In the field of astronomy, Maunakea is known as a prestigious site for observing and science. In Native Hawaiian culture, Maunakea is revered as the connection between past, present, and future generations and their ancestral lands of Hawaii. We have reached a juncture at which it is necessary to allow and enable Native Hawaiians to pursue careers in astronomy, especially on Maunakea. This paper serves to tell the accounts of four Kanaka astronomers and raise awareness of the barriers they have faced while pursuing astronomy careers. The authors identify issues that the community faces due to the disconnect between astronomy and Hawaii communities and propose resolutions to lead the way forward.