First on the list is wood. This one might seem obvious, but it's often overlooked. You have to know what kind of wood to use, how much of that wood you're going to need, and how much it'll cost you. Some woods are easier to work with than others, and not all types of wood work with every project. You probably don't want to go broke buying your materials, so the price is very important.
The next problem you could face if you decide not to use plans is figuring out what tools you will need for the project. Again, this comes down to experience. If you've worked with wood before, knowing what tools to use won't be a problem for you.
Tools can give you a real headache if you're new and inexperienced. As a rule of thumb, most small and simple wood projects can be completed using basic carpenter tools. Larger, more complicated projects usually require special tools.
So you've got the wood situation all figured out, and you know what tools you will need to do the job. The last problem you could run into is measurements.
Measurements are very important, especially for the beginner. An experienced woodworker could see the project in his or her mind, and be able to guess at the measurements for each part. Their guess would probably be pretty close, and the project would turn out fine. This is NOT the case if you are a beginner.
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