Gail Wong, ACC – Founder of Live True and Co-Founder of Ladies Investment Club Singapore

For this week’s edition of FinanciElle “$tatements”, I had the opportunity to interview Gail Wong, ACC, Founder of Live True and Ladies Investment Club Singapore. Like myself, Gail is also a SheEO Activator.

After reading her three part series on LinkedIn about her first year of women investing in women, I knew I wanted to interview her.

Paolina: Why did you design Courageous Conversations about money? What do you want the women who participate to take away from the program?


Despite an Ivy League degree in Finance and a top-notch corporate finance career, I struggled for some years to invest my personal wealth and navigate life changes that brought uncertainty e.g. switching career paths and entrepreneurship.

I had a persistent feeling there was more to such decisions than paper analysis. My breakthrough came through exploring emotions and unspoken narratives about money that lay beneath – a meandering and solitary process of half a year.

It was some time after, sharing with curious friends the newfound joy and results working with my money, that I discovered I was far from alone with that vague intuition. There seemed to be a hunger from women for a safe place, structure, and support system to process what’s “difficult” about money.

Finance blogs and Google explain analytics and financial concepts but the struggle and source of anxiety and conflict comes from the meaning(s) we associate with money. Some of us might be blind to the fact that every human being has a relationship with money that drives how we operate in that area. Financial literacy somehow misses out on equipping human beings with the awareness, tools, or language to navigate our money narratives. Neither the selling process for financial products, nor our everyday money conversations, gives room to explore our relationship with money productively.

I didn’t start with a charted roadmap or any intention to create a program to sell. I was fortunate to have the coaching skills to guide myself through the wilderness into light. It occurred to me that being trained to curate a learning experience for others; I might eliminate the loneliness, uncertainty and missed opportunities that I experienced for others.

The women whom I seek to serve have individual circumstances, but share a commitment to work with and leap over – once and for all – the persistent uneasiness with their money. I want them to know themselves better, write loving narratives around money that support them in moving forward, and discover freedom, joy and Zen with finance. I want to see them be courageous in financial decision-making and negotiation, proud to be advocating for themselves, and discovering their economic power in a myriad of ways.

Paolina: What tools can women use to have courageous conversations about money?


Emotional awareness is one beginner tool I employ in my work. By adolescence, we have internalized how critical money is to our survival and self-worth. So, emotions like admiration, fear, shame and guilt can be incredibly primal forces, hidden from us.

A simple example: how do you feel when reviewing credit card statements? Putting a word to our feelings helps us find our bearings. From there, one can gently inquire: Why do I feel this? What’s behind that emotion? What is driving me to hide, deny or push back?

This awareness alone can create space for small but powerful steps of change: to pause, instead of run; to ask, instead of assume. The best way to build confidence and self-trust is through intentional actions.

I recommend focused bursts of thinking for this sort of awareness – 15 minutes journaling, a 30 minute mindful walk without music or mobile. Sharing your observations with an active listener can be powerful.

The other critical tool that works hand in hand with emotional awareness is Self-compassion. This was the hardest life skill for me to “get” and is a continual challenge to practice – it is often said that women are their worst self-critics. The feeling of inadequacy, being alone in struggle, is the biggest barrier to starting such exploration; and that is why it is mission-critical to integrate community and safe spaces in both my coaching and investing activities.

Paolina: What is the most common finance/money issue you see with the female business leaders and/or women you coach and what’s one piece of advice you give them?


To continue from my previous response, the common thread is: “I don’t know enough” or more fundamentally, “I am not enough”. While their backgrounds and circumstances vary, my clients are highly intelligent and driven women who are often right about the gaps they see. By the time we start working together, they usually have “thrown the kitchen sink” at the problem and are feeling so challenged that they simply don’t believe a breakthrough is within their reach, or they are deserving of one.

Much of our work together is about pivoting that fierce commitment to develop a growth mindset for them. I help them find ways to learn to talk to themselves as the unstoppable girl of wonderful possibilities they have forgotten they once were. I often ask myself when walking my talk: what would I say to my 7 year old daughter if she was in my current shoes? This can shift self-talk from downtrodden flagellation to upward flight.

Paolina: What advice do you have for a woman looking to start investing in other female led ventures, who might not know where to start?


Take charge of your learning experience – Whatever your experience level, this is something you have power over from day 1. How can this journey, and it is a lifelong one, be an enlivening adventure, rather than a path of eggshells in darkness?

Be curious – about the world and trends; about other women investors or women entrepreneurs. How does your consumption or investment decision impact the world?

Accept that no one knows everything – I’d recommend an active learning plan e.g. understanding bonds in March, and building a simple model in April. At the same time, expect mistakes as the most valuable part of your learning. Celebrating wins and progress, however small in your mind, is equally helpful.

It’s more fun with people –follow your instincts about who the right people to surround yourself with are. It is inspiring to see communities around investing sprouting around the world – there has got to be a local version of SheEO, Ladies Investment Club or entrepreneur’s community around you, which can open up your perspectives and provide accountability.

Paolina: In shifting from becoming an investment banker to an entrepreneur, what has been a courageous conversation you’ve had to have about money and your business?


What’s required the most courage in this transition (and every few months still) is Self-Leadership. So the courageous conversation, first and foremost, is with self.

Up to this point in life, I have walked the beaten path of conventional success very well, and never had to develop self-leadership. I resented that workplaces “owned” us, until discovering just how uncomfortable it is in the wilderness. The absence of a supervisor defining my next project, the obvious next step, a household brand name/ important title behind me, fancy suit or colleagues as a reference point was absolutely terrifying. I’ve had to confront answering basic questions like:

Who am I? (Or rather, what are you doing these days?)

What do I do next?

“Entrepreneurship is the Olympics of Uncertainty”, is a phrase I’ve been sharing recently. Unlearning “should’s” are a necessary condition for innovation yet it’s much harder to close the door on should’s when it is all we have known. Add to the mix that the Singapore culture is extremely rules-based – I started with quite an unproductive mindset for entrepreneurship!

There is so much heart and excellence to every purpose-driven entrepreneur but articulating it powerfully and concisely to an outsider took years of courageous formulation. In my experience, it is not as simple as stringing together nice-sounding words and selling a story; it had to be a story reflecting my beliefs that I could authentically own. I’ve just found satisfactory expression – which is why my website (the first sh*tty draft) is only – and finally – up, 3.5 years after launching my professional coaching practice. It is only in the last year I have stopped routinely second-guessing my self-introduction and got comfortable speaking publicly about myself and what I offer.

Self-conversations allow me to take action in the face of the unknown and have external conversations that also require courage.

For instance, how do I deal with opening a conversation with people who may become clients, before validating my answers to the expected questions? That includes answering questions like “How much do you charge?”

I started out quoting external data points, and gradually shifted to confidently stating a rate that I truly believe reflects my value and commitment to the client. I still get butterflies in my stomach sometimes – what if they disagree? I am guided by the knowledge that rejection never hurts more than self-betrayal (acting against what I know).

Other examples: Playing full out, without guarantees of any traction or pivoting after investing a whole month into a project that doesn’t feel right.

I’ve discovered freedom and joy in “having no right answer”. In accepting the unknown, I create my own race, the only imperative being: to express myself authentically and work with clients who would value and benefit powerfully from my service. I discovered that I can often be wrong about what I’m capable of, under-estimating myself. I’ve learnt that my instincts are reliable indicators to be heeded. I branded my practice as Live True – for I know through experience that the quest to live true to one’s core can be the most courageous inquiry a human being can undertake.

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