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In this episode, Dray sits down with Sharon Markowitz, founder of Your Career Wings and former product marketing leader at Zoom, to unpack what it really takes to navigate today’s job market.

From experiencing layoffs firsthand to coaching professionals through career transitions, Sharon shares practical strategies that cut through the noise.

You’ll learn:

• Why layoffs are often not about you and how to reframe them
• How to avoid the “spray and pray” job application trap
• A smarter, more intentional approach to job searching
• How to use AI tools like Google NotebookLM to prepare for interviews
• The right way to network (without sounding transactional)
• How to position your experience when changing industries

Sharon also shares real client examples, actionable frameworks, and free resources to help you take control of your career path.

🔗 Resources Mentioned:

• Sharon Markowitz | LinkedIn
• Career Transition Checklist (free)

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off with code DRAY30 → jobhire.ai/job-matcher/?imutm=dray (you must use that link)

👉 Follow on TikTok

👉 Subscribe on YouTube

👉 Connect on LinkedIn

👉 Buy me a coffee or leave a tip to support the show 💸

🎧 All links: https://linktr.ee/draycation

Thanks for supporting The Reboot Era — every follow, share, and tip helps me keep making content for anyone navigating layoffs, pivots, and everything in between.

Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.

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What happens when a 17-year career comes to an unexpected end?

In this episode, I sit down with Steve Fiore, who shares his journey from long-term corporate leadership into an unplanned chapter of reflection, creativity, and reinvention after being laid off.

We dive into:

• What it’s like to spend nearly two decades at one company and how it feels when it ends
• The financial and emotional realities of navigating a layoff
• Why Steve chose to “practice retirement” and what that actually looks like
• The creation of his lifestyle blog Rooted & Refined Living, inspired by a trip to Hawaii and a deeper appreciation for sensory experiences
• The realities of monetizing a passion project (spoiler: it’s not overnight success)
• How storytelling, food, and craftsmanship intersect in meaningful ways
• The power of alumni networks and organic connections
• Lessons from teaching, mentoring, and delivering a TEDx talk on productivity
• Why slowing down might actually be the key to moving forward

This is a conversation about perspective, about finding value beyond your job title and learning to reconnect with the things that make life rich.

🔗 Connect with Steve on LinkedIn
🔗 Check out his blog Rooted & Refined Living

If you’ve ever faced a layoff, questioned your path, or thought about starting something of your own, this episode is for you.

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off with code DRAY30 → jobhire.ai/job-matcher/?imutm=dray (you must use that link)

👉 Follow on TikTok

👉 Subscribe on YouTube

👉 Connect on LinkedIn

👉 Buy me a coffee or leave a tip to support the show 💸

🎧 All links: https://linktr.ee/draycation

Thanks for supporting The Reboot Era — every follow, share, and tip helps me keep making content for anyone navigating layoffs, pivots, and everything in between.

Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.

Send us Fan Mail

In July 2025, 9,000 employees were laid off in a single day.

Quentin Cobb was one of them.

After 17 years in the gaming industry — working across studios owned by Sony, Bethesda, and Microsoft — Quentin suddenly found himself asking the same question thousands of professionals face:

“What now?”

Instead of returning to another AAA studio, he decided to build something of his own.

In this episode, Quentin shares the raw, emotional, and practical realities of:

• Navigating your first layoff
• Detaching identity from job titles
• Competing in a brutal remote job market
• Starting a company with friends
• Hard creative conversations
• Founder burnout (and the December breaking point)
• The importance of support systems
• Why networking is about relationships — not requests
• And how to prepare for layoffs before they happen

This isn’t a highlight reel startup story.

It’s honest. It’s emotional. And it’s deeply human.

If you’ve ever been laid off, feared a layoff, or wondered whether you could build something on your own — this episode is for you.

Connect with Quentin on LinkedIn:
👉 https://www.linkedin.com/in/quentin-cobb/

💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off with code DRAY30 → jobhire.ai/job-matcher/?imutm=dray (you must use that link)

👉 Follow on TikTok

👉 Subscribe on YouTube

👉 Connect on LinkedIn

👉 Buy me a coffee or leave a tip to support the show 💸

🎧 All links: https://linktr.ee/draycation

Thanks for supporting The Reboot Era — every follow, share, and tip helps me keep making content for anyone navigating layoffs, pivots, and everything in between.

Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.