"Esperantisto de la Jaro" is a famous title given every year by the periodical La Ondo de Esperanto. The award recipient is selected by an international jury led by Halina Gorecka, without any clear criterium. What should an Esperantist do to be more likely to receive this prize?
I feel qualified to answer this, because I was last awarded the prize of Esperantist of the Year!
There is a nominating committee that chooses candidates and then a jury who votes on these candidates. Everyone in both bodies tend to be older, so if you were focused on winning this prize, you should do something for the Esperanto community that has an impact as well as being visible to the older generation. For example, founding the Esperanto Wikipedia wasn't big enough to earn the prize.
Also, the action typically has to have had a huge impact in that particular year. Thus, the Esperanto Wikipedia kept growing at a constant rate and there was no year where it was particularly impressive. In fact, by the time Wikipedia was very large, I was no longer very active there. But 200,000 people starting to learn Esperanto in 6 months? That's something clearly understood by everyone.
In any case, if you're gunning for this prize, I'd recommend thinking strategically about what the Esperanto movement and community needs most and work on that. If you keep building and joining teams and work strategically to improve the Esperanto community and/or culture, you may have a good shot at it, but only one person wins it every year, so nothing is a guarantee. Bonŝancon!