Bret Stephens from the New York Times published the following quote: “Mindless optimism is the only antidote to rational despair.” He made the quote in a political context, but it reminded me of a comment from someone else who described a dedicated salesperson as someone who, in the face of countless ‘no’s’ winging past their ears, trudges forward looking for a ‘yes.’
Launching a new business is one of the hardest things anyone can do. The success rate is terrible, and the odds are stacked against you. Early stage entrepreneurs face numerous peaks and valleys of optimism and despair. They start with a bright idea, or at least an idea that they think is bright, and it often feels like the inertia of the entire world is resisting their success.
I have been involved with mentoring early-stage entrepreneurs for years, and I continue to be blown away by their courage and commitment to getting their businesses off the ground. As a mentor, advisor, board member, it is often challenging to know just how much reality to inject into the conversation when an entrepreneur describes their optimistic plans, or how much optimism to expound when the entrepreneur falls into the trough of despair. That is why the quote from Stephens hit home with me.
It is not a simple binary choice between mindless optimism and rational despair. Entrepreneurs need a healthy balance to keep trudging forward. I see the role of advisor as providing brutal honesty blended with a heavy dose of encouragement. When things are bleak, we help the entrepreneur to problem solve, and when things are all sunshine, we help them to prepare for rain. My general operating philosophy is to always question the premise behind the optimism or the despair. Whenever anyone tells me there is only one possible outcome or path forward, my lifelong response is to question the premise, and often it has spurred creativity or opportunities that were otherwise overlooked.
One approach I frequently employ as an advisor is to focus on a different timeframe or horizon than the one on which the entrepreneur is fixated. When the optimism or despair is driven by short-term thinking, I try to open the aperture to consider the implications for the longer-term. Conversely, when the fixation is on the longer-term, I tend to narrow the view to evaluate the short-term drivers that lead to the longer-term. Shifting the focus often unlocks creative alternative paths forward.
A tool I learned years ago is to clearly identify the facts that define the current state of affairs, and then articulate the desired situation at a point in time in the future. Once the two ’bookends’ are clear, then agree on a series of steps that have to take place in order to get from ‘now’ to ‘then.’ Next, assign a target date or timeframe to each step. Think of the picture as a staircase where each step is a meaningful milestone along a path to the goal. Several things are often revealed in this analysis:
The most common revelation is that the sum of the timeframes for each step will far exceed the original timeframe for the ultimate goal. The entrepreneur has an ambition to achieve a grand goal (mindless optimism) in two years, but when we look at the steps to get there, it becomes clear that it will take much longer, or require considerably accelerated achievements in the near-term. In this example, bringing the long-term goal back to the near-term, and questioning the premise about what it will take to get to the goal results in a dose of realism that can unlock creativity to accelerate or alter the path forward.
When the entrepreneur is in a trough of despair about the current situation, shifting the focus to the small steps required to achieve the ultimate goal can create perspective. It may be that the cause of the current despair is really only a speed-bump and not a brick wall, and the entrepreneur just needs to lift their sights to see beyond the bump in the road. Alternatively, the despair may be coming from the scale of the challenge ahead to reach the ultimate goal. The staircase approach helps to break it down into small steps. ‘The longest journey starts with the first step’ or ‘the way to eat an elephant is one bite at a time.’ Questioning the premise that the current crisis warrants despair can help to bend the thinking to see past the roadblock.
This staircase, and other techniques to keep the focus on future outcomes are powerful tools to offset the near-term binary choice of mindless optimism or rational despair. The most important contribution from an external advisor, mentor, or board member is to assist the entrepreneur to be realistic and creative, and to open the discussion to explore alternative paths and outcomes that temper the mindless optimism or the despair.