Barack Obama wasn’t born into a life of privilege, but he knows how his life changed when it came to finances. He had an easy way of marking his economic change by taking a look at his Hawaiian vacations with wife Michelle Obama over the decades — they went from couch surfing to the lap of luxury.
This revelation came in a frank discussion about money with singer Bruce Springsteen on their Spotify eight-episode podcast, Renegades: Born in the USA. Barack was reflecting on an impressive Christmas present he gave Michelle last year — it was five stars all the way. “I arranged for us to have a dinner on the top deck of this hotel overlooking Waikiki. Left the girls behind. Some friends arranged this Hawaiian trio,” he shared. “It was a good setup. Watched the sun go down. I was quite pleased with myself.”
With that once-in-lifetime moment, the couple looked back to where they started in the 20 years they had been visiting Hawaii together. The first time they stayed on his grandparents’ couch — not exactly the Four Seasons hotel — but they managed to upgrade to a motel room that “was like five miles from the beach” the following year. Those milestones meant a lot in the lean years when just having the privacy of a room away from family meant a lot to them.
Things got really fancy when they “moved to a legit hotel that had a pool in the general vicinity of the beach.” For a decade they settled into the Sheraton. “You’re gettin’ there,” joked Springsteen. The well-known hotel chain is where many families are happy to stay — it’s a nice, clean room to rest your head after a day at the beach. But the Obama family thought things were getting really fancy when they were able to afford a junior suite so mom and dad could have some alone time.
But the lesson in the family’s growing wealth didn’t come from nicer hotel rooms, it actually came from the realization that it was the time spent together that mattered more. “You can track, sort of, our economic status, right, over the years through our vacations,” the former president said to Springsteen. “You can almost see every place that we had stayed, but the pleasure of it was reminding ourselves that we were just as happy in each of those places.”
Barack did admit that he’s just like all of us when he got excited by things like tiny bottles of shampoo and soft robes to wear — and yes, he did try on that robe — but it was the vacation moments that cost nothing that he still remembers. “After that initial moment, it was still the sunset that mattered and you holding hands,” he revealed. “It was still the sound of the girls laughing as they were running after each other in the sand. It was the free stuff that had nothing to do with the places you were staying at.”
Springsteen, who also has a sizable fortune from his years as a successful musician agreed with his co-host, “Those are the elements of joy.” So while it’s fantastic to have a swanky room on vacation in Hawaii — and yes, we are happy to join the Obamas on their next vacation — Barack still thinks he would be just as content in that small motel room five miles from the beach. He didn’t remember the Sheraton as much as he remembered the snapshots in his mind from his joyous family moments.
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