Mountain, Balloons and Jail Balls

I drew this picture after a coaching session with my client recently. As I reflected, I realised that the person in the picture could easily be me, just by changing some of the words on those "jail balls".

Mountain, Balloons and Jail Balls

After more than 20 years as a corporate executive with big titles and a stable income, I stepped fully into the freelance world in January 2024 — with only an idea that I could be a corporate consultant — as that was the only role I knew I could play from my past experience.

I still remember my first humble paycheck, RM5,000 (which is hardly S$1,500), for some work that I did for a Malaysian company.

I knew clearly why I left the corporate world — limited growth, misaligned leadership style, stifling corporate culture. I crave for more time autonomy and flexibility, so I can spend more time on what matters to me — my family and health— and try crafting my career on my own. That is my mountain, and I am committed to climb it.

However, for someone who has never stepped out of the corporate world for more than 20 years, the free-lance world seems daunting — no office hours to follow, no office space to work in, no titles, no brand name, no monthly paycheck. The path felt lonely and uncertain, and I've got 2 school-going children and mortgage to pay for. I noticed the "jail balls" dragging behind me are labeled with fears:

• Fear of the unknown

• Fear of rejection

• Fear of being judged

• Am I good enough?

• Can I make it?

And then came another, more empowering question:

“What am I doing about these jail balls?”

To some of these jail balls, I already hold the key — it’s just a matter of recognizing it and releasing it. 

Other times, it’s about focusing on the mountain ahead and adding more helium to my balloons — the things that lift me: purpose, growth, service.

Most of the time, it is simply this: Taking small, sometimes painful, but consistent steps, putting one foot in front of the other — strengthening the “muscles” or the core of who I am, until one day the weights feel lighter. Some of the weights never really go away, you just became stronger.

If you're standing at the edge of something new — uncertain, excited, afraid — you’re not alone.

What are your "jail balls"? And what’s one balloon you could fill today?