“My legal training made me risk-averse and perfection-obsessed — both of which helped in my legal career, but which were liabilities in an environment demanding quick decisions and high productivity.”

November 17th, 2011

A lawyer-turned-entrepreneur comments how his legal education helped–or hurt–him in his current vocation.

I am not particularly risk-averse, and I shun perfection. I find it to be a waste of time. The marginal cost of perfection is just too high.

Don’t demand perfection. Producing excellent work is critical in the working world. However, the pursuit of perfection can become counterproductive. I realized that the countless hours I spent making excellent work perfect could have been more valuable put to use in other ways. The risk of neglecting sales calls or employees outweighs the risk of missing that improperly italicized comma that I was trained to find.

And this is why I never read leases or other documents. It’s usually not worth it. And if the shit hits the fan later, litigation works.

For example, one of my first entrepreneurial tasks was to secure short-term office space in a building at Farragut North. Once I found a suitable spot, I met with the landlord, who presented me with a four-page lease. Having studied countless contract cases, and litigating a few since, I found my legal training and lawyerly instincts taking over. I spent literally days on that four-page document, researching D.C. law, correcting typos and spacing and inserting provisions on assignment of the contract and forum selection, to name a few — just as I had been trained to — until the old document was unrecognizable. While the new contract seemed perfect to me, it was totally excessive for a month-to-month agreement. The reality was that I had just wasted tons of time that I could have spent identifying client prospects, without which I couldn’t pay the rent due under that lease.