We’ve all felt it. That moment when there are no more options. The deadline is approaching and, seemingly, the only way out of it is failure. The stress level is high, the caffeine intake is equal to the stress, and there is the constant thought of, “if this only had happened, it all would have been ok.” But it’s not. But don’t focus on that. Focus on the task at hand. Just push through. One more night, one more day, one more week, it will be ok. This, ladies and gentlemen, is what I call the squeeze.
I tell a lot of people that the secret to being an entrepreneur isn’t the idea, it’s the resiliency. But it is also the art of being comfortable with the uncomfortable. And the squeeze is definitely uncomfortable. In fact, it just plain sucks. But you don’t have to be an entrepreneur to feel it. It can be in a relationship, a school assignment, a work promotion, an athletic goal, it comes when you are pursuing something that is more difficult than expected. It’s a feeling that we feel many times in our lives and for some reason, it never seems to get any easier. But one thing is true, the current squeeze always feels better than the previous.
So what causes these squeezes? Well, remember when I just mentioned that you are pursuing something more difficult than expected? Well that is the way through it all, expectations. Expectations are at the center of what we call living in the modern world. We are expected to get good grades in school, we are expected to find a good job, we are expected to be responsible, we are expected to do a lot. In fact, it is basically programmed into us from day one. We are expected to reach a certain level in order to be considered “worthy.” Seems like a lot to take on at a young age. I remember one of the first times I didn’t meet the expectation. It was actually a spelling test in 1st grade. I was expecting to get 100% on the spelling test. I had done my studies (yes, I studied at that age), and I was prepared. When I got the test back, I had missed one word… “But.” Any guesses to how I spelled it? I added an extra “t” at the end. To this day, I’m not quite sure how I was wrong because I was technically correct with what the teacher said, but oh well. But the more important part is that I was expecting to perform at a certain level and I didn’t. It was frustrating and stressful, even that age. I had this feeling that I had to do even better, every single time, from here on out. While a great motivator, I believe that motivation can come from other sources than expectations.
I’m sure we all remember a date where we expected things to go well and they went quite the opposite direction. It also hits even harder with the first heartbreak. You feel that things are going to always be amazing, and you begin to expect it. Suddenly, the unexpected happens and you split up. It’s crushing. After this happened to me a few times, I began to shift the perspective to “no expectations.” Instead of being disappointed, I was always pleasantly surprised because I didn’t know what to expect. As I got older, I found this lack of expectation to be a powerful tool in overcoming difficult, stressful, and very much overwhelming situations. But it wasn’t always easy.
When you decide to live life with expectations, there then exists this delicate balance between pessimism and realism. Without the expectation of success, it is easy to expect failure. And choosing to not expect success and instead just feeling like you are aimlessly going through the world can feel like a lack of direction. So began the difficult balancing act of learning where the line is between a positive mindset, setting expectations, and remaining motivated. I’ve always believed that anything is possible. Sometimes, it can be a reckless ignorance around the potential downsides of a decision. But the entrepreneurial side of me thinks that if you believe in the positive, it reduces the chance for the negativity to enter the mindset. However, especially in an entrepreneurial context, I have experienced a lot moments where I leaned more into the expectation of success and was wildly disappointed. What I began to practice was almost a reserved acceptance of the present.
I’ve been a Formula One fan since the time I could stand, LONG before it became popular in the US. It is the one job I wish I could still have. One of the most important things for a driver, and for athletes at large, is to always remain even keel about everything. Never let the highs get too high, or the lows get too low. Just be focused on the goal and improving everyday at the task at hand. It seems semi emotionless but it allows for more space to perform. This skillset is also present with some of the world’s top performers. The entrepreneurial journey, much like an athlete, is a wild roller coaster of success and failure, hope and depression. It is all about managing the mindset through everything. So rather than setting an expectation of success, set a focus of improvement. If you hit the goal, wonderful. Take a moment to appreciate it, anchor the win in your mind, and move to the next thing. If you miss the goal, that’s ok. Take a moment to evaluate what could have gone better, learn from it, and move to the next thing. I never quite understood, when I was younger, why some of the best people in the world at their given talent seem so calm in some big pressure moments. But this is exactly why, they had prepared for the squeeze and didn’t set expectations.
One of the first major squeezes was when my company ran out of money, completely. And it was bad. I thought I had reached the end of the road and we’d have to close the doors. I couldn’t sleep, I thought about all the things that could have done differently, and I mostly just felt defeated. But stepping back, and it wasn’t super easy, I noticed that, yes, it was unfortunate but it also allowed an opportunity for innovation. What could I do to generate value for the company with absolutely nothing? This was the moment that I realized that, as uncomfortable as the squeeze is, it forces progress because there is no other path. It is what a lot of companies call a pivot to make it sound more like a thoughtful decision than a necessity in the moment. But for the founder, it is do or die. One of the most valuable things I have experienced in building my company has been the squeezes because the business model has changed to a place that not only is more valuable, but more profitable and manageable. The key is to remain even keel about it all and learn to go with it, no matter what is happening. The answer in a squeeze won’t always be correct, or a major breakthrough. But that is ok too. It is more about getting through more and more squeezes. They will never stop but they will get easier to deal with. But every once in a while, a big squeeze will come and that is when all the lessons learned from all the practice come together.
One of the squeezes that come along will be life changing in the best way. So don’t be afraid of the squeeze. It is a beautiful moment.