Kai Islander delivering a speech at a graduation ceremony at Main Street Scholars. 

Last Wednesday, Kai Islander gave the commencement speech for an intimate gathering at Main Street Scholars, which was celebrating the promotion of two eighth-grade students and one high school graduate: Islander himself.

“I am not the greatest with public speaking,” he began, “but I once heard that the world belongs to the courageous, so I’ll do my best to be courageous.”

The 18-year-old has had some practice being brave. He has spent the last seven years forging his own nontraditional path through school. It has allowed him to write his own ticket to the college of his choice with a sizable scholarship and a year’s worth of college credit under his belt.

From a young age, Islander was destined for a different path.

He is the third of four brothers and went to public elementary school like his siblings until fifth grade. But unlike his brothers, Islander never felt comfortable there.

“Even from the time he was a little boy, school in a regular setting never felt right for him,” said his mother, Jennifer Islander. “He felt like it was a waste of his time.”

Things came to a head when Kai went to Cunha Intermediate School for sixth grade. Kai’s grandmother, Jamie Weintraub, remembers getting her daughter’s phone call, about halfway through the year, saying they couldn’t send Kai to school one more day.

“He was crying. He had stomachaches. He was being bullied,” she remembered. The family decided to pull him out of Cunha right away.

The Islanders home-schooled Kai through seventh grade, then Weintraub quit her job and opened Main Street Scholars to teach him. When she started in the fall of 2014, she had Kai and two other full-time students.

After two years full time at Main Street Scholars, the Islanders enrolled Kai in the College Connection Concurrent Enrollment Program at the College of San Mateo. The program allows current high school students to enroll for free in up to 11 units and earn college credit.

Kai said CSM was a little intimidating at first, but he soon felt right at home. “I was pretty tall, so most people couldn’t tell that I was just 15.”

Kai took the bulk of his general education courses at CSM, where he received both high school and college credit. The rest of his classes he took through Main Street Scholars, including French, economics and a class on Shakespeare run by Half Moon Bay Shakespeare founder and artistic director Robert Pickett. 

He applied to 13 colleges and was accepted at 12, all honors programs, with sizable scholarships at every private school. He ended up choosing Juniata College, a small liberal arts college in Pennsylvania that allows students to design their own major.

“It’s been pretty awesome so far,” said Kai. “I’ll be going to college with over a year’s worth of units.”

Kai’s high school years were void of what some may consider traditional teen milestones like football games and senior prom, but his mom said that those aren’t really important to her son.

Instead, Kai was able to devote his time to the subjects he was passionate about. He had time to read voraciously and discovered a love of history. His current plan is to pursue a degree in law, with a dream of one day sitting on the U.S. Supreme Court.

Printed on Kai’s commencement program were the well-known words of Robert Frost’s poem “The Road Not Taken.” Frost’s words are an apt sentiment for this teen who was compelled to forge his own path:


... Two roads diverged in a wood, and I – 

I took the one less traveled by,

And that has made all the difference.


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