The Reboot Era

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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. She shares how she built a career on her own terms, the highs and lows of freelancing, and why AI ultimately pushed her to pivot again — this time into business development in New York’s electrical industry.

We discuss:

• Why freelancing can be both freeing and unpredictable
• How to build a personal brand on LinkedIn that actually drives opportunities
• The realities of AI’s impact on creative careers
• Why blue-collar entrepreneurship may be one of the most future-proof industries
• How to recognize — and act on — the right career pivot

📍 Connect with Vivian on LinkedIn: Click here

If you’re rethinking your career path or curious about freelancing, entrepreneurship, and AI’s role in shaping the future of work — this is an episode you don’t want to miss.

💼 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

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👉 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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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 can help fix it
• Free features Jobbyo offers, like job tracking, resume market analysis, and ghost job verification
• Paid features that save serious time, including AI-powered auto apply and inbox integration
• The importance of building community during the job search

🌐 Links & Resources Mentioned:

• Jobbyo Website: https://jobbyo.ai/
  
  
• Join the free Slack community: Click here
  
  
• Learn about the Jobbyo Scholarship Program: Click here
  
  
• Connect with Hilary Torn on LinkedIn
  
  
• 🎁 Use code REBOOT at checkout for 15% off paid plans until December 23rd 2025

If you’ve been laid off, are burned out from the search, or just want smarter tools to land your next role — 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.

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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 the “finally breathe” simplicity)
• What’s next: portfolio/booking public page, more payment methods, broader country support
• How to give feedback now (DM Valentina) and via the post-beta survey

Try it: Join the Go Lancer beta at golancer.io and follow Go Lancer on LinkedIn. Connect with Valentina to share feature ideas.

Perks: If you help them as a beta tester to improve the app, you’ll get a free month and two months 20% discount as a reward!

Note: Go Lancer is not a marketplace (yet); it’s the back office for freelancers who already land clients via email, LinkedIn, IG, etc.

Links:

• Valentina's LinkedIn - https://www.linkedin.com/in/valentina-cvackova-53065167/
• Golancer.io

💼 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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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 isolation, shame, and rumination (community, journaling, movement)
• Why your skills and wins still belong to you (Ship of Theseus analogy)
• Rebuilding identity beyond your job title—and why that makes you more resilient next time

Try this (from Steve’s framework):

• The 15-minute daily reset: 5 min journaling → 5 min movement → 5 min outreach (one text/DM to a real human).
• Replace “derailed” with “detour” in your language for one week; note what changes.

Links & mentions:

• Book: The Layoff Journey (available on Amazon; ask your local bookstore to order)
• Steve Jaffe
  • Website: thestevejaffe.com
  • Substack: Steve Jaffe on Substack
  • Instagram: @stevejaffethelayoffjourney
  • LinkedIn: https://www.linkedin.com/in/jaffesteve/
• Contact: [email protected]

💼 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

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 question behind the question—how to tailor without memorized scripts.
• The STAR method the Reboot Era way (convert vague prompts into real wins).
• Deconstructing job descriptions fast—especially for next-day interviews.
• The 15-minute post-interview self-eval to improve without spiraling.
• Layoff storytelling: the negative-sandwich answer that shows momentum.
• Conversations > applications: building the network that builds offers.
• Extrovert and introvert paths to “positive and prepared.”
• The Amazon “folders” prep story—and how to adapt it for your next loop.

Links & mentions:

• Book: Interview Speak (Publisher: Manning) — 45% off with code TRElimmer
• Laura Browne LinkedIn - https://www.linkedin.com/in/laurabrowne/
• Barbara Limmer LinkedIn - https://www.linkedin.com/in/barbaralimmer/
• Laura’s site: CareerCoffeeBreak.com

💼 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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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 Southeast Asia is his “in case funds dip” landing zone. We map the early route (Frankfurt → Berlin → Casablanca/Taghazout → Florence), talk surfing world-class Anchor Point, hostel living, Workaway gigs, staying safe in unfamiliar cities, and growing from zero social presence to daily updates. Also starring: Iris, the border collie he hopes to eventually reunite with abroad.

What we cover

• Why a near-promotion pushed him out, not up
• Budgeting an open-ended trip (fixed costs, subscriptions, loans)
• Cheap-flight routing & spontaneous detours
• Hostels vs. hotels, shower reality, “go-fasters” (feet) & hitching
• Workaway, odd jobs, writing, and other income ideas
• TikTok/YouTube Shorts strategy for raw, daily updates
• Safety mindset + trusting people while trusting your gut
• The emotional side: leaving family and a beloved dog

Links mentioned

• Riley on TikTok: https://www.tiktok.com/@unemployed.riley
• Riley on LinkedIn: https://www.linkedin.com/in/riley-simmons/
• Riley on Instagram: https://www.instagram.com/simmy613/
• Workaway (volunteer & cultural exchange app): https://www.workaway.info/

Call for connections
If you’re in Germany, Morocco, Italy, Greece, Turkey, Poland, Romania, Lebanon—or on a great surf break anywhere—DM Riley. Local tips, hikes, cheap eats, and spare couches welcome.

💼 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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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 perfection) is the key to getting started
• The AI tools he actually uses daily — including ChatGPT, Suno, HighLevel, and more
• Where to find reliable updates on the fast-changing AI landscape

Whether you’re brand-new to AI or looking for ways to level up, this episode will leave you with practical steps and fresh inspiration.

🔗 Connect with Dan on LinkedIn: Dan Sanchez

🎧 Check out his podcast: The AI Driven Marketer

💼 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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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:

• Preparing for layoffs before she happen
• Turning corporate skills into entrepreneurial income streams
• Navigating Upwork as a freelancer—the highs and the scams
• The mental and spiritual toll of layoffs (and how to heal)
• Building purpose-driven work and multiple streams of income
• Why your 9-to-5 is actually the blueprint for your business

📚 Mentioned in the episode:

• Anatomy of the Spirit by Caroline Myss – on Amazon, click here
• Connect with Shelia (Flower) on LinkedIn: https://www.linkedin.com/in/sheliabenson/

This conversation is a reminder that even in the hardest transitions, you can reinvent yourself and find a new path that’s aligned with your passion and purpose.

💼 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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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 reality of ageism in tech. Nellie also shares how networking — done with kindness and curiosity — has fueled her career, and why she’s optimistic about what’s next. If you’re in gaming, tech, or just navigating a career pivot, this one’s packed with real talk and takeaways.

Links Mentioned:

• Connect with Nellie on LinkedIn

💼 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

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 audiences
• Creating daily content for over 2,000 days straight
• Preparing for a natural bodybuilding competition this year

We dig into:

• How to build a layoff-proof life with multiple income streams
• Structuring your days to fit in career, fitness, creativity, and community
• Why your job title should never define you
• The mindset shift that turns setbacks into launchpads

🎧 Listen now and learn how to reclaim your time, energy, and purpose after a career shake-up.

Connect with Patrick Lyons:

• LinkedIn: https://www.linkedin.com/in/patrick-a-lyons/
• TikTok: https://www.tiktok.com/@patrick_lyons
• Instagram: https://www.instagram.com/patricklyons/
• The Lion Shred: https://lyon.training/

💼 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.