What Leaving 5 Jobs Has Taught Me About My Purpose

What Leaving 5 Jobs Has Taught Me About My Purpose

2 years ago, I was recovering from my near-last employment.

More precisely, I was recovering from my quarter-life crisis — when your life looks neat on the outside but chaotic on the inside.

On one hand, I enjoy a materially comfortable and intellectually interesting life. On the other hand, I was unfulfilled with my career.

I have changed 5 jobs over 2 years.

My titles & achievements failed to fill the void of an escalating misalignment and an emerging sense of purposelessness.

The question I ached to answer: What does my journey reveal about my life’s work and my purpose?

For decades, I had internalized others’ validations and expectations for my success.

Equalizing my work with my worth, I became deeply ashamed of my journey.

Instead of confidence, my career decisions and performances were based on fear.

I approached workplaces the way circus lions learn to act ‘Hold your breath. Perform the right steps. Or be punished’.

It was exhausting and intimidating.

Eventually, I hit rock bottom. And got too paralyzed to escape.

So I took my time in the deep end, learning to embrace this darkness.

The arms of my family, my partner, and my coach helped me out of the pit.

Returning to light from that darkness, I learned life-changing lessons about my career, my purpose, and my life.




Career development is increasingly similar to software development — it’s increasingly agile. The linear, or waterfall model no longer serves everyone. Our career is as individualistic as our characteristics.


Lesson 1: Career development is agile and individualistic.

Here are the paradigm-shifting truths about career development:

  • Similar to software development — it’s increasingly agile.
  • The linear, or waterfall model no longer serves everyone.
  • Our career is as individualistic as our characteristics.

Whereas waterfall careers follow a linear milestone-by-milestone structure of progress, agile careers advance through a fluid, loopy flow of experiments and iterations.

Some would call it a ‘squiggly’ career.

Great software and applications aren’t built with all the known variables and pinpoint accuracy at every step. They were initiated with hypotheses and validated through as many tests as necessary.

Think of our career as our lifetime project.

Most of us started out with limited clarity about ourselves. We develop hypotheses, validate them and repeat that loop as we go.

What’s more, software & applications are evolutionary throughout their lifecycles. Like how our careers evolve as we transform.

Where is the room for our career to evolve freely if we tie ourselves to the rigid structure of a ladder or a narrow definition of success?

To quote Helen Tupper & Sarah Ellis in their book, ‘The Squiggly Career’, the linear career concept ‘assumes we’re all motivated by the same thing (becoming more senior), that we all work in places where endless promotions are possible (at a time when organizations are looking to reduce hierarchy) and that any direction but ‘up’ is bad’

Our society’s hyper-fixation on the linear, or waterfall, career concept not only comes from traditional employment structure but also from toxic achievement culture.

But if engineers are no longer sticking to a waterfall model, why are we still holding onto a linear career concept?



My career flows with the flow of my personal growth. The overseeing process of professional evolution harmonizes my outer and inner journeys. It’s larger than any single form of occupation.

Lesson 2: Regardless of your career shape, it always contributes to your life’s work

  • What if my journey was not at all interrupted? But simply a fluid experience of a serial project?
    The way any episode of a Netflix series contributes to its plot.
  • What if my career was not merely a collection of separated employment? But a continual process of professional evolution?

I was a business development manager who was ultra-sensitive, bone-deep introverted, and highly intuitive.

I read between the lines. Saw through clients’ emotions and intentions. Told converting stories. And developed winning teams.

But I didn’t shine at any random business.

After another 2 years of digging up places to find my spot, my business development nature co-founded my consulting business and co-acquired freelance projects.

To this day, my business development career is the cement of my work. Because of it, my coaching venture is fortified.

You see, our career is only an expression of our evolution. It runs the flow of our personal and professional growth.

It’s larger than any single form of occupation.

Like a river, this flow can be straight and fierce at one part, winding and murmuring at another.

But no matter the different shapes my career takes, it always contributes to my life’s work.

