Chasing Waves: A Careers Podcast for Career Reinvention and Leaving Corporate

Retrenchment from a big tech job can take your career identity with it. Tomi Grainger rebuilt his as a portfolio career after TikTok.

👉 FREE LIVE OCTOBER WORKSHOP: Navigating a career transition? Join "Who Are You Now?" to map out your next move https://chasingwaves.co/workshop/

When someone asks what you do, they almost never ask what you value. So when the job that answered that question disappears, it can feel like you disappeared with it. Tomi joined TikTok Australia as one of its first ten employees and spent four years as "Tomi from TikTok." After the redundancy, the hardest part wasn't the job search. It was working out who he was without the name badge.

Today he is Group Strategy and Influencer Director at WPP Media and runs his own speaking and coaching business alongside it. This conversation is about how he got there, and why he stopped measuring success in KPIs.

We cover:

- What to do in the first days after a redundancy, before you apply for anything

- How to find your values when the big brand name is gone, starting with what freedom actually means to you

- Why a portfolio career lets you test a new path while keeping a steady income

- How Tomi landed a client at a dinner party, and the networking reframe that takes the awkwardness out of asking

If you are in the messy middle after a layoff, you are not starting from zero. Everything you built comes with you. Take a breath, then go chase your next wave.

👉 Take Tomi's Future Proof quiz: https://www.tomigrainger.com/futureproof.html

Connect with me:

- LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/

- Instagram: https://www.instagram.com/chasingwaveswithjo/

- YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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Retrenchment from a big tech job can open the door to a second career you never considered. Alaina Appleman found hers in luxury travel.

👉 FREE LIVE OCTOBER WORKSHOP: Navigating a career transition? Join "Who Are You Now?" to map out your next move https://chasingwaves.co/workshop/

Alaina and I worked together at Meta. After the 2023 layoffs she spent months chasing roles in tech, hospitality and startups all at once, until a single introduction pointed her toward a path she had never pictured for herself. Today she's an award winning luxury travel designer at Blue Sky Escapes, a Singapore based host agency, planning everything from a quick hotel stay in Siem Reap to a 35 day journey through South America.

We cover:

- Why running every career option at once can leave you with zero direction

- How to trial a new career before telling LinkedIn

- The launch mistake that brought in 100 requests before her first booking

- Why trusted people on the ground matter more than an AI itinerary

If you're facing retrenchment or wondering whether leaving corporate could lead somewhere better, Alaina shows what one quiet experiment can turn into.

Connect with me:

- LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/

- Instagram: https://www.instagram.com/chasingwaveswithjo/

- YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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A career change after 40 almost never starts with certainty. Yvonne Lam put it simply when we spoke: I quit my corporate job, and I figured the rest out on the way. She left banking in Hong Kong and is now an interior designer.

Yvonne took an introduction to design course during maternity leave, then a full year diploma with five real client projects, then an internship where she was the oldest person in the room taking direction from designers half her age.

In this episode, you'll hear Yvonne's story and learnings:

• How to test a hobby before you bet a career on it, in the exact order Yvonne did it
• Which JPMorgan skills transferred straight into design work, and why she says you are already halfway there
• How she handled the friends and family who questioned her decision, and why some of them ended up questioning their own
• The one technology gap she used to out execute designers with far more experience

If you are somewhere in the middle of a career change after 40, or you have been quietly drafting the email that starts with I quit my corporate job, this one is for you.

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/
• Instagram: https://www.instagram.com/chasingwaveswithjo/
• YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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Leaving corporate rarely looks like one clean leap. Nic Law changed careers from corporate lawyer to master gin distiller, and the part nobody sees is the two years in between with no salary and his savings draining.

This is a Spotlight episode, where I go deep on one bold career change and the thinking behind it. Nic quit his law job in Hong Kong out of the blue after seven years, with no plan and no idea what came next. What he did next is the useful part: he took a distilling diploma, talked his way into an internship in Scotland in his thirties, and called every government department in the city until he found the one that could grant a license nobody believed still existed. Today he is co founder and master distiller at N.I.P., one of Hong Kong's first gin distilleries, named as the opposite of VIP. https://www.nipdistilling.com

In this episode, you'll learn:

How to tell a calculated risk from a reckless one when you are the one taking it

Why he tested the idea in small steps before committing a single dollar

What actually transfers from the career you are leaving, and why his legal training was the reason the business exists at all

How he kept moving when every answer he got was vague

We also get into runway, which is where most of these decisions actually get made. Three months, six months, a year. How long you need before you jump, when a bridge role is the smarter move, and why a long runway is not always the safe one.

