Aaron Khoo spent almost three decades building technology at Microsoft, Axon and Amazon. He walked away without another job waiting, and learned that fear doesn’t get a vote in what comes next.
There was nothing obviously wrong with Aaron Khoo’s career when he began questioning it. He had spent almost three decades in technology — working at Microsoft, helping build Axon’s early body-camera business, and spending nearly ten years inside Amazon Web Services. He had built products at scale, managed teams and reached a level of seniority many people spend entire careers trying to attain. Yet this was not the first time Aaron discovered that being good at something did not mean he should keep doing it.
Years earlier at Microsoft, Aaron had received strong feedback and been promoted, and on paper his career was moving in exactly the right direction. Internally, something was changing. “I don’t need this promotion,” he remembers thinking. “It’s not about the level or the money.” He could not fully explain the feeling at the time. He simply knew that coming to work no longer felt right, and he did not want to stay until discomfort turned into resentment. So he left, eventually joining Axon to help build its body-camera business, wanting to put the only skill he had — technology — toward something practical. “Something being better is better than nothing being better,” he says of the decision.
The same instinct eventually told him to leave Axon too. Staying could have been financially rewarding, but the work no longer felt like the right long-term fit, so when an opportunity at AWS appeared, he took it — and stayed for almost another decade.
By 2025, Aaron was no longer just wondering which technology company to join next. He was questioning whether he needed another conventional job at all. Over breakfast, a friend asked him a question he had not seriously considered: “Have you thought about not working?” His first reaction was disbelief — he had worked almost continuously for close to 30 years. But she suggested the growth might lie in the very thing that made him uncomfortable, and recommended Annie Duke’s book Quit. Aaron read it on a flight and landed with his decision made. What he recognised was that most of his hesitation wasn’t excitement about continuing his career. It was fear of losing what the career already gave him.
He left Amazon on December 1, 2025, with no new role waiting. The adjustment was harder than he expected — for years, part of his identity had come from being an executive at a respected company, with the authority and status that came with it. Suddenly he was home with his dog. “The dog wasn’t gonna listen to my opinions,” he jokes. Behind the humour was a real recalibration: without a title, what answers the question “What do you do?”
Today Aaron has a different answer: “I want to experience life.” He has approached that with an engineer’s instinct for systems, deciding to learn something new every year rather than leave curiosity as an abstract ambition — taking improv classes, learning to sing and play bass, writing a detective novel, and choosing selective technology projects partly because they expose him to unfamiliar people and ideas. Work has not disappeared. Its role has changed.
Near the end of the conversation, Aaron reduces much of what he has learned to a single principle: “Fear doesn’t have a voice. You can feel it, but it doesn’t get a vote in what you do.” He still feels anxiety about unfamiliar plans, including months spent living in different cities. The difference is that he no longer assumes the feeling should decide the outcome — weighing the realistic downside of a few months somewhere new against the upside of an experience he might carry for the rest of his life, and finding the answer usually favours trying.