The way rivers always reunite with the ocean. The way my business development career prepared me for my entrepreneurial journey in coaching.

I am here to direct the flow of my career in the orientation of my purpose.

Lesson 3: My career was a plant that needed to be repotted.

At my 5th workplace, the more I tried to inhabit, the more my aliveness withered. I buried my head under the pillow, screaming, ‘What was wrong with me?’

Not a thing.

Being good in business development is one thing. Choosing where to devote that skill is another.

I was lost because I struggled to distinguish the two.

Our seed of talent needs to be planted in the right environment so that we can grow. Many times, the unfit is not due to the environment, but our own outgrowth.

I learned that my strength didn’t get weakened. It was my purpose that got awakened and demanded to be realized.

  • My long-repressed value for freedom and impact was aching.
  • My maturing passion for personal development came aflame.
  • My unexpressed talent for writing was tickling.
  • My mission for helping others break free from the norms of this achievement culture was vocalizing.

The corporate / start-up world was no longer accommodating my evolution.

My career was a plant that needed to be repotted.

Our purpose is where our innate talents, values, passions, and mission meets. It is the compass helping you navigate your life’s work.

The truth is we are all differently talented. But similarly labeled and categorized by the same social standards and norms.

Instead of measuring ourselves up to external parameters, let’s learn to calibrate our career with our internal purpose compass and regain sight of a world of possibilities to be actualized.




Instead of measuring ourselves up to external parameters, let’s learn to calibrate our career with our internal purpose compass and gain sight of a world of possibilities to be actualized.


2 years of reinventing myself took me on a deeply fulfilling adventure.

I did not only transition out of my business development career, and pivoted toward an entrepreneur in consulting and coaching.

But I also shifted out of my urban life and became a beach-town resident who enjoys a walk among the horizon-filled paddies at sunset.

The fourth lesson sat deep in my soul.

‘What else could I do to realize my purpose?’

I inquired. Something I had known the answer to.

Your voice matters. Your story matters.’

I pondered the clue until one day, I acknowledged an impulse. A heart-originated dialogue.

‘Write. Share it with the world’

‘What could I possibly offer?’

‘Your insights. Your soul. Your wholehearted candor in a world troubled with divisiveness and prejudice’

2 years have passed since that moment, my story has changed lives.

Readers of my blog and growth-letter have found empathy, wisdom, and inspiration to take a deep breath into their hearts, a deep look into their souls, and a leap of faith in their journeys.

Clients of my coaching practice have re-connected with their purpose and regained their confidence. So that they could embark on the adventure of their dreams.

‘I can’t remember how I could live my life ignoring my longings for such a long time. Since our last meeting, I applied for […], I had the chance to see how fulfilling it was to follow what I wanted. I’m so thrilled to be ‘in the flow’, and very much grateful for the journey to becoming who I am now’, said my coaching client.







The biggest lesson of all: none of us is meant to journey all on our own. Enlist support, and be assisted to rise beyond the voice of doubt and fear, and dare to live the life we deserve.




The biggest lesson of all: none of us is meant to journey all on our own.

Enlist support, and be assisted to rise beyond the voice of doubt and fear, and dare to live the life we deserve.

If you aspire to plant the seed of a vision, a purpose, and cultivate a life that makes your heart sing, can I support you?

My Navigation session is specifically designed to help you

  • define your authentic success
  • gain clarity on what’s holding you back
  • identify the key next steps for you to get there.

The session is complimentary. Sign up here to start getting the right support for your success.

3 Comments

  1. S

    Only when you turn around, you will able to see the journey u have walked through… reflection is lonely and often filled with doubts, regrets or guilts… but remind yourself with all the happy moments you had !!! (And many will come… ) all that is also because the “wrong” turn you took prior… there is no right and wrong in how to live a happy life… but there is way to love yourself … which is to understand and accept whoever you are at this moment of time… easy to say , but just to observe the negative emotions and being objective in reflection is not a easy task…

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