Chutes and Ladders: A metaphor for life and entrepreneurship

As a ritual, every evening I prepare for the upcoming coaching meetings I have the following day. I review our previous meeting notes, the task I assigned to the entrepreneur and the status of the startup at the time of our last meeting.


This practice of taking time to prepare in advance of a meeting is a tool which I train and coach the entrepreneurs I work with to adopt. Even setting aside 3 min before each meeting will generate focus, sharpness, clarity, and help you specify what the goals of the meeting are and the desired outcomes. Because when we are clear with ourselves, it is easier for us to mobilize and motivate the person in front of us.


There are many pearls of wisdom written in my notebooks from entrepreneurs' coaching sessions. I note things that emerge during meetings either from me or from the entrepreneur. We often speak about the manic emotional cycles of the entrepreneur experienced through the daily ups and downs. We speak about how each and every email from an investor or customer elevates us or sets us back emotionally and how to manage that.


In one of my last meetings, one of the entrepreneurs shared a sense of dejection because an investor had withdrawn on investment at a relatively late stage. He went on to describe to me the challenging feeling of ups and downs as “chutes and ladders,” just like the board game. This phrase stuck with me. Life, and specifically the life of an entrepreneur is just like a game of “chutes and ladders.” Sometimes we climb the ladder and make quantum strides ahead. And just when we believe everything is set with goals to keep progressing forward in the upcoming month, suddenly, we are hit with a setback.


Life is an ongoing climb between setbacks

Last week, my targets were set, my calendar full with upcoming meetings and I felt energized to propel my business forward. Suddenly at 2 in the afternoon, I was notified that my whole family, husband and 3 young sons, needed to enter two weeks of quarantine due to COVID exposure at my 5 year old son's school. I instantly felt my freedom was taken away - freedom to choose, to move, to go out. It felt like the only possibility was to dangle the rope and rappel to the next level down until this period would pass and I could climb back up the ladder.


The same entrepreneur who had experienced an investment setback finished our last meeting having reflected on how he operated during the investment process. He considered what he could have done differently and in the process developed skills to use data and storytelling effectively. He saw how the process empowered his team and enabled them to see his reality; how he acts as a CEO with intense and anticipatory conversations with investors on the one hand, and disappointment experienced on the other. Through reflection, he was able to realize the value gained, even when the investment didn’t come through. We learn to accept what is and the circumstances for which we can not control. Our ability to look ahead, to continue moving forward with motivation and inner confidence until the next ladder comes is what is important above all.


We continue to jump between squares of the game, throwing the dice, and noting that there are a number of options that are possible to actualize. Even in quarantine or lockdown, the work continues and so does learning, education and volunteering. What works for me, is to keep things in proportion counting my blessings that everyone is healthy and this situation is only temporary. I must draw out what is best in the current reality.


So continue on, with all your strengths, find the ladders, and don’t be afraid of the moments when we repel down. As we inevitably repel down, take a moment to notice what we learned on the way up. This way, we can forge a new or alternative path forward as stronger, more wise individuals and entrepreneurs.