Let me tell you: a silent auction hates to see Selenid and me coming.

We learned this the last year.

Every winter, the local ski mountain where we spend most of our weekends with the kids, Holiday Valley, hosts an event called the Penguin Paddle. It’s a full day of fun, with the main attraction being kids (and a few brave adults) wearing garbage bags and sliding down a quarter of the mountain on their bellies for a $1 donation to the adaptive ski program. Our kids have done it the past two years and love it.

There’s also a raffle, a cookout, and a silent auction.

Last year was our first season spending significant time at Holiday Valley. We wandered into the silent auction almost by accident. It was spontaneous and fun, and we ended up winning a few prizes. Ever since, we’ve been looking forward to it.

This year, it wasn’t a surprise. It was part of the plan.

The Silent Auction Strategy (Or Lack Thereof)

After grabbing some food and watching our kids crash into each other at the bottom of the hill, we walked into the auction room ready to play.

We had no budget.

No limit on how many items we’d bid on.

And this wasn’t some black-tie gala with five-figure packages. The biggest-ticket item was probably a signed Buffalo Sabres jersey. Most bids ranged from $2 to $150.

We circled the tables, writing our names down and enjoying the process. Our only rules were simple: if a kid outbid us, we were out. And if someone was clearly hovering over an item, obsessing over it, we’d let that one go despite our competitive streak.

At the end of the auction, we walked away with 17 of the 110 prizes.

Total spent: $750.

On items we did not plan to buy at the start of the day.

On nothing we truly needed.

So, did we just waste $750?

Was It Irrational?

From a purely practical standpoint, you could argue yes.

This was not a carefully planned purchase. It was unintentional spending. Impulsive. Made under time pressure.

But that’s not the whole story.

Life and money are rarely black and white. No expense is entirely practical or entirely emotional. Even the most “rational” financial decision has some emotion behind it.

This one likely falls right in the middle.

First, it gave us a ton of joy. Why? I’m not entirely sure. But we love the event and are already looking forward to next year.

Second, every dollar went to a fantastic cause. That part was very intentional.

Third, we bid on things we will actually use or that others we know will enjoy. I picked up some cigars and bourbon, occasional guilty pleasures. Selenid won kitchenware and skincare items she genuinely loved but would never buy for herself. We grabbed a few toys for the kids. None of it was essential. All of it will get used.

Fourth, we can afford it. Decades of hard work and a physician income have blessed us with strong cash flow. More importantly, our financial habits have us firmly on the path to financial freedom. A one-time $750 expense is not going to derail anything. If anything, directing it toward charity makes it feel even better.

What’s the Real Point?

I get labeled as overly frugal all the time. Just today, a reader asked when doctors can finally stop delaying gratification. I think the misunderstanding is that people assume I’m anti-spending.

I’m not.

If I were, I wouldn’t have been able to spend $750 on silent auction items without losing sleep.

I’m pro-intentional spending.

And yes, by the strictest definition, today’s purchase was not intentional. But here’s the nuance: when you build your financial foundation early, you create room for flexibility later.

If I had leased two luxury cars, bought a home three times my income, joined multiple country clubs, and inflated my lifestyle right out of training, that $750 would absolutely cause stress. Fixed expenses would leave little wiggle room.

Instead, I paid off my commercial and student debt. I built a savings rate above 20 percent. I invested in index funds and bought cash-flowing rental properties.

That’s what creates days like today.

And I can tell you, it’s worth it.

One Last Thought

If your current situation looks more like the high-expense example, don’t get discouraged. It’s never too late to change direction. Start today…here are some tips.

So what do you think? Did we overdo it? Was that $750 thrown down the drain? Or was it money well spent? I’d love to hear your take in the comments.