[3] Following high school, Jakobek attended the University of Toronto, intending to become a teacher and graduating with a degree in public administration.
[3][5] During the time he represented the district on the School Board, he attended college and worked at a liquor store to pay off his campaign debts and tuition.
He became city of Toronto budget chief in 1990, and held the position for the next ten years despite an attempt by Barbara Hall and others to oust him in 1994.
After departing from the City Council, Jakobek took a break from politics to pursue a master's degree in Health Sciences at the University of Toronto.
[3] At the center of Jakobek's platform was a proposal to pay off Toronto's then $2 billion debt by selling city-owned parking lots, golf courses and unused municipal buildings.
[9] In the early 1990s, the City of Toronto planned to tear it down due to its deteriorating condition and to its location which was subject to flooding and erosion, forcing it to be repeatedly moved to higher ground.
[9][10] To prevent its destruction, Jakobek partnered with historians Gene Domagala and Glenn Cochrane to create a group called “Save Our Station (S.O.S.
[9] As of July 2020, it was still in active use when Jakobek and other Beach area dignitaries celebrated its 100th anniversary, its lifeguards having rescued an estimated 6,000 swimmers over the course of its existence.