Raymond’s Life Timeline

This page is the personal encyclopedia’s chronological entry point, complementary to thematic entries (beliefs, decisions, low points, strategies, etc.): thematic pages answer “What kind of person is Raymond?”; this timeline answers “How did his story develop over time?” Dates and numbers use RAYMOND_TIMELINE.md as the single source of truth. Each milestone links to its corresponding thematic entry, allowing readers to jump from any year into the full context of an event.

Before high school

See Childhood and Adolescence

Junior high: Earned his “first pot of gold” by playing online games.
Ninth grade through high school: Joined the Knight Korean pop dance team, then the dance club at The Affiliated Senior High School of National Taiwan Normal University. He left the street-dance scene because of its seniority system and tacit monopolization, developing the insight that “commercial value can save a culture” and a rebellious streak (see Childhood and Adolescence).
High school: Worked part-time at tutoring centers and in food service; stopped taking money from his family at age 18.
Age 18: Traveled independently in India for 35 days, his first solo trip abroad.

2012–2018 — Six years at NCKU

See Six Years at National Cheng Kung University: Changing Majors Twice and Extending Graduation, multiple roles, launching projects from zero, and From Freelancer to Business Operator

2012: Entered the Department of Chemical Engineering at National Cheng Kung University.
2013–2014: Founded N Power Workshop, Tainan City Wanderer, and Co-Creation Era; participated in the Taiwan–US Student Conference.
2014: Began writing and sharing on Facebook.
2015 (second year): Began fully remote contract work, became a freelance instructor, and paid his own tuition and living expenses.
~2015–2016: Changed majors for the first time, from chemical engineering to industrial and information management.
~2016–2017: Changed majors a second time, from industrial and information management to the university-wide interdisciplinary program (first cohort). Established the core belief: “Competence is the means; passion is the end.”
Fourth year: Joined the Korean company JANDI as a remote worker.
~2018: Graduated after six years at NCKU, having extended his studies by two years because he changed majors twice.

2017–2018 — Writing takes off

See Writing Takes Off (2017–2018), Three Breakthroughs When Writing Changed His Life, Writing Is the Best Investment for Ordinary People, and The Tortoise Philosophy and Blue-Collar Roots

~2017: Published the “turtle exploring the ocean floor” declaration, sharing his background and growth story publicly.
2017: Began writing on Medium and became a Top Writer in Productivity.
~2017: Was invited to speak at TEDx on “The Power of Sharing”; launched his first online course on Hahow.
2018: His interview-guide series passed 500,000 views; his writing led to a job opportunity at a multinational company.

2019 — Beijing, marriage, and a fire

See The Beijing Period (2019–2020), Why Beijing, The Late-Night Fire at Raymond’s Tainan Home in 2019, and Yuzu (Song Zhiyou)

2019: Invited by Dedao App to Shenzhen for its Knowledge Spring Festival Gala (a livestream watched by tens of thousands).
2019/03/17: The Late-Night Fire at Raymond’s Tainan Home in 2019 forced him to move.
2019/07/21: Married Yuzu (Song Zhiyou).
2019/08: Joined Keep in Beijing as a product-operations specialist; at the same time, served as a digital-transformation consultant to a Taiwanese brand group. His annual salary exceeded NT$1 million.

2020 — Leaving employment and starting a business; year one of the company of one

See The 2020 Retreat from Beijing to Taiwan and the Birth of Raymond Thirty, From Raymond Hou to Raymond Thirty, Leaving Employment at 26 to Build a Company of One with Yuzu, Starting a Business with a NT$1 Million Government-Backed Loan and No Ads for Three Years, Launching Paid Membership Subscriptions from the Brand’s Earliest Stage, Raymond Thirty Podcast, and Raymond Weekly Newsletter

Early 2020: Returned from Beijing to Taiwan for Lunar New Year and could not go back after the pandemic began.
2020: Formally left traditional employment; Starting a Business with a NT$1 Million Government-Backed Loan and No Ads for Three Years; co-founded “Raymond Thirty” and 「柚智夫妻」 with Yuzu.
2020/03: Began recording the Raymond Thirty podcast.
2020: Launched the Raymond Weekly newsletter (100 subscribers in its first month).
2020/09/16: Reflected on Beijing and Keep’s layoffs on his 25th birthday and declared that he would build content products and a community ecosystem (“Make some noise”).
2020/09/21: Published “Why Did I Stop ‘Dancing’?”, looking back on his street-dance experience from junior high through high school and developing insights about “commercial value can save a culture” and institutional systems.
2020/11: Began thinking about a paid membership subscription.

2021 — Subscription service, courses begin, and home purchase

See Notion Online Courses and Boot Camp, Lifehacker Premium, Moving from Medium to Self-Hosted WordPress (2020), Naming the Company “Nomadic Youth Digital Content”, and The Subscription-Service Low Point: Payment Became a Barrier to Getting to Know Each Other

2021/01: Began learning about investing; registered the company “Youmu Young Digital Content Co., Ltd.”
2021: Bought a resale home in Taipei; launched Notion Online Courses and Boot Camp; launched a paid membership subscription (Lifehacker Premium); moved from Medium to self-hosted WordPress.

2022 — Moving into the new home and getting into smart-home technology

See Smart Work Home, Keelung: A Startup Studio That Began in a Three-Ping Living Room, and Work-Life Integration (Not Balance)

Early 2022: Raymond and Yuzu turned a 3-ping (approximately 9.9-square-meter) living room in Keelung into a studio.
2022/08/15: Officially moved into the new home and built a smart home office.
2022: Began experimenting with smart-home technology (Aqara → HomeKit → Home Assistant).
2022–2023: Raymond and Yuzu practiced “living frugally” and kept detailed accounts to control expenses.

2023 — Smart-home office goes viral; AI exploration begins

See Smart Work Home and Use Real-Life Experience to Counter AI Mediocrity

2023: Completed the DIY whole-home smart upgrade (more than 25 Aqara devices).
2023/09/16: Re-edited the transcript of his 2019 graduation speech at the NCKU interdisciplinary program, establishing the hub-page principle of centering blog posts around core articles.
2023/10: A smart-home video went viral and passed one million views in a week.
2023: Studied AI applications at work and launched the ChatGPT Work Methods course (TRIRO framework).

2024 — Standing firm at thirty

See The Super Individual: A Definition for Today’s Professionals, Attention > Time > Money, and Multiple Identities

2024/02: Interviewed by “i Living Circle | My Home” about a live-work smart home.
2024 Q1: Lifehacker Premium exceeded 12,000 members.
2024/07: Celebrated the fifth wedding anniversary with Yuzu in Beijing.
2024/09/17: Turned 30 and published “What I Learned About Turning 30 Over the Past Decade.”
2024/10: Published “Raymond Hou’s User Manual”; had taught or spoken more than 500 times.

2025 — Super Individual course, digital nomadism, and a burst of content

See The Super Individual’s Way of Working (55-Unit Online Course), The Super Individual: A Definition for Today’s Professionals, Digital Nomad Map, The Low Period and Restart Week of the Second Half of 2025, and Thirty Days of Breakdown

From 2025: Frequently traveled while working (India, China, Malaysia, Singapore, Japan, Thailand, and New Zealand).
2025/06: Began fundraising for The Super Individual’s Way of Working (55 units, KIT model).
2025/09/16–17: On the last day of being 30, completed the review of Part Two and Assignment 6 of The Super Individual’s Way of Working; the full course went live the following day.
2025/09: The Super Individual’s Way of Working officially launched.
2025: The blog passed 300 articles; Raymond Weekly passed 25,000 subscribers, with an open rate above 65%.
Second half of 2025: The Low Period and Restart Week of the Second Half of 2025.

2026 — The AI Agent era begins

See A Full Shift to AI Agent Collaboration in 2026, Raymond’s AI Double, The Super Individual and AI Agent Era (2024–2026), and Build a Custom Hacker Coins System and Choose Teachify for Discord Integration

2026/01: Reflected on the six-year paid subscription service and decided to continue.
2026/02: Began building the AI agent Raymond’s AI Double from scratch with Claude Code; named it “Kairos” on 2/8 and launched it in the team Discord on 2/13.
2026/02: Refactored and slimmed down CLAUDE.md (513 → 120 lines); established an AI Agent teaching series.
2026/09/17: Reflected on five and a half years of entrepreneurship on his 32nd birthday, summarizing the shift from the labor stage to the systems stage, recording family upheaval and the wisdom of “the raft,” reminding himself to “finish well and sleep well,” and announcing that in 2027 he and Yuzu would “step away from the screen” to bring the first half of their business to a considered close.

Ten core turning points (for a book or talk)

Stopped receiving money at age 18: Survival pressure drove him to study productivity.
Changed majors twice at university: Chemical engineering → industrial and information management → university-wide interdisciplinary program; extended graduation by two years (see Six Years at National Cheng Kung University: Changing Majors Twice and Extending Graduation).
Started writing on Medium in 2017: Went from zero followers to Top Writer, leading to TEDx and Dedao App invitations (see Three Breakthroughs When Writing Changed His Life).
Beijing and marriage in 2019: Chose to leave despite an annual salary above NT$1 million, saying, “I still like assigning work to myself” (see Why Beijing).
Started a business during the 2020 pandemic: Borrowed NT$1 million at age 26 to start from zero (see Leaving Employment at 26 to Build a Company of One with Yuzu).
Notion course in 2021: An uncommon online-course case that grew to 13,000 learners (see Notion Online Courses and Boot Camp).
Smart home goes viral in 2023: One million views in a week; “recording life is the best content” (see Smart Work Home).
Turned 30 in 2024: More than 500 talks and 12,000+ members; “Don’t push too hard; leave room to breathe.”
Super Individual in 2025: Summarized seven years of experience in a 55-unit course (see The Super Individual’s Way of Working (55-Unit Online Course)).
AI Agent in 2026: Shifted from using AI to building an AI counterpart: “The greatest byproduct of training AI is understanding yourself better” (see Raymond’s AI Double).

Raymond's User Manual