- 9 minutes 46 secondsYour First Job Might Never Exist
Is AI really replacing jobs? Or is something even more dangerous happening?
Everyone is asking whether AI will take our jobs. I think we’re asking the wrong question.
The real disruption isn’t that experienced professionals are being replaced. It’s that the first step of the career ladder is quietly disappearing.
In this video, I explore:
* Why AI helps junior employees more than senior ones
* Why companies are hiring fewer entry-level workers
* What happens when AI takes over the work people used to learn from
* Why today’s graduates face a very different job market
* The hidden risk businesses are creating for themselves
* What leaders, managers, parents and young professionals should do next
Using research from MIT, Stanford, Harvard and real-world examples (including the ATM revolution, factory electrification, and the Air Canada chatbot case), I explain why the biggest AI problem may not be automation, but the disappearance of apprenticeship.
Whether you’re a CEO, manager, HR professional, student or parent, this is a conversation we need to have before it’s too late.
👇 I’d love to hear your thoughts.
Is your company still hiring junior talent?
Or has the entry door quietly started closing?
Leave a comment below.
If you enjoy thoughtful discussions about AI, work, leadership and the future of careers, consider subscribing. New videos every week.
Timestamps:
00:00 AI Hiring Paradox
00:22 Homework Without Struggle
01:05 ATM Story Misleads
01:55 AI Levels Skills
02:39 Entry Jobs Vanish
03:48 Apprenticeship Gets Cut
04:36 Where Seniors Come From
05:34 Why AI Pilots Fail
06:54 Redesign Workflows
08:08 Trust and Accountability
09:05 Protect the Bottom Rung
Get full access to Will That Work? at www.adriantan.com.sg/subscribe2 August 2026, 3:05 am - 10 minutes 56 secondsI've Lost My Job Six Times.
Someone is going to get retrenched today — and they have no idea. After 11 years inside recruitment and hundreds of conversations with blindsided professionals, I can tell you retrenchment is almost never actually a surprise. The signals show up weeks or months early. Most people just don't know what they're looking for. This video names all 9 — and the 4 quiet moves to make before you ever need them.
🔎 Track live layoffs in Singapore → https://layoffsg.com
⏱️ TIMESTAMPS
0:00 – Someone gets retrenched today (they don't know yet)
0:17 – Why it feels like a surprise (but almost never is)
1:11 – Two things to understand first
1:16 – Why the people who know aren't allowed to tell you
1:43 – Companies retrench roles, not people
2:22 – The signals are structural, not personal
2:37 – Signal 1: The hiring freeze
3:15 – Signal 2: External consultants arrive
4:01 – Signal 3: Communication becomes careful
4:44 – Signal 4: Your manager's behaviour changes
5:32 – Signal 5: You're asked to document your processes
6:21 – Signal 6: Budget quietly disappears
6:48 – Signal 7: A reorg or "strategic review" of your function
7:23 – Signal 8: New leadership with no history with your team
8:08 – Signal 9: Your scope quietly shrinks
8:54 – The two wrong responses (denial vs. panic)
9:20 – Move 1: Update your resume now
9:34 – Move 2: Activate your network quietly
9:49 – Move 3: Build visibility outside your company
10:08 – Move 4: Know what you're entitled to
10:28 – LayoffSG.com — the layoff tracker I built
10:53 – Final thought
Get full access to Will That Work? at www.adriantan.com.sg/subscribe12 July 2026, 3:29 am - 15 minutes 32 secondsThe Iron Rice Bowl Was Never Yours to Hold
I'm an introvert. Small talk drains me, and walking into a room of strangers is the last thing I want to do — so for years my "networking strategy" was finding the food table and looking busy with my coffee.
And yet people still walk up to me at events (and once, at a night market) already knowing who I am. That's not luck. It's reputation infrastructure — 8 specific moves that put your name into the world before you ever show up in a room, so trust is already built by the time someone reaches out. I used these moves while running my career coaching practice, and
I'm using them again now as I build my fractional career.
In this video, I break down all 8:
00:00 Intro
03:52 Move 1: Write a Book
05:57 Move 2: Speak at Events
07:21 Move 3: Academic Affiliation
08:14 Move 4: Win Awards
09:03 Move 5: Join Industry Bodies
09:57 Move 6: Get Board Positions
11:17 Move 7: Media Bylines
12:24 Move 8: Podcasting
None of this works in 30 days. But if you're moving into fractional work or self-employment, this is the difference between chasing clients and having them come find you.
