I cannot think of a project that the orbital sander was not used. Whether painting, staining, or just applying a clear finish, you will want to sand to some level to smooth out the wood. Even when using barn-wood or reclaimed wood, I often at least sand the edges to get rid of sharp edges and revel some of the underlying fresh wood. I usually have about 4 or 5 different grit sandpaper on hand for my orbital sander, here is my favorite brand.
Just like a hammer and tape measure, a drill is something a lot of people already keep on hand for small household projects. Danny and I started out on a SUPER cheap drill when we first got married and quickly learned that this was not something to cheap out on.  If you plan to do much woodworking, invest in a quality drill.  It doesn’t have to be the best of the best, but do at least get a mid-grade drill.
You’ll find here, quite a comprehensive list of YouTube woodworking channels, and I must thank the woodworkers of reddit for helping me put this list together. I did originally decide decide that a channel needed to have a minimum of 1000 subscribers to be included on the list but after a lot of feedback I decided to include every channel that was sent to me (as long as it was woodworking themed). There were a couple of channels (Clickspring and Inspire to Make) that were on the list that I have removed because they weren’t strictly woodworking, but still do think that they are definitely worth checking out.
Thanks for the suggestion. At this point my plan is to focus on keeping things as they are. Many people have stated that they appreciate the current format. The videos are not necessarily intended for everyone, however they are for people that have a curiosity and a desire to learn woodworking. These are the people that will watch and raise questions and then ask the questions.
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About Youtuber LAB11 Created designer furniture from scratch from wood and recycled materials like pallets or customizes and repairs existing furniture. The watchwords for our creations and customizations are: Pretty, durable and solid things. Here are the videos of some projects creations but also of layout of the workshop, A video per month out at least. 

Flea markets and swap meets are great sources of old tools, but unless you are able to rehab and sharpen them, they aren't going to do you much good. You can always find lots of chisels and planes at these places, and they can be brought back to life. I wouldn't waste my time on any saws though, unless they are relatively rust-free. If a saw is rusty, you will have to re-file and re-set the teeth, which requires a good deal of expertise and some specialized tools.

I have been around woodworking my entire life.  I have always been intrigued by how you can take something like lumber and turn it into a wonderful, beautiful piece of furniture.  Once I graduated high school, I kind of got out of woodworking.  I wanted to go a different route.  I was going to college and just trying to make ends meet on the bills.

The best advise I can give you is to get and read the book "Hand Tool Essentials" by the staff of Popular Woodworking before buying any tools.  It is sort of an inexpensive crash course in hand tools.  Chris Schwarz's book "The Anachrist's Toolchest" is another good source of information on handtools that I found to be a fun read.  Use the internet to learn all you can about a tool before buying.  The tools you need are dictated by what you want to build.
Non-Standard Miter Slots - This one is a downer.  One of the primary advantages of having a table saw is access to jigs that expand the saws functionality.  This is a major issue if you plan on buying after market jigs.  Given that we are limiting the cost of this buildout to $500, I am guessing that after market jigs are probably low on the priority list.  Your going to want jigs once you start researching what they enable you to do, my advice is to build your own - there are plenty of plans online.  
Another staple in the beginner woodworkers tool kit has to be the cordless drill. Used for either drilling holes or driving fasteners, this tool gets used on almost every project. There a tons of options here regarding size of batteries, aka power, but something around the 18-20 volt range is a good all-around size that will not leave you constantly wishing you had something larger or smaller. Here is a large accessory kit at a good price that should give you most of the drivers a bits you will need.
We made the decision for my wife to be a stay at home mom - it was a decision we both felt was a good one before we ever even discussed it. Being a single income family does sometimes have financial drawbacks, but the blessings of my wife being a stay at home mom are blessings that money can't buy. Eventually, when our son (and any future children we may have) are in grade school, my wife will look at finding a job. She's also looking at the possibility of starting to do in-home daycare for 2 or 3 children in our home, which would bring in some extra money. 

