I attended the first day of Big Omaha yesterday and was really impressed with the conference. It was my first time there and I plan to be a regular attendee. At the end of the day there was a general Q&A with all of the day’s speakers. One of the questions asked was “If you could go back in time and talk to your 15-year-old self, what would you say?” When I heard the question I immediately thought of two things.

First, I would tell myself that many of the choices you make in life have consequences, and that regrets in life will stay with you forever. I would say that I should begin training myself to consider the potential regrets that may result from a decision or choice I make, and to make the choice that would result in the potentially lesser regret. These choices come in many forms. As a simple example, for most of my adult life I have kept to a personal pledge of never going to bed after a serious disagreement with someone I care about without bringing it to closure — even if I had to be the first to apologize. Another example of this was when I made the choice to leave eSellerate to start my own company. This was a very difficult type of decision that many people face. Before I made my decision, I saw two potential regrets: 1) that I would have left a comfortable job to start a company that ended up failing, and 2) that I would look back in 10 or 20 years and regret I had not done what I had always wanted to do by trying to start my own company. When I pondered this I realized that I could recover from a failed startup, but there was nothing I could do to ease the regret of never trying in the first place.

Secondly, I would tell myself one of my favorite quotes: “No battle plan ever survives first contact with the enemy.” What this means to me is that it is ok to have a plan, but once you start down a path you need to be flexible by adjusting and reacting to new information and opportunities. Where I am today has very little to do with up-front planning and more to do with recognizing and pursuing opportunities I found interesting and that I felt would expand my perspective. I am afraid many people get so laser-focused on achieving a particular goal and headed down a particular path that they fail to see unique and interesting opportunities that come across their path because they don’t fit into their plan.

Shervin Pishevar of Social Gaming Network spoke at Big Omaha about the personal side of being an entrepreneur and had an interesting quote: “It is far more important in life to collect experiences and not things.” I think that quote can be used as a guidepost for keeping vigilant and recognizing opportunities.

Avoid regrets and focus on collecting experiences over material things — that would have been great advice for myself at 15.

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