Every six months I do something that most financial advisors would call insane and I am a better person for it.

My wife and I take a 4-day getaway at a hotel that’s a stretch for us to afford.

If you asked most “responsible” adults, they’d probably say it’s reckless. You’ve heard the advice a thousand times: live within your means, don’t waste money on frivolous things, put it in your 401k.

And the thing is, they’re right. I agree with them. But they’re also missing the point.

Because the value of these trips isn’t in the dollars spent. It’s in what they create.

For us, the point is twofold.

The first is connection. My wife isn’t just my partner in life… she’s my partner in business. Our days at home are a blur of meetings, deadlines, coaching calls, raising our son, and trying to keep everything running. Evenings are usually a mix of catching up on emails and making sure our son actually brushes his teeth before bed. It’s easy for the “marriage” part of our relationship to get buried under the weight of everything else.

But on these trips, all of that falls away. My mother-in-law takes care of our son, and for four days it’s just us. No school runs. No laundry. No work Slack messages lighting up at odd hours. We get to be a couple again (talking, laughing, and remembering why we chose each other long before we chose spreadsheets and staff meetings).

The second is inspiration.

Right now, as I’m writing this, I’m in a Bali-style villa with an infinity pool that spills into the horizon of a private lagoon. We’ve ordered room service that costs ten times more than if we just walked out of the hotel. And every time the bill comes, my heart skips a beat. Honestly, I’m almost certain I’ll need to fight off a minor heart attack when I check out.

But here’s the twist: that pain, that shock, is the motivation.

You see, I don’t want this level of beauty, peace, and comfort to only exist for me four days every six months. I want it to be my family’s daily reality. Not in the sense of size… I don’t care about a massive house or gold-plated door handles… but in the sense of how it makes us feel. Calm. Restored. Surrounded by beauty.

That’s the gift of these getaways. They remind me what I’m building for.

It’s easy to get caught up in the grind of work and forget why you’re doing it in the first place. You check Slack, you sit through another meeting, you wrestle with numbers in a spreadsheet, and after a while, the days blur together. It’s like running in place… exhausting, but not necessarily moving forward.

But then I sit in this villa and look out over the water, and the why comes roaring back.

I’m not working just to pay bills. I’m working to create a life where my wife and I don’t just reconnect twice a year, but every day in little ways. A life where my son grows up surrounded by peace and beauty, not stress and scarcity. A life where experiences like this don’t feel like a guilty splurge, but a normal part of how we live.

That’s what these weekends give me. Not only a stronger partnership, but a stronger tie to my yearning. They reset the hunger that gets dulled when you’re buried in the day-to-day.

And that’s the point that most financial advisors miss. They’re right about the numbers, but wrong about the fuel. Saving every dime is logical, but it doesn’t always light the fire that pushes you forward. Sometimes you need to stretch, to feel a little uncomfortable, to remind yourself why you’re hustling so hard in the first place.

Today is our last day here. Tomorrow I’ll go back to early mornings, calls, projects, and everything else. But I won’t go back the same.

Because I know six months from now, I’ll be back in another hotel, taking another stretch trip. And I hope that one will be one small level higher than this one. A slightly nicer room, a little less heartburn when the check comes.

Progress measured not just in revenue, but in experiences.

That’s my reminder. That’s my why.