You do not need to take big chances with your money but you do have to trade reward/risk. We will use the chart of CTY, the ultimate belt and braces Trust as they have paid increased dividends for over 50 Years.

The chart with a simple re-invest the dividends plan has gone up from £3.25 to £9.30.

Looking at the chart, you will notice the price never moves up in a straight line, after 4 years the price is where you started from, although you own more shares. The recent price action, compared to it’s history, indicates the price is overbought.

The dividend has risen gently from 16.45p to 22.1p. A yield on buying price of 6.5%

Having achieved the Holy Grail of Investing, using a lot of hindsight, you could sell some shares, whilst retaining your original stake, buy two more positions to try and do it again, while still earning income from CTY, that sits in your account at zero, zilch, nothing.