20 Questions to Help You Get Clear on the WHY behind Your Biz

By Kelly Elizabeth Scott, Leadership & Wellness Coach

With anything new, we’re going to feel some amount of fear. We often manifest & justify this fear in one of three ways:

  • We freeze & become indecisive (“Maybe I’ll start next week…”).
  • We fight & get angry (“I just can’t do this!”).
  • We flight & make an excuse to run (“I don’t have time for this.”).

Over the last few weeks, I’ve felt quite a bit of fear. I felt fear when I went to my first coaching conference in Arizona (and didn’t know a single person!). I felt fear when I hired my own mindset coach and put down a deposit. I even felt fear the first time I told someone about a new video series I’ll be starting this year. I felt fear around all three of these events, even though I was really excited about each of them.

For me, fear most often manifests as a desire to flight. I feel a ton of resistance and I want to run, to back out, to stop, and to throw my hands up and call it a day.

Even though I’ve felt a lot of fear over the last few weeks, I’ve been able to keep taking action anyway. I participated in the conference. I made friends. I put down the deposit. I told a second person about my video series. I’ve been able to recognize the fear, sit with the uncomfortable feeling of resistance, and not run to the nearest exit. (Confession: I won’t say there haven’t been tears, though.)

I’ve been able to move forward towards my goals in spite of the fear I felt because of the time I spent getting clear on the why behind my work. 

Before I started trying to get visible in my business, I spent weeks crafting a core message for my business. I spent time diving into why I do what I do, what values I am driven by, and what future I’m trying to create for myself and for the world.

“People don’t buy what you do; they buy why you do it. And what you do simply proves what you believe.” ― Simon Sinek, Start with Why: How Great Leaders Inspire Everyone to Take Action. (Watch his TEDX talk on the subject here.)

In his TEDx talk, Simon Sinek discusses why great leaders are actually great leaders. He claims they all think, act, and communicate the same way.

Great leaders understand why they do what they do and what beliefs they are inspired by. Great leaders have a great purpose.

To become the visible, successful boss ladies we want to be, it’s important we spend time setting a core message and getting clear on what’s most important to us. It’s important we craft a message that will help us say “no” more often, so that we can say “yes” by design rather than default.

In his book Essentialism, Greg McKeown talks about the importance of this type of clear message. In gathering data from more than five hundred people, he found a consistent reality: “When there is a serious lack of clarity about what the team stands for and what their goals and roles are, people experience confusion, stress, & frustration. When there is a high level of clarity, on the other hand, people thrive.”

Women’s Leadership Coach, Nisha Moodley, also talks about the importance of this core message as a simple statement that expresses the heart – the primary belief(s), meaning, reason, & purpose – behind our work.

She says, “When you have a clear message, you feel more grounded, confident, focused, enthusiastic, and clear. When times come that you feel lost or confused, your core message helps you reconnect with your North Star (what you desire for yourself & for the world), and get out of your head and into your heart, so you can get back in action. Your core message will inspire those who it’s meant to reach, by allowing their hearts to connect with resonance to yours. This opens the doors to more raving fans, more customers, and more opportunities to have your voice be heard.”

When you don’t have a core message, then you may feel unclear, unmotivated, and disconnected in your work. It will be harder to step forward in faith and in spite of fear.

To start crafting your core message today, so that you can step out in faith and in spite of fear, follow these steps outlined below! Take your time and know that you’ll probably draft more than one statement. In truth, you might draft hundreds of statements! That’s ok. Keep drafting and redrafting your core message until it feels completely aligned to you.

Crafting a core message:

1. Start with awareness.

In this first step, you simply want to gain awareness around your current behaviors and where they came from. Start to notice your thoughts about the work you do, and even begin to dive into where they are coming from (your beliefs).

What things, topics, or people light you up?

What tasks do you love doing?

What’s your body position like during the day? (I.e. Are you hunched over and breathing shallow or are you sitting tall and breathing deep?)

What triggers different emotions in you? (These triggers may be task, event, situation, or people related.)

2. Release all judgment.

In order to get clear on your big why, you must release any and all judgment you have towards any of your thoughts, emotions, and desires. Focus on speaking to yourself (& to others) with curiosity and compassion rather than judgment.

What situations have had the biggest impact on getting you where you are today?

What battles have you been through? Do you notice any patterns?

In those battles, what did you want to happen? What did you wish for?

What have you overcome?

How have you been set free?

