10 November 2011

Be willing to be uncomfortable. Be comfortable being uncomfortable. It may get tough, but it’s a small price to pay for living a dream.

Peter McWilliams


While at my old job, I had the benefit of working closely with people who had much more experience than I did. At most internal meetings, I was twenty years younger than the next youngest person in the room. As a result, I got exposed to a lot of important business lessons from people who had used these lessons to achieve great success.

One of the most interesting things someone told me was that his top personal development goal was to become more comfortable in uncomfortable situations. He said that he had seen many successful and unsuccessful people over the years, and the most important differentiating factor was whether people were willing to have uncomfortable conversations. The number of uncomfortable conversations you have is directly linked with your overall success; double your uncomfortable conversations, double your success.

His business was the money management business, both as a financial advisor and later as a manager of other financial advisors, and it’s easy to see how this advice is true for money management. When their clients lose money, some financial advisors call half as much, and some call twice as much; guess who is more successful in the long run?

When I think back to my past, there were many times where if I was able to have composed difficult conversations my life would have been much better. After college, a close friend and I had massive yelling matches for months over something that could, in hindsight, have easily been solved if we were able to just sit down and have a difficult conversation. I nearly lost a good friend, and our friendship still hasn’t completely recovered. It’s one of my biggest regrets.

For those wondering how to practice being comfortable in uncomfortable situations, the answer is simple; practice. Everyone has important conversations that they put off; such as asking for a raise or firing an underperforming employee. Start having those conversations. When you feel a sinking feeling in the pit of your stomach, that’s when you know you’re doing what you should be doing. While you’re in the conversation, focus on being calm and collected. After you’re done, think about what you could have done better. Repeat.