As part of my daily evening ritual, I prepare for the next day's coaching meetings. I review notes from the previous session with my client, the task items I assigned to the entrepreneur, and the startup's status at the time of our last meeting.

This practice of preparing for a meeting in advance is a tool that I encourage and train my entrepreneurs to adopt. Setting aside just 3 minutes before each meeting will improve your focus, sharpness, clarity on desired outcomes and help you hone in on your goals for the session. When we are first clear with ourselves, it is easier to mobilize and motivate the collaborating person.

There are many gems of wisdom I've written down from my sessions coaching entrepreneurs. I take note of things that emerge throughout our meetings, either from myself or the entrepreneur. My mentees and I will often discuss the manic emotional cycles they experience throughout their daily ups and downs. As another example, we will also speak about how each email from an investor or customer can elevate us or set us back emotionally and how to manage it.

In a recent meeting, one of my entrepreneurs shared a sense of deep dejection after an investor had withdrawn their investment at a relatively late stage. He described the challenging feelings of ups and downs as "chutes and ladders," just like the board game. This phrase stuck with me. Life, specifically the life of an entrepreneur, is just like a game of chutes and ladders. Sometimes, we climb the ladder and make great strides, and just when we believe our goals and progress are set for the coming month, we suddenly slip into setbacks.

Life is an ongoing climb between setbacks

Last week, my goals were set with my calendar full of upcoming meetings, and I felt energized to tackle them to propel my business forward. When suddenly, one day at 2 in the afternoon, I received notification that my whole family, including my husband and three 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 of choice, to move and to go out taken away from me. At that point, it felt like the only possibility was to throw the rope over the ledge and rappel to the next floor down until this period would pass and I could climb back up the ladder.

The same entrepreneur who experienced the investment setback finished our last meeting reflecting on how he operated during the investment process. He considered what he could have done differently to develop skills to leverage his data and storytelling more effectively. He saw how the process empowered his team and enabled them to see his reality from his perspective. He felt that he acted as he needed to as a CEO, on the one hand, pleased with his conviction and anticipatory communications held with investors, but utter disappointment on the other. After further contemplation, he eventually recognized and understood the value gained, even though the investment didn't come through. We learn to accept things as they are and the circumstances in which we have no control. Above all, what is most important is our ability to look ahead, to continue moving forward with self-confidence and motivation until we reach the next ladder we climb.

We continue to jump between the game's squares, roll the dice and acknowledge that there are several possible options to pursue. Even in quarantine or lockdown, our work continues, as well as learning, education, and volunteering. What helps me keep things in perspective is to count my blessings for everyone I love being healthy and knowing that this situation is only temporary. I must proceed with what is best under the current circumstances of our new reality.

So move forward using all of your strengths, find the ladders, and don't be afraid of the moments you may need to climb down. Ultimately, what goes up must come down, so take a moment to notice what you learned on the way up. In doing so, you can forge a new or alternative path forward as a stronger, wiser individual and entrepreneur.

Sep 23, 2020
by Gali Bloch Liran 

Chutes and Ladders: A Metaphor for Life and Entrepreneurship

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