During his time in the sport, the Brazilian established himself as one of the most loved and exciting drivers on the grid, amassing a huge following around the globe.
With a second retirement -- Massa first quit F1 in 2016, only to be lured back for another year -- on the horizon, it looked as though the 37-year-old was going to enjoy some well-earned time away from the spotlight.
But no sooner had Massa climbed out of an F1 cockpit than he was signing a contract with Venturi to be its main driver for the 2019 Formula E season.
"I love to race," Massa told CNN's Supercharged show at the Venturi launch in Monaco. "And it was the right time to stop Formula One.
"I'm really happy with my decision but I wanted to keep racing, so I think Formula E is the championship that is growing more.
"I like new challenges so it's definitely a new challenge for me -- and I'm looking forward for this new experience in Formula E, especially with the Venturi team."
'Huge asset'
Massa's presence for the upcoming season, which begins this weekend in Saudi Arabia, is quite the coup for Formula E.
Considered one of the world's fastest growing sports, Formula E attracted more than 300 million viewers globally to watch at least one race on TV last season, according to Forbes.
An average of 27.1 million watched each individual race, a huge increase on the 18.6 million that tuned in for each race during the 2016-17 season.
Its rapidly increasingly global reach is one of the main reasons high-profile drivers like Massa are scrambling to become a part of the sport.
But connections in the world of motorsport help, too, as Venturi discovered when trying to convince Massa to dot the i's and cross the t's on his new contract.
The Monaco-based team, the brainchild of Monegasque businessman Gildo Pallanca Pastor, boasts Susie Wolff as its new team principle for the upcoming season.
Wolff made her name in F1 as a test driver for Williams, in 2014 becoming the first woman to take part in a race weekend for 22 years.
It was also the same year Massa joined Williams to begin his four-season stint at the British team.
"But I can't take credit for Felipe, because Gildo was already speaking to Felipe when I joined," Wolff tells Supercharged. "So I just finished off the last negotiations.
"He's a huge asset to the team. First off, I just really like him as a person a lot, but (also) the experience he can bring having been in motorsport at such a high level for so long.
"The fact that he lives in Monaco, so he's easy to get to the office to be in the simulator. It really is for us, I believe, one of the strongest pairings in Formula E with Felipe and Edo."
No guarantees of success
Venturi, co-owned by Hollywood actor Leonardo DiCaprio, has endured a difficult first four seasons in Formula E.
Having competed since the series' inception in 2014, the team has only managed a best championship finish of sixth place, along with a seventh and two ninth-place finishes.
Venturi are also yet to win an E-Prix, but Wolff is optimistic that can change this season.
"I'm realistic, it's going to be a huge challenge," Wolff admits. "We are a small team but I think that's the beauty of Formula E, just because you're a manufacturer doesn't guarantee success.
"I believe that we have the chance for success. If we get everything right, if we find the reliability, the speed we know that is there, I have no doubt that we can come away with some great results.
"Can we string that together enough for a championship? I believe we've got more work to do before that's possible, but I respect the competition massively because I know what they're capable of, but I do believe and I wouldn't go racing without the belief that we can achieve success with Venturi."
Despite his wealth of experience in motorsport, joining FE has been a steep learning curve for Massa.
While F1 and FE may appear to share some similarities on the outside, the differences once you're sat in the cockpit are vast.
Even drivers already well acquainted with the sport will have to get to grips with the new "Gen2" cars and all the changes that come with it.
But Massa is hoping he can be the missing piece of the puzzle for Venturi to finally record a first E-Prix win.
"It's a new challenge for Venturi as well, to be bigger and to be more important, to be more successful and I'm happy to be part of it," Massa said.
"I really hope it will change. But it's better not to say anything and just concentrate on the races, on the job, but yeah, I think it's possible to change that number.
"I will really try hard -- me and Edo (Mortara, Venturi teammate) hope we can change only one time that number, but many times."
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