Skip to content

Caleb Tupili

Caleb Tupili was one of the first ever High School Day (HSD) speakers at the 2019 Homeschool Convention. The Homeschool Gazette sits down with him as he shares about his presentation and HSD experience.

Jessica Shepherd: Thanks for sharing with us, Caleb. You were one of seven speakers who shared at the very first High School Day during the 2019 Homeschool Convention. Can you tell us what it was like to have the opportunity to share your homeschooling journey–specifically your high school years?

Caleb Tupili: Hi Jessica, thank you for this opportunity! As you already mentioned, 2019’s High School Day was the first of its kind, and I am really thankful to have been a part of the event’s pioneering batch. I think it was a great opportunity as I really learnt so much more about myself in the preparation process. It came very timely, as in the weeks prior to the event, I was choosing what exams to take and considering different paths of education. I found it especially helpful to count my blessings, and appreciate the little things in life that led me to where I am.

Jessica Shepherd: You focused greatly on how homeschooling provided you with opportunities to practice responsibility, how have you seen the impact of this in your life?

Caleb Tupili: My parents have always believed that faith and character ought to take primary focus in one’s education. The most important years in my homeschooling journey would undoubtedly be the first few. In the book Outliers, author Malcolm Gladwell comments that it takes roughly ten thousand hours, or approximately 417 full days of practice to achieve mastery in any field. So quite naturally my initial years of homeschooling ingrained principles and habits into my lifestyle. I realised after homeschooling, that I took some things for granted in school. I had a habit of cleaning up my desk at school, and hence was elected the cleanliness manager and got this little shiny badge for keeping the classroom neat and tidy. I got recognition! However, at home there was no such thing. Having to absorb some chores and help at home awakened me to the importance and rigour of real-life skills. I slowly learnt how to balance my education with chores, family-life, and church, all which inculcated principles of ownership that I am especially thankful for today

Jessica Shepherd: When approached to share at High School Day, what was your initial reaction? It must have been exciting to be one of the pioneers for this event.

Caleb Tupili: I won’t lie, I was initially reluctant to share at the event, stemming from an unawareness of what it would entail. As you mentioned, this was the first SG High School Day in our history. It is always scary to do something new about which you have little information. At the same time the idea of pioneering a new event sounded really lucrative. This second emotion took prevalence over my initial worries, and I am really thankful that I accepted the opportunity. I would really like to express my gratitude to the mentors who walked me through the event, namely Aunty Dawn Fung and John Hoy, who encouraged me along the way and built me up with their honest feedback.

Jessica Shepherd: Can you share one of the main hurdles you learned to overcome related to this event; either in your preparation for the event or during your presentation?

Caleb Tupili: I really did not know what to expect at the start of the preparation process. I have spoken on many platforms, but never in a “TED-like” format. But that was not my biggest struggle. There have been phases in my life when I really challenged my decision to homeschool. I was going through one such phase. I had a terrible mental block while writing my High School Day speech because I could not find something positive in my education and in my lifestyle. I was really encouraged by this anonymous statement: Success is going from failure to failure without losing your enthusiasm. The entire experience reminded me of the impact homeschooling had on my life, and I am glad to have rediscovered that.

Jessica Shepherd: As you wrote your speech, what impact did you hope it would have on your audience, and have you seen that?

Caleb Tupili: My intention was to really speak from a position of honesty. I hoped to relate with the struggles that maybe one-or two of the members in the audience have faced before. Every cloud has a silver lining, and I wanted to place more emphasis on the silver lining rather than the storm cloud life often sends our way.

Jessica Shepherd: What was some feedback you received after your presentation?

Caleb Tupili: The youth speakers all did an amazing job! The event was a huge success, eventually resulting in all the youths being reinvited to speak at another engagement. I was really moved by the number of people who approached me after the event, sharing that they related with what I had to share. It humbled me to learn that I am not the only one who faces doubt and struggles when it comes to my education. It was an eye-opening experience, and I am glad that I could share my personal outlook with others.

Jessica Shepherd: What was the most influential aspect of High School Day 2019?

Caleb Tupili: 2019’s High School Day was crafted to present a unique dynamic; a lineup full of teenage homeschoolers, and a predominantly adult audience. It was amazing to see the next generation rise up and shake the platform. The most influential aspect was definitely the diversity between the speakers that was so intentionally orchestrated to paint an honest and ‘full’ picture of homeschooling. I admire the synergy between the speakers, and I am glad to have worked alongside such passionate and charismatic teens.

Jessica Shepherd: Do you think it meets a need of many parents–homeschooling and non homeschooling?

Caleb Tupili: After the key notes, a good 45 minutes were allocated for QnA. This segment in the event catered perfectly to the array of questions bubbling in the room after the keynotes. I personally felt that this segment was the most effective in meeting the needs of the parents in the room.

Jessica Shepherd: After the success of last year’s event, High School Day will be returning in 2020; what are you hoping to see come out of this event; what is some advice or encouragement you have for the next speakers and will you be attending?

Caleb Tupili: This year, it is my pleasure to be working alongside Aunty Dawn Fung, and Uncle Mark Lim, in a media related role. I look forward to working with the speakers and to promote what they have to share. If there is anything I would like to encourage our new lineup of speakers with, it is this: Speak from your heart, and be honest with your sharing. Each one of you are unique. Embrace that individuality, and do not be shy to share your struggles. More than success, people relate with struggle, perseverance, and growth. Do not be afraid to go against the grain.

The Homeschool Convention 2020 tickets go on sale from 1 Feb 2020. Please visit for more information or click to join the Convention’s FB Event Page

Photo of Caleb Tupili by Hoon Sze Siang of Snapshot Imaging

One thought on “Caleb Tupili Leave a comment

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: