Why Buy And Hold Investing Doesn’t Work For All

If you are starting your investing journey than you should consider the best methodology to achieve your objectives. Some popular theories include John Bogle suggesting to buy 50% in a stock index and 50% in a bond index. This is a set and forget move that only requires periodic rebalancing. I am sure this works for many investors. Then, there is the buy stocks for the long haul like Warren Buffett and others to let them appreciate in value and grow dividends over the lifetime of your portfolio. Most investors subscribe to this theory for managing their investments. I prefer to more actively manage my portfolio and focus on multiple steams of income.


You may have heard the old adage that the best way to make a small fortune is to invest a large fortune. Another one is that the most difficult time to invest is always now. Mark Twain famously considered every month of the year was peculiarly dangerous for investing in stocks. And there is the wall is a thoroughfare that begins in a graveyard and ends in a river.

Sometimes Wall Street analysts urge the public to buy stocks they know are poor investments as they are probably selling in private deals. Insiders can play games using their superior information because they hold insurmountable advantages. Even Jim Cramer has acknowledged how easily stocks are manipulated by big-time money managers.

To some, this theory is referred to as buy and hope.

As you learned from the past two decades, stocks don’t always go up. Remember the market downturn not so many years ago. Some people buy stocks at the end of a bull market after listening to the crowd full of bull market stories for years only to watch their stocks for years through a bear market. If you are in your 30’s this may not be a concern. But if you are approaching middle age or retirement, do you have time to wait out a secular bear market?

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The market went up an average of 8-9% in the last century but the key word here is this is an average. There have been periods of time when stocks turned in negative returns for several years. I know retirees who had their portfolio cut in half by market corrections. At that age, you no longer have the wherewithal to make earnings via working. A history lesson in it toke 20 years for the market to make gains after 1966. The latest bull market is being fueled by those prepping for retirement but eventually they will spend those dollars during retirement. You know what this means for the market.

Picking stocks that will last a lifetime to grow in value and appreciate in price is tough. We had debacles such as Enron and others and today bell weathers such as GE are in trouble. Yet to get rich in these stocks the security must perform well in all areas. Most of these stock picks are based on the fundamentals of the stock. However, there are many factors that affect long-term success such as changes in technology and markets. I am thinking of Amazon, Google, Facebook, Netflix, and others. Where have all the books stores gone? Who was the major search engine before Google? Why are brick and mortar retailors going away because we shop on Amazon?

In general, buy and hold does not produce income. Stocks just lying around the portfolio doesn’t produce any cash flow unless they pay dividends. Growth stocks that are likely your home run stocks usually don’t pay dividends. If you asked a successful entrepreneur their opinion of tying up precious cash in a non-producing investment for years with the risk of a bear market, what will they say? They will probably tell you it is all about the cash flow. When income is not being produced, you are hoping stocks will increase enough overtime to produce wealth.

The buy and hold investing ties up your capital without producing income to use in your life. If stocks are higher, then you can sell them, take gains and access the money. But if stocks are down, you are digging into your capital in order to get your hands on some cash. And it is all because stocks are not producing income.

Then there is the value investors. You know them, they buy low and sell high to capture the true value of the stock. Generally, the market moves all boats and your value investment will likely flow with the tide. Value is a relative term based on the perception of the assets as all do not agree on the correct value. Therefore, you had better be right if you are a value investor. Some stocks may be value plays for years!

Wall Street tends to be traders so they don’t do buy and hold investing but you are listening to their recommendations. Odd that Wall Street would tout a strategy they don’t follow themselves. There no mystery that Wall Street needs buyers for stocks. They turn their money generating cash flow all the time. Shouldn’t you?

Remember seeing two market crashes with one in 2000 and the next in 2007 with a span of 10 years. Some investors were ruined twice within a decade. With stocks at all-time highs, when will the next crash happen? Are you prepared to protect your capital?

The smartest strategy would be to buy stocks that pay dividends at the market bottom in 2009. You get the market rebound and cash flow from income. You may have picked up yields of 5% or more during this period.

Then, the best approach would be writing calls on your portfolio stocks to generate more income. A declining market is a perfect time to write calls on a long-term holding. The stocks are declining anyway so why not produce income out of them?

Instead of buy and hope investing, you should try income investing using a conservative approach that can produce an average monthly return of 3-5% which builds wealth quickly using dividend stocks. Think about it, you get dividends from the stock and premium income from writing covered calls.

Imagine that: you can force a stock to generate excellent income – paying you rent – while defining and limiting risk at the outset. And you can choose how much risk to undertake.

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