Aug 17, 2025
For years, Simon Alexander Ong told his strict Asian father that the job was "going okay." What he didn't say was that he'd already quietly started coaching clients on the side - building a business in secret, evenings and weekends, until he had three paying clients and a decision to make.
Today, Simon is a bestselling author, international keynote speaker, and one of the most-watched creators in his space - his video "I'm 40. If You're In Your 20s or 30s, Watch This" has 3.9M views. In this episode, we go behind the highlight reel: the double life, the conversations he had with his father once he finally had something to show, and why he says the biggest mistake career-changers make is quitting cold with no foundation.
TIMESTAMPS
(00:00) Introduction
(01:26) Being boxed in by titles
(03:35) Becoming a brand
(06:14) Simon’s objections
(08:52) A partner who supports your goals
(15:44) The pressure of having it together
(18:05) A compelling vision
(19:49) Learning vs being an expert
(23:05) Creativity as a differentiator
(25:18) What Simon is working on
(26:41) Transferable skills
(27:40) Does your family get what you do?
(31:14) Should I quit my job?
(35:00) How to do it all
(40:25) 3 Tips for entrepreneurs & creators
(46:01) Actionable takeaways
CONNECT WITH SIMON ALEXANDER ONG
YouTube: https://www.youtube.com/@simonalexandero
Website: https://simonalexanderong.com
Book: https://simonalexanderong.com/book
Newsletter: https://simonalexanderong.com/shots-of-energy
Instagram: https://www.instagram.com/simonalexandero
LinkedIn: https://www.linkedin.com/in/simonalexanderong
CONNECT WITH CHERYL LAU
Website: https://cheryllau.com
YouTube: https://www.youtube.com/@cheryltheory
Instagram: https://www.instagram.com/cheryltheory
LinkedIn: https://www.linkedin.com/in/cheryllau
WORK WITH CHERYL LAU
I produce distinctive and deeply resonant podcasts for leaders and organizations who want their content to command attention, spark meaningful conversations, and attract high-value opportunities.
I ensure your podcast isn’t just another show in the feed - it’s an asset that elevates your authority and moves your work forward.
Here are 3 ways we can work together:
✨ 1:1 Editorial Podcast Production
✨ Corporate Podcast Producing & Consulting
✨ Hosting for Corporate Shows
Schedule a discovery call for us to explore what working together might look like: https://cheryllau.com/discovery
CONTACT
Please email hello@cheryllau.com for business inquiries.