My favorite part of being an entrepreneur:

The month-long adventures I get to go on with my family every year.

✅ 3 years ago it was Mexico
✅ 2 years ago it was Colombia
✅ Last year it was Turkey

This year it’s Utah and all of us are getting pretty darn good at skiing if I do say so myself.

I was telling a friend about these trips recently and he asked a great question:

“Why do you make your vacation so drastic each year?”

I hadn’t been asked in quite that way before, so it really got me thinking.

For my wife and I, it was a decision that we were going to spend $10k – $15k per year on experiences and making memories as a family.

That number might have a sticker shock,
But not once you break it down.

We looked at this a few years ago and decided we had 2 options:

1️⃣ Buy a 6 bedroom house so that everyone could have their own room for the next 15 years, then we could begin downsizing.


2️⃣ Put that money towards experiences each year.

We thought about it and came to the conclusion that when we look back
– when our kids look back –
We will remember these times much more fondly than we would remember having a nicer house.

I don’t think my kids will look back when they are older and think:
“Gosh I wish our house had had 6 bedrooms instead of 4 and that we had 5,000 square feet instead of 3,000.”

I think they are much more likely to remember Mom & Dad taking them all over the world or on an epic ski adventure and the memories that come with that.

These trips aren’t cheap.

But when you look at them in the grand scheme of things,
They’re worth every penny.

🔔 Follow Brian on Linkedin: Brian Pillmore




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