What tools are needed to start woodworking? Well, this list can vary greatly depending on your budget. The best beginner woodworking tools are subjective but can vary largely depending on how much money you are willing or able to invest to start out in woodworking. It can also vary depending on if you are wanting to start out woodworking just as a hobby or as a side-hustle business. Most of the best beginner woodworking tools on this list are either tools I own, have owned, or at least have used in the past.
We made the decision for my wife to be a stay at home mom - it was a decision we both felt was a good one before we ever even discussed it. Being a single income family does sometimes have financial drawbacks, but the blessings of my wife being a stay at home mom are blessings that money can't buy. Eventually, when our son (and any future children we may have) are in grade school, my wife will look at finding a job. She's also looking at the possibility of starting to do in-home daycare for 2 or 3 children in our home, which would bring in some extra money.
Ron Paulk is an extremely likeable mystery and I think he deserves 10x more subscribers than he has. I'm convinced he's a secret millionaire - he has a workshop in what seems to be the 20-car garage of a multi-million dollar mansion - which he claims belongs to a friend and he's only using it temporarily while they sell the house.  I think it's been five years now that he's been there.  But anyway, Ron is mainly a finish carpentry contractor - that's things like baseboard, fireplaces, kitchen cabinets etc.  He is a master craftsman.  What makes him unique is his approach to working - he is all about being portable, mobile and lightweight.  Every year he seems to fit out a new van or trailer as a mobile woodshop.  I've built Ultimate Workbench, Chop Saw station and fitted out a van following his designs.  He introduced me to Festool, which was a costly mistake for me!  I've built a lot of his projects, and I learned a whole lot along the way.
Every woodworker needs a couple of levels. You probably won’t need one of the 6-foot levels used in construction, but 48” is a good length for many of the woodworking projects you’ll do. Usually, you’ll also need an 8” level too, usually known as a torpedo level. You’ll check the level and plum of your construction. Level means horizontal, and plumb is vertical.

About Youtuber Here you will find everything from money saving tips, woodworking projects, jigs and completely wild contraptions. I have been building and designing since I was old enough to swing a hammer. With a mind for out of the box thinking and an unusual mix of artfull design and engineering interest, you never know whats going to happen next.

Ok, the leap from $1,000 to $2,500 is a big one.  I certainly didn't make it at one time.  It took me years.  But I know folks that decided they wanted to get into woodworking and dropped at least $2,500 getting themselves outfitted.  When you do make the jump, the thought process becomes much less about making sure you can get the job done and becomes more about having quality tools to get the job done. 

You need an out-feed table to support work exiting the table saw and band saw. By placing the tools close together, I was able to make one out-feed table that works for both tools. I put four pivoting wheels on the table, allowing me to shift the table in any direction. By placing a shelf below the table, I gained some much needed storage space for portable power tools. Finally, since this is a large work surface, the table also serves as a true, flat assembly table.
It's funny how some interests (or trades) got onto YouTube very early.  Woodworking has been popular on there since the video-sharing behemoth got started.  I suspect this is because the US has a strong tradition of TV shows about woodworking - two great examples being Norm Abram's New Yankee Workshop and Roy Underhill's Woodwright Shop.  With a plethora of channels available on cable, and a bigger population, broadcasters were able to air more niche, and thus detailed shows.   Over in the UK we had four channels, and so if something wasn't going to appeal to at least 5% of the population (or it was cultural) then it didn't stand a chance.  

Check with Habitat for Humanity.  If they have a store you may find several good items such as a bench, bandsaw or etc.  When I retired and moved I donated  a complete shop full of woodworking power tools and hand tools to Habitat.  They sold them, I deducted them from my income tax.  Unfortunately I could not retire my desire to woodwork and at age 78 I built a shop and use only hand tools and a bandsaw.  Good exercise pushing  a LN #7.   Build yourself a solid bench with some southern pine with a moxon vise that can be built by hand.  Get some holddowns!
Only comment would be to start with manual machines -once you have them mastered, then worry about CNC. I'm only 71 at this point, but I still have a lot of things left to master! Try to find even a HF mini-lathe and mill used, and get started. The sooner you start, the sooner you become experienced, Just a warning though - machining is just as addictive as wood working.
An assortment of chisels should be part of every workbench. Chisels are not just for wood carvers. Any woodworker will need chisels to clean out joints and saw cuts. Look for chisels made of high-alloy carbon steel or chromium-vanadium alloyed steel. Hardwood grips are best, especially if they have metal caps on them. This will keep the end of the handle from becoming malformed when you hammer on it.
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Just how small?  Will you have an extra bedroom for your shop or will you be doing woodworking in your living room?  Do you have to put the projects and tools away every time you want to entertain or will you leave everything set up all the time?  A while back FWW had a video tour of a shop in Japan that was smaller than small.  I'll try to find it and get back.  Found it...  shows what can be done in a small space but this shop was not on a small budget so no help there.
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