It is a good habit to regularly check bike chains for wear. Bike chains are consumable parts and they wear out. When worn out, they stretch and this can cause a number of problems.
I check bike chains for wear every time I either wash my bike or when I am installing a freshly waxed chain. I was washing my bike this evening, and as you can see from the photograph, this chain needs to be replaced. The chain checker tool has easily slotted into the chain, indicating the chain is stretched.
I will be replacing this chain immediately. The main reason for quickly replacing a worn chain, is that it can save money. A worn chain starts to wear out other parts of the drivetrain; namely cassettes and chainrings. Chains are relatively cheap to replace. Replacing a chain, the cassette and the chain rings get pricey.
A worn chain is also not as crisp, when it comes to gear changes and it doesn’t run as smoothly as a new one. There is also an increased risk of chains breaking, if they are old and worn out.
So buy yourself a chain wear indicator tool and get into the habit of checking your chains. The tools are readily available and cheap (mine cost me about $12).