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The Career Advice HR Will Never Tell You: Build Skills Outside Your Job [W&S 155]

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What if you’re doing everything “right” - climbing the ladder, hitting milestones, building stability, but deep down… success still doesn’t feel secure?

We dig into a growing mid-career reality: more professionals are quietly building skills outside their job; not because HR asked them to, but because they’re trying to protect their future. Because in today’s world, even the most stable job can start feeling… temporary.

This episode’s guests:

  • Dawn - Author of Take Back Control of Your Money and host of Wise & Shine (but today, she’s in the hot seat sharing her personal journey)
  • Roy Teo - A comms & marketing professional of 18 years who made a bold pivot into real estate advisory (and hasn’t looked back since)

We unpack:

  • Why mid-career professionals are upskilling even when things seem “fine”
  • The moment “job security” starts feeling like an illusion
  • What corporate life teaches you… and what it never will
  • The uncomfortable truth about visibility, personal branding, and being seen

The mindset shift that makes skill-building possible (even when you’re exhausted)

This isn’t another “hustle harder” conversation.

It’s about optionality.
It’s about resilience.

And it’s about building the kind of skills that no one can take away from you, no matter what the economy, tech, or workplace throws next. Tune in and discover why the smartest professionals aren’t waiting until it’s too late.

What We Discuss:

  • 02:27 What skills have you been building outside your main job?
  • 11:43 What skills from your corporate job do you still find useful?
  • 15:20 What insecurities did you face while building these skills?
  • 19:19 Did you consider skills that don’t require visibility?
  • 21:58 What mindset did you need to change to build these skills?
  • 24:37 How do you manage your time while learning a new skill?
  • 31:06 How has building these skills helped shape your future?

Episode Resources:


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