Matt Jonkman, a 52-year-old retiree, has chosen an unconventional lifestyle aboard his 50-foot houseboat anchored near Navy Pier in Chicago. Since April, Jonkman has embraced the freedom of life on the water, accompanied by his feline companion, Monty. As summer winds down, he is preparing to journey south to Kentucky for the winter, with the intention of returning to Chicago’s picturesque waters by spring.
Jonkman’s decision to live aboard his boat stems from a desire for adventure and a close connection to his adult daughter, Savannah, who resides onshore. “I told myself I’d live like this for at least a year,” he stated. “Now I don’t want to get off yet.” His choice to become a “liveaboard” offers him a chance to enjoy the scenic backdrop of the Chicago skyline while avoiding the high costs associated with traditional docking fees.
Living on the water has its challenges, but Jonkman finds joy and satisfaction in the simplicity of his floating home. He has crafted a cozy living space complete with a kitchen, lounge chairs, and even a flatscreen television. “Making dinner is the best part of the day,” he remarked, highlighting the breathtaking views he enjoys each evening.
Anchoring overnight in public harbors has allowed Jonkman to minimize expenses while occasionally renting a spot to pick up supplies or visit local attractions. His boat has become a familiar sight to both fellow boaters and those passing by onshore. Tour boat captain Karina Zuniga noted, “I always wave at that man, and he always waves back. He basically has his whole life right there.”
Jonkman, a former cybersecurity expert, has a rich history that includes dropping out of college, serving in the Army, and founding a successful security software company. Following a near-fatal plane crash in 2020, which left him with significant injuries, he decided to embrace a more relaxed lifestyle. “The accident made me slow down,” he reflected. “I was this hard-charging tech guy. I’m not that anymore.”
Despite the tranquility of his new life, Jonkman acknowledges that living on a boat requires constant vigilance. He has faced the unpredictability of the weather and the maintenance demands of his vessel. “Thirty percent of the time you’re trying to stay alive,” he explained, referencing the challenges posed by thunderstorms and other hazards.
His daughter Savannah expressed mixed feelings about her father’s new lifestyle but noted the positive impact it has had on him. “He seems happier being so self-sufficient,” she said. “I’ve seen him become more sure of himself. He’s kind of got a mission.”
While Jonkman revels in the solitude and independence of boat life, he also seeks connection. He has made friends among fellow boaters and finds the experience of living on the water enriching. “On the water, everyone has something in common,” he noted. “I learned that there’s a lot I could tolerate that I didn’t think I could.”
As Jonkman prepares for his journey south, he reflects on the challenges and joys of living on the water. “I feel more settled now than ever,” he remarked, though he admits uncertainty about what lies ahead. “But I still don’t know what the f— I’m going to do.”
His journey embodies a unique blend of adventure, resilience, and self-discovery, demonstrating that life on the water can offer both challenges and profound fulfillment.
