Some trips are fixed.
Some trips are flexible.
Some are mostly cash.
Some are almost entirely points.

The mistake is thinking those are different games.

They’re not.

In this special session, JGOOT Advisor Ajay breaks down two completely different trips booked back-to-back:

• A fixed-date Hawaii family trip for five
• A three-month Asia adventure starting in late February

One required specific dates and limited flexibility.
The other leaned heavily into optionality and points.

One used a mix of cash and over 90,000 points.
The other unlocked nearly $18,000 in travel for around $1,000 out of pocket.

Different constraints.
Different strategy.
Same skillset.

It’s time for:
Two Trips, Two Strategies: See What’s Possible When a JGOOTer Masters the Skillset.

Ajay will walk through how he thinks about flexibility, how he chooses when to use cash versus points, and why there’s no such thing as “a points trip” or “a cash trip” inside JGOOT.

Inside this session, you’ll learn:

• How to approach fixed-date travel without abandoning strategy
• How flexibility dramatically increases leverage
• How to decide when to deploy points and when to preserve them
• How JGOOT becomes a skill you use on every trip, not a tactic you turn on and off

This isn’t about showing off a big redemption.

It’s not about extremes.

It’s about understanding that once you master the skill, every trip becomes an opportunity.

Whether you’re planning a family vacation with fixed dates or dreaming about a long-term adventure, you’ll walk away seeing exactly what’s possible when strategy compounds over time.