How I gained confidence in myself

I came across a recent post on reddit: How do Singaporeans become more confident? 

This person grew up in a controlling environment where their mother’s harsh and demeaning behaviour left little room for self-expression or social growth.

Constant negativity has deeply eroded their confidence, something even their boss has noticed.

Despite these challenges, they are seeking ways to rebuild their self-esteem and create a more empowered future, showing courage and a desire for change.

The thread has some useful advice. At the same time, I thought I would share my journey as someone who struggled with insecurity in my early and mid-20s.

At work, I had a boss who, despite my consistent efforts and achievements—hitting and exceeding targets quarter after quarter—offered little genuine recognition or encouragement.

While I felt there were areas where I could grow or perhaps could have taken the initiative to provide feedback and help him improve his leadership skills, the lack of support and constant criticisms left me feeling stuck and unfulfilled.

Each morning, I faced the day with a sense of dread, questioning whether my efforts would ever feel truly valued or enough.

In my personal relationships, I encountered challenges that tested my resolve and understanding. I had a partner with many admirable qualities, but he found it difficult to fully support my career growth.

He sometimes questioned why I attended networking sessions, misinterpreting them as opportunities for meeting new men rather than professional development.

Even when I achieved meaningful wins at work, I often held back from fully celebrating, concerned about how it might impact his sense of security.

It was a delicate balance, and while it was difficult, it taught me a lot about navigating different perspectives in a relationship.

Outside of work, I pursued volunteering and writing about socioeconomic issues—causes I felt deeply passionate about.

While many appreciated my efforts, there were also some who misunderstood my intentions, dismissing them as attention-seeking.

Rumours began to circulate, and I later traced them back to a lady who spread these toxic rumours as she thought I was too close to someone she had a crush on.

These moments were challenging, but they also became valuable lessons in resilience. self-belief and empathy.

As difficult as it was to navigate these experiences, they ultimately became part of my growth journey.

Looking back now, five years later, I’ve grown into someone much more confident.

Interestingly, there wasn’t a single therapist, or life-changing event that sparked this shift.

After all, confidence is not something that appears overnight. It is something we nurture, often in the face of setbacks.

Instead, it was the accumulation of small wins that helped me build up my self-esteem. I found my life improving.

The first step was joining Salesforce. This was a turning point in my career in SaaS. I was 27 years old then and the youngest AE in the team.

I felt like I had big shoes to fill and everyone was better than me. I felt small in front of clients.

However, I reminded myself it was not easy to land a role in this company. Also I had a boss who believed in my potential and spent a lot of time training me.

After leaving Salesforce, I had a significant salary increments with each step I took. Within a period of 5 years, I almost tripled my annual income.

My experiences in this company has become such an important part of my story. I some times tear up when I pass by Suntec Tower 5.

Outside of work, my content began to take off. I was recognized as one of LinkedIn’s Top Voices in Singapore, and have also been featured on platforms such as Channel News Asia, Her World and Dollars & Sense.

What gave me the most encouragement was hearing from others about the impact I have left on their lives, be it finding a career they are passionate about.

With each step forward and the help of many many benefactors (贵人), I found myself surpassing many who had stood in my way.

They stayed stagnant or fell from where they used to be as the tech winter began.

I’ve come to firmly believe that building skills and achieving small wins are among the most powerful ways to grow self-esteem.

These are gifts you earn for yourself—treasures no one can take away.

When people are nasty to you, it is on them

I wish someone told me this when I was younger. I hope that by sharing this, it will benefit someone who felt small in some ways:

When people are mean to you, it is a bigger reflection of them versus you.

Reflecting on past experiences, I’ve realized that when people act in hurtful or unkind ways, it often stems from their own emotional struggles or insecurities.

They might fear losing someone they care about, compare themselves to you, or simply lack the tools to communicate or lead effectively.

Someone once told me, "Hurt people hurt people," and it resonated deeply.

In truth, I’ve never known a genuinely happy person who intentionally tears others down—it almost always comes from a place of fear or insecurity.

That’s why it’s so important not to internalize their behavior or let it define your worth.

Instead, remind yourself that their actions are a reflection of their own inner battles, not a reflection of your worth.

Food for thought: Is your calendar reflecting your priorities?

Your calendar is the most brutally honest autobiography you'll ever write.

While you claim "family first" and your Instagram shows gym selfies,

your calendar reveals the truth: endless Zoom calls that could have been emails, pointless meetings for projects your barely involved in, and endless project updates for projects that never seem to move forward.

Each hour on your calendar is a decision about what matters, stripped of pretense and rationalisation.

Your calendar isn't just recording your time—it's exposing your lies.

-Shane Parrish 

Every week, I share actionable ideas on how we can optimize our wealth; health and relationships.

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