The Reboot Era
Layoffs. Burnout. Reinvention. Welcome to the messy middle of career change — and the community that's not afraid to talk about it. Hosted by Dray Jankowski, a former tech program manager laid off in 2025, The Reboot Era is part unfiltered storytelling, part emotional support group, and part career comeback plan. Through weekly solo episodes and candid guest interviews, we explore what it really means to rebuild your life — professionally, emotionally, and financially. We’re not here to sell you hope. We’re here to tell the truth — with humor, heart, and a little chaos. Each episode dives into one of our seven pillars: • Layoffs & Unemployment • Motivation & Momentum • Strategy & Income • Redirection & Reinvention • Mental Health & Renewal • Closure & Reflection • Identity & Calling If you’ve ever screamed into a throw pillow after reading a rejection email — this is your place. 🎧 New episodes every week. 💬 Got a story of your own? Come tell it. This isn’t just my era — it’s ours!
Episodes
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 h...
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 realit...
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, Q...
In this episode of Reboot Era, James shares the emotional aftermath of being laid off, the uncomfortable silence of job applications going nowhere, and the pivot that led him to launch Wonderfish, a podcast booking agency built around one core belief: helping people share their stories is the fastest way to build trust and influence—especially in the age of AI.
We talk about what James actually did at Forbes on...
Layoffs may be framed as business decisions—but for the people impacted, they’re deeply personal.
In this episode, Dray sits down with Mark Nickerson, a leadership and management coach with 30 years of experience in the tech industry, who was laid off for the first time in his career in 2025. Mark shares what it was like to navigate that moment, how compassionate leadership made a difference, and why so m...
AI is changing everything — but not in the way most people expect.
In this episode, I sit down with Oleg Danyliuk, Founder & CEO of Duanex and Co-Founder & CTO of Insyghtful AI, to talk candidly about tech layoffs, the shrinking demand for developers, and how AI tools are reshaping both sales and software development.
Oleg shares firsthand insights from running offshore teams in Ukraine and Poland, ...
In this episode, Dray reconnects with two returning guests from season one who faced job loss, uncertainty, and career pivots head-on — and came out stronger on the other side.
Rob Sarro shares how he:
- Walked away from a role that wasn’t the right fit
- Took on a global QA leadership position
- Built a successful AI-powered family organization app part-time
- Uses modern AI tools to work faster, smarter, and mo...
Season two of The Reboot Era is officially here.
In this kickoff episode, I reflects on everything that’s happened since season one ended — landing a new job, navigating a completely new company, dealing with the emotional whiplash of another layoff announcement, and realizing that being “back to work” doesn’t mean the fear goes away.
This episode sets the tone for season two:
- Why layo...
When I started The Reboot Era five months ago, I had just been laid off and was staring down one of the hardest job markets in recent memory. What began as a way to process my own story quickly grew into something bigger — 25+ conversations about layoffs, pivots, side hustles, resilience, and rebuilding.
In this 12-minute season finale, I read a letter to the version of myself who didn’t see the layoff co...
Last guest episode of the season and it's with a thoughtful, candid conversation about DEI with Lilian Argueta—first-gen American, Human Development grad (UCSD), and DEI operator with experience at UC San Diego, UC Santa Cruz, Google, and CrowdStrike.
Context & Care: This is a sensitive subject. We’re not here to argue, but to share perspectives and invite inclusive dialogue. Two people, r...
In this episode of The Reboot Era, I reconnect with my fellow Bryant University alum Vivian to explore her unconventional career path — one defined by global adventures, freelancing experiments, and fearless reinvention.
After graduating in International Economics, Vivian skipped the corporate route to pursue a fellowship in LA, a cultural exchange in Brazil, and eventually five years of freelancing as a writer...
In this episode of The Reboot Era Podcast, host Dray Jankowski sits down with Hilary Torn, co-founder of Jobbyo, to talk about burnout, failed startups, and the messy reality of career pivots.
Hilary shares:
- Her unconventional path to becoming a co-founder (spoiler: it started on Reddit)
- How multiple failed startups prepared her for Jobbyo’s success
- Why today’s job market feels broken — and how AI ...
Guest: Valentina — Founder of Go Lancer, a centralized freelancer workspace (tasks/projects, time tracking, invoicing, booking, AI income forecasts). Started Jan 2025; now in beta.
We cover:
- Why freelancers don’t need another marketplace—they need a workspace
- The feature set: projects, tasks, timers, invoices (1-click), booking, AI nudge/forecasting
- Early user feedback (copywriters/designers love t...
Guest: Steve Jaffe — author of The Layoff Journey; 25 years in marketing/advertising; laid off four times; now helping people navigate the emotional side of job loss.
In this Reboot Era episode, we cover:
- The myth of meritocracy—why layoffs often feel arbitrary and unfair
- The seven grief stages applied to layoffs—and how to shorten the distance from dismissal to discovery
- Practical tools to counter...
This week on The Reboot Era:
HR insiders Laura Browne and Barbara Limmer show you how to stop guessing and start translating interviews—so your answers are authentic, on-target, and memorable. Perfect for anyone in a career reboot, navigating layoffs, or gearing up for a high-stakes loop.
You’ll learn:
- Why most candidates think they “nailed it” (and why interviewers disagree).
- The questi...
At 25, Riley Simmons decided the safe path wasn’t his path. After a stint in the Marine infantry and a climb into corporate finance, the promotion he’d been eyeing crystallized one truth: he didn’t want that life. So he saved, simplified, and bought a one-way ticket. In this episode we unpack the real planning behind a bold leap—monthly burn, student loans, keeping an apartment, and why South...
When Dan Sanchez — better known as Danchez — was let go from his startup role, he could’ve played it safe. Instead, he leaned into what he saw as the next big thing: artificial intelligence.
In this episode, Dan shares:
- How a career setback became the catalyst for his pivot into AI
- The progression of learning AI, from first-time ChatGPT user to building custom GPTs
- Why experimentation (not perfecti...
After being laid off twice in just a few months, Shelia Benson—better known as Flower—turned her pain into purpose. In this episode, Flower shares how her intuition helped her prepare for job loss, how she leveraged her insurance and CRM skills to launch her own freelance consulting business, and how spiritual practices like Reiki and sound healing helped her rebuild confidence and clarity.
We talk about:
...In this episode of The Reboot Era, I sit down with Nellie Hughes — a design director with 20 years in the gaming industry, most recently at Xbox Publishing. Nellie shares her journey from creating open-world experiences to navigating a layoff at one of the biggest names in tech. We cover everything from building creative teams and advocating for accessibility, to spotting layoffs before they happen, to the rea...
What would you do if you were laid off… twice… in just six months?
Patrick Lyons didn’t just bounce back — he built forward. In this episode of The Reboot Era, Patrick shares how he turned back-to-back Microsoft layoffs into an opportunity to fully invest in his passions:
- Launching and scaling multiple fitness businesses, including The Lion Shred
- Performing improv comedy to packed audience...
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