After two decades building Alibaba into a $460 billion business, Ma is now pivoting full time to philanthropy. He started the Jack Ma Foundation in 2014, and has cited the Bill and Melinda Gates Foundation as an inspiration for his charitable endeavors.
"Jack has been signaling for some time his interests in philanthropy, environment, women's empowerment, education and development," said Duncan Clark, the author of "Alibaba: The House That Jack Ma Built."
But he's also a former English teacher, and has often talked about his passion for education. The date that Ma chose to formally step down, September 10, is Teachers' Day in China, "so there's some messaging in that," Clark said. It's also Ma's 55th birthday.
Ma referenced his previous career to explain why he was stepping down from his company.
"Teachers always want their students to exceed them, so the responsible thing ... for me and the company to do is to let younger, more talented people take over in leadership roles," Ma said last September.
The current knowledge-based approach of teaching will "fail our kids" who will never be able to compete with machines, Ma said. Children should be taught "soft skills" like independent thinking, values and teamwork, he added.
In 2017, Ma's foundation pledged $45 million over 10 years to help discover and cultivate future teaching talent in rural China.
Ma has also taken his teaching beyond China to other emerging markets, according to Clark.
Ma and Alibaba have hosted a biennial conference in China on women and entrepreneurship since 2015. The events have drawn names such as Arianna Huffington and Vera Wang. This year's conference included a video message from Rihanna.
Ma said that gender equality is one of the most-important issues in the 21st century, noting that "if you want your business to succeed, it is critical to appoint enough female leaders."
The revelation came amid rising concern over the tighter grip being exerted on China's private sector by the Communist Party under President Xi Jinping.
Ma is stepping away from Alibaba at a relatively young age. He has said in the past that he wants to retire earlier than Bill Gates, who stepped down as chairman of Microsoft at the age of 58 in 2014.
"I got rumors from outside China, saying: 'It's because the government wants to push you down.' Nobody can [push you out], if you don't want to leave, right? Because I know it's nothing about the politics or government," Ma said.
Still, some observers say that Ma had flown a bit too close to the sun, and leaving Alibaba is partly about self-preservation. The charitable projects Ma has signaled he is interested in pursuing in retirement have the added benefit of being unlikely to cause waves with China's leadership.
The final chapter in Clark's book on Ma was titled "Icon or Icarus."
"He's keen to secure his legacy. He's not fully exiting the company. But this move is a smart way to leave on a high," Clark said.
"To avoid being Icarus you have to ... not only avoid flying too close to the sun, but also avoid crashing into the waves. So you have to still be ambitious. In philanthropy, education, environment he has plenty of room to soar yet. Areas where the government will be tolerant if not encouraging," Clark said.