(I037) The 2 Questions I Ask Myself Before Quitting Anything
There are days when leadership feels less like a calling and more like carrying a mountain on your back. You wake up heavy, your mind fogged, and one thought keeps whispering louder than the rest: “Maybe it’s time to quit.”
I know that feeling. I’ve been there — staring at projects, businesses, even entire career paths, wondering if I had the strength to keep going. What I’ve learned is this: the moment you want to quit isn’t weakness. It’s a signal. A signal to pause, breathe, and ask yourself two questions that will tell you whether you’re facing fear… or facing truth.
Step 1: Name the Narrator — “Whose thought is this?”
The first thing I do is pause and name the voice inside my head. Is it my inner saboteur — I call her “Annie” — or is it my authentic voice?
Annie’s voice is fear, doubt, and the pull toward comfort at all costs. Annie is the source of my internal drains (–ROE). She wants me to stay small and safe.
My authentic voice — my Kokoro (心) — is the quiet pulse of purpose (heart/mind/spirit). It doesn’t promise comfort, but it fuels my internal energy (+ROE). It seeks growth and alignment, even if it feels uncertain.
By naming Annie, I can separate the fear from the truth. I can say, “That’s not me. That’s just the voice of safety talking.” It gives me space to choose who’s actually in charge.
This practice has carried me through countless storms — even the hormonal swings of perimenopause that made me question every decision. Naming Annie gave me a container for those thoughts, without letting them define me. It’s not about silencing fear, but about choosing whether fear gets to drive.
Step 2: Go to the Historian — “What would my 80-year-old self tell me?”
Once I’ve named the voice, I consult the best strategist I know: my 80-year-old self.
I imagine her looking back on this moment, telling the story. What does she regret? What is she proud of? Which story would she never forgive herself for writing?
This is what I call an Ensō Pause (間) — a conscious gap in the rush of decision-making, where I can check for alignment before I move forward.
A Real-Life Example: Leaving Corporate
In my final months in the corporate world, Annie was loud:
“You’re not an entrepreneur.”
“You don’t have what it takes.”
Classic Internal Drain (–ROE). Comfort over courage.
But when I asked my 80-year-old self, the answer was undeniable. She said,
“If you stay safe, you’ll spend the rest of your life wondering ‘what if.’ You’ll regret choosing comfort over courage.”
That story was unacceptable. The alternative story — uncertain, messy, but brave — was about experimenting, failing, laughing, learning. It was about choosing the HA-HA-HA moments until I found the AHA. That was the story I wanted to tell. That was the story I chose.
Why This Practice Works
These two questions shift me from being reactive to being creative. They stop me from quitting out of fear and allow me to choose from wisdom. They ensure that the authentic me — not Annie — is driving the engine of my life.
When you’re burnt out, it’s tempting to think the only answer is to walk away. But sometimes what you really need is not to quit — but to pause, name the voice, and listen to the future you who already knows.
Take the Next Step
This practice works best when you’ve defined the 80-year-old self you’re consulting. That vision is your Kokoro Canvas — the map of the life you’re designing.
If you’re ready to create yours, I invite you to join my upcoming webinar: Create Your Kokoro Canvas: Design a Life Driven by Purpose and Growth
In this live session, you’ll learn the equation of Return On Energy (ROE), uncover your own “Annie-like” excuses, and design a life of unshakable alignment.
