(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as  YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.

In episode 72, former lawyer-turned-creator Jen joins Ross to trace how childhood curiosity and a fearless career pivot led her from courtrooms to full-time travel storytelling. Together they unpack why continuous learning, embracing uncertainty, and treating every trip—near or far—as a chance to reset can unlock both personal fulfillment and entrepreneurial momentum.

The conversation then shifts to hands-on tactics: hacking airfare costs with flexible dates and flight-alert services, planning bucket-list detours, and empowering solo travelers through research and readiness. Alongside tips, they trade anecdotes—from $70 Japan tickets to therapy-dog training—and preview future podcast guests and a new recording setup poised to keep their global-minded community inspired.

Jen Ruiz’s Social Media:

⁠Jen’s Website⁠

⁠Jen on a Jet Plane⁠

⁠Instagram⁠

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.

Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.