The past 8-odd-years-or-so I have been on a constant quest to learn how to make all the things... ALL the things. I've picked up a random assemblage of skills through a combination of trial and error, internets, and bothering people who know more than I do. While this may not be the most efficient way to learn something, it's a process that allows me to form a unique perspective on traditional methods and ultimately develop a deeper understanding of "how stuff works."
So clearly, I like this DIY attitude, HOWEVER, when I decided to pick up woodworking, I didn't feel like this was the best approach. One must exercise caution while cultivating new skill that poses a significant risk to your safety. When there is a sharp learning curve and significant safety risks involved, it's best to look before you leap and listen before you lose an eye...
The following are a list of steps for how to pick up this skill set, with some specific recommendations for people in Chicago:
1. Try a 1-time beginner's class
Before investing your time and money into this hobby, test the waters and make sure you enjoy it. A lot of people like the general idea of building stuff without realizing that woodworking is all about accuracy, precision, and meticulous attention to detail. Only go down this path if you DEEPLY enjoy measuring twice, cutting once.
Woodworking is super "in" right now, so lots of arts centers, home goods stores, and salvage sites will offer "make it and take it" classes catered to beginners. For people in Chicago, I recommend checking out ReBuilding Exchange's workshops. They offer a wide selection of beginner projects and even do themed classes for couples (if you're into that.) The quality of their instruction is high and, on a personal note, I find roaming their stock one of the most inspiring/Romantic things to do. So much reclaimed wood, so little time!
2. Invest in an intro level class series
I strongly encourage people to investigate options for an intro level course. A good class will cost you in the range of $500-$1,000, but it is money very well spent if this is something you intend to take seriously (and would like to avoid loss of limb).
The class I took at Woodsmyth's consisted of 10, 3-hour classes during which you made 3 projects: a bookshelf, storage box/seat, and a tool box. The quality of instruction was really high and the value of the projects alone is worth the price!
The instructor framed the entire 10-week class as about safety and risk management. The first day of class on on shop safety felt a little bit like a "scared straight" lecture, but it was very effective. The two biggest ways to manage risk in a woodshop are 1. NEVER lose your focus and 2. use the right tool for the job. Sounds simple, but it takes a lot of knowledge to really understand the capacity of these tools. Some straightforward instruction and dedicated time in class will give you a huge leg up in learning how to use tools appropriately and navigate your way around a woodshop. SAFETY FIRST PEOPLE.
3. Get access to some equipment and community
This could be the most difficult step, depending on where you live. Owning and maintaining a personal woodshop requires lots of: money, space, and time (3 things us young urbanites have in scarce supply). And even if you do have all those things, belonging to a community of people who can give advice and collaborate with on projects is so helpful when you're just beginning.
So, search your local area for a place that offers memberships or whatever kind of paid access that fits your needs (daily, monthly, annually). Depending on which place you go to, they might require you to have taken classes or at minimum, get certified on tools. So make sure to investigate these things before buying any classes (as per steps 1 and 2).
I belong to Pumping Station: One (otherwise known as the greatest place in the world). They have a full wood shop in addition to welding equipment, 3d printers, laser cutters, electron microscope (wut?), a knitting machine (woah), and lots lots more. It's a monthly-membership fee (a pittance at $40 or $70/mo. if you want storage and community voting rights).
4. projects, projects, projects!
You've done all the learns and legworks now, so get building! There are lots of free plans online. Ana White is one of my favorite resources; the projects are well-curated and very pro-lady-building. I recommend starting off with projects ear marked as "beginner" or using only 2 X 4s. There are lots of simple projects out there you'd like to have in your home, so don't snub them. Build your skills up slowly. No one becomes Ron Swanson overnight!