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. 4D AGO

    Laid Off After 30 Years: What Corporate Leadership Still Gets Wrong

    Send us a text 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 many companies fail to handle layoffs with transparency and humanity. Together, they unpack: What companies get wrong (and occasionally right) about layoffsWhy transparency is rare—and how it can also be used to hide bad decisionsThe hidden burden placed on middle managers during reductions in forceWhy performance alone shouldn’t determine who stays and who goesHow poor leadership training fuels toxic work environmentsWhy Mark chose to start his own coaching practice instead of returning to corporate lifeMark also introduces Leading With Meaning, his leadership coaching practice focused on helping managers lead more humanely—and shares why he’s making foundational leadership tools available for free to anyone who needs them. This episode is especially relevant for: People impacted by layoffsManagers navigating uncertainty or changeAspiring leaders who want to do things differentlyAnyone questioning the current state of corporate leadership🔗 Resources Mentioned: Leading With Meaning (Free Leadership Tools Library): https://leadingwithmeaning.com/ Connect with Mark 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.

    47 min

  2. JAN 28

    How AI Is Changing Sales, Hiring, and Tech Careers

    Send us a text 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, building AI-powered products, and transitioning from a deeply technical role into sales leadership — a move that ultimately inspired the creation of Insightful AI. In this episode, we cover: Why tech layoffs feel different in the AI eraHow AI is reducing the need for large development teamsThe shift from “just coding” to proactive, business-focused engineeringReal-time AI sales coaching during live Zoom callsHow Insightful AI helps sales reps handle objections instantlyCareer advice for developers navigating uncertaintyWhy networking and relationships matter more than everWhether you’re a developer worried about your future, a founder adapting to AI, or a sales leader looking for an edge — this conversation offers real, grounded perspective from someone building in the middle of the shift. 🔗 Connect with Oleg on LinkedIn 🔗 Learn more about Insyghtful AI (sales coaching with real-time AI prompts) 💼 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.

    25 min

  3. JAN 21

    Career Comebacks: Building, Belonging, and Better Fits

    Send us a text 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 fitTook on a global QA leadership positionBuilt a successful AI-powered family organization app part-timeUses modern AI tools to work faster, smarter, and more intentionallyLillian Argueta opens up about: Navigating months of rejection in the DE&I spaceLanding a Manager of DE&I role at AdidasWhat the Adidas interview process really looked likeTransitioning from fully remote work back into a hybrid environmentWhy in-person connection matters for people-first rolesBalancing career growth, accessibility, and personal milestones🔗 Links & Resources Mentioned: Rob Sarro’s family organization app: FamoramaAI tools referenced: GitHub Copilot, Claude, GPT models, Lovable, ReplitWhether you’re rebuilding after a layoff, thinking about starting something of your own, or searching for a role that actually aligns with your values — this episode offers honest insight, encouragement, and proof that forward momentum is still possible. 💼 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.

    35 min

  4. JAN 14

    The Return of The Reboot Era

    Send us a text 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 layoffs aren’t going anywhereHow being rehired doesn’t erase traumaThe importance of financial cushions and communityFighting for people from inside the systemWhat it really feels like to rebuild… againSeason two will feature returning guests from season one, new voices, and unfiltered conversations about work, leadership, hiring, firing, and everything in between. 🎁 JobHire.ai Giveaway – Official Details 50 free one-month JobHire.ai trials over the course of five weeks (10 PER WEEK). 🗓️ Giveaway Timeline Start: January 14, 2026 End: February 17, 2026Entries open every Wednesday w/ new Podcast episode and close the following Monday at 11:59 PM PSTWinners announced every Tuesday✅ How to Enter (Required) To enter the weekly drawing, you must complete all of the following: Follow JobHire.ai on LinkedInFollow or connect with Dray Jankowski on LinkedInSend Dray a LinkedIn message stating you are entering the giveaway and include:The usernames/handles of any social platforms you followed (for entry tracking)⭐ Bonus Entries (Optional) You can earn additional entries by following more accounts. Each additional follow = one extra entry. Follow JobHire.ai on TikTokFollow JobHire.ai on InstagramFollow Dray Jankowski on YouTubeFollow Dray Jankowski on TikTokBe sure to include the usernames for these follows in your LinkedIn message to receive credit! 50 winners total. One free JobHire.ai month per person. One-time use. Va 💼 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.

    23 min

  5. 09/30/2025

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

    09/29/2025

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

    09/26/2025

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

    09/25/2025

    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 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
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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!

Information

  • Creator
    The Reboot Era
  • Years Active
    2025 - 2026
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © 2026 The Reboot Era
  • Show Website
    The Reboot Era