How To Decide: The Best Story You’ve Never Heard

Towards the end of August I embarked on a short road trip to Boston. The reason for the trip was half active procrastination before making a potentially life altering decision, and half salvaging what remained of my east coast summer. The warm, soothing weather was dwindling down, and so was my time to decide.

The decision revolved around my move to San Francisco to work on my venture full-time, or to move on to new projects. When that thing you’ve been seeking is finally in the grasp of your hand, closing your fingers around it can be daunting. I knew what I had to do, but was I ready?

I had a term sheet; do I scribble my name on it? I just graduated college; is this supposed to happen? The two thoughts seemed to be stuck together.

As I paced aimlessly around Harvard Square one afternoon, frustrated and nostalgic as the eager college students moved into their dorms, I called Derek:

Derek. What the fuck should I do?

He didn’t tell me what to do; he never does. But, he did reply to my question with a story that I’ve thought about every day since:

I never wanted to sell CD Baby, but I was noticing that I was less enthusiastic about the company, and losing interest.  Around this time I had three different companies wanting to buy it, but had always said no.  I asked my friend Seth for advice and he said:

“If you care, sell it.”

Derek’s interpretation, and mine as well, was that if he was even considering selling CD Baby, he would be doing the company little justice by continuing to run it. The thought alone was unfair to the organization he not only managed, but built from the ground up. It required dedicated attention.

The answer to Derek’s dilemma was apparent in the decision-process alone. Meaning, if he truly cared about the company, it was best to pass it on to someone who didn’t have the intent to sell.

The result? Derek sold.

In my situation, I knew I cared enough to stick with my own company. I wasn’t actively considering other opportunities, even though they existed. And even if I was, I knew I’d add little progress to someone else’s project with my own startup nagging me in the back of my mind. How could I not give it a try?

The reality of my situation was that I cared so much, I was having difficulty dealing it.

There was only one way to resolve it. I signed.

The decision making process can be more telling than a decision itself, even if the most obvious choice is the hardest one to make.

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