Get full access to Will That Work? at www.adriantan.com.sg/subscribe28 June 2026, 4:00 am - 6 minutes 52 secondsThe Side Hustle Rule Your Boss Breaks Every Single Day
My former CEO stood in front of the whole team and said: no side hustles. Too distracting. The company needs your full commitment.
He had three board directorships, two committee seats, and multiple rental properties.
He wasn’t lying to be cruel. He was protecting what he’d built — and hoping you wouldn’t notice the gap between what he said and what he did.
I noticed too late. I went all-in on one company for a decade. $5M revenue, 30 staff, everything I had in one place. Then the partners changed, the investors pulled out, and I spent three months not knowing what to do with myself at 9 am on a Monday. Then I drove Grab.
This video is what I learned from that — and what your boss already knows that nobody taught you.
What is covered:
00:00 Side Hustle Hypocrisy
00:27 Leaders Diversify Quietly
01:41 The Loyalty Deal Died
02:18 All In Then Burnout
03:04 Uber And Identity Loss
03:21 Diversify Without Seniority
03:49 Build Assets Under Your Name
04:03 Writing Builds Reputation
04:30 Fractional Work And Niches
05:43 Commitment Versus Concentration
06:06 What Equity Are You Building
06:42 Do As They Do
Get full access to Will That Work? at www.adriantan.com.sg/subscribe16 June 2026, 7:18 am - 13 minutes 19 secondsFractional Work Explained (From My Experience): Money, Clients, Pricing & Sustainability
After my CNA article on fractional work went live, I received many LinkedIn DMs, so I’m answering the most common questions in this video.
00:00 Intro
00:37 What is Fractional Work?
01:58 Can It Work Financially?
03:14 Handling Dry Spells
05:24 Do You Need a Big Network?
05:59 Set Up a Company or Operate Individually?
06:29 How to Land Your First Client
07:35 What If a Client Wants You Full-Time?
08:11 Retirement & Exit Strategy
09:06 Which Industries Work Best?
11:51 How to Price Yourself
Get full access to Will That Work? at www.adriantan.com.sg/subscribe26 April 2026, 2:00 am - 8 minutes 59 secondsDie With Zero: Retire With Memories, Not Money
I reflect on Charlie Munger’s wish for more time and share three ideas from Bill Perkins’ Die With Zero that changed how I think about money and life.
First, you don’t retire with money—you retire with memories, and some experiences have real physical expiry dates, so postponing them can mean missing them forever.
Second, I reframe retirement planning by treating net worth peak as a date, not a number, and explain how dying with unspent money can represent thousands of hours worked for nothing, while the fear of running out is often bigger than the math.
Third, I walk through Perkins’ “time bucketing” exercise—mapping life in five-year blocks and assigning goals to realistic windows—plus my own buckets for travel, family, and work changes, to stop drifting and start choosing intentionally.
00:00 Munger’s Wish for Time
00:27 Book That Changed Me
01:05 Retire With Memories
02:06 Experiences Expire
03:19 Peak Net Worth Date
04:11 Fear of Running Out
05:09 Time Bucketing Method
06:16 My Time Buckets
07:07 Bucket List vs Buckets
07:54 Closing Takeaways
Get full access to Will That Work? at www.adriantan.com.sg/subscribe1 March 2026, 7:20 am - 8 minutes 3 secondsReflections on Content Creation, Imposter Syndrome, and Staying True to Your Voice
I'm back after a six-month hiatus to discuss the origin of his podcast, his experiences with imposter syndrome, and his journey in content creation.
I reflect on the evolution of content creation from blogging to contemporary practices involving AI, and emphasise the importance of maintaining authenticity in one's tone of voice.
Also, a shout-out to Typeless: to help you align spoken and written content, and announces plans for more monologue episodes. Stay tuned for a candid look into the world of content creation and personal growth.
00:00 Welcome Back: Where Have I Been?
00:11 The Journey of My Podcast and Book
01:16 Current Work and Future Plans
02:14 The Evolution of Content Creation
03:09 The Importance of Authenticity in Writing
06:03 Tools and Tips for Content Creation
07:20 Conclusion and Future Episodes
Get full access to Will That Work? at www.adriantan.com.sg/subscribe1 February 2026, 9:21 am - 29 minutes 58 seconds166 - Why Florence Foo QUIT Her Job & Launched FOUR Businesses!
In this revealing episode, Florence Foo shares her incredible journey of quitting her corporate job while pregnant with her second child to launching four successful businesses. From starting a boutique digital marketing agency to organising large-scale events, introducing sunscreen dispensers on demand, and exploring groundbreaking LED technology, Florence navigates the rollercoaster ride of entrepreneurship. Discover her insights on time management, overcoming challenges, and the strategies behind her diverse business ventures. Don't miss this inspiring story of ambition, resilience, and innovation!
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This episode is brought to you by Deel, the all-in-one platform simplifying global team management with payroll, HR, IT, and compliance solutions, trusted by over 35,000 businesses worldwide. Learn more at https://deel.com/adriantan.
00:00 Leaving the Corporate World
01:11 Introducing Florence
01:32 Florence's Career Journey
02:12 Starting a Digital Marketing Agency
05:00 Expanding into Event Organising
08:59 Venturing into Sunscreen Business
10:26 Exploring LED Lighting
11:51 Balancing Multiple Businesses and Family
17:34 Managing Work-Life Balance
18:22 Health Impacts of Overworking
19:44 Lessons from Nine Years in Business
20:09 Starting as a Solopreneur
21:35 Dealing with Client Challenges
25:36 Prospecting for New Business
27:28 Adapting to Digitalisation
28:08 Advice to My Younger Self
28:53 Future Plans and Contact Information
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Where to find Florence Foo:
LinkedIn: https://www.linkedin.com/in/florence-foo/
Oakwood Media: http://www.oakwood.sg
Where to find Adrian:
LinkedIn: https://www.linkedin.com/in/adriantanck/
Website: adriantan.com.sg
📕 No More Bosses: https://amzn.asia/d/abmPxU6
Get full access to Will That Work? at www.adriantan.com.sg/subscribe28 July 2025, 9:11 am - 44 minutes 59 seconds165 - Eric Tan EXPOSES The Harsh Truths About Starting Your Own Business
In this eye-opening episode, Eric Tan, a seasoned entrepreneur and chartered accountant, reveals the staggering realities and misconceptions of starting your own business. From the relentless grind and overwhelming stress to the illusion of having more control over your time, Eric shares his journey from working for Pricewaterhouse to running his own successful accounting and consulting firms.
Tune in to uncover the brutal challenges faced by new businesses, the importance of setting realistic goals, and why you should think twice before diving into entrepreneurship. Plus, get invaluable insights on the best business structures and tax considerations to ensure your startup's success. This is a must-watch for aspiring entrepreneurs!
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Eric Tan is a Singapore Chartered Accountant and Certified Management Consultant, best known as the co-founder and Managing Director of The Resource Group Pte Ltd. With a career spanning over 15 years in finance, business advisory, and human capital development, Eric has played a pivotal role in equipping small and medium enterprises (SMEs) with the expertise and resources needed for growth and regional expansion
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This episode is brought to you by Deel , the all-in-one platform simplifying global team management with payroll, HR, IT, and compliance solutions, trusted by over 35,000 businesses worldwide. Learn more at https://deel.com/adriantan.
00:00 Introduction
01:08 Meet Eric: A Multifaceted Professional
02:21 Eric's Career Journey: From Audit to Consulting
03:21 The Decision to Go Independent
04:49 Balancing Family and Entrepreneurship
06:51 The Reality of Being Your Own Boss
11:20 Navigating the Challenges of Entrepreneurship
20:24 The Changing Business Landscape
25:50 Understanding F&B Business Failures
26:12 Case Study: My Cousin's F&B Journey
27:55 Lessons from Starting a Recruitment Business
28:41 The Importance of Accurate Financial Projections
29:20 Acquiring and Retaining Consulting Clients
30:43 Networking Strategies for Business Growth
34:20 Choosing the Right Business Structure
38:12 Tax Considerations for Different Business Entities
40:19 Common Accounting Mistakes to Avoid
44:30 Final Thoughts and Contact Information
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Where to find Eric Tan:
LinkedIn: https://www.linkedin.com/in/eric-tan-15034111/
The Resource Group: https://theresourcegroup.asia/
Acce Advisory: https://acceadvisory.services/
Where to find Adrian:
LinkedIn: https://www.linkedin.com/in/adriantanck/
Website: adriantan.com.sg
📕 No More Bosses: https://amzn.asia/d/abmPxU6
Get full access to Will That Work? at www.adriantan.com.sg/subscribe6 July 2025, 12:08 am - 37 minutes 14 seconds164 - From Gang Fights to Gender Fluidity | Shawn Lim's Journey of Authenticity & Resilience
Join Shawn Lim as he opens up about his transformative journey from being arrested as a teenager to becoming a successful content creator and podcaster.
Discover why he prefers the term 'content creator' over 'influencer' and learn about his platform, Human Algorithm, which aims to promote authenticity in the age of AI.
In this eye-opening podcast, Shawn shares deeply personal stories for his neurodiverse daughter and offers insights on how to navigate life's struggles while staying true to oneself.
Don't miss this compelling conversation filled with valuable lessons on vulnerability, authenticity, and the art of being human.
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Shawn Lim is a Singapore-based media entrepreneur, journalist, and advocate for diversity, equity, and inclusion (DEI). He is best known as the founder and creator of Human Algorithm, a storytelling-led media platform and podcast that spotlights underrepresented voices at the intersection of business, technology, media, and DEI
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This episode is brought to you by Deel, the all-in-one platform simplifying global team management with payroll, HR, IT, and compliance solutions, trusted by over 35,000 businesses worldwide. Learn more at https://deel.com/adriantan.
00:00 Introduction: Content Creator vs Influencer
01:14 The Human Algorithm Platform
01:29 Podcasting Journey and Background
02:13 Transition from Corporate to Independent
04:57 Balancing Work and Family Life
16:04 Building a Personal Brand on LinkedIn
20:12 The CEO's Storytelling Journey
21:04 The Importance of Authenticity
21:49 Balancing Authenticity and Oversharing
23:52 Writing with a Target Audience in Mind
26:07 The Human Algorithm on Substack
28:16 Leveraging AI Tools for Content Creation
32:11 Creating a Content System
35:07 Masterclass and Final Thoughts
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Where to find Shawn Lim:
LinkedIn: https://www.linkedin.com/in/mediumshawn/
Human Algorithm: https://humanalgorithm.substack.com/
Where to find Adrian:
LinkedIn: https://www.linkedin.com/in/adriantanck/
Website: adriantan.com.sg
📕 No More Bosses: https://amzn.asia/d/abmPxU6
Get full access to Will That Work? at www.adriantan.com.sg/subscribe28 June 2025, 1:01 pm - 35 minutes 51 seconds163 - She SKIPPED COLLEGE to Build a Startup During the Pandemic! Amanda Cua Reveals Her Journey
In this captivating episode, Adrian and Amanda Cua discuss her unexpected decision to skip college and embark on an entrepreneurial journey during the pandemic.
Amanda shares how she utilised a gap year to create a successful newsletter company, BackScoop, in Southeast Asia.
She delves into the challenges she faced, the strategies she used to grow her subscriber base, her thoughts on the media landscape, and her experiences with impostor syndrome.
Tune in to learn about Amanda's inspiring journey and get valuable insights on building a startup from scratch.
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Amanda Cua is a Filipino entrepreneur known for founding Backscoop, a popular newsletter focused on Southeast Asian tech and business news. She started the newsletter after deciding not to pursue university, aiming to provide easily digestible information on startups in the region.
Backscoop has gained a significant following, including investors and startup founders. Cua has also hosted the podcast "One More Scoop" and has been featured on Forbes' "30 Under 30 Asia" list.
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This episode is brought to you by Deel, the all-in-one platform simplifying global team management with payroll, HR, IT, and compliance solutions, trusted by over 35,000 businesses worldwide. Learn more at https://deel.com/adriantan.
00:00 Introduction
01:39 Who is Amanda Cua
02:00 The Evolution of BackScoop
02:48 Challenges and Inspirations
03:32 Skipping College for Entrepreneurship
04:11 The Decision Between UK and US Education
05:05 First Steps into the Startup World
08:16 Building a Network from Zero
11:23 Growth Hacking Strategies
14:16 Newsletter Evolution and Team Challenges
17:00 Challenges in Content Creation
17:59 Dealing with Imposter Syndrome
22:19 Daily Routine and Health Focus
24:00 Impact of Moving to Singapore
26:37 Opportunities in New Media
33:13 Advice for Aspiring Founders
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Where to find Amanda Cua:
LinkedIn: https://www.linkedin.com/in/amanda-cua/
BackScoop: https://backscoop.com
Where to find Adrian:
LinkedIn: https://www.linkedin.com/in/adriantanck/
Website: adriantan.com.sg
📕 No More Bosses: https://amzn.asia/d/abmPxU6
Get full access to Will That Work? at www.adriantan.com.sg/subscribe22 June 2025, 10:04 am - More Episodes? Get the App