How do you know which drill bit to choose?

This will no doubt win the stupid post of the month award, but I'm serious. I have a little plastic case of drill bits, some are missing and some fit more than one slot, several are duplicates. It doesn't say (can't see that well) what size they are on the bit, but above the slots in the case the size is molded in there.
The last time it was a window box, and picked to small a drill bit and had trouble getting the screws in so I took my drill bits to the hardware store to buy some more screws (dropped a couple and could not find them in the dirt) and ask which bit to use, little things in the house no big deal but I'm doing to do some bolting, screwing and drilling through two thicker layers of wood. Right now it happens to be attaching stakes on a stepladder plant stand, a screen door trellis, and also some supports to reinforce the door. Next project, who knows what I'll run into.
I have noticed if I don't choose the right size drill bit, it is hard to get the screw in and you get it so far in and the slot or plus (phillips) starts getting stripped, sometimes because I didn't drill the hole deep enough and sometimes because I used too small a bit.
Do you just eyeball it and guess? For my knitting needles and crochet hooks, I have a little template that I can poke the thing in and find the exact size. Do they have something like that for drill bits? Maybe I could use that somehow. Poke whatever I've got in there and follow with a drill bit until I find a good fit.
Maybe I answered my own question here. Buy the bolts and use the knitting needle thingy.
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A drill gauge is inexpensive but you don't need one. Hold the screw up and look at how much metal is under the treaded parts and choose a bit closest to that size or just a little under. You can use a lubricant on the screw to ease installation, beeswax, an old candle or bar soap. Here is a chart from the web.
Wood Screw Pilot Hole Size
Screw Size Hard Wood Soft Wood Countersink Size Tapered Bit Straight Bit Tapered Bit Straight Bit 2 3/32 1/16 5/64 1/16 1/4 3 7/64 5/64 3/32 1/16 1/4 4 7/64 5/64 3/32 1/16 1/4 5 1/8 3/32 7/64 5/64 5/16 6 9/64 7/64 1/8 3/32 5/16 7 5/32 7/64 9/64 3/32 5/16 8 11/64 1/8 5/32 7/64 3/8 9 3/16 9/64 11/64 1/8 3/8 10 13/64 9/64 3/16 1/8 7/16 12 7/32 5/32 13/64 9/64 7/16 14 1/4 11/64 15/64 5/32 1/2 16 9/32 3/16 17/64 11/64 9/16 18 5/16 7/32 19/64 13/64 5/8 20 21/64 15/64 5/16 7/32 3/4 24 3/8 17/64 3/8 1/4 3/4
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That makes sense.
You can

I'll try to remember that, happen to have all three.

The chart makes little sense but I saved it anyway, thanks. I haven't graduated to countersink yet, but by golly I will.

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wrote:

Looks like the poster forgot the way proportional spacing (and other things) can really make a mess of a well aligned table.

--
Mark Lloyd
http://notstupid.laughingsquid.com
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Yeah, I cut him some slack on that - and myself. A link might be helpful if one exists.
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The pilot hole should be the same size, or just SLIGHTLY smaller, than the central shank of the screw, and at least as long as the screw is. Even then, th e bit can slip out of the screw slots if you don't press with enough pressure or if you don't hold the drill perfectly parallel to the screw and the direction you're drilling.
A lot of people ruin their screwdriver bits by violating one or both of the above. A common third reason is trying to go too fast. Take your time, line it all up. Start the drill slow for a couple of turns, then speed it up, then come to a stop, WITHOUT releasing pressure, just as the screw gets in. You shouldn't need any lubricant, but I often just put a little spit on the screw, especially if it's a long one or the wood's real hard. It helps a lot (and it's fun and cheap) to just practice. Get a couple of 2x4's or 1 4X4 and a 5 lb. box of screws and have at it.
B.S.
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That part I have now, thanks to another post, but I have trouble drilling straight sometimes. Plus, I know it's dumb, but I forget to toggle the switch to back it out and drill away and wonder why nothing is happening :-). Or you run into a nail. Or something.

I wish you were kidding, but I fear you are not. If I didn't have so much going, that probably is a good idea. I'm going to practice on my projects. I have learned to settle for less than perfect, just did the darned sloppiest paint job I have ever done, party due to working in too confined a space and partly due to I want to get it done and three coats is a lot of work with a brush. Nobody's going to look that closely outdoors. Yes, of late, I go too fast because I can only do a little at a time, take it outside or try to find a place inside, and you have to drag it all back in and out, too hot, blah blah.
Some people just get stuff done like the Energizer Bunny, buy it early in the day, done by evening. Not me. Except my window box. That was an exception and it took an extra trip to the hardware store and I spilled all the plants I bought. But I got it done in one afternoon and early evening. I'm not talking just planting; I'm talking putting up the brackets. That was an exception.
Never did I imagine that I would have to learn to fix things and if I want something, do it myself if I possibly can. I mean girls didn't take shop back then. We learned to sew.

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snipped-for-privacy@rock.com, 7/24/2006, 1:45:57 PM,

What are you talking about here? Isn't it the hole that needs lubrication? Maybe I should use your method.
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http://images.meredith.com/wood/images/pdf/screwchart.pdf
You should note that a lot depends on whether you're drilling in soft wood or hard.
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True. Most of my stuff is soft in the house, no oak trim for me, also so far with my various projects. Hardwood is expensive.

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