This part of owning your story – every single piece of it – is so important. Can you talk about every part of your story (everything that’s happened in your life)? If not, why not? Where are you still holding judgment or shame? What might you have to let go of?

3. Dig in.

Here is where you really dive in!

What struggles, challenges, or experiences have you been through?

If you could give one thing to the world, what would it be?

If you could solve one problem, what problem would you solve?

What has been your “medicine” – the thing that most changed your life?

What do you value most at the end of the day? 

What matters most to you?

Why do you believe it should matter to others?

How do you most like to serve?

What do you believe about yourself and about the world?

What’s your vision for the future of the world? For your future self?

Why is your service or product worth the price?

While there is absolutely no right or wrong way to answer any of these questions, here are a few examples to get you started.

  • How have you been set free?

After a year of feeling lost & stuck in the “what am I supposed to do with my life” phase, I quit my job as a Systems Engineer for the Department of Navy. It was a leap of faith I felt called to take, and one that opened the door for growth in so many ways. But, there was one thing I wasn’t prepared for…starting my own business & becoming an entrepreneur brought up every single tiny insecurity I had and ever had. It’s an emotional roller coaster, but one that is ultimately setting me free. It’s forcing me to strengthen my faith, break down my insecurities, and bring to light every little thing that is holding me back. It’s bringing me to two of the greatest freedoms: God & self-love.

  • What do you believe about yourself and about the world? 

I believe we are here for a reason. That we were created to step wholeheartedly into our current and desired roles, sharing our gifts despite fear. That we were created to leave a beautiful footprint on those in our lives, by fully exploring, stepping into, living, and expanding who we are. I believe in myself, I believe in you, and I believe in our ability to make a difference.

  • What’s your vision for the future of the world? For your future self? 

Imagine living the life you know you’re created to live. Imagine being filled with laughter, happiness, positive energy, meaningful connection, a deep sense of purpose, and unconditional love. Imagine absolutely adoring your body, waking up excited to work each day, and feeling more at peace with yourself than ever before. Imagine feeling oh-so-confident that you’re on the right path and moving towards the business (and life) of your dreams. That’d be pretty amazing, right? Next, imagine if everyone else woke up feeling the same way. What would that world be like? What more could we do?

  • What do you value most at the end of the day?

I value celebration. I value real, meaningful connection, a deep sense of purpose, continual service, unconditional love, nonstop personal growth, and complete peace – body, mind, & soul. I value mega comfy socks, getting shushed for laughing too loud at restaurants, cheesin’ for the camera, and eating dessert daily. I value never letting anyone hang out on a limb alone, acknowledging even the tiniest of wins, doing nothing on a regular basis, and speaking with curiosity & compassion rather than judgment. I value chasing dreams, believing fully in ourselves, and leaving the biggest, most positive footprint possible (though I don’t care if that footprint is left on one person or thousands of people). I value knowing we’re enough – no matter what we do or don’t do – because we were chosen even before the foundation of the world.

  • How do you most like to serve?

I most like to serve by uncovering and celebrating the beauty of another – by drawing out their God-given gifts, their core values, their secret passions, their big dreams, & their true desires – and then creating a life and a foundation that reflects exactly who they are and want to be. I most like to serve by helping women see themselves fully, wholly, and truthfully, so that they can stand firm in their value, loud in their voice, tall in their story, and strong in their why. So that we can create the life & business that both makes them come alive and is the change they wish to see in the world. The thing that has been hardest for me to see in myself (oh yes, I am my own harshest critic) is the way I am most delighted to serve others.

As you go through these questions, give yourself full permission to be messy. Give yourself permission to write whatever you feel and whatever you think – without the need to filter. Have fun, be curious, and dig deep as you get clear on the why behind your biz.

[1] These questions come from a mix of my experience and the teachings of three leaders I admire: Nisha Moodley, Katie Den Ouden, & Stephanie May Wilson.


About the Author

Kelly is the leadership & wellness coach for kindhearted, purpose-driven women ready to leave a bigger footprint in their work and personal lives. She’s passionate about helping you build your strongest foundation for success (hint: that’s you) first and focuses her efforts on deep self-care, confidence, leadership, lasting change, and the common blocks that hold us back. Visit http://www.kellyelizabethscott.com/a-free-gift-for-you.html to download her free guide with 5 powerful questions to ask yourself daily.


Hi there!

I’m Jessica

The wellness work you are doing is needed now more than ever and I created the HEA to help you with the business side of things.

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