I tend to over-think things and second-guess most decisions I make, especially when they’re money related. Most of the money-decisions my wife and I have made to-date about our plan to retire early were automatic – spend a lot less than we make and put all of the spare money we have against the outstanding mortgage.
Now, I actually have to do stuff – making lots and lots of investing decisions over the next (hopefully) 60 years. This month will mark the beginning of having funds available to start investing – which will be quite a change in my money-spending lifestyle.
I read a lot of stuff – a good chunk of it is money-related. Like most things on the Internet, a lot of the information available is contradictory. Some sources say that the market is at a peak right now and it would be ridiculous to buy anything. Other sources say that there’s never been a better time to invest in “Stock X”, or “REIT Y”. As an almost total rookie investor, and someone who is a constant second-guesser, this is the point where I get intimidated.
My whole investing plan centers around buying income-producing assets, which slowly (but hopefully surely) replace my wife’s and my salary, until we have enough money to be able to not work anymore. At a 5% return, every $1,000 we invest is going to increase our annual income by $50. I really try to keep these kind of numbers in mind when I go to spend money on something that is unreasonably dumb, because all of those decisions are doing nothing but adding to the time it will take us to achieve our goal.
In order to achieve my goal, I will probably start investing sooner rather than later, increasing our current annual income now. I will hopefully pick assets that will not result in me flushing money down the drain. I guess the good thing about having what could be called a somewhat stable job, is that if 100% of my decisions are wrong, I’ll still be able to eat. In some way of thinking, I think I’ll treat my retirement investing career the same way I’ve treated sports betting. With gambling, I assume that everything I put in is probably going to be gone. For someone who will hesitate to buy some random $5 item, explaining to my wife that this is within the realm of possibilities does give me a bit of a cushion when making these kind of decisions.
While I would prefer to not shovel money out the door, this pessimistic level of thinking does allow me to overcome my decision-making paralysis and continue down my path to financial independence.
How did you decide when to start investing? Do you try to time the market, or just find investments that fit your set criteria?