So You Want to Cast Off the Shackles of Corporate Oppression and Strike Out on Your Own

Good for you! Here are some things to consider.
  1. How much money do you have?
    Because, no joke, and no matter what you do, you can realistically face a three-year slog to get where you want to be. It takes time to build a business.
  2. How much do you rely on the cadence of a steady paycheck?
    Corollary to question one, but a nuance. Until you establish yourself you may go through extended dry periods. Even if you've got money set aside, psychologically it can be difficult and you may freak out.
  3. How much do you crave the social aspect of office life?
    Because that shit will be gone. You will work alone at your desk most of the time, or optimistically in a cafe surrounded by strangers.
  4. How much do you like the steady pattern of a work week?
    Depending on what you do, you'll need to get used to the idea of using alternative days as your "weekends" or, maybe, working every day. Maybe not a full day, but every day.
  5. How much time are you willing to commit getting work versus doing work?
    Initially that balance will be grim. It gets better.
  6. How disciplined are you at pushing yourself to achieve without someone giving you assignments or deadlines?
    It's all on you, all the time. You are your own CEO.
  7. Do you have a life partner?
    And are they prepared to put up with all of the above? Will it matter if your schedule, your money flow, and your interactions change drastically? Is your relationship strong enough to survive inequity?
  8. Are you ready to be truly happy?
    Because if you can survive all of the above, I can almost guarantee you will be.