Known as "Dr. Tsai"
after completing a doctorate at the London School of Economics, she's also the first woman in Asia to be elected head of state without being part of a political legacy.
While Tsai is known for her steely calm and understated manner, Freddy Lim
is famous for his over-the-top stage antics as the frontman for Chthonic, one of Asia's leading black-metal bands.
The rocker beat a ruling party veteran to earn a legislative seat for the New Power Party, a smaller opposition party that emerged from the 2014 Sunflower Movement protest against a trade pact with China.
Fellow New Power Party candidate Huang Kuo-chang
is also a legislative election victor. He can now walk into parliament as an elected official, just two years after he stormed and occupied parliament as a Sunflower Movement activist.
All are colorful candidates in a vibrant election that forced the ruling Kuomintang party to lose the presidency as well as its parliamentary majority for the first time in history.
"The change is really, really good," says Sunflower Movement student leader Lin Fei-Fan.
"Our democracy is only 20 years old, and this is the most interesting election in Taiwanese democratic history."
Taiwan's boisterous, multi-party election stands in sharp and telling contrast to the single-party state next door that is tightening its grip on dissent.
And it's all happening at a time when Taiwan is distancing itself even further from the mainland.
According to Taiwan's national research center,
a growing number of young people on the island are identifying themselves as Taiwanese rather than Chinese, choosing to identify with their birthplace as opposed to the homeland of many of their ancestors.
They have governed separately, but Mandarin Chinese is widely spoken in both places.
Under Taiwan's incumbent president Ma Ying-jeou, ties have warmed with the introduction of direct flights and closer trade links.
But a new Taiwan has voted for change, and an increasingly organized youth movement is wary of closer ties to China.
"We definitely want a peaceful relationship with China," says politician and Sunflower Movement activist Huang.
"But that doesn't mean we have to sacrifice our way of life."
The political ascent of Taiwan's Sunflower Movement has captured the attention of youth activists in Hong Kong who have been protesting against China's rising influence in the territory.
Umbrella Movement student leader Joshua Wong traveled to Taiwan
to witness and learn from their election process.
But while Wong could travel freely to Taiwan, Huang could not travel to Hong Kong.
After being invited to a special CNN taping in Hong Kong, Huang says his online visa request to travel to the city was denied. Huang says he was previously denied entry in 2014 after the Sunflower Movement protest.
CNN reached out to the Hong Kong government for comment and was informed that the Immigration Department does not comment on individual cases.
Pop star's apology
Although Hong Kong is part of China, it enjoys a high degree of autonomy under a governing principle called "One Country, Two Systems."
The case of Hong Kong's missing booksellers has also sparked fears over freedom of the press and illegal arrests in the territory.
So when a teenage Taiwan popstar
was forced to apologize for waving the Taiwan flag on South Korean TV, many people in Taiwan were angered by what they saw as one of their own kowtowing to the growing influence of China.
And this has emerged as a key challenge for Taiwan's new president -- finding a way to work with China, while affirming Taiwan's own identity.
Taiwan cannot afford to alienate China, it's number-one trade partner.
But inside Tsai's DPP party, there's a greater call to move Taiwan's trade links gradually away from China, especially as the giant's economic engine slows.
"The solution lies in something that Tsai has said repeatedly: the 'Go South Policy' to further engage countries in South and Southeast Asia," says J. Michael Cole, editor-in-chief of Thinking Taiwan, a news and analysis website founded by Tsai Ing-wen.
"Even if Taiwan does not have official diplomatic ties with those countries, a lot more can and should be done to revitalize Taiwan's economy."
At her first international press conference as the new president-elect, I asked Tsai Ing-wen about her plans to assert Taiwan's identity on the world stage.
"Only through strength, can we gain more respect and protect our people and our democratic way of life," she replied.
That response may be lacking concrete policy details, but it does reveal a major theme of her upcoming presidency.
Taiwan must stand as tall as it can, to step out of the shadows of the giant next door.