Why she gave up a $600k banking job to choose values over money

What happened?

In Singapore, success is often measured in numbers. Salary, bonuses, job titles, net worth. The higher they are, the more secure and accomplished we are assumed to be.

But what happens when the numbers stop telling the full story?

In this week’s Beansprout podcast, we spoke with Gail Wong, former Wall Street banker turned founder and CEO of Live True, about why she chose to walk away from a high-paying banking career and redefine success on her own terms.

At just 27, Gail was advising billion-dollar deals across three continents. By conventional standards, she was on a clear path to senior leadership, financial security, and status. Yet beneath the surface, she began to question whether the life she was building truly reflected who she wanted to be.

In this conversation, Gail shares candidly about the realities of life in investment banking, the emotional and physical toll of an all-consuming career, and the difficult trade-offs involved in choosing values over money.

We also explore what it really means to align our financial decisions with our values, how identity and self-worth are often tied to income and job titles, and why wealth is more than just a number on a balance sheet.

Catch the full conversation in the video below.

Key takeaways for investors and professionals from interview with Gail Wong, Founder & CEO of Live True

#1 - Success is often inherited, not consciously chosen

Gail reflects that for much of her early life, success was something she never stopped to question. Growing up in Singapore, the path was clear. Do well in school. Clear each academic hurdle. Take on the next difficult challenge and excel at it.

This mindset carried her into banking, where excellence and endurance were rewarded. Long hours, intense pressure, and personal sacrifice were treated as the price of success.

Only later did she begin to shift from asking “Can I do it?” to the more uncomfortable question, “Should I do it?”

That shift, she explains, is critical. Many of us are capable of enduring very demanding careers. But capability alone does not mean alignment.

#2 - Money can validate you, but it rarely fulfils you

One of the most honest moments in the conversation comes when Gail describes receiving her first bonus cheque. It was a six-figure payout, and it felt like proof that she was valued.

That feeling became a reference point. For several years, she found herself chasing the same high, believing that the next increment, the next promotion, or the next deal would finally deliver lasting satisfaction.

But while the numbers grew, the internal experience did not.

Gail explains that what kept her in banking longer than she expected was not joy, but external expectations. The belief that many others would fight to be in her position. The idea that questioning such privilege was ungrateful or indulgent.

#3 - High-paying careers often normalise unhealthy behaviour

Life in investment banking is intense, and Gail speaks openly about how pain tolerance became a measure of performance. Yelling, vulgar language, and verbal abuse were part of daily life.

Over time, these experiences became normalised. When behaviour is repeated often enough, it stops feeling wrong, even when it clearly is.

As Gail moved into management, she began asking herself a confronting question. Is this how I want to show up in the world?

When work consumes 70 percent or more of your waking life, the culture you are immersed in shapes who you become. That realisation played a major role in her decision to leave.

#4 - Leaving is not just a financial decision, it is an identity shift

From a financial standpoint, Gail was clear about what she was giving up. The earnings trajectory in banking is well known. Friends reminded her she had left just before the most lucrative years.

But the harder part was not the loss of income. It was the loss of identity.

Without a prestigious job title, she noticed how quickly social dynamics changed. Attention shifted. Conversations ended sooner. Status was quietly reassigned.

Gail explains that many people underestimate how deeply their sense of worth is tied to their professional identity. Letting go of that can feel destabilising, even when finances are secure.

#5 - Freedom sounds appealing, but structure still matters

After leaving banking, Gail expected freedom to feel blissful. Instead, it was disorienting.

In banking, your time is fully structured. Tasks are assigned. Deadlines are clear. Once that disappears, you must learn to design your own days.

Gail shares that autonomy is not the same as ease. Many of us still need structure to thrive, even when we are no longer working traditional hours.

This period of transition eventually led her into personal development and coaching, where she began to uncover the deeper fears driving many of her past choices.

#6 - Aligning money with values requires conscious trade-offs

Today, Gail works with professionals to help them align their financial lives with their values. This does not mean rejecting money, but understanding what trade-offs you are willing to make.

She speaks about knowing your numbers, not just income and expenses, but what is truly non-negotiable for your wellbeing.

This philosophy extends to investing. Gail chooses not to invest in certain industries, even when that decision may reduce returns. In difficult market years, such as 2022, this choice had a tangible cost.

Yet she is clear. Being able to sleep at night matters more than maximising every dollar.

#7 - Wealth is an experience, not just a number

Gail reframes wealth as something lived, not just accumulated.

She has met people with significant financial resources who feel empty, and others with modest means who feel rich in generosity and peace.

Beyond a certain point, she notes, more money often leads to lifestyle inflation and rising expectations rather than deeper fulfilment.

For her, wealth is about leaving people and places better than you found them, and living in a way that feels internally consistent.

#8 - Parenting brings values into sharper focus

As a parent, Gail feels these questions even more acutely. Navigating Singapore’s education system, she is keenly aware of how early children begin to tie their worth to grades and comparisons.

She hopes to teach her children two things. Always do your best, and honour yourself.

Without self-honour, achievement becomes hollow. You become a walking CV rather than a whole person.

#9 - Choosing values has a cost, but also a return

When asked to calculate the return on leaving banking, Gail is honest. Financially, she is earning far less than she could have. On paper, the opportunity cost is significant.

But the non-financial returns are priceless.

Quiet mornings. Peace of mind. Self-acceptance. Freedom from imposed striving.

These are not easily measured, but they fundamentally shape the quality of life.

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