Can you wing it?
Should every woodworking project start with plans? Usually I’d say yes. However, the best answer is simply “it depends”…
Sometimes you just wanna hit the workshop and see where a project takes you. While this approach may not be ideal for a specific client or customer project that has to be built to specification, it can be GREAT for your connection to the craft of woodworking. It’s also a great way to break loose and just let the work flow and develop naturally. 
Let me be clear. Having plans BEFORE you jump into cutting, ripping and squaring up timber for the project at hand is invaluable. There’s nothing worse that being in the middle of a project and realizing you’ll be short a few board feet or that the timber you have is the last of a particular grain style. Plans are especially important for client projects as you can look ahead for costs, materials, shop space allocation and a number of other things to better ensure the final outcome is what you and your customer expect (or at the very least what you expect which should be MORE than what your clients expect). The tried and true statement of “measure twice & cut ones” certainly means plans…plan it out, write it out, draw it out – whatever works!
What about those projects that aren’t ‘scripted’ though? The ones that are simply an inspirational vision or design you see in your head and just have to try? My opinion? Go for it. Don’t overthink materials and other things – just get started and pivot/adjust along the way. Now I’m not saying you should dive into a huge dining room table that seats 16 here, but perhaps that artistic piece you’ve been wanting to try or a mini version of something you’re dreaming up. A few months back I had never worked with epoxy and decided to just go for it. I didn’t have any templates or specific designs in mind, but I started small. One turned out great and the other was 50/50 – (I say 50/50 because the front looked great and the back was toast!).
Overall I’m not saying throw caution to the wind every time you set foot in your workshop. I am saying that once in a while building from a pure free-flow creativity mindset can be a wonderful recharge. Plans have their purpose and are very often needed on a build – but give your ‘artsy’ self a try once in a while and see where it leads you.
Built something creative recently without plans? What did you think of it overall?