Timing Isn't Everything

Let’s get something obvious out of the way first: good timing is clearly better than bad timing. But an obsession with perfect timing is perhaps the worst enemy of any entrepreneur or investor.
Worrying about whether it’s the right time to enter a new market, start a business, buy real estate or make financial investments is a recipe for inaction, not a path to smarter decisions. Those who live by such indecisiveness are doomed also to be the same people  years down the road expressing regret for missed chances to buy underpriced equities, for businesses that could have been great if they had actually been started, for ideas that were brilliant and ahead of their time before someone else went on to execute them.
Simply put, doing things is generally a lot better than doing nothing. This philosophy certainly holds true even in the most cyclical of industries, because the past behaviour of individuals (if not of markets) is usually a strong indicator of future behaviour. It may be comforting to look at down markets as validation for one’s decision not to invest in real estate, for example, but, never investing because of anxiety about timing is a terrible thesis for long term wealth creation.
Perhaps the best insurance against timing anxiety is to focus more on the concrete reality of people and what they need vs. the abstract reality of markets and what they might do. Warren Buffett has shown himself to be better at advocating for and sticking to this approach than any investor in modern times. His approach is perfectly expressed in that part of his 2011 letter to shareholders discussing non-productive investments in general and gold in particular.
There’s a strong correlation between investors and entrepreneurs who are indecisive and fearful and those who seek out non-productive investments that are a hedge against bad things happening. In 2011, all of the world’s gold reserves were equal in value to, in Buffett’s words:
“…all U.S. cropland (400 million acres with output of about $200 billion annually), plus 16 Exxon Mobils (the world’s most profitable company, one earning more than $40 billion annually). After these purchases, we would have about $1 trillion left over for walking-around money (no sense feeling strapped after this buying binge).”
Buffett goes on to express disbelief that anyone could possibly prefer a metal with little utility, which costs money to extract and store, over the returns offered by investments that spin off cash by producing the things people need. Whether farmland is currently “expensive” or “cheap” in relative terms, it is always useful and needed, and this utility and need far surpasses the rationale not to buy it because the timing isn’t quite right.
The bottom line: there’s never a better time than the present to start executing your plan.