Unless you have very specialized requirements (and quite possibly you do) the solution is usually to unhook yourself from thinking of needing specific programs and to instead focus on needing to perform specific tasks. (Then finding the Linux way to perform that task.)

Barring that, the codeweavers suggestion is a good one. I used it in my early days when I thought I couldn't live without particular pieces of Windows software and although that was several years ago, even then it was pretty good about being able to easily run arbitrary Windows software. IMO it's cheap enough to be worth the investment.

If you truly have bespoke requirements that just can't be satisfied by either of the above, staying on Windows may legitimately be your best option.

More generally - if you decide to take this step, expect to have to learn to use a computer substantially differently than you have in the past. It's not harder; in many ways it's easier. But if you are very experienced and comfortable with Windows, a lot of concepts are going to feel foreign to you. Tackle one task at a time and your experiences will build upon each other. Go into it expecting to have to learn, and you'll do fine. Bizarrely I find the least tech-savvy folks sometimes have the easiest time transitioning.