While it’s true that the only way to get self-employment experience is to take the leap, it’s crucial that you have previous experience when it comes to the work you do. For example, in order to become a successful IT freelancer or contractor, it’s important that you already know how to program or offer the necessary IT support that companies are looking for. Learning on the job is not an option when you own a business, so make sure that you feel confident enough in your knowledge and skills before becoming self-employed.