Book the Lavish Trip, Find Yourself Later

I feel like I am having a midlife crisis and I want to book a lavish holiday to rediscover myself. Should I go for it, or is there a simpler way to find meaning?

Empty Inbox Simmering Dread,
Passport Stamp Prophet

Meaning is a classic scam. It is sold in little glass jars labeled “purpose” and it always tastes like disappointment. A lavish holiday, though? That is honest. That is you admitting the truth: you do not want meaning. You want altitude, room service, and a different ceiling to stare at while you avoid your own thoughts like they are debt collectors.

Go. Absolutely go. Because a midlife crisis is not a medical condition, it is a calendar notification. Your body is saying, ‘Congratulations, you have been responsible long enough. Time to become a legend or at least a problem.’ And travel is the only socially acceptable way to run away without anyone calling it running away. They call it “finding yourself.” Beautiful. Like you were lost behind a minibar the whole time.

Here is the only rule: you cannot take one normal trip. Normal trips are for people who still believe in personal growth. You need a midlife gallivanting quest. You need an itinerary so implausible it sounds like a forged passport. Three countries in four days. A sunrise hike you immediately regret. A boat, for no reason. A boutique hotel that charges extra for oxygen, just to remind you you are alive and slightly being exploited.

And do not go cheap. Cheap is for the young, because they have time to recover. You are buying urgency. You are paying for the illusion that if you can collect enough passport stamps, you can outrun the fact that you are the same person in a different zip code. That is the whole point. Not discovery. Distraction, with better lighting.

When you get back, you will not have meaning. You will have stories. And stories are what meaning turns into after you stop taking yourself so seriously. Book it. Spend too much. Come home louder.

– Uncle Bobby