Have you ever wondered what points lessons other travelers learned the hard way—so you don’t have to?
Today’s episode is a little different. I recently crowdsourced the biggest points lessons learned in 2025 from members of my community, and the responses were so good. Some were tactical, others were mindset-shifting, and more than a few had me laughing because they highlighted mistakes that are just so relatable in this hobby.
In this episode, I’m sharing the most insightful, surprising, and valuable takeaways from real travelers across the spectrum of experience—from those just starting their rewards journey to seasoned award travel veterans. I’ve organized these lessons around five main themes: be proactive and be prepared, stay curious and creative, don’t let perfect be the enemy of done, automate and plan ahead to prevent year-end stress, and high-value specific tips you need to know.
From transfer timing surprises and phantom award space to the power of flexibility and actually spending your points instead of hoarding them, these real-life lessons will help you earn more strategically, book better redemptions, and navigate award travel with less stress in 2026.
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Point Me to First Class is the show for professionals and business owners with higher-than-average personal or business expenses, who want to learn to leverage these expenses into credit card points they can spend on travel.
Each week, I share valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points, so you can expand your travel and expand your experiences.