1. Starting Notes
2. Points Vs. Miles (And Their Value)
3. Envisioning a Goal
4. Checking Your Credit
5. Choosing an Airline
6. How to Pick a Card (Or Two)
7. Real Life Examples
8. Score!
9. How to Keep It Going
10. Keeping Track of It All
11. Wonderful Side Effects
12. Final Words
13. Resources

Award booking with Skymiles. 85,000 miles to visit Barcelona, Amsterdam, and Madrid. Early 2013 New York departure.
Award booking with Skymiles. 85,000 miles to visit Barcelona, Amsterdam, and Madrid. Early 2013 New York departure.

So you’ve selected a card or two, saved up your points and miles, ran your spending through your new card(s), and are looking at your ideal reward flight. Congratulations!

Let me tell you what a great feeling it is to press the final button that secures you a ticket and generates your itinerary. After it’s all gone through and the trip is booked, you look at the screen in disbelief. Is it really so easy? It is! Why don’t more people do it? Various reasons: perhaps they’re not interested in travel or would rather earn cash back than airline miles. Maybe they don’t trust themselves to responsibly use credit. Or maybe they’d rather pay full price for all their trips instead of get them for free to earn status on a particular airline.

The real reason is that most people don’t want more to remember, more accounts to keep track of, more numbers to think about. In the next section, I’ll outline how to automate your earnings. It’ll take 30 minutes max to set up and you won’t have to think about it ever again – until you’re ready to redeem your free travel, of course.

But for now, immerse yourself in the feeling of reaching your goal. You haven’t yet? Envision it instead. Plan your flights, think about where you’ll stay, what you want to do, or just bask in the knowledge that it will soon be real. Scoring a free flight is awesome, if it’s your first time or your hundredth.

What’s so great about scoring a free flight is that you have the opportunity to fly on a multitude of airlines thanks to the alliances and their partners. You can connect in a number of airports, or fly direct if you’ve chosen a nonstop flight. You’ll encounter different kinds of aircraft, new cultures, all types of people, food, and experiences. It all forces you to evaluate yourself and your preferences, which makes you more savvy, well versed and cultural, and of course more well-traveled.

By seeking out things that you enjoy and that you’re passionate about, you won’t notice or mind the little time it takes to set it all up. In fact, you may be anxious about beginning your journey. The point is that this hobby is worth its rewards. You get more than a free trip. You’ve found a way to live a fuller, richer life that will give you memories that you’ll get to keep with you forever. That’s ultimately why I spend so much time figuring out new ways to accumulate and redeem points and miles. For airlines, getting me to a destination is business as usual, but for me it’s special to plan a new trip every single time.

Next up: How to Keep It Going

Announcing Points Hub—points, miles, and travel rewards community. Join for just $9/month or $99/year.

BEST Current Credit Card Deals

  • Capital One Venture X Rewards—Earn 75,000 Venture miles once you spend $4,000 on purchases within the first 3 months from account opening, plus a $300 annual statement credit for travel booked through Capital One
  • Ink Business Preferred® Credit Card—Earn 100,000 Chase Ultimate Rewards points after you spend $15,000 on purchases in the first 3 months and 3X bonus points per $1 on the first $150,000 spent on travel and select business categories each account anniversary year
  • Amex Blue Business Plus—Earn 15,00 Membership Rewards points once you spend after you spend $3,000 in purchases in the first 3 months of Card Membership and 2X bonus points on up to $50,000 in spending per year with NO annual fee

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