Talk to someone who is already working in the career you desire.
Do some research and find people who are working in the career field you want to enter. Write, email or call them and ask if you can set up an informational interview. Most people are willing to talk about their careers if they have the time available to do so.
Make sure your approach is not-threatening. Make it clear that you are only want to obtain information and not to steal anyone’s job!
Be willing to take risk.
Sure, you were a lot more willing to take risks in your twenties. More than likely you didn’t have a mortgage, kids, car payments and 401k to worry about. However, if you are committed to change then be willing to take the plunge into uncertain territory. Be willing to take a pay cut or a less secure job in order to get experience. If you are giving up a comfortable job that brings in a steady paycheck every week in order to pursue your dreams as a writer then make the realization in advance that you will no longer be able to count on that money going into your bank account on a regular basis.
Make a financial plan.
Even though you are going to have to take risks, a good financial plan can ease your career transition. Make sure you have money saved for the times you might not be earning money or for the times you are earning considerably less money. If you need to go back to college then you will need money to pay for it. Figure out if you will need student loans to pay for school or if you can pay for it yourself up front.
Come up with a budget to live on and make cut backs in areas where you tend to splurge. Although you must be willing to face the fact that sacrifices might be necessary in order to make a career change, you must also realize that certain things cannot be sacrificed. You will still need to eat and you will still need health insurance, especially if you have children. Factor these necessities into your budget.