That's awfully wide, but I suggest you try a different way of thinking. Instead of "I'd like to drive the week of January 15th," followed by "Oh god, I did not plan my ski trip" and intensify panic panic until you get "too late," try the other way round.
List some things you like to do. Examine some of them more closely. Do not ask people to recommend places or places. Just like here it is too opinionated. Instead, think about what you care about: cheap transportation from the airport, great views, food, quality of skiing, how busy it is at any given time of the year, and so on. Explore these specific things. Ask friends about these specific things. Heck, ask here. Not "What is the best X in Y?" but "is X full in January?" "How much does it cost to get from the airport to X?" and so on.
Plans are starting to develop. You will begin to feel that a particular place is calling you. For skiing, food, the picturesque train ride, whatever. Now you can assign a date to this plan to your plan. Not before that point. Now you can look at the prices and find out how to book and how to do it. You know how many days this place needs. You know your options to get there. You know the cost of hotels and access to things. Half of the work is done, maybe more. There is no need to panic.
If you get to this point and it is only a few weeks to your allocated vacation time, then this vacation will not be the trip. This holiday will be a little easier and easier, maybe you did that earlier. The next vacation will be this trip calling you. After all, there is always a next vacation.
I often spend a year planning a trip. A journey on a 26-part 11-island island took two years. I enjoyed every minute. Dream of the volcano, the beaches, the walks, the museums. Make a list of the things we would see and do. The reality was even better, but dreaming was a big part of it. If you stop looking at this stage of dreaming and planning as painful, but as part of the joy of traveling, you will better plan it and Have fun planning and traveling.