5 Core Reasons You Should Always Aim For Failure

The scariest thing in the world is winning. We don’t talk about it. We might ignore it because of all the benefits of winning. But the fear looming inside of our win is incredibly real once it sinks in. This is because winning causes something that is very hard to reverse.

When we win we feel invincible, which is when we are most at risk. The false security of winning leaves us in a dangerous position of no longer learning, adapting, or growing. Above all else, once we’ve won, we don’t want things to change, because we have suffered and worked for so long to win that we want things to stay that way, even though we know that everything is constantly changing. In other words: winning blocks us from being objective. And that’s a very scary place to realize you have trapped yourself in.

So if winning is bad, what is failure? Perhaps failure is the key to understanding that even with constant progress, objectivity and change management is essential to your future as an entrepreneur and leader.


Here are 5 core reasons you should always aim for failure:

1.  Negativity Doesn’t Exist.

When you are focused on one single outcome being the only acceptable outcome (i.e. winning) you surround yourself with a lot of negativity. The reason for this is pressure. You know that so many things have to go right for you to win that one false move could set you back or make you fail. It creates an environment of negativity, of a need to have a very controlling work environment, and to be incredibly strict with particular deadlines and outcomes expected from teams. This creates a very competitive and hostile work environment which often leads to instability in your teams because people do not thrive or find happiness in places where they are constantly monitored and evaluated. Frankly, it is unnatural for humans to work that way, but still today it is how we think about winning. Winning is achieved through control.

When failure is an option the pressure is off for everyone involved. Which means that the time spent reporting to team members how they haven’t performed well enough can be spent on building empathy and trying to understand your business through the eyes of those engaging with it daily. There is no need for negativity because everyone is trying their best. And if you feel they aren’t, you can talk to them and learn to understand, without feelings like time is being wasted by having a conversation with someone you work with daily.

2.  You Can Expect Things Not To Go The Way You Want

Things change. Things go wrong. Sometimes nothing goes wrong internally, but externally it goes very wrong (think a badly received PR campaign). When you accept that things won’t go as planned it means you can build the kind of company culture that is agile and can shift at a moment’s notice. There is more room for creativity and more meaningful collaboration because the focus is on relationships. Both relationships internally as well as the company’s relationship with its mission, both can change at any time, it is expected, and therefor systems exist where those sudden changes can be gently managed and nurtured rather than ignored or made to feel irrelevant to the bottom line.

It is incredibly difficult to problem solve in a controlled environment, because you are focused more on the likelihood of your idea being rejected, rather than the rest of the company feeling relieved and excited about your idea solving the problem everyone is feeling. When failure is okay, it means bad ideas are welcome, and sometimes the best way to find good ideas is to start with bad ones – but for that to happen, people need to feel okay being vulnerable and sharing ideas that might not be obviously a winner.

3.  Your Dreams Get To Be Humongous

Our big achievements as people have been achieved by people who, if you asked them, most likely will tell you that they never thought it would happen. Airplanes. Landing on the moon. They didn’t know it was possible, let alone had any certainty of winning. Why could they achieve it? Because when you dream is so big that it seems impossible, if you get the right minds together, the attempt alone is incredible. To try is such a privilege because it is your dream. To even get close would mean such a huge step forward that any progress is worthwhile.

Certainty is possible, but only when your dream is tiny. And you have to pay people a lot of money to care about a small dream and show up at work every day. When your dream is huge, almost impossible, people will sacrifice a lot to be a part of it. So set your goals, then double it, then triple it. That way even when you don’t quite get there, you are further than you would’ve been had you settled for your first goal.

4.  Everyone Fails Together

Who is the team we love more: the team who we know will win, or the team who shouldn’t even be in the final? We will choose the underdog every single time because of one simple thing: the story. A life well lived is a life of adventure, going against the odds, making it happen because you believed in it. We all want to feel like a hero in some way, and that’s impossible if winning isn’t assumed as the only option.

When everyone knows they can fail, they also know that it is something that they will fail in together. It is why the film “300” was so popular. We believed in them because they were outnumbered, it seemed impossible. Imagine the power and conviction of any group that stands together regardless of the possibility of failure? Wouldn’t you want to be part of that?


5.  We Accept Our Weaknesses

When you only think about winning you very rarely think of reasons why you won’t, because doubt is the opposite of certainty. To want to win means you are blind to your weaknesses, which only means you are unlikely to grow any stronger.

When the possibility of failure is accepted, so are our weaknesses. We are able to inspect ourselves and our teams, to better understand how things could be even better. In other words: to accept failure is to be humble and to be hungry for improvement at all times. Improvement is impossible without accepting weakness, and in a company talking about weaknesses and struggles of team members only strengthens the whole.


When our goals are larger than life, and our teams are growing stronger and closer to each other daily, failure becomes irrelevant, because progress is constant. The focus for everyone is on something they all believe in, whether they trust that it is possible or not, and every day they get closer to something that is seemingly impossible. All that failure means is that there is more work to be done.

The truth is that failure is not the opposite of winning, because failure is not losing. Failure is when you haven’t reached your ultimate goal. Losing is when you are no longer are welcome to try.


Post Author: First365