Why you should always sharpen your farm tools
You're not going to do agriculture work without sharp tools, it's unavoidable. You'll eventually need to cut something.
You should sharpen tools as much as you want to use them. If you notice that you're putting in more effort to cut something with the tool, it's a clear sign it's not sharp and it definitely needs work done on it.
If you have a dull hoe, it will not cut, it will drag and you might even end up hurting yourself in the process, so by using an inefficient hoe, you will be pushing harder and sweat more because instead of cutting weeds, they will just bend over and pop right back up. What a waste of time and energy on the land.
If the hoe was sharp, it would cut the weeds' heads off with one good strike, at most two strokes.
If you cut brush with a dull cutlass, after an hour of using it a dull blade will bruise the stems of brush and even bounce off the brush. A dull cutlass also tires your arm out very quickly, this is an issue of maintenance or the fact that you're not strong enough to never give up. The tool you're using is making the work harder for you, period.
The solution to the problem of not sharpening your tools is to sharpen them frequently and properly. It looks obvious until you see someone forcing to use a blunt Cutlass to clear his land and you ask why he has not sharpened the knife and he says he's ok.
The way to sharpen your hoe and cutlass is to use a flat file at the appropriate angle with steady strokes until the edge is back to its original shape. To sharpen your hoe and cutlass, you can use a bastard file to do it.
If you're looking to use the bastard file, when the file touches the edge, you should draw the bastard file along the edge in smooth and long strokes. I'm sure you've seen this in blacksmith movies before if you have seen in real life.
To sharpen shears, you should use light pressure and only sharpen the bevel side, the flat side must remain flat.
If you ask me, I'll say the sharp tools should be sharpened throughout the entire season. If you are using a cutlass to do heavy brushwork, you should sharpen it every thirty to forty minutes, and carry a pocket stone with you to use throughout the day to save your energy until the end of the day.
The time to sharpen is less than the time it'll take to use blunt knife.
Your tools should always be cleaned and oiled after using them. Doing this will prevent rust from rotting away the tool and it will also save you time at the end of the day, because it takes about ten seconds to clean and oil your tool after using it. Some people just don't clean or oil their tools, and so when their tools rust or fall apart they have to go out and but new tools. Spending money they didn't need to.
The true test of a sharp tool is how little effort it takes to make a cut. A sharp hoe will easily penetrate the soil without the need for your weight behind it. You will be able to make a cut through a branch in one smooth stroke with a pair of sharp shears. This is how the tool has been designed to be used. Anything besides this is unnecessary work you're adding to your life.

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