For several years, Silicon Valley entrepreneur Timothy Draper has sought to break up California, citing its unwieldy size as damaging to the state’s schools, livability and the economy. In November, California residents will get their chance to vote on his latest proposal: to divide the world’s fifth-largest economy into three separate states.

Draper, who made his fortune investing in startup companies, is proposing that the state of 40 million people be split into three entities with roughly the same populations. Northern California would comprise the upper part of the state, including Silicon Valley and San Francisco; Southern California would include a vast swath of the inland’s verdant farmland, stretching to San Diego; a third state, simply called California, would hug the coastline from Santa Cruz to Los Angeles.

If Californians approve the controversial ballot measure, which academics and others say faces many obstacles, it would still need the blessing of the California Legislature and the U.S. Congress. Politicians, for one, may be wary of splitting up a state that has long voted Democrat.

Vikram Amar, a professor and dean of the College of Law at the University of Illinois in Urbana-Champaign, said California’s conservative-leaning inland empire (which would be part of the new Southern California) could swing Republican.

“That is a risk Democrats in California and Washington, D.C., will be loath to run,” he said.

Californians have long debated whether they were better as a whole or in parts.

In 1941, a group of secessionists along the border of Northern California and Southern Oregon proposed creating a new state called “Jefferson.” It was called the “Yreka Rebellion” then, and was initially dismissed as a publicity stunt. It gained momentum as rural voters sought autonomy from their urban counterparts, a common refrain among Californians.

In 1993, Stan Statham, a Republican state assemblyman, proposed splitting the state into three parts, promoting a smaller-is-better agenda when it came to governing. More recently, a group of Californians proposed the state leave the union altogether (they called it Calexit) after Donald Trump was elected president in 2016.

It is not Draper’s first attempt to divide California. In 2013 he proposed carving the state into six. The proposal did not garner enough signatures to be included on the November 2016 ballot and cost Draper about $5 million. Opponents feared that California’s rural towns would suffer compared with the coastal communities, which generate higher tax revenues.

On Tuesday, the California secretary of state’s office certified that Draper, who submitted more than 600,000 signatures from voters, had garnered enough for the initiative to appear on the ballot.

A breakup would be complex, as the state’s businesses and universities — even its water system — are interconnected and dependent on one another. Employees and entrepreneurs who split their time between Hollywood and Silicon Valley would essentially be working in two different places with their own tax structures.

College students from Northern California who go to school in Los Angeles (and vice versa) would also be affected. “Now they would be going to out-of-state schools and paying higher tuition,” said Amar.

And, of course, there is the psychological shift.

While Californians in the northern and southern parts of the state have long perceived themselves as different from each other, they all identify with their home state.

“Who gets to be called the real Californian?” said Amar, who grew up in Walnut Creek. “Even though there is a rivalry, we are frenemies.”