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 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 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.