He made his debut on opera stages in 2004 as Otton in Monteverdi's L'incoronazione di Poppea, staged at the Warsaw Chamber Opera. On stage, he presented himself both in the Baroque repertoire (including the eponymous part in Orlando, Goffred in Rinaldo, Tirinto in Imeneo, Polinesso in Ariodante and Tolomeo in Händel's Giulio Cesare, Pompeo in Vivialdi's Farnace), classical works (Cherub in Le nozze di Figaro, Ramiro in La finta giardiniera, Annio in La clemenza di Tito, Farnace in Mitridate, re di Ponto, as well as Ascanio in Ascanio in Alba by Mozart), as well as in 19th century repertoire, including his title role in Rossini's Tancredi and contemporary roles (title roles in Krauze's Polieukt and Pałasz's Ja, Kain, Artur in Tango and Fior in Dobrzyński's Operetka, as well as L'Ospite in Sciarrino's Luci mie traditrici. He also cooperated with the The Mazovia Musical Theatre Operetta (the role of Prince Orlofsky in Strauss's Die Fledermaus), Podlasie Opera and Philharmonic, the Grand Theatre in Warsaw and Łódź, and the Baltic Opera in Gdańsk.

As a soloist of the Zurich Opera Studio, he performed at the Zurich Theatre as Oberon in Britten's Midsummer Night's Dream. The singer took part in the recording of unique collections of Polish baroque music - collected works by Grzegorz Gerwazy Gorczycki and Stanisław Sylwester Szarzyński, Caldara's oratorio Maddalena ai piedi di Cristo, as well as Händel's Giulio Cesare opera in Warsaw Chamber Opera. The artist’s oeuvre also includes recordings of contemporary music, including Marc-André Dalbavie's Sonnets sur un poème de Louise Labé for countertenor and orchestra, Giya Kancheli And Farewell Goes Out Sighing for the same ensemble, Penherski’s Lamentations and Breviary for Men's soprano and String Quartet, Britten's Seven Sonnets of Michelangelo, Liszt's Sonetti del Petrarca and Mykietyn's Shakespeare's Sonnets.

Jan Jakub Monowid is a laureate of two Fryderyk Awards,he also won the Jan Kiepura Theatre Music Award for the best singer. In 2011, he won 3rd place in the counter-tenors' competition during the 5th edition of Gianni Bergamo Classic Music Award.