It was 2017 – May 8th in fact – when I took my first foray into moving money around and trading stocks. I had absolutely no idea what I was doing.

Of course, I purchased the requisite books one must purchase at the beginning of their stock trading journey, many of which were just as over my head as the entire process would prove to be in the coming months and years.

It was safe to say that I was lost, and felt very vulnerable. I was afraid of losses, and completely unaware of my risk tolerance. I had no idea how to maintain control of, or even begin to face my emotional impulses concerning money. I had never had money before. And I felt incredibly awkward having any power and influence over any sizeable amount.

When I first began to dabble in trading, the thought of losing money rippled through my body like a seismic tremor. It was hard to function when it came time to press the buy or sell button. Simply transferring it between accounts made me nervous. In short – I was not in any condition to be transacting money in the open market. The saving grace was, I knew and recognized all of these things.

My father had died in February of the prior year. I was paid by the estate to organize and supervise contractors, as well as take part in the renovations. The hours were long, the work was decent, and the money began to accumulate, certainly as the estate began to settle, and the disbursements began to arrive.

I was low man on the totem pole as far as the will was concerned (“sucking hind teat” as my father would have called it), and stood to gain the least for my efforts.
My dad would angrily and quite vindictively rewrite his will during bouts of inebriation, and had subsequently damn near written me out of the will entirely. That part of the story is probably best saved for later.

To this day, I believe the circumstances surrounding the finite source of the money made it more valuable to me. I was not going to easily let it go. And my desire to do something with it, turn it into something as some final act of defiance, burned deep. It still burns deep today. Maybe I’ll finish that part of the story at some point, but I digress…

In the end – when all was said and done – and after some help from my sister who tried to atone for some of my father’s unfairness by giving me a piece of what was coming to her – I had accumulated a decent egg. Rather than go drink it away, I put it into a Roth IRA and began my journey of learning a different way of viewing and thinking about money. My first most important quest was to figure out how to preserve what was in the account. Outside of saving throughout the year and making contributions, I had not yet learned how to grow what was there.

My first few fearful and feeble attempts at growing the money though trading stocks would do little to increase the principle amount. I made a few small, low-risk trades, never losing anything as I didn’t dabble in high-risk assets or methods. But I did succeed in getting money trapped in poorly timed trades that took forever to appreciate. These experiences were not without their positives, as I learned the “art” of averaging out of bad trades, taking the money and deploying it in other, hopefully greener pastures.

I understood the concepts of successful trading, but lacked the confidence to step up to the plate and actually make trades, certainly trades of any significant amount. I was restrained by a severe lack of trust in the information I was relying on to make what I thought were knowledgeable, fact-based decisions.

I was incredibly suspicious of anything I read, heard or viewed on the internet or television. I still am. One cold, hard, fact about trading, rather than investing – one that I could discern quite easily, and know deep down in my bones, is that the vast majority of what you hear, read, or see about the stock market, is absolute bullshit. Without going into some diatribe (maybe later), good companies and solid trading strategies do not need hype to survive and flourish.

Market manipulation and pump-and-dumps on the other hand, do. Those my friends, are words to live by.

My aversion to loss and reluctance to trade, paired with my overall ignorance about the market, would keep me on the sidelines for the next five and a half years. During this time I would miss out on several boom-busts, as well as several successful trading opportunities, and years of compounding… I would also spend that time watching, reading, studying, educating myself and saving, month after month, year after year… and the time has come to re-enter the marketplace – in a way that works for me.

In the next part of this series I will share some of the steps I took along the way to make finance, savings and the stock market work for me. I have found internal peace – and my view of the market has evolved. I now see it as the land of opportunity, rather than feel at every turn that I was always going to be chasing after mythical gains and percentages, and never achieving my goals. That journey from fear – to here – is the one I would like to share with all of you…

Stay tuned…