In 1998, while still a student at the Estonian Academy of Music and Theatre, Jakobson was cast in the role of Jane Peterson on the long-running
Eesti Televisioon (ETV) television drama series
Õnne 13; a role Jakobson has, to date, been performing on the series for over twenty years. The same year, she appeared as Stella in the
Peeter Simm directed comedy-drama
Kõrini! In 2006, she appeared as Maarja in the comedy-drama
Tabamata ime, based on the 1912 play of the same name by author
Eduard Vilde and later the same year played the role of Helina in the Veiko Õunpuu directed drama
Tühirand, based on the story of the same name penned by
Mati Unt. The following year she appeared as Laura, a single mother in the Veiko Õunpuu directed drama
Sügisball for which she won the Best Actress award at the 11th
Tallinn Black Nights Film Festival on 9 December 2007. On 11 February 2006, she was among ten European actors selected from twenty-one candidates, each representing their country, to be presented with the European
Shooting Stars Award by the
European Film Promotion (EFP). The event took place during the 56th
Berlin International Film Festival. In 2012, she appeared in the
Petri Kotwica directed Finnish-language joint Estonian-Finnish coproduction
Rat King as a German language teacher for
Allfilm and Making Movies Oy. In 2013, she appeared as Loviisa Maidla in the
René Vilbre directed family-adventure film
Väikelinna detektiivid ja valge daami saladus. The following year, she appeared as Karmen in the
Andres Maimik and Katrin Maimik directed romantic drama
Kirsitubakas. In 2016, she appeared as Juta in the René Vilbre directed
Taska Film comedy
Klassikokkutulek opposite actors
Mait Malmsten,
Genka, and
Ago Anderson. The film proved to be extremely commercially successful in Estonian theatres and Jakobson reprised her role for the 2018 sequel
Klassikokkutulek 2: Pulmad ja matused, and the third installment
Klassikokkutulek 3: Ristiisad in 2019. In 2018, Jakobson had prominent roles in two films: as Aunt Liilia in the
Moonika Siimets directed historical drama
Seltsimees laps, and as the titular character's mother in the Estonian-Icelandic crime-drama
Mihkel, directed by Ari Alexander Ergis Magnússon. In 2023, she had a starring role as Laine in the
Ergo Kuld directed comedy film
Suvitajad. She also starred in
Marko Raat's romantic drama film
8 Views of Lake Biwa as Jänesesilm, and has a minor role in Miguel Llansó's science fiction thriller film
Infinite Summer. Apart from her decades-long role on
Õnne 13, Jakobson has also had prominent roles as Annette on the
Kanal 2 mystery-drama television series
Nukumaja in 2017, and as Monika on the ten-part ETV drama series
Miks mitte?! In 2021, she appeared as Liivia Kurm in the
Priit Pius directed television drama
Süü. ==Personal life==