Should You Quit Your Job? How to Know When it’s Time for a Career Pivot | E39

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The Art of Letting Go: Navigating Life Transitions and Rediscovering Purpose

In this episode I unpack the complexities of quitting your job, the value of introspective tools, and the growth that comes from aligning your values with your choices so that you can go on to serve your purpose.


The Challenge of Quitting: More Than Just Walking Away

Leaving a job is rarely as simple as handing in a resignation letter. The experience is emotionally difficult, even when you know that it’s the right decision.

For many, the act of quitting a role brings up waves of uncertainty. Will others judge your choice? Will you disappoint colleagues or bosses? I shares how I navigated the emotional turbulence of quitting, from anxiously figuring out the logistics to quit, to the anticlimax of a brief, impersonal response. The anticipation and worry leading up to the moment often feels far heavier than the event itself. It’s a testament to how much we attach our self-worth to external validation from others, even when we know we’re moving on for the right reasons.

Quitting, is hard not because the decision is unclear, but because finality presses us to confront what we truly want, on our terms alone.


Learning From the Past: Unpacking Previous Goodbyes

I also get into other job quitting transitions and lessons I’ve learned from past farewells. Early in my engineering career, I quit from a place of resentment and a desire to “stick it” to the man. This experience, however, was humbling. The event was met with indifference rather than drama, underscoring a key insight: quitting to get back at someone or to elicit a reaction is rarely satisfying.

Another transition I made during the height of the pandemic had to be done virtually. This time I was encountered much to my surprise with empathy and understanding. These contrasting experiences drove home the importance of quitting for personal growth and alignment, not as a reaction to others’ behaviors.


Tools for Transition: The Books That Changed the Game

I credit a trio of transformative books that gave me not just encouragement but practical strategies for reevaluating my life:

  1. Rebel: Find Yourself by Not Following the Crowd by Graham Cochrane
    This book helped reenforce the challenging of societal expectations and clarify personal desires. Through targeted exercises, I was able to get a clearer picture of the life I want, separate from external pressures.

  2. The Artist’s Way by Julia Cameron
    With its structured program and exercises like Morning Pages (daily journaling) and The Artist Date (weekly solo adventures), this book’s activities helped me uncover what I actually want out of life.

  3. The Big Leap by Gay Hendricks
    Perhaps the most impactful, this book pushed me to envision a life built on strengths and passions, moving past fears to embrace a bigger purpose.

These tools did more than inform, they activated change. They encouraged self-inquiry, highlighted patterns of self-doubt, and outlined actionable steps toward a future with deeper meaning.

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Living Your Values: The Heart of True Alignment

A significant revelation from my journey of quitting is the importance of identifying and living by your values. Recognizing a misalignment at my job helped clarify that the discomfort I felt wasn’t about “winning” or being “right,” but about pursuing a life aligned with my true self.

Writing down your values, and reflecting honestly on whether your environment supports them can help you determine if what you’re doing is working for you. This can be both daunting and illuminating, and one that doesn’t have to be finished, but more so an ongoing process.


Embracing Uncertainty: Moving Toward Your Purpose

Transitions are messy, emotional, and never quite as dramatic as we picture them. But as my story shows, they’re also profoundly necessary. The discomfort of leaving something behind is balanced by the excitement of pursuing purpose, creativity, and authenticity.

The journey isn’t always linear, but with self-reflection, supportive practices, and a focus on values, you can make the leap. Perhaps one small change will inspire a butterfly effect of positive change in your own life and the lives of others.

If you’re contemplating a leap, remember: it’s rarely easy, but it’s always worth investigating what you truly want to work toward.


Looking for more?

Check out my Substack for written reflections on purpose.

Book a free 1:1 purpose coaching call with me.