The Reboot Era

The Reboot Era
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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!

  1. SEP 30

    Reboot 26 | Season 1 Finale - A Letter to My Pre-Laid Off Self

    Send us a text 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 coming — the me who thought relationships were real until they went silent, the me who didn’t yet know how powerful vulnerability, consistency, and community could be. This episode is about heartbreak, rejection, ghosting, and loss. But it’s also about what came next: posting honestly on LinkedIn, landing a brand partnership with JobHire.ai, finding an incredible new role, launching this podcast, and building a community that reminds all of us that we are more than our job titles. If you only have a few minutes, start at minute 1:47. Some words are more powerful when heard than when read. 👉 Thank you for being part of Season 1 of The Reboot Era. Season 2 is coming soon. Until then: keep rebooting! 💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off in Sept. 2025 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.

    12 min
  2. Reboot 25 | LU7 - Inside DEI: The Work You Don’t See (and Why It Matters)

    SEP 29

    Reboot 25 | LU7 - Inside DEI: The Work You Don’t See (and Why It Matters)

    Send us a text 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, real experiences, open minds.What we cover: Clear, practical definitions of diversity, equity, inclusion, belongingPay equity: where bias sneaks in and why interviews ≠ impactERG reality check: why a “simple” cultural moment can take 6+ monthsComms & credibility: how missed messages send the wrong signalSelf-ID & compliance: why your profile matters (even if it feels optional)What moves the needle: top-down commitment and empowered managersLinks & mentions: Connect with Lilian Argueta on LinkedIn – Click HereWork with Lilian: Open to DEI strategy, ERG leadership, and org-wide inclusion roles. 💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off in Sept. 2025 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.

    45 min
  3. Reboot 24 | RR7 - The Future Belongs to the Unconventional: Vivian’s Story

    SEP 26

    Reboot 24 | RR7 - The Future Belongs to the Unconventional: Vivian’s Story

    Send us a text 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 unpredictableHow to build a personal brand on LinkedIn that actually drives opportunitiesThe realities of AI’s impact on creative careersWhy blue-collar entrepreneurship may be one of the most future-proof industriesHow 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 in Sept. 2025 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.

    34 min
  4. Reboot 23 | MM4 - Rebooting the Job Search with AI: A Conversation with Jobbyo’s Co-Founder

    SEP 25

    Reboot 23 | MM4 - Rebooting the Job Search with AI: A Conversation with Jobbyo’s Co-Founder

    Send us a text 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 successWhy today’s job market feels broken — and how AI can help fix itFree features Jobbyo offers, like job tracking, resume market analysis, and ghost job verificationPaid features that save serious time, including AI-powered auto apply and inbox integrationThe 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 2025If 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 in Sept. 2025 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.

    41 min
  5. Reboot 22 | RR6 - Go Lancer; The Only Workspace Freelancers Need

    SEP 24

    Reboot 22 | RR6 - Go Lancer; The Only Workspace Freelancers Need

    Send us a text 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 workspaceThe feature set: projects, tasks, timers, invoices (1-click), booking, AI nudge/forecastingEarly user feedback (copywriters/designers love the “finally breathe” simplicity)What’s next: portfolio/booking public page, more payment methods, broader country supportHow to give feedback now (DM Valentina) and via the post-beta surveyTry 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 in Sept. 2025 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.

    30 min
  6. Reboot 21 | SI4 - Why Layoffs Feel Unfair (and What to Do Next)

    SEP 17

    Reboot 21 | SI4 - Why Layoffs Feel Unfair (and What to Do Next)

    Send us a text 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 unfairThe seven grief stages applied to layoffs—and how to shorten the distance from dismissal to discoveryPractical 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 timeTry 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 JaffeWebsite: thestevejaffe.comSubstack: Steve Jaffe on SubstackInstagram: @stevejaffethelayoffjourneyLinkedIn: https://www.linkedin.com/in/jaffesteve/Contact: steve@thestevejaffe.com💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off in Sept. 2025 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.

    35 min
  7. Reboot 20 | SI3 - From Layoff to Offer: Authentic Answers that Win in 2025

    SEP 16

    Reboot 20 | SI3 - From Layoff to Offer: Authentic Answers that Win in 2025

    Send us a text 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 TRElimmerLaura 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 in Sept. 2025 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.

    49 min
  8. Reboot 19 | RR5 - A 25-Year-Old’s Reset

    SEP 8

    Reboot 19 | RR5 - A 25-Year-Old’s Reset

    Send us a text 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 upBudgeting an open-ended trip (fixed costs, subscriptions, loans)Cheap-flight routing & spontaneous detoursHostels vs. hotels, shower reality, “go-fasters” (feet) & hitchingWorkaway, odd jobs, writing, and other income ideasTikTok/YouTube Shorts strategy for raw, daily updatesSafety mindset + trusting people while trusting your gutThe emotional side: leaving family and a beloved dogLinks mentioned Riley on TikTok: https://www.tiktok.com/@unemployed.rileyRiley 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 in Sept. 2025 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.

    33 min
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About

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!

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  • Creator
    The Reboot Era
  • Years Active
    2K
  • Episodes
    27
  • Rating
    Explicit
  • Copyright
    © 2025 The Reboot Era
  • Show Website
    The Reboot Era