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How to overcome the fear of making a leap? 5 ruthless questions to ask yourself

I was on the running track one day, thoughts racing in my head.

I could taste fear and anxiety, a sort of existential crisis that wasn’t estrange. I felt that I hadn’t lived up to my best self, I felt that clock is ticking faster as I approached late twenties, I felt torn between choices, wondering why I circled back to crossroad.

I had come through a long way to reach this point, thinking that my path will become clearer as I gained more clarity.

And yet, when I came across opportunity that scares me, the battle between head and heart reignited, fear clouded my head to do its job – to protect.

I smiled.

The inner battle and discomfort were here for a reason. With every turmoil comes self-questioning, with ruthless and honest questions come truth.

Where am I on my own path? Do I rule my fears, or do they rule me? What is the basis of fear? What does that say about my character? What is the hard decision I’m avoiding?

I truly believe that we need to break in order to build. My brokenness often leads to a leap that changes the course of life, that makes life uniquely mine.

Are you happy with your life?

In my first corporate job as auditor, I had to vouch a few hundred samples in one assignment.

Spending days in a dim file room, digging through invoices, delivery notes, and payment vouchers, I started to question myself, why are you vouching documents? Are you growing? Is there better way you can contribute to the society?

When I told myself that I was wasting life instead of time, it was a word so strong that it urged me to think deeper and take action.

Making a big leap from professional industry into food and beverage industry marked the start of my non-linear career path.

It was the first time I took full ownership in an important decision, where I defined risk, values, success, and happiness for myself.

Can you see the path of growth?
Joining a start up coffee chain, I felt liberated being able to manage my time and responsibilities, dealing with vibrant spirits in food and beverage industry.

After one and a half year, even though the company was growing, I couldn’t see where I was heading in my own path.

In a one-man marketing team, I had no one to guide me or help me improve my work. It was frustrating to feel that I was doing everything and didn’t excel in anything.

The time bomb exploded when a new year started.

With little benefit improvement and weak explanation from my boss, I was pushed to decide for myself – could my time, my life and my potential be fully maximised in this environment?

It wasn’t a hard question. My colleagues and I decided to quit the company and start our own business.

Is your work aligned with your inner drive?

When we started a café consultancy company, I was totally ignorant to the fact that 90% of start up companies fail.

Even though I didn’t quite understand the essence of building a business or creating unique value for people, I didn’t have time to grill myself when we had to start paying bills.

The challenges pushed me into corners and tried to break me. In those moments, I learned about who I was, what I stood for, what I was capable of, what were my guiding values.

As time passed, I was working in a company I founded instead of working on it. It was a founder trap that I struggled to pull myself out of.

When I realised that there was a gap between the company and my drive for growth, connection and contribution, I went through personal struggle, questioned my life purpose, shattered my identity, changed my narration, and sold my share eventually.

It was an important process that set me up for more challenges in the future.

Are you using your strength to do the right thing?
When I thought I was leaving behind F&B industry, I took on a café operation manager role that looked good and sounded good. I quickly realised the mismatch – I had no experience in operation despite having set up multiple cafes.

The day I told myself to try, I lost the beautiful vision of building community, embarking on a journey of losing myself.

Why am I here? Am I going backwards in life? Should I stay? Should I go? Is it too early to leave before trying? Am I a millennial who couldn’t withstand hardship?

For 3 months, my mind was so noisy that I couldn’t hear my own voice.

I was lucky to come across a book project during this period. When I started writing, I felt powerful being able to create meaningful work.

The moment I decided to leave the job that didn’t suit me, my mind was like blue sky once again.

What is your vision for future self?
I thought I’ve reached the destination when I started a content writing company for businesses and agencies.

I was finally able to make a living doing what I love – to write.

However, it didn’t take me long to learn that there was a difference between writing from my heart and writing to get paid. Without a purpose, writing is simply a skill with utilities.

In my quest to create meaningful work, I reached out to a mentor.

After a couple months of exploration in high level MICE industry, I was given an opportunity that encompassed my passions although I was underprepared, unqualified and fearful of whether I would succeed.

The stake of making mistake was high. Uncertainties and self-criticism got the best of me at times. I had to keep reminding myself to focus on the goal and the person I would become if I pushed to the end.

Despite learning to ask the right questions and be honest with myself, making a quantum leap never got easier.

It means grabbing the opportunity instinctively before it slips, choosing the harder path and bearing higher risk in order to be more.

It might be painful but the upside is limitless.

Are you willing to do it for your future self?

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