Trained by my engineer grandfather as well as shop teachers to always carefully plan my work, it was a bit of a deviation to create these 2 projects. Both were done entirely freehand without even a clear idea of what the end products would look like, just a simple idea. These also should not be considered any kind of example of woodworking, but I feel the approach warrants mention as an occasional mental exercise.
In the case of the garden gate, I knew that I needed some serious bracing to keep it rigid through the seasons, and angled braces natually lend themselves to the diamond pattern. That was the only vision I had, so I made the diamond first, then attached hardware cloth to make a "window" (I had envisioned a solid door). The built-in flower box just organically emerged as the shape filled out. I'm quite pleased with how it turned out and many of our guests seem to enjoy the flowers in an unexpected location. Sticks near the in-place construction site begged to become the trellis, and the rest just happened.
After building a rather complex chicken coop according to some very thorough plans, I decided to simply wing it for the 2nd coop. In this case, the only guiding concept was that I had some hand-split cedar shakes to use as shingles, so it needed to have a sloping roof. I also noticed that the birds seem to enjoy shade, so I elevated the entire structure to provide them a shelter while still "outside". The double-fence of our chicken moat provided the support posts for the coop and again, the design just unfolded as I built it. It is definitely rustic, some might even say an eyesore-grade bit of redneck engineering, but in general I don't mind it and it fits into the quirky nature of our property rather well. It certainly suits the birds just fine.
In general I do prefer to be detail oriented, thoughtful in my planning, and exact in my execution. However, I think this type of freeform work is excellent when an occasion allowing flexibility presents itself. The type of problem-solving and mental gymnastics required to "wing it" are much different than the skills needed to design and follow a plan. I believe both approaches are valid for various situations, and practice makes perfect (or close enough).