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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 more intentionally

Lillian Argueta opens up about:

• Navigating months of rejection in the DE&I space
• Landing a Manager of DE&I role at Adidas
• What the Adidas interview process really looked like
• Transitioning from fully remote work back into a hybrid environment
• Why in-person connection matters for people-first roles
• Balancing career growth, accessibility, and personal milestones

🔗 Links & Resources Mentioned:

• Rob Sarro’s family organization app: Famorama
• AI tools referenced: GitHub Copilot, Claude, GPT models, Lovable, Replit

Whether 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.

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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 anywhere
• How being rehired doesn’t erase trauma
• The importance of financial cushions and community
• Fighting for people from inside the system
• What it really feels like to rebuild… again

Season 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, 2026
• Entries open every Wednesday w/ new Podcast episode and close the following Monday at 11:59 PM PST
• Winners announced every Tuesday

✅ How to Enter (Required)

To enter the weekly drawing, you must complete all of the following:

1. Follow JobHire.ai on LinkedIn
2. Follow or connect with Dray Jankowski on LinkedIn
3. Send 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 TikTok
• Follow JobHire.ai on Instagram
• Follow Dray Jankowski on YouTube
• Follow Dray Jankowski on TikTok

Be 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.

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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.

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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.

What we cover:

• Clear, practical definitions of diversity, equity, inclusion, belonging
• Pay equity: where bias sneaks in and why interviews ≠ impact
• ERG reality check: why a “simple” cultural moment can take 6+ months
• Comms & credibility: how missed messages send the wrong signal
• Self-ID & compliance: why your profile matters (even if it feels optional)
• What moves the needle: top-down commitment and empowered managers

Links & mentions:

• Connect with Lilian Argueta on LinkedIn – Click Here

Work 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.

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 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

👉 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 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.

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 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: steve@thestevejaffe.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.