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I'm no expert but being a wood guy forced me to learn how to sharpen free hand. It took me a lot of trial and error but there are plenty of you tube vids on the subject. To me there's two kinds of sharp, tearing sharp and honing sharp. On soft metal blades (cheap knives) I feel it's a waste of time to hone them because they'll dull so fast anyway. I quickly sharpen those to tearing sharp with a diamond steel. Not razor sharp but sharp and will cut a tomato cleanly. On quality knives, my good chisels and hand plane blades I want honing sharp. I have diamond plates 400 and 1000 grit but only use those if the edge is damaged or a 22° edge needs to be established. My wet stones get the edge honing sharp. I finish with 8,000 grit and leather strop which are both polishing. When the blade can shave hairs off my arm I know it's sharp. I use my 400 diamond plate to keep my wet stones flat which is important for chisels and planer blades. It's a learning curve to hold a blade on a stone consistently and that's just a feel I had to figure out (how to hold my fingers to apply equal pressure) Deburring is essential for a honing sharpness too. The " sharpening steel" in the knife drawer doesn't actually sharpen, it simply straightens the burr. To deburr chisels and planer blades i hold dead flat on the fine grit stone for just a couple of sideways passes
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