MyPunchblog

Since I started MyPunchbowl.com a few years ago, I’ve noticed a few times where I’ve felt “in over my head.” Sometimes it’s when I have a million things coming at me at once (like this week) and I have to brutally prioritize my list of to-do’s. Other times it’s when I’m in a high-level meeting with an investor or potential partner and I feel overwhelmed by the importance of presenting MyPunchbowl well. Other days I can feel overwhelmed by the reality that our employees and contractors have put their faith and livelihood into Punchbowl Software.

Jeff Bussgang (Flybridge Capital Partners) wrote about this phenomenon today, and specific passages really struck a chord with me.  I remember in the early days of Punchbowl a lot of nights as Jeff describes in his blog post: “I would come home at night, shake my head as I recounted to my wife the decisions I was responsible for making, and reflect that I really had no idea what I was doing.”

Jeff continues his blog post with a description of the 80/20 rule for entrepreneurs: 80% of the time you should be in control of what you’re doing, and 20% of the time you should be in over your head.

I like the spirit of this 80/20 rule, but I would amend it a little. For me, I think it’s important to concentrate the feeling of being in over my head into a burst. I think it’s important that once in a while — for a stretch of a few days in a row – to push myself out of my comfort zone and feel in over my head. Sometimes this will take the form of attending a conference where I have to do a lot of meet and greet with executives way over my level, and sometimes it takes the form of tackling a really hairy product or technical issue with our development team. The key for me is to concentrate that feeling of being “in over my head” into a few specific days, and then get back to the tasks and objectives that I want to achieve for the month.

If you’re an entrepreneur and you never feel “in over your head” then do whatever it takes to stretch yourself to that place. It’s not comfortable while you’re there, but soon you’ll look back and see how far you’ve come, who you’ve met, and what you’ve learned.

Thanks to Jeff Bussgang for tackling this important subject.

This entry was posted on May 8, 2008 at 10:14 pm and is filed under Startup. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.