Inflection points in life and embracing the unknown

Last month marked the first anniversary of the day when I made some big decisions in my life. One year is an arbitrary time, not that long, but long enough to look back and see what happened.

What happened

November 22nd, 2021, I had just started a one-week annual Thanksgiving vacation with my family. It began with a seven-hour drive which gave me time to think through and finalize the decisions brewing for years.

I had been considering changing something about my career for a long time. I had been feeling “stuck,” and despite various changes in my work in regard to my role, I remained unsatisfied and restless.

I kept trying things, such as working on problems that interested me—doing fewer management tasks and more technical work. I would feel great for a few months, and then the unsatisfaction would creep back up.

I felt being pulled in too many directions at work and home. The three kids have been growing up and taking on various interests. With my wife working crazy hours, child care mostly felt in my domain. I felt like I was failing my kids. Not enjoying my time with them as much as I used to, and I was often very distracted in my head, thinking about ten different things. Family, coding, stocks, crypto, work, trading, family … all mixed up.

The idea of quitting my job kept on creeping up. It was scary and felt foolish. Quitting job? Quitting income? What would others think? How would that look on the resume, and on and on and on? Yet there it was, creeping back up over and over again and showing many benefits that I could experience. Potentially. I didn’t really know if I would experience those benefits. I imagined I would, but there is no way to know until you jump off the cliff, so to speak, and go for it.

And that’s what I did, driving that day, I told myself it was time to pull the trigger. I decided to quit my job, where I had worked for the past 15 years. And to finance the break, I made a perhaps equally seismic decision to sell the speculative stock portfolio that I had built in the past three years. Seismic shift. Super scary. But it had to be done so I could try something different and see how it feels.

On the decision to liquidate the portfolio

I can’t say I made that decision because I could see the market continue to tank badly. The situation was getting worse, but being a positive and hopeful person, I was hoping that the drops would stop and the markets would return to normal.

However, from countless hours reading various investing and trading books, I took away the idea that hoping is not a good strategy. You need to be more concrete and more direct. Taking no action is good if that’s what you think you should do. But don’t do it based on hope. Do it based on a plan.

The decision was difficult because it took me years of work to build that portfolio. You also have this feeling of greed, or perhaps fear, or both, pulling at you and tempting you to wait for more. Since the summer of 2019, I had spent evenings and weekends slowly chipping at it, adding stocks, doing research, and doing well. Of course, not because of my skills, but simply because I got lucky with the tides of wealth rising post covid and carrying all the good and the bad to the skies.

I wish I could tell you I got out at the top. Not at all. By November, my portfolio had contracted by about 40% from the absolute peak. But again, that’s neither here nor there. You make a decision and go for it.

In hindsight, it was an excellent decision. By my rough calculations, I would have seen the total amount contract by about 80%. Instead of seeing that waste away, it has financed my stay at home.

The odds are high that the overall markets will recover, and there will be a new bull run. But you can never know if what you had in your portfolio will ever see its highs again.

How has it been a year later

I think it was one of the best decisions I could have made. The amount of time I spend now with my kids has increased dramatically.

I still code like a maniac, just look at my github activity stream:

I just love tech and coding so much that I doubt I will ever give it up. But this time, it’s for personal projects, research, and some of the systems I use today to trade. I do hope to return one day and code for others, but for now, that’s on hold, and I hustle on my stuff.

The time spent with my kids is where we saw the biggest change. We suddenly have a handful of neat routines with the kids that I believe are adding a healthier way of life for all of us.

We spend time together on school work, I am there for their homework, and I am there with them when cooking food. They participate in our grocery store trips, cooking, and meal planning. We do so much together now, and I feel like they learn much more about life, and their academics, when I can guide them along.

We have added a few after-school activities and can do them all with zero stress. Previously I would have to rush from work to pick them up and rush to an activity if we had one. It always felt like being on a run. It was definitely not fun for me, I can’t imagine it was that much fun for them.

I thought I would be reading more, but that has remained pretty much the same. One book per month or so. I guess I am just too excited about spending time with the kids and coding.

Embracing the unknown

I love the “theme” of discomfort, and this was exactly that: embracing the suck and that feeling of discomfort.

Making big decisions, such as quitting a long-term job or liquidating a portfolio, is scary and feels super uncertain. But sometimes, these inflection points can lead to positive changes and even new opportunities. You will never know how it will turn out until you take the leap of faith.

It helps to do so with safeguards in place and with family support. You will never be 100% ready. Make your odds of success as high as possible, and then go for it.