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How often are you in over your head?

Today is November 28 and the Navigate the Chaos question to consider is “how often are you in over your head?” American writer and comedian Elna Baker wrote “Impossible is just a big word thrown around by small men who find it easier to live in the world they’ve been given than to explore the power they have to change it. Impossible is not a fact. It’s an opinion. Impossible is not a declaration. It’s a dare. Impossible is potential. Impossible is temporary.”


If you want to navigate the chaos and translate one dream after another into reality you will need to come to an understanding with the word impossible. What is your current relationship with impossible? How often do you even think about your relationship with impossible? Have you often wondered how someone accomplished something you thought impossible? One such strategy people use to achieve the impossible is to be in over your head. Today’s reflection involves three different components of being in over your head: remain fearless, buy time, and pushing yourself further than you ever thought possible.


The first example of remaining fearless comes from a woman entrepreneur. In a 2017 interview with Amelia Diamond published in “It’s Never Too Late: 3 Women on Second Chances and Changing Careers,” Polly Rodriguez, Chief Executive Officer, and founder of Unbound said: “Be relentless and fearless about learning as much as you can. To be a successful entrepreneur, you have to enjoy constantly being in over your head. There is this sweet spot between, “I GOT THIS!!!” and “…Holy shit, I’m gonna barf” that you live in every single day. You also have to be obsessed with getting feedback from people who will tell you the truth. For Unbound, I got my friends who had never owned one of our products before to try one. Every single person was obsessed with the products after they used them, and that was how I knew we were onto something. I also think that, sometimes, you can just feel it in your bones. I could so clearly see what Unbound was destined to become and how it could be so much more than just selling products, but really giving women a sense of entitlement to enjoy their bodies.” When you are in over your head and fearless you can move confidently in the direction of your dreams.


Sometimes, when you are in over your head it helps to buy time in order to give yourself space to figure out your next step. According to legend, when a king sentenced a man to death the man told the king he could teach a horse to fly in two years’ time. The king granted him permission. Hearing of this the man’s family thought him insane. “Don’t worry,” he told his family. “First, no one has ever tried to teach a horse to fly, and the horse might well learn. Secondly, the king is already old, and he might die. Thirdly, the horse might die and then I will be given another two years to teach the new horse. And even if everything remains exactly as it is, I will still have gained two years of life.”


So, yes, telling the king that he could teach a horse to fly placed the man in a situation where he was in over his head. But he relied on a strategy that would allow him to buy time. For some people who navigate the chaos, being constantly in over their head is the preferred way to go through life.


The third example of being in over your head involves pushing yourself further than you thought possible. For example, financial planner and author Carl Richards noted in a September 25, 2017, New York Times piece “I’ve learned to prefer being in over my head. It is definitely scary; that never changes. But it also forces me to perform in ways that the shallow end never does. I go from thinking I am capable of ‘X’ to very quickly performing twice or three times that amount — and sometimes even 10x. Think of being in over your head as a little magic box. In one side goes the old you and out the other side comes a 2x or 10x version of yourself. Wouldn’t you buy a box like that if you could? The truth is you don’t have to buy anything. All you have to do is confront your fears and dive in deep.”


In an Inc. article Jessica Stillman, noted the value of ambition and the likely inevitability of getting in over your head. According to Stillman “ambition is all about pushing yourself beyond your perceived limits. If you’re not taking on reach goals and slightly terrifying challenges than you’re unlikely to reach your full potential. Which all sounds good in theory, but there’s a little discussed byproduct of this can-do attitude. Sometimes you’re going to get in over your head -- way over.”

  • How often are you in over your head?

  • What is your current relationship with the word impossible?

  • How often do you even think about doing the impossible?

  • Do you know anyone who ever did something you thought impossible?

  • Has it ever occurred to you that you may have accomplished something someone else thought was impossible?

  • Who or what is stopping you from getting in over your head?

  • If you are not getting in over your head, what are you afraid of?

  • How ambitious are you?

  • Are you willing to get ‘in way over your head?