The Adrian Tan Show

Adrian Tan
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This is my podcast, where I speak with folks to explore the nuances of modern work and its idiosyncrasies. Beyond just the enablers and vendors transforming this space, I will also include intimate conversations with people navigating newfound career pivots. They have successfully transitioned to their new careers, and I hope to distil their ups and downs in this unstructured journey so the rest of us can learn from their best practices. www.adriantan.com.sg

  1. 2d ago

    Your 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/subscribe

  2. Jul 12

    I'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/subscribe

    I've Lost My Job Six Times.

  3. Jun 28

    The 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/subscribe

    The Iron Rice Bowl Was Never Yours to Hold

  4. Jun 16

    The 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/subscribe

  5. Apr 26

    Fractional 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/subscribe

    Fractional Work Explained (From My Experience): Money, Clients, Pricing & Sustainability

  6. Mar 1

    Die 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/subscribe

  7. Feb 1

    Reflections 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/subscribe

    Reflections on Content Creation, Imposter Syndrome, and Staying True to Your Voice

  8. 07/28/2025

    166 - 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! --- 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 --- 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/subscribe

    166 - Why Florence Foo QUIT Her Job & Launched FOUR Businesses!
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About

This is my podcast, where I speak with folks to explore the nuances of modern work and its idiosyncrasies. Beyond just the enablers and vendors transforming this space, I will also include intimate conversations with people navigating newfound career pivots. They have successfully transitioned to their new careers, and I hope to distil their ups and downs in this unstructured journey so the rest of us can learn from their best practices. www.adriantan.com.sg

Information

  • Creator
    Adrian Tan
  • Years Active
    2020 - 2026
  • Episodes
    180
  • Rating
    Clean
  • Copyright
    © Adrian Tan
  • Show Website
    The Adrian Tan Show