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  • Gail Wong

6 Years: An Investing Milestone

Last week I opened an automated email from Interactive Brokers ☝️ that transported back to the moment I began investing “with no guard rails”... and it sparked a reflection and celebration about how far I've come.


A line in the sand


The reason this moment is significant to me was - despite my Wharton pedigree (and degree) and the billion-dollar advice I gave my corporate finance clients, I had never made 100% independent decisions about my own money until then. (Why? Keep reading.)



So the mundane act of opening a low-cost trading account was the beginning of an uncomfortable, “first toe in the water” bid to test a hypothesis:

❓What am I really paying others for? Can I do this as well - or possibly better - than my wealth advisors, without the bells and whistles and security blankets?

On that day (26 July, 2017), I took 10% of my investment funds and started managing it myself. I wanted to see how a regular adult - without special access to financial tools or products through connections or their job - could sustainably DIY-invest.


I was not gunning for the top-quartile performance of professional investors, nor to replicate that amount/ depth of work - I had the rest of my life to live!


My plan was to set aside an hour each week for an “investing date” to:

  • Develop a thesis.

  • Research instruments.

  • Assess risk exposure at an individual holdings and portfolio level.

  • Input trades on my mobile.

  • Systemise my process and then simplify it.



What am I acknowledging, 6 years on?


These are 3 highlights among the many lessons I've taken from this ride.


1️⃣ I did it all, and didn’t “lose it all”.


"Losing it all" was my worst fear, and at the heart of why I had abdicated to third parties.


For the time I put in - weekly in the first 2 years, then quarterly thereafter - the portfolio met my requirements of high single-digit annual return. It clocked 9% annual return on a buy/hold strategy (and that’s with >20% cash drag and 0% leverage - because, cautious). All but 1 of my calls are in the money today.


And I got to sleep at night.


In contrast, most of my outsourced investments produced tepid to disappointing performance. It seemed like the only folks who made money were the banks/ intermediaries! (Another reason I advocate doing this yourself!)


2️⃣ I CAN do this.


For a girl whose mom was an active retail (and property) investor, I still carried a whole bunch of gender stereotypes that I deconstructed with every investment call I made.


To be able to declare that “I AM an investor!”, and own it as one of the things I do - alongside singing in perfect pitch or baking bread - was the beginning of a completely unplanned, unimaginable evolution that saw me:

  • running an angel investment club,

  • teaching other women to invest in the most opaque asset class,

  • starting a VC firm and (most of all…)

  • being consulted as a gender-lens investing expert

  • adopting a mission to re-imagine capitalism, and redefine how capital is allocated.



3️⃣ I trust myself, with deep conviction.


If you look beyond the spreadsheets, tools and mountains of disclosure, investing is ultimately a practice of holding fear, shame, uncertainty and voluminous information all at once without getting overwhelmed... then choosing consciously.


Over the 6 years, I have honed investing into a form of active meditation that strengthens my growth mindset and self-trust. The victory is an internal one, over a default programming of “what am I missing?” and other financial trauma (more on that another day…) that used to paralyse me.


In trusting, I have accepted that

  • Stepping out into the markets means dealing with its large unknown forces.

  • Forget about defying nature, success in investing is simply the ability to ride those waves and respond to changing conditions.


Easier said than done - our nervous systems don’t like that!


To believe that I know enough, and I am enough to rise to whatever shows up - externally and internally….


To wean myself off reliance of third-parties, to come to terms with "bad" trades and rookie mistakes...


This kind of trust was alien to a detail-oriented, analytical, highly-sensory, lifelong people-pleaser, who used to manage her acute sense of danger via control.


Trust is unshakeable, but not blind. I still do plenty research. There is much (I know that) I don’t know - and don’t touch. I got here through continual “self-work” - unlearning, and active healing of my relationship to money - in parallel to the homework - the learning and action plan I set out with. It has yielded me this unexpected gift of self-belonging that no one can ever take away, which also helps me as an investor.


Why do I share this?


You might wonder - "this person sure talks about investing in a really hokey way". Isn’t investing simply “buy low, sell high”? Why the personal development fluff?"


I can understand that sentiment with good humour 😂 Many of my close peers invest for a living and we have been trained to approach it dispassionately (albeit knowing that a 10% drawdown on their book. Investing courses dangle the promise of easy, "sure-win" strategies. Former-Me from that world - who wore black suits and pumps and walked on Wall Street (and its equivalents in the UK, Hong Kong and Singapore) - would not have been receptive to, or ready, for my message here.


If you’re thinking, “Yup, that’s me,” then here’s my question to you:

do you feel truly, wholeheartedly, GOOD when investing?

If not, then maybe my sharing will make you think again.


I write this for the people who are ready and open, who have had enough of transactionality and compartmentalising and want something more.


My lived experience - a transformed experience of investing - says: it is possible to interact with money (including investing) free of fear, shame and guilt. You may even discover along the way other riches such as joy, curiosity, a sense of purpose/fulfilment.


Wonderfully, I have found others in this world who are similarly and collectively re-inventing the experience of investing. Far from monks or hippies, these are people with jobs, mortgages, kids and pets, retirement accounts, self-made wealth, modest inheritances and who pay taxes.


Some of them I’ve taught to know themselves - their risk tolerance, values, holdings and relationship with money - and find their own way, grounded in their individual financial reality and local contexts.


Many others are new friends, co-conspirators and mentors. We introduce to each other new opportunities and approaches to evaluating them. We learn about the world - it’s current day problems, and it’s infinite futures through the businesses created to solve those problems. With a whole-person approach, there is always room for our emotions and values along with common sense in our decision-making.


All this might seem like A LOT for someone at their beginning, who might wonder…


Can I get there too?


Yes, emphatically, yes.


When I started, all I wanted was to “not lose money” and take the load off my overworked husband. From my 13 years as a coach, I know that my breakthrough - and the immense sense of accomplishment and celebration - is available to anyone willing to show up. And they will probably get there much faster than resistant, scared me 🙈 who insisted on doing it all by myself, for too long!


The markets have shifted significantly over the past year, and presents opportunities for change and action.


Here are some resources to get you started:

  1. Investing Mini Quiz - See for yourself where you stand in investing.

  2. Financial Wellness Diagnostic - For those seeking a holistic assessment of their finances, and ready and open to work.

  3. My meandering investing journey was the central motivation for designing my first group coaching program around money in 2017 - to shortcut the change process for others, and curate the support and community that I found myself wanting. 6 years on, I am opening registration for Jumpstart, a trauma-informed upgrade of the original program. It is a container intended for regular folk taking their first steps to mastering money in sync with their soul and values. Book a suitability call with me to learn more.



Ultimately, I am for every person’s peace and happiness with money, and cheering them to take the next constructive choice for their financial wellness. I am here to offer anyone feeling lost, wanting to go beyond informational courses and willing to make change in their financial life, a place with others like you. Whatever your level of wealth and knowledge, moving forward is always a growth journey. Together, we can go further, faster.

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