208 | Travel During Your "Go-Go" Years: Success Story with Bret Crawford
Tue Feb 03 2026
Are you waiting to travel "someday" when you have more time or money? Portland realtor Bret Crawford shares how he went from barely earning enough Southwest points to flying free multiple times a year – and why the book Die with Zero convinced him to stop waiting. In his 60s, Bret's embracing the "go-go years," traveling as much as he can before he gets to the "slow-go" and then "no-go" years. Whether you're in your go-go years or approaching your no-go years, this episode is your reminder that tomorrow isn't guaranteed. Start using those points and making those memories NOW.
In this episode, Bret shares:
Booking 10-13 free trips annually (New Orleans, Los Cabos, Palm Springs, Hawaii and more!)Leveraging Hyatt points for stays in prime locationsPlanning a dream family Hawaii trip for his adult kids – paying for everyone's flights with pointsHis strategy for booking multiple options, then choosing what works best for his wife's teacher scheduleAbout Families Fly Free: Ready to stop waiting and start traveling? Families Fly Free teaches families a simple system to fly for free using travel rewards. Join our community at FamiliesFlyFree.com.
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Are you waiting to travel "someday" when you have more time or money? Portland realtor Bret Crawford shares how he went from barely earning enough Southwest points to flying free multiple times a year – and why the book Die with Zero convinced him to stop waiting. In his 60s, Bret's embracing the "go-go years," traveling as much as he can before he gets to the "slow-go" and then "no-go" years. Whether you're in your go-go years or approaching your no-go years, this episode is your reminder that tomorrow isn't guaranteed. Start using those points and making those memories NOW. In this episode, Bret shares: Booking 10-13 free trips annually (New Orleans, Los Cabos, Palm Springs, Hawaii and more!)Leveraging Hyatt points for stays in prime locationsPlanning a dream family Hawaii trip for his adult kids – paying for everyone's flights with pointsHis strategy for booking multiple options, then choosing what works best for his wife's teacher scheduleAbout Families Fly Free: Ready to stop waiting and start traveling? Families Fly Free teaches families a simple system to fly for free using travel rewards. Join our community at FamiliesFlyFree.com.