Pivoting from hotel front-desk agent to something new (update)

After 7 years as a hotel front-desk agent I am thinking about moving into a different field. I have been trying to stay organised about it. My family is supportive but nervous. Has anyone made a similar move?

Thanks for writing this out. I went through something close to it 11 months ago, and it got easier once I kept a simple log of every call and form.