In the last month, I've had the pleasure of meeting with at least 50 people in the Boston startup community. Every conversation includes some form of a personal story exchange. I tell what I've done over the past 10 years, they tell what they've done, and we look for the common ground to continue to conversation. Through this, I've realized not only how important a good personal story is, but also that it is no place for self-deprecating humor.
I don't think I am alone when I say that I get uncomfortable when talking about my own succeses. I've realized that I deal with this discomfort by making fun of myself when telling my story. When talking about my degree in computer science (something I am quite proud of and which has served me well) I make a joke about the fact that it's from a liberal arts college. When talking about the 230 episdoes of HubSpot's video podcast I co-hosted over 4 years, I make a joke about how crazy HubSpot was to let me speak publically for the company. I never stopped to think about how others were percieving my personal story, until I started telling it over and over and seeing others tell theirs.
There is no doubt that telling your story is an art. You want to highlight the high points, without bragging. You want to share the details, without talking for hours. You want to entertain, but not dimish what you are saying. A couple of weekends ago, on a drive to NH, my husband and I worked to retool my personal story. It's something you tell over and over, and I had a script. I needed to rewrite that script to take out the parts where I make fun of myself, and remove the parts that went into too much detail (another problem I have when talking.)
It's taken a couple of weeks for me to feel comfortable with my new story. I think it tells what I have been up to in the last 10 years much more effectively, while also showing my best side. I expect others have different weaknesses in their own personal story. I'm expect it's easier to see what those are when you are telling it multiple times a day, but I encourage you to think about how you would answer the question, "Tell me your story?" Where are the weaknesses and what can you do to improve your story?
