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When you make more than your friends

BrewerBob said:
What follows is not important in the grand scheme of things. It will probably fall under the "I wish I had that problem" category for some of you. Still, for those interested in offering advice I am all ears.

I am at a point in my life where I am well off financially. It took a while. I worked at Wal-Mart and at an animal kennel and I delivered pizzas. Then I spent 20 years in the Army and when I got out I started my own business. I am finally at that stage where my money is working for me rather than the other way around. And I am not ashamed to say that I like to treat myself now that I can finally afford to do so. I'm not into fancy cars, jewelry or expensive clothes or anything like that. But I do like to travel.

Other than my wife, my favorite people in the world are my best friend (who is a Chief Petty Officer in the Coast Guard) and my younger step-brother, who works for a non-profit organization that finds housing for homeless vets. Like me, they are married and have young children. They are solidly middle class guys living on a budget. Just as I was most of my life.

I love those guys and I want to take a kick-ass trip with them. I have a few ideas but they are all fairly pricey. I am certain it would be a financial burden on them. Which is why I would be more than willing to pay their way. My wife thinks they might be insulted and think I was giving them charity. The way I look at it is that paying for their shares is just part of the cost of an awesome trip. It WON'T be as much fun without them. But I don't want things to be awkward between us, either.

What would you do in my spot? How would you feel if you were in my friends' spots?
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First of all, congrats. Success is earned, and you deserve it.
I have a simple solution to your problem. Ask those guys how they would feel, ask them for suggestions. If you are really good friends, they won't mind but give you an honest answer. Take it from there.
I have been on both sides, and what I appreciate most from anyone is honesty.
 
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