Taking Risks

Some people naturally love risk. I have skied, I ride a Harley, I have backpacked through parts of South East Asia but I am not a natural risk taker. Truth be told, I liked to ski on green and blue runs, I bike with full gear all the time, rarely in the city, and never in bad weather or in the dark. And when I went to Asia, I didn't have reservations but I did have detailed plans and always kept to the safe parts of the countries, never traveled alone, and had several guide books with me. I am rarely seen as a risk taker or a thrill seeker in life.

The same was true at work for me. I was naturally inclined to follow the well known paths. But I got good advice early in my career that made me view risk differently at work, and made me more willing to take bigger risks. My greatest successes came when I followed these two simple rules:

1. I was told to trust my own judgement and make things happen. If I saw a new or better way to do things, I should go for it. Leaders lead they don't follow. Sadly, my early tendency was just to complain about what was happening even when I could see a better way. It was much more satisfying and effective to take the risk to lead and fix the problems.
2. More importantly, I was advised that "if your stomach doesn't hurt a little, you probably aren't taking enough risk". A mentor of mine, Randal Leavitt, shared that with me in my late twenties after I told him that I was feeling very queasy on my current project because there were so many unknowns. He pointed out that that was good; with risk will come rewards. He did add that if I felt like vomiting, that was probably too much risk :-). I took his advice and my project was very successful. I still use "the stomach test" to this day as it has never let me down.

If you want to be a leader then you need to take calculated risks. You do not need to take crazy risks but you are not a leader if you just do standard repeatable mundane tasks. Challenge yourself and challenge your teams. Make a difference.

Less confident people are more successful

I liked this article in the HBR.  I am one of those people who consistently questions themselves. Despite being a consistent high achiever, I used to really lack self confidence. But over the years, I learned to trust my judgement and my abilities, and gain a reasonable amount of confidence. But I still avoid "winging it" and like to be prepared, I am still self-critical, and I believe that I rarely seem either arrogant or deluded. Looks like my lack of confidence, which troubled me for some time, was really a helpful trait.