I've been camping in the backcountry all of my life. As a kid I went on adventure summer camps, exploring relatively controlled environments with groups of fellow younglings and marginally older adults. Once I became an adult myself, I started camping more regularly and expanding my comfort zone. Camping in the fall? Crispy. Springtime camping? Maybe a little chilly. Winter camping? Who does that? Maybe me!
Eventually I started camping nearly year-round. I'd miss a month or two and would feel bummed out that I didn't make it all twelve months. It seemed the only way I was going to camping every month of the year was to make it a goal and stick to it. In 2016, that's what I did. Since then, I haven't missed a month yet. Even though some months I camp multiple times, these only count once for that particular month. No double dipping in July so I can skip November.
Check out each year and see where I've been below. In addition to camping every month, I try to mix up where I go so things don't get stale. Sub-goals include seeing how many months of the year I can camp without a tent, and how many months of the year count as winter camping.