If you are stuck in your career and waiting to feel certain before leaving corporate, Nic's story is the one to sit with.

Connect with me:

LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/

Instagram: https://www.instagram.com/chasingwaveswithjo/

YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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Every career pivot starts before you have proof it will work. Tim Wong was told bands don't work in Hong Kong, then played to seven people.

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Tim is the lead singer of Dear Jane, one of Hong Kong's biggest rock bands. Before that he was on a TVB contract that his father's connections helped arrange, and when he told a supervisor he wanted to leave to do music, the answer was that bands don't work here.

What happened next is the part nobody puts in the highlight reel. A first show after signing to Warner that drew seven people. Roughly eighteen months dormant between labels. A founding member walking away. Falling over on stage twice in the middle of a guitar solo.

I wanted this conversation on the show because the mechanics are identical whether you are leaving a stage or leaving a corporate job. You are making a career decision without certainty, in front of people who have opinions about it, with no way to know if the thing you are betting on will land.

The line from Tim that I keep coming back to: "if you think you have one hundred percent certainty, you do not know enough yet.

We also get into what it feels like when the room finally sings your song back, and why he taught himself to become a director.

⏱️ CHAPTERS

00:00 Told bands don't work in Hong Kong

01:17 Welcome to the studio and how Tim and I met

02:34 An accidental start in acting at TVB

05:03 Starting Dear Jane and the pushback that followed

07:05 Back to indie roots and finding a singing voice

09:36 Falling over on stage twice, mid solo

13:28 Playing to an audience of seven

19:42 Losing a founding member and rebuilding the sound

25:23 How to take the leap without a guarantee

30:56 The night the whole room sang it back

33:50 The cover that exploded on YouTube and brought the audience back

39:24 Why waiting for one hundred percent certainty keeps you stuck

41:17 Learning to direct and being a beginner again

45:39 What to do if you are standing at a crossroads right now

47:31 Fan questions and where Dear Jane is touring next

Onwards: Bonus content, Show & Tell and scenes that didn't make it into the full episode.

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A short message before Thursday, on why career change takes longer than the internet says and why you don’t have to figure it out alone.

👇 LAUNCHING SOON: THE CAREER CHANGE ACCELERATOR 👇

I’m putting together a small career change accelerator for people who are ready to stop overthinking their next move and start taking action.

It will be a small group, max. of 10 people, with live online sessions, practical frameworks, accountability, and, perhaps most importantly, other people who are in the messy middle of figuring out what’s next.

I’ll be sharing the first details soon. Join our email list for the latest updates! https://chasingwaves.co/list/

My conversation with Tim Wong of Dear Jane drops Thursday, Aug 27.

Tim talks openly about the years when the band had no traction and no proof it was ever going to work. That’s the part social media leaves out. And it’s often the part that matters most when you’re in the middle of a career change, quietly wondering why it’s taking you so long.

In this short message:

• Why the “I did it in two months” story can make you question your own progress

• What Tim’s slow years actually looked like

• Why taking action while you’re still uncertain matters

• Why you shouldn’t have to navigate a career change alone

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/

• Instagram: https://www.instagram.com/chasingwaveswithjo/

• YouTube: https://www.youtube.com/@Chasingwaveswithjo

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Thinking about a career change but unsure where to start? If you are changing careers, looking for career clarity, or wondering how to make hard decisions about leaving corporate, this episode will show you why you do not need to have everything figured out before you start.

After more than 15 years leading commercial teams at AstraZeneca and Johnson & Johnson, Angela made the leap from corporate into entrepreneurship. Today, she is the co-founder of Bentou, a science-backed oral care probiotic brand for pets. Her journey was not driven by a single life-changing moment, but by years of reflection, small experiments, and the willingness to keep taking the next step.

In this episode, Angela shares why she always knew she wanted a second career beyond corporate, how becoming a parent influenced her career decision, and the practical steps she took before making the transition. From building a side project during evenings and weekends to evaluating her financial runway and expanding her network, she offers a realistic blueprint for anyone considering career reinvention.

If you are feeling stuck, overwhelmed, or waiting for the "right time," this conversation is a reminder that clarity often comes through action, not certainty.

In this episode, you'll learn:

• Why you do not need a perfect plan before making a career transformation
• How small experiments can help validate your next career move
• The role financial planning plays before leaving corporate
• How networking creates unexpected career opportunities
• Why taking consistent micro steps builds confidence over time
• How to overcome overthinking and self doubt when making a big career decision
• What high performers can bring from corporate into entrepreneurship

Whether you are exploring a midlife career change, planning your next career pivot, or simply trying to find a career you love, Angela's honest insights will encourage you to stop waiting for certainty and start moving forward one step at a time.

If this episode resonated with you, share it with someone navigating a career transition and subscribe to Chasing Waves for more practical conversations on building a fulfilling career with confidence.

Loved this episode? You can buy me a coffee ☕️ It’s a small way to show your support and means more than you know.

buymeacoffee.com/chasingwaves

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/
• Instagram: https://www.instagram.com/chasingwaveswithjo/

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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Imposter syndrome does not disappear after leaving corporate. It just changes shape. You can be experienced and still be completely new, and that mix is where career reinvention hits hardest.

I spent years as an exec at Meta and Spotify. Then I left it all to start over, and last week I caught myself at midnight, ninety minutes into one thumbnail, wondering why I had walked away from a fancy title to feel this clueless.

In this quick episode, we'll cover:

• Why chasing validation is the trap that makes most people quit right before it would have paid off
• How to catch yourself scoring your own progress against other people's applause
• The one weekly practice I use to measure mastery instead of recognition
• Why a real transition takes six to eighteen months, not the few weeks we secretly expect

I am still in this one with you. I have not beaten the validation trap either. I just know what to do when it shows up.

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/
• Instagram: https://www.instagram.com/chasingwaveswithjo/ 
• YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us!

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Leaving corporate isn't about a perfect exit plan. It comes down to three honest questions: how much runway you actually have, what you won't trade away, and one piece of real proof that your idea can work.

In 5 minutes, you'll learn:

• How to think about your real runway, and why the number matters less than what it tells you about your options right now
• How to identify your own non negotiables
• And the importance of testing and experimenting to find proof for your next move

This isn't about quitting your job this week. It's about running the number, naming your trade off, and finding one piece of real world proof, so you can start moving without blowing up your life.

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/
• Instagram: https://www.instagram.com/chasingwaveswithjo/
• YouTube: https://www.youtube.com/@Chasingwaveswithjo

Enjoyed the show? Hit "Follow" and leave a review to help others find us.

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Feeling stuck in your career is not the same as knowing what you want instead. What do you do when your career no longer feels right, but you have absolutely no clue what you want instead?

When you’re feeling stuck, it’s easy to think you need a massive 10-year plan or a sudden "lightning bolt" of inspiration before you’re allowed to make a change. But clarity doesn't come from sitting at your desk overthinking it—it comes from gathering real-world information.

In this episode, I share how I left a 20-year corporate career at companies like Spotify and Meta without a perfect roadmap, and the exact step-by-step process I used to find my way next. We’re breaking down how to stop chasing fancy job titles and instead figure out what kind of ordinary working life you actually want.

Plus, we tackle a major trap that trips almost everyone up: learning how to untangle whether you want to quit a new path because you genuinely dislike it, or if you’re just facing the uncomfortable "tax" of being a beginner.

What we dive into:

• The Passion Myth: Why waiting for an "aha!" moment keeps you stuck, and what to do instead.
• The Ordinary Tuesday Test: How to design a career around the daily life you want to live two years from now.
• Fear vs. Dislike: A simple trick to tell if you’re resisting something out of fear or true misalignment (featuring my own messy video-editing rabbit hole).
• Your Experiment This Week: A low-stakes, real-world action step you can take today to get your first piece of honest evidence.

📺 WATCH THIS EPISODE ON YOUTUBE Prefer to see the faces behind the mic? We are officially on camera! You can watch the full video version of this episode, complete with visuals and behind-the-scenes moments, on our YouTube channel. Click here to watch and subscribe: https://youtu.be/BvwyHARf4tA

Loved this episode? You can buy me a coffee ☕️ It’s a small way to show your support and means more than you know.

buymeacoffee.com/chasingwaves **

Connect with me:

• LinkedIn: https://www.linkedin.com/in/joannawong-chasingwaves/
• Instagram: https://www.instagram.com/chasingwaveswithjo/

Enjoyed the show? Hit "follow" and leave a review to help others find us!

Hosted on Acast. See acast.com/privacy for more information.