So you’re happily drilling a hole, and suddenly, your drill is right up against the material. You can’t go any further, because your drill bit isn’t long enough!
The first time that happened to me, I was like “uh, now what?” Luckily, there are a few easy fixes!
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Invest in a Longer Drill Bit
If your drill bit is too short – good news, they make longer drill bits!

These are sold both individually and in sets, so if you just need an extended drill bit for one size, you don’t need to break the bank.
That said, if you expect to have this problem regularly with different sized bits, it could be worth investing in a set.
If you’re not sure how often this happens, I’ll say this: I’ve only needed an extended length drill bit once. I’m sure there are applications where the drill bit is too short more often, but I’m not sure what they are.
These extended length drill bits are usually either 6″ or 12″ long, and range in price from $3 at Harbor Freight to $15 at Home Depot.
I’ve usually been happy with the cheapo Harbor Freight bits, but I also rarely need to use an extended length bit, so the cons (aka, short lifetime) of a cheapo bit aren’t really an issue yet.
Get a Drill Bit Extender
One of the MVTs of my shop is this little drill bit extender:

It makes it so much easier to drive screws with a hex bit, so I use it literally every time I use a hex bit.
However, the secondary advantage is that it lengthens the drill bit by a few inches, giving you a couple extra inches of reach.
They’re also great in narrow situations where you can’t fit the whole drill.
Note that these drill bit extenders only work with hex bits, not twist bits or anything else that has cylindrical shank.
Also, these little things are like, $2. I’m pretty sure Harbor Freight used to offer them as freebies, but Harbor Freight’s freebie days are mostly over, so you’ll likely need to pay a couple bucks.
Expose More Shank
This is a beautiful sight:

The twist drill bit is firmly clasped by the chuck of the drill. It won’t wiggle or wobble or anything else annoying when you go to drill the hole.
But it’s not going to drill a very deep hole. You know how this same drill bit will drill a deeper hole? By inserting the drill bit like this:

By having the chuck clasp the shank further down the drill bit, more bit is exposed, created a longer drill bit and drill.
This won’t always be enough length for your drill bit, but it’s a good place to start if you’re not up for a drive to your local Home Depot.
Drill From Both Sides of the Wood
If you’re in a pinch, and don’t want to drive out and purchase a new tool, there is a technique that can mimic the “longer drill bit,” however it’s a little complicated and only works if you’re actually drilling a hole, not just driving screws.
Step 1: Drill a Normal Hole
Start by drilling the hole normally, until the chuck of the drill hits the wood.

At this point, stop and back the drill bit out of the hole
Step 2: Punch a Hole with an Awl
Place an awl in the hole you’ve made. Then hammer it into the wood, until it reaches the other side. You can read more about this technique here, in my post about how to drill a hole without a drill.

Note that this technique works best if there’s only a little bit of wood that the awl need to punch through – like 1/2″ to 1″ of distance. I tried this on a 2×4, and promptly got my awl stuck in the wood.
Once it reaches the other side, you should have a small hole that goes the entire width of the wood. It might not be big enough. That’s okay.
Step 3: Drill from the Other Side
Since the awl reached the other side of the wood, you now have a small hole that can act as a pilot hole for your larger drill bit.
Line the drill bit up with the pilot hole, and drill the hole as normal.
Halfway though the wood, you should hit the place where you’ve already drilled.
Note that this only works in cases where the wood is less than double the length of the original drill bit. Otherwise, even drilling from both sides won’t make the drill bit match.