This talk is for all those looking for a guide into how to break into a cyber security or information security career with local tips for those living in Wisconsin. Whether you are still in college, debating going to college, or an experienced professional looking to change careers, I wrote this talk for you as I wished this guide existed when I changed careers. Flashback to four years ago where something changed, I woke up and was no longer passionate about what I was working on like I used to be. The challenges were still there and a management career was just around corner but cyber security looked so much more exciting and got me excited to get up and out of bed in the morning. So with no previous cyber security roles or training, I made a hard career pivot from a well paid and stable Principal Engineer job at a large international company to an entry level security role and enrolled in a security degree program. From there, I ended up changing roles a few more times with different companies while picking up many cyber security certifications along the way. Before I knew it, I was invited or selected to speak at many local Wisconsin cyber security conferences and was speaking in front of my peers at local cyber security focused organizations. This talk is a summary of my experience to break starting a cyber security career down into a simple strategy while providing an overview of the information sources, certifications, local communities, and trade offs to consider for someone starting down this path.