The Story-Reality Gap

Not long after a recent conference, I was comparing notes with an early-stage social entrepreneur about pitching to potential investors. The pitches at the conference had been heavy on dreams, lighter on reality, and we got to talking about how big the gap should be between the stories we tell on stage and what’s happening on the ground. 

Specifically, in service of telling our stories, when do we push the truth so far as to reach a breaking point?

Like all good questions, the answer to this one begins with recognizing the limits of black and white thinking: there aren’t just two types of stories, one full of puffery and half-truths and the other a grim, warts-and-all picture of reality so sober and honest that no one would ever dream of funding us.

Indeed, the real truth is this: we owe it to our ideas to tell stories big enough that there’s space for others in them.

Our job is to describe a future reality that will only come into being if the listener rolls up her sleeves with us to help make it happen. This reality can be a few steps, maybe many steps, removed from today, because the question the sophisticated listener is asking isn’t “is this exactly what they’re doing today?” it is, “do I believe that this person with this team, together with my help and support, can get us from here to there?”

With this as a given, we all have our own sweet spot for how we tell stories in ways that mesh with our personalities and worldview.  I’ve been persuaded both by big-picture dreamers and cranky cynics, the former because they help me see something that feels impossible but just-in-reach, the latter because if, with all their negativity, they tell me that they can make something important happen, I’m inclined to believe them.

My own version of selling builds off how I’m wired—I deeply value transparency and authenticity, and as a listener I want to understand where gaps lie and that an entrepreneur is thinking two steps ahead. So I pitch in this same way, always trying to walk the line of painting a big vision and acknowledging what doesn’t exist yet, the potential pitfalls, an how I’m going to address them. This is the balance that works for me, the space between a story I cannot tell authentically (because it feels un-grounded) and one that is thinking and playing too small.

Of course your sweet spot will be somewhere slightly different, a comfort zone with a natural set point on the spectrum between dazzle/charisma/vision and grounded, sober reality.

The non-negotiable bit is that, regardless of which style is most comfortable to you, it’s everyone’s job to share an evocative vision of an as-yet-unrealized future and help others see it.

Storytelling is just that…story-telling, and the stories you want to tell are stories about the future.

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