While I love the Eleanor Roosevelt quote, “Do one thing every day that scares you,” I can’t say that I have lived it. A scary task on a daily basis just seems too much. But, I have lived by the rule of doing one thing every year that pushes me way beyond my comfort zone.

Early in my career I started an annual ritual of sitting down and having a very frank conversation with myself. The conversation typically occurs in the fall when the leaves are turning and the air is becoming cooler. I prepare one of my favorite beverages, a mug of piping hot tea or a glass of a hearty Cabernet.

I spend time thinking about the past year and identifying my strengths and weaknesses. The area of focus for the year always emerges with great clarity, sometime before I have finished my tea or wine. I then devise a plan for how I ‘ll tackle the thing that truly scares me. The plan involves establishing a bold goal and then crafting a step-by-step plan for how to achieve it.

I remember the year when the “thing “was public speaking. I dreaded public speaking so much that I honestly hoped to get hit by a bus on the days when I had to stand in front of others and try to be coherent. But, I could see where my career was headed and knew that being able to speak well, and perhaps even enjoy it, would be a major asset in my career.

I signed up to speak at a major conference, knowing the audience would be in the thousands. In the eight months leading up to the conference, I hired a coach, I picked out my outfit, I thought about the audience, I developed my speech, and I practiced, practiced some more, and practiced even more. The day of the conference I didn’t think about being hit by a bus; I only focused on how I could deliver the best and most authentic speech possible. And, well, I must admit that I nailed it.

I discovered that it is truly invigorating to tackle something really hard. Forcing myself to do this practice year after year made a significant difference in my career.

At this stage of my career, my annual thing is sometimes professional and sometimes personal. My thing this year is to learn how to sail. I’ve spent hours on a sailboat; I’ve even taken some lessons. But, for some reason I still have an extreme lack of confidence and comfort out on the water. In June I will board a sailboat with a group of women and a master instructor and we will sail in Casco Bay for three days straight. The instructor assures me that after three days I will step off the boat as a true sailor. I’ll admit that I keep wondering if there are busses that run in that area of Maine.