For the last few years, Jason Dion was running his cybersecurity training business, Dion Training, from his guest room in his home in Mayaguez, Puerto Rico. However, his remote-first company recently acquired office space near Orlando, Florida, where he and his family are now located. Although he does appreciate moving his office and recording equipment from his house to a shared location, he continues to work with his employees and contractors in six countries using primarily remote-work strategies. Some of these strategies include asynchronous communication using Slack and offering flexible work hours for everyone, except for their once-weekly meeting. Jason makes his own hours and still works from home on occasion; so, he feels like he has tremendous flexibility, even as the lead instructor and founder of a growing business. In this episode, Jason shares how he transitioned from a naval officer to a college professor. He has worked as a network engineer, director of network operations and security center, and as an information systems officer for large organizations around the globe. He eventually needed more flexibility with his schedule, which led to him teaching cybersecurity courses on Udemy. Between the basic Udemy courses and the more robust courses on his website, his training program has grown to 1 million students. Dion Training now prepares students for IT, project management, and cybersecurity certificates. Many people who go through this training program will end up in remote-work positions, as IT work lends itself well to working from a home office. Jason explains that there are dozens of roles within the cybersecurity realm, with something for nearly every personality type. Of note, most entry-level cybersecurity positions do not require a college degree, so he encourages high schoolers and recent high school graduates to seek experience in an IT help desk situation while earning certificates so they can enter a career position making $70-200k within a couple of years. Job seekers need to obtain specific certificates for different fields, and sometimes a combination of more than one is required. Jason personally holds multiple information technology professional certifications, including Certified Information Systems Security Professional (CISSP), Certified Ethical Hacker (CEH), Certified Network Defense Architect (CNDA), Digital Forensic Examiner (DFE), Digital Media Collector (DMC), CySA+, Security+, Network+, A+, PRINCE2 Practitioner, and ITIL, among others. He also holds a master of science degree in information technology, specializing in information assurance, but he reminds the listeners that the bachelor’s and master’s level degrees are usually only needed for management and higher positions. Dion Training does offer a track that includes career counseling which is especially useful for those who are pivoting their careers.