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Why Are We Still Doing That?

Blog / Podcast

Our blog and podcast dive into the real stories and everyday strategies behind building a No Vacation Required life. We challenge outdated norms, share fresh perspectives, and explore what it means to find fulfillment right now—in a world that rarely makes it easy.

Why Are We Still Doing That?

No Vacation Required

It’s 2021 and we’re hanging out by the pool – well, one of the pools – at our swanky resort in Cabo.

Those who really know us know that coastal Mexico is not our scene. But the pandemic was rough, we needed a travel moment, and Mexico was, like, right there. Like so many others reentering the world, we wanted easy above all else.

Anyhow, we’re hanging out at the pool listening to the various, boisterous wedding attendees (remember the post-covid wedding rush?!) around us celebrating in and around the infinity pool. It’s the oddest combination of people. Hillsong-ers, bros, impossibly attractive women, reunited friends, a clump talking about how cool table-side guacamole is (hello 199X!).

Cabo San Lucas, Mexico. Photo Credit: No Vacation Required

The scene

Five Euphoria-high-like, soon-to-be bridesmaids returning from a morning booze-cruise excursion are clumsily snaking their way through the pool area’s lounge chairs only to end up plopping down…right in front of us.

One convincing woman is insistent that another one is dating the wrong guy, and she won’t stop until she wins this fight. The other three (um, wisely) slink off into the pool while these two have it out.

“Two jalapeño margaritas, an order of fish tacos, and a burger!” shouts the buzzed Convincer to a server who has clearly dealt with this shit before.

I zone out.

The plot

“Hey! Hey! Hey you guys! She should go for someone as great as she is, shouldn’t she?”

I’m brought back to reality. The Convincer (who must be in Sales, she’s sooooo convincing) thinks it would be smart to invoke us in making the case that her friend needs to date someone who is her equal. Her poor friend, by the way, is so out of it from that earlier party-boat excursion that she can barely navigate getting the burger into her mouth. She really does not need that margarita.

So we start asking questions like we do.

“Well, what do you mean ‘her equal?’”

Then comes lots of talk about jobs, and money, and status. You know, those typical measures of success.

Cabo San Lucas, Mexico. Photo Credit: No Vacation Required

I interrupt these proceedings to provide some context

When we started our No Vacation Required life back during/after The Great Recession, there was a part of us that felt like we practically invented the concept of deprioritizing traditional measures of success. I mean, to our credit, we were once named a “top 50 travel/lifestyle blog.”

But we weren’t pioneers. 😂

Now, friends send us “links we might be interested in” only to find current-day websites of wide-eyed people who think they invented the concept of living a self-directed, deliberate life.

How dare they.

And now we’re done with the whole, click-worthy “living like we’re dying” thing that got us all those ‘page-views’ in our early No Vacation Required life. Now we’re all about “life after living like you’re dying.”

The climax

The wind in Cabo is evil. It keeps you from realizing how fried you are getting in the sun. Pink and tender, we learned that on day 2 of this trip and we’re not falling into that trap again. Our pool time is over.

So, as we start to gather up our towels and iPads and pool stuff, we spew some Kent and Caanan Pearls of Wisdom® to the loquacious, lubricated young women in front of us.

We talk about the fact that a person is made up of stuff other than their job and their income. And that other stuff? That’s the good stuff; the stuff that matters.

We then talk about the stuff of life that’s soul-stirring – having big dreams, living those big dreams, wanting to be better, wanting to do better, thinking beyond your own self-interest, and having compassion.

I think they get it. They seem grateful – a little in awe.

And now, your wise gay uncles need to get out of the damn sun.

The lesson

We’re done living like we’re dying. We’re proof that there’s life after living like you’re dying. We’re done with the bucket list.

We’re post bucket list.

Once again, we are not pioneers, but there aren’t too many templates for the No Vacation Required we’re living.

And in this chapter of our life – just as in the last chapters – we’ll share our contrarian viewpoints with anyone who will listen. Because, although we didn’t invent this lifestyle, people still need to hear the voices of those of us urging people to look at life and success differently.

And to constantly ask: Why are we still doing that?*

Onward & Upward,

*This may or may not be the title of our forthcoming podcast. 😏


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