Aaron Khoo

Aaron Khoo’s career began far from the Seattle technology industry where he would eventually spend much of his professional life. He grew up in Malaysia and moved to the United States at 18 after receiving a substantial scholarship to Knox College in Illinois. Drawn to mathematics and computer science, he later completed a PhD in robotics at Northwestern University.

After graduate school, Aaron joined Microsoft. He initially worked in games before moving through Windows and Xbox, including much of the Xbox 360 generation. Microsoft was also the first environment where he remembers experiencing something resembling imposter syndrome. Surrounded by highly capable engineers, he responded by learning from them rather than retreating from the challenge.

The experience also gave him an early appreciation for building technology at enormous scale. Working on Windows when software was still distributed on CDs meant that mistakes could not simply be corrected with an immediate cloud update. A seemingly small failure rate could affect millions of installations. That discipline around quality would follow him into later roles.

After roughly ten years, however, Microsoft no longer felt right. Aaron had recently been promoted and was succeeding by conventional career measures, but the level and money were no longer enough. Rather than wait until that discomfort became resentment, he left and spent the next few years co-founding startups.

In 2014, a series of shootings prompted him to think more seriously about where his technical skills could make a practical difference. He joined the small body-camera team at Axon, then known as Taser. For Aaron, the attraction was not a title. Body cameras offered a tangible way for an engineer to contribute to a problem he cared about.

After about a year and a half, Aaron again recognised that it was time to move. Staying at Axon could have been financially rewarding, but the environment no longer felt like the right long-term fit. Around the same time, AWS approached him. He spent almost another decade there, working across AWS Config, AWS Backup and AWS Control Tower.

By 2025, the question had changed. Aaron was no longer simply deciding which company should come next. He was beginning to question whether another conventional technology job was what he wanted at all. A conversation with a friend introduced a more uncomfortable possibility: perhaps the next step was not another job. Reading Annie Duke’s Quit helped him recognise that much of what was holding him back was fear of losing what he already had.

Aaron left Amazon on December 1, 2025 without another full-time role waiting. The transition initially brought an unexpected loss of identity and authority after decades of being defined partly by senior positions and teams. Over time, that discomfort gave way to a different way of thinking about work and life.

Today, he has not abandoned technology. Instead, he chooses where to apply his experience while leaving space for writing, learning and experiences outside the industry. The shift is less a retirement from work than a move from obligation toward choice.