Going on ‘Offense’ in Your Life

A couple of conversations this week made me think about living “a life of offense.”

In one example, a friend is finally thinking about leaving a job to pursue something better. In another case, another friend is getting more comfortable taking on risk, both in personal and work situations. Both are leaning forward. Before, both seemed to be hanging back, almost in a defensive posture.

I don’t think that you can always be on offense or defense at all times with your decision-making. And, there are periods in your life, such as adolescence, when defense is natural. During that period, you may be signaling confidence, when interiorly, you are not, as you still try to figure out who you are.

For me, I started to lean forward and go on offense more and more in my mid-30s. The big step was starting a new VC firm, and from there, it spread to more parts of my life. Previously, I had a very “standard” career track: college, investment banking, management consulting, getting a MBA, joining an established VC firm.

It all changed when I decided to walk and do my own thing. Doing something entrepreneurial means that life has become more risky, but it has been much more emotionally fulfilling. It was terrifying to quit my job. It was even more terrifying to fundraise alone for an institutionally backed VC fund back in early 2007.

I am so grateful it all worked out. It makes me think of the old adage: no pain, no gain.

I see this attitude every day when we work with our portfolio companies. Some are doing very well. Others are deep in the sausage-making process. It is very inspiring to see people creatively tackle problems and persist.

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