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Leslie’s Leadership Lesson: Letting Go Of Relationships

How Letting Go Of Negative Relationships Can Help Us In The Long Run

This leadership lesson is about me and letting go of a long time friend of mine. It’s about disassociating oneself from unethical friends. It’s also about setting deep boundaries and making serious personal statements, too.

I had a friend, Gary*, for the better part of ten years. Gary was an underdog that I befriended in high school, my college friend, and a collaborator on several personal and professional projects. When I started working in a serious professional setting, I sent my specific business needs to him. Since I knew every step of his professional development, I trusted him. I referred business to him and even brought him on when I first took my business to the next level.

I was on a limited budget, so we bartered with each other to make up the difference. I helped him land a full time job before he graduated college and coached him as he made the transition to a real, grown-up professional. Then, things started to change when Gary wasn’t meeting deadlines that we agreed to. He was ignoring my messages for weeks at a time. He gave me one hundred and one reasons why he couldn’t follow through on his side of the deal.

Being his friend and compassionate of his personal situation of disabilities, financial issues, and relationship issues, I brushed off his lack of commitment to these problems. When I could afford to pay him what his work was worth, that didn’t even do the trick.

I confronted him several times explaining that my trust was waning and that his professional reputation was directly affected by his ability to meet his obligations and communicate problems. I even threatened to pull the plug on the project and go with somebody else. Time and time again, he apologized and gave me another deadline that he would inevitably miss.

This, unfortunately, spanned a time period of one year. I thought to myself over and over – I am telling him how I feel, I’m meeting him half way, and I am doing my best to resolve the situation – what the heck am I doing wrong?? I began to question my own judgment.

Then, one day, it hit me that I was allowing him to take advantage of me simply because he had the title of friend. Dur, that’s a no-brainer. I was looking back to our history and making decisions on the good memories, totally turning a blind eye to the fact that Gary wasn’t being a friend – let alone a reliable business partner. Even worse, here I am preaching boundary setting to my clients and I am not following my own advice to end relationships with unethical people.

Friends are friends because they trust and like each other. I didn’t trust or like the person Gary had become. After wasting time, losing money, and stressing out for a year on a project that would never get done I realized that I had to do the right thing and end the relationship. It’s like that old expression goes, “Fool me once, shame on you. Fool me twice, shame on me.”

One day, I just stopped talking to Gary. I didn’t even bother to try to get the money I had lost. I disconnect my online affiliations and I stopped referring business to him. Was it hard to disassociate myself from an old friend gone bad? Yes. It hurt. Was it necessary? Yes. Do I feel bad about it today? No. In fact, Gary didn’t even bother to contact me after the cease of communication. I suppose he understood why I ended the relationship.

Have you ever had to make the tough decision to end a personal or professional relationship? What was the experience like and what have you learned from it?

*Names have been changed to preserve privacy.


Leslie, Inc. offers solutions for finding happiness through one-on-one coaching, mindful leadership retreats, and digital products. If you’re ready to GET HAPPY, check out Leslie’s guide packs. For more tips on achieving your state of happiness, sign up for Leslie, Inc’s weekly newsletter.

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