Don’t Train the Curiosity Out of Yourself

A friend of mine is looking for work, and recently someone suggested that she meet a woman involved in catering and food trucks. The whole thing was vague. Nobody seemed entirely sure whether there was a job, a project, or simply a conversation that might lead somewhere.

My friend was cautious, which was entirely reasonable. I reacted differently. I wanted to know who this woman was, what kind of food trucks she worked with, what she might need help with, and when we were going to meet her.

As I heard myself, I realised that there is still a golden retriever living somewhere inside me.

Someone says there may be something interesting happening, and before the sensible part of me has had time to ask what the meeting is about, the golden retriever has already found the lead, fetched its coat, and positioned itself by the door. It does not know where we are going, but apparently that is not a problem.

I have accumulated enough experience to know that this reaction is not always rewarded.

I receive messages from people who say they want to connect, exchange ideas, or explore possible cooperation, only for the conversation to reveal itself as a badly disguised sales call. They have often done no research beyond finding my profile, and they have little idea whether I need their product or am even the right person to speak with.

I have also offered my help to founders, accelerators, and investors who sounded genuinely enthusiastic and said we should absolutely continue the conversation, after which I never heard from them again. Job applications often end the same way, disappearing without a rejection, an explanation, or any indication that another human being has looked at them.

After enough of this, caution begins to look a great deal like intelligence. The hit rate really is terrible, and the cost is real, because every attempt consumes some time, energy, and willingness to believe that this particular conversation might be different.

It would therefore be easy to conclude that the sensible response is to participate less. Take fewer unclear meetings, stop offering help so readily, apply only when the fit is almost indisputable, and leave unfamiliar doors closed until somebody can explain exactly what is behind them.

I understand that response, but I do not want to live by it.

The trouble with repeated disappointment is that it does not only teach us to recognise bad opportunities. Over time, it can also teach us to suppress our interest before we know whether the opportunity is bad at all.

We become careful with enthusiasm, and somewhere in that process good judgement can begin to look uncomfortably like dullness.

That worries me more than another wasted conversation.

It is sensible to ask what a meeting is about, to do enough research to protect your time, and to recognise when somebody has disguised a sales pitch as personal interest. It is also sensible to stop chasing people who repeatedly promise to return and never do.

But there is a difference between qualifying an opportunity and requiring it to justify its entire existence before it has even begun.

Many of the things that came to matter in my life did not begin with much clarity. They began with conversations, introductions, half-formed ideas, or somebody saying that two people should probably meet. Some of those vague conversations have led to paid work, collaborations, friendships, and directions I could not have planned beforehand.

Many others led nowhere, and a few were a complete waste of time.

That is the irritating arithmetic of it. One good conversation can make up for dozens that produced nothing, and the meeting you nearly declined can occasionally change the direction of your work for the following year.

There is no reliable way to identify those meetings in advance. If there were, curiosity would hardly be necessary.

My own compromise is to qualify the opportunity without trying to remove all uncertainty from it. I ask what the conversation is about, check whether the other person has made a reasonable effort, and decide how much time I am prepared to risk. After that, I try to leave some room for the possibility that neither of us yet understands why the meeting might matter.

The golden retriever does not understand any of these precautions, of course. It has heard something moving in the bushes and would like to investigate.

It may be a rabbit, although experience suggests that it is probably a plastic bag.

Experience should teach us when to shorten the lead, but not hold it so tightly that the dog eventually stops looking.