The 4 most unexpected coaching situations

By Kenneth OhJun 23, 2015


Life coaches have seen it all! We ask some of our life coaches to recount one of their many unusual, wacky or fun experiences with their clients.

Coach 1: My client asked me to go skinny dipping with him. He was aiming to build up his courage and worked with me to come up with a list of wild and wacky things to do. We drove to a nearby swimming pool early one morning and took a dip – stark naked – into the cold waters for a good 15 minutes!

Coach 2: My brother asked me to coach him on love relationships, which was completely unexpected because I didn’t think that he would ask me of all people to coach him. To put it in context, he was also being coached by my fellow colleagues at that time. Moreover, he understood that relationship coaching tends to be a bit tricky since you can’t be biased towards either party, and him being so closely related to me could have resulted in an unbalanced assessment. But he trusted me to remain neutral and told me that he had one of the most productive and eye-opening coaching sessions in his life.

Coach 3: I had a client who spent years in and out of prison, not because he was a bad person but because of his desire to help the people around him that got him ending up on the wrong side of the law. He once called me up to ask me to lend him some money since he was flat broke after serving another jail term. I asked him what he needed it for. He said, “I need some change to take a bus. I’m going to a seminar to find out if I can be a real estate agent.” As a coach, you can’t give money to your clients, so I said, “No.” But I continued, “Here’s your chance to be creative. Do you wear a watch? You could sell it. What skills do you have? Can you clean houses or cars for your neighbours?” He replied, “Ok, sure. I can do that.” 2 weeks later, he called me and said, “I just wanted to thank you. I’m a very happy man!” He had just sold a property and earned a commission of $35,000!

Coach 4: My client wanted me to busk with him in the train station as a counter-challenge to my challenge to him. As a coach, I couldn’t back out of this request so I did. He played the ukelele while I sang. We did it for 15 minutes and earned a grand total of 20 cents – not bad for such a short session for newbies in the busking scene!

Have any other requests for your coach? Find one at to challenge yourself today for a more fulfilling life!