He is best known for his work on massively multiplayer online role-playing games (MMORPGs), mainly as director and producer of Final Fantasy XIV: A Realm Reborn and its expansions.

Yoshida is credited with the revival of the original Final Fantasy XIV project by commentators like Game Informer, which was initially criticized for poor quality.

His career choice was influenced by two Nintendo Entertainment System games: Mario Bros. shocked him with the idea that people could control what was shown on television and the possibilities of multiplayer design; Dragon Quest III made him want to become a writer due to how engrossed he became by its story, more so than those of books and films.

[8][9] His formative years were lived in Hakodate, where he balanced high school studies with a part-time job running the entire game corner of a toy store.

[14] He applied to Chunsoft, his preferred choice, but the internship meant he could start earlier at Hudson: since Yoshida was going through difficulties at the time, he opted for the latter to give his mother peace of mind faster.

His role kept expanding, eventually working under Oji Hiroi's supervision on the original Far East of Eden III: Namida  [ja], which was ultimately moved to the PC-FX.

[16] He faced a harsh environment: programmers held control over productions, saw designers as useless, would not realize documents if they found them boring and had no patience for people that did not understand or tried to broach their field.

[9] A partnership with Enix saw them develop a Windows online action RPG with randomly generated dungeons and a Diablo-like system, designed by Yoshida and produced by Yosuke Saito [ja].

A sales meeting by management concluded a story mode was required, but since the team already had to rework it twice due to their demands, a debate ensued over how to inform the developers, which ultimately led them to shelf it instead.

[21] Following the game's shelving, Saito invited Yoshida to "take his revenge" by moving to Tokyo and working on what was then called Dragon Quest Online.

[9] Yoshida joined Square Enix in 2004 as the fourth member of the Dragon Quest X team;[20] as chief designer, besides handling the writing alongside Yuji Horii,[19] with Jin Fujisawa [ja] as director.

Eventually, that game required his full attention to be completed, so circa late 2007, he appointed Yoshida as acting director for Dragon Quest X—an arrangement that lasted over a year and a half—due to his "indisputable competence" and trustworthiness.

[22] The idea to loan player characters as NPC party members came as a result of preserving series integrity: "When working in all Dragon Quest projects, the theme is not about complexity but having a game that's really easy to get into".

Elsewhere, a desire to make a card game that parents and children could play together led Yoshida to conceive the car-centric Chōsoku Henkei Gyrozetter for arcades.