Someone once asked a great philosopher which he would rather have—a gift of money or a gift of friendship. “Friendship,” replied the philosopher, “because money is spent but friendship can last forever.”

“I shall think of that advice forever,” the questioner responded, “as a mark of your friendship.”

“Sorry,” the philosopher apologized, “my friendship is free, but my advice isn’t. Pay up.”

As you will see in this chapter, money is but one of the ways to lose friends.

1. Go into business with…

George has been your personal friend forever. You do everything together. So you and George become business partners. A few months into this grand alliance, a few chinks appear. It turns out that George’s work habits are a bit different from yours.

You’re an early riser. George thinks early is anything that happens before noon. You’ve put in four hours before George puts in an appearance. You’re a detail person. George can’t be bothered with the fine print; he’s a charmer. That can be just dandy, if your Mr. Inside/Mr. Outside arrangement is viable. But even though George is handling sales to take advantage of his people skills, you’re in a business where your customers still carry slide rules and want everything done by the numbers. George no can do. What can you do?

2. Buy something from…

You’re finally going to add that three-season porch your spouse has been wanting for the last 23 seasons. Good Old Ollie’s just getting started in the remodeling business. Why not let him do it? Though G.O.O.’s bid is 25 percent higher than anyone else’s, he assures you that “you get what you pay for.” He must have meant leaks and broken tiles. You can’t very well turn him into the Better Business Bureau, so you just bite the bullet while someone else fixes Ollie’s follies.

3. Sell something to… (reverse of 2.)

Your dad goes into a nursing home. He has a three-year-old car with very low mileage. You were going to advertise it, but your friend Sid pesters you to sell it to him. You do, and take a $500 haircut. Then after three months the transmission goes out. Sid seems to think that’s something you should pay for. Funny, you and Sid don’t get together as much anymore.

4. Hire…

Friend Ralph worked for a Fortune 500 company and says he was downsized out of a job. He’s an accountant, and you have a serious bean-counting deficiency. A marriage made in heaven? Not quite. You discover that the corporation that canned Ralph may have been onto something more than just a routine restructuring. It seems that learning new ways to do things is not to be found on Ralph’s balance sheet. You never bothered to check him out, of course, because this is a guy you’d known for 20 years. Too bad, because after six months Ralph “doesn’t work here anymore.”

5. Go to work for… (reverse of 4.)

You took early retirement and decided to go to work for your old fraternity brother Alex, a self-made zillionaire who was two years ahead of you in college. Boy, Alex was a real wild man in those days. Unfortunately, he still is. He screams. He curses. He harasses. Alex thinks it’s still Hell Week and he has the paddle. You depledge.

6. Go on an extended trip with…

Greg and Lisa are great company, so this long vacation with them would be a guaranteed blast. Well, it was a “blast” as in “explosion” or “bomb.” You’ve always been a generous tipper. Not Greg. He’d stiff any waiter or waitress if he had the chance. It used to seem kind of cute, but not anymore, not when it got repeated over and over, every day, every meal. No amount of nudging or teasing seemed to work. Toward the end of the trip, you’d have to sneak back to the table and throw down a couple extra bucks to make up for Greg’s cheapness. And no bill was ever split 50/50. Greg always found a way to shave a few pennies off his end. Punctuality wasn’t one of Greg’s virtues either. Every day you’d wait for them in the lobby before you could get going. Little things? Oh yeah. But they sure can get big in a hurry.

7. Lend to or borrow money from…

All of the above problems are minor compared to this one. More friendships have been trashed because of money than all the other reasons combined. Do your banking with a banker.

Mackay’s Moral: Friends are made by many acts… and lost by only one.

Excerpted from Pushing The Envelope All The Way To The Top