I want you to close your eyes for a moment and imagine the worst client that you ever had. Come on, we all have had those relationships where if we see their name pop up when we look at our calendar on Sunday, our week is ruined. But no matter who that client was (I hope it is a was!), the client was probably not the issue—we were.

My worst client was someone I’ll call Bob. It was the early to mid-’90s and Bob was charming, charismatic, alcoholic, an inveterate gambler and wealthy. This was relatively early in my partnership with Wil Heupel, and we were at best doing only OK. I was professionally smitten with Bob, what we could do for him, and what he could do for us. Things went pretty well until they didn’t.

Bob once called early in the morning from a casino in Las Vegas where his run at the blackjack table left him up around $100,000. He was drunk, but I agreed that when the banks opened, we would call to get his winnings wired into his bank account back home. Somehow, we got the call lined up and as we were going through the last digits of the wire, Bob hung up. He was no longer reachable. Needless to say, he came home with only some of those winnings.

Eventually, although we were doing comprehensive planning, Bob grew tired of the way we managed money. He didn’t like asset allocation. In fact, he bought one of those late ’90s go-go newsletters and began trading aggressively on margin using the model portfolios. He was doing unbelievably well; we were not. We warned him of the risk he was taking, but he metaphorically hung up on us. When we eventually parted ways (I am not quite sure who fired whom), he was highly leveraged investing in the model portfolios. He paid little attention to the other things we were working on like his estate plan, college funding and some of the business planning.

Bob’s departure was very expensive for us, because he was our biggest client at the time. It turned out to be far more expensive for him, though. The go-go newsletter’s investments completely blew up in early 2000. I can’t imagine how much Bob lost, but when the margin calls hit, I suspect it was close to everything.

But in looking back, Bob was not the problem. I was. Here’s why.

First, I tried to fix him. The problem with trying to fix someone is that you are assuming they are broken. When we treat others as broken, then we are not treating them as equals. We make ourselves superior to them and the relationship changes. Bob didn’t want to be fixed, yet I was inserting myself in ways that did not prove useful to him. I could offer a certain kind of help, but that help was not appreciated. If he hadn’t been such a major client, I probably would have suggested we part ways sooner, but I am sure that I was attracted to not only the chance to fix him, but to be paid for it.

Second, I tried to save him. In this situation, I made him a victim. Bob was a proud guy and he would be the last person who would want to be viewed as a victim. My need to be a hero overrode this. If I could have saved Bob, then I could have put his house in order, tied up things in a neat little bow for him and his family, and felt great about the role I played in making a difference. Generally, most of us wish to make a difference. We feel the best about our work when we can do so. But again, when we are saving someone, we are elevating ourselves above them. Working with someone is different from saving them. The first makes it about them, the second makes it about us.

Third, I tried to change him. I clearly saw the things that were not working for him—the alcoholism, the gambling—and tried to change him. That’s pretty arrogant, isn’t it? I’m right, you’re wrong. In what part of your life have you been successful in changing anyone? People may choose to change, but it is their decision. The only people we can legitimately change are ourselves.

Fourth, I wanted to be liked by him. Isn’t that sort of weird? I had placed myself in a position superior to him and yet still sought his approval. Because I sought his approval, I don’t think I fully acted with integrity. I should have walked away from the relationship far sooner than we parted.

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