I find the hardest thing is initiating, once I’m doing something then I get quite into it. On the rollers I’m more motivated watching a riding video as I feel connected to the purpose/outcome. Getting out at this time of year will pay dividends when the dust comes back, recognise the effort when it’s made.
Maybe a performance or process goal would help? Something objective like a faster time in a race/segment, better cornering etc. Apply the old SMART process to it, having something to work for which you gain at the end can feel pretty good as long as it’s planned properly.
Don’t be too hard on yourself, it looks horrible outside. But when you’re out there it’s still fun, you just need to be prepared a bit differently. Sometimes a new bit of kit helps to get excited about riding, you can never have too many tyres or comfy things to wear when it’s fierce outside.
By the way, while you have a cold focus on a bit of recovery and figure out an indoor training routine (in the week I do rollers for 5 days with yoga before bed, plank pose exercises at the weekends as my easy days). Write it down and set it around your week ahead. A training diary can help keep track of what works so you can adapt/increase load/focus on specifics as needed.
I’d be erked by creepy train tracks in the dark, that plan to ride with your mate sounds like a great idea 🙂