Still Not Working

After watching Twilio stick crash from over $450 to under $125 in less than a year, I am still not thinking about going back to work.

Go to a good college, get a good job, and take care of your family. Money is still on my mind. It hurts when you lose over a million dollars in the stock market.

My wife is still working and receiving a steady income. So we don’t need to dip deeply into our reserves for the time being, but that doesn’t make me question all my financial decisions.

Money shouldn’t drive my life, but it’s hard to ignore. Unfortunately, capitalism will do that to you.

To feel successful in America is to amass capital. So when you lose a third of your wealth in a few months, you feel like a failure.

People say that there’s nothing you could do and you can’t time the market, but that’s just a coping mechanism. You decide when and where to invest your money. If I had invested all our money in the S&P 500 in July 2021, we’d have the same amount now. Instead, Twilio(TWLO) has lost two-thirds of its value. Other mid-tier tech companies like Shopify(SHOP) saw significant drops. A fund with many of these companies, ARKK, is now worth 43% of what it once was.

In 2008 you can look at a company like Salesforce (CRM) and see it lose 70% of its value. Of course, if you invested at its local peak of ~$18.80, you would have seen an eleven-fold gain. The S&P500 went from $1500 in 2007 to $750 in 2008 to $4200 today. Currently, it has only lost 12.5% of its all-time high.

I fear a significant drop in the total market will push TWLO down even further. But is that where my focus should be?

Numbers Don’t Always Give Answers

I need to remind myself that I quit working to spend time with my kids while they still want me to spend time with them.

My son is 13 now and already prefers to spend time in his room instead of with me. Of course, we will still play catch or the occasional video game, but he’s trying to figure himself out.

Meanwhile, my daughter is ten. Much of her time is spent at school and with her sports activities. I still make them breakfast, and we have dinner together every night. In four years, they will be in high school and college. If we somehow managed to burn through all our cash by then, I could return to work.

The people I know my age don’t love their jobs. Some enjoy them as a challenge. Others find them mind-numbing but necessary. Few are genuinely willing to think about not working because it’s not a short-term option.

I am a lucky person, and I need to continue capitalizing on this opportunity.

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