Investing as a full time job

It was a long road to finding a job that I could commit to and enjoy. Along the way I did everything from working as a personal trainer, teaching English in Japan, answering phone calls in an automotive company, to setting up online courses at a university. All were varying degrees of purgatory for me. But finally after a 10 year period of ‘purification’, I’ve been able to move on to what feels like heaven.

For the longest time I had no idea of what my version of work heaven is. Despite the challenges, I always believed deep down that I would find my way out of the maze.

It’s hard to pinpoint exactly what led me to investing, but I think there are a few critical pieces of the puzzle that I’ll list here. Perhaps they might help you if you are still searching for your place.

1) Experiment and try many different fields

From very early on I was interested in almost anything and everything. As a kid I loved going to the science museum, the zoo and reading books where they explained how things worked with cross-section diagrams. Later I would read through encyclopedias at random, learning about what they produced in Colorado or about gorillas in the Congo. At school once I could choose subjects, I chose from both the sciences and the humanities, enjoying for example political studies and biology equally. That was all well and good and even from a young age I had decent general knowledge, but it came with one glaring problem. What on earth was I going to choose to study at university and then go on to a career in? So I bounced around. The upshot of this is I got to try a whole bunch of different jobs. Meet a lot of people. And got a really good idea of what I don’t like. From that point you just need to reverse engineer. So the first step is to have as much fun as possible trying out different jobs and activities to see what resonates and what doesn’t.

2) Take a large number of aptitude/personality tests

After a period of trying things out you will be in a position to gather some data. Personality tests are fine, but if you are still quite young I don’t think they are as valuable and perhaps even counter-productive. That’s because they are only testing your aptitudes/interests that you are currently aware of. As an example, let’s say that you are a great public speaker, but perhaps out of fear or lack of opportunity you have never tried it, how would you know? But if you have been proactive, by the time you reach your mid to late 20’s you should be getting a pretty good idea of who you are and at that time, the tests are very useful indeed.

A big piece of the puzzle was the CliftonStrengths test, which you can get access to for free if you buy the accompanying book StrengthsFinder 2.0 - Tom Rath. It is designed to identify your top 5 strengths in a work context. The strengths fall under 4 broad categories: executing, influencing, relationship building, strategic thinking. ALL of my top 5 stregnths fell under the strategic thinking quadrant. That was the first lightbulb. I realised then that the reason I had struggled so much in the routine office jobs I’d been doing is that I was almost never using my key strengths.

My very top strengths related to learning new information. At the time I thought, “well that’s great, I like reading. What the hell am I supposed to do with that!?”

3) Keep learning

If reading isn’t your thing, another approach is to talk to people and get information directly from the source. The point is to expand your mind and be exposed to ideas that may give you hints about which direction to move in next. If you’re stuck somewhere you don’t want to be, the absolute worst thing you can do is to go home and watch TV all night, or spend hours on social media. A better use of the time is to learn what you don’t yet know, so that you can prepare yourself to step into something else.

Having worked out that learning was my key skill, I leaned in to it. I ramped up my reading and spent every spare moment doing it. I was determined to find answers.

4) Make the most of opportunities

One book changed the course of my life, Antifragile by Nassim Taleb. After earning his stripes as a trader on Wall St and making “FU money”, he transition into an academic career and wrote a series of books that culminated in the masterpiece, Antifragile. It’s not the easiest read, but it’s packed with very useful ideas. One of which was using puts to hedge a portfolio of investments. A put makes money when the price of something goes down. You can think of it as an insurance policy for stocks. As I was reading Antifragile in January of 2020, news of a novel virus spreading in China broke. Although it was in the news, it wasn’t yet a big deal. The financial markets hardly reacted, if at all. Things had been so good for so long, that people had become apathetic. Fresh from reading Antifragile I realised there was a chance that this new virus would have serious implications, that it would be a “Black Swan” event. I opened up my brokerage account, answered a questionnaire that upgraded my account to allow me to buy options and proceeded to buy some puts. I didn’t realise it at the time, but the options I was buying were cheap, dirt cheap. They were priced as if nothing bad could ever happen again in the financial markets. They were the equivalent of buying car insurance for $100 on an expensive car.

With little cash on hand I scrounged around for whatever I could spare. It wasn’t much. But within a month the virus was spreading globally and financial markets were in freefall. The value of my puts went up exponentially and a month after buying them I sold them for a 3400% return. I’ll never forget going into the bathroom at work, so that I could login in to my account and sell those puts. Walking back to my desk I just couldn’t contain myself, I smiled and laughed out loud. I had just made a third of my annual salary by pushing a button. It was more than that though, I had used my strengths in learning and strategic thinking to do it. For the first time in my working life I saw a way out of the seemingly endless purgatory I had been enduring all those years.

5) Once you decide, commit fully

Having moved around so often and had one ‘brilliant’ idea after another for a decade, at first I really doubted myself. What if this was just another grand idea that failed miserably and I lost interest in it after a while? So I took my time and thought it through. I went away for a long weekend. Spent the time alone. No social media, no distractions. I took walks in nature and thought about it from every angle.

Investing wasn’t perfect I figured, but for my strengths it was far better than anything else I’d found. I determined that come what may I would make a go of it. At some point you need to do that because all of us only have so long in life. There is no perfect career. You have to look at your options and say, this is the best one I’ve got and make it work.


In closing, it’s hard to know when the puzzle will come together. In my case the saying, “the night is darkest before the dawn”, held true. You only realise that in hindsight. For those of you going through it, if there is one key it is: never ever give up. Keep moving forward. Keep learning. If you do those two things, success is a matter of when, not if.

As for me, I still consider myself a novice investor. But I’m committed and learning. If I can write a little on the side, even better.

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