

Where is my why?

Is my Why driven from inside or outside of me?

I was so deeply, unconsciously immersed in the hard work that I had no idea there was even a distinction. Of course it’s coming from me. {Duh}

One day in 2009, in the depth of the economic recession, I was driving home after a long day at work. I was worried about the viability of my high-end stationery boutique that was suddenly taking a huge hit as spending on discretionary goods and services came to a screeching halt.

As I turned into my upscale neighborhood filled with luxury homes and vehicles, my primary thought was “What will the neighbors think of me if my business fails?”

Wait, what?! THAT’s what I’m most worried about right now?

That was the day I began to see that I was driven by an external Why.

I needed to be successful because the Playbook {and seemingly the whole world} told me this was the way to happiness, security, and all the other things that seemed to exist outside of me ~ like approval, acceptance and even love.

Little did I know I had opened a Pandora’s Box full of many more questions….

Whose why is it anyway?

“What will they think of me?”….

Who is the “they” who seems to be driving all this hard work and my relentless pursuit of success?

Are they the nameless, faceless authorities who wrote the almighty Playbook?

The neighbors? the other parents at my children’s school? my mother, husband, children?

The inner critic who mercilessly cracks the whip and tells me I should be doing all of it better?

Is there a me who lives beneath the “taskmaster me”? And if so, is this what she really desires? Or would she have an altogether different Why?

Why is this my why?

Is my Why driven by fear and conditioned programming or by my own genuine desires?

What am I afraid of? of not being able to take care of my family? of not being accepted or loved? of ending up poor and homeless?

Are these fears real or instilled from challenging experiences in my childhood?

Am I operating from a belief in scarcity? believing that I need to grab whatever success I can before someone else gets there first? that I need to be more successful or powerful than others so that I can be sure my family and I will have what we need?

If I could get to a place beyond the fear, doubt, insecurities and conditioned beliefs, would I still choose this?

So. many. questions….

And the more I asked, the more something deep inside began to stir. I began to connect with the me who knew there had to be so much more to living than merely surviving, so much more than all the hard work, struggle and sacrifice.

My conditioned self was seeking success and survival. My authentic self, my soul, was craving something much more.

Simon says successful leaders start with Why.

Thriving leaders go even deeper.

As a leader who’s moving beyond surviving, sacrificing and chasing success, you go deeper. You open Pandora’s Box and you keep asking questions until you get to the essence of your true Why.

Because your most authentic Why ~ the Why of your soul ~ is the one that leads you to fulfillment rather than burnout, the one that inspires aligned action, and the one that allows you to make a truly meaningful impact.

And because now, more than ever, the world is crying out for what you have to bring ~ your unique What that is inspired and abundantly sourced from your deepest Why.

💭 I’d love to know what it is that’s inspiring you. Share your big Why {and even your What} in the comments below.👇 🌊 To help generate a tsunami of thriving, please Like, Comment and Share this post.

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Holly McCann
Grail Leadership

Founder & Vision Keeper of Grail Leadership, helping pioneering leaders thrive by aligning core mission, essential genius and the regenerative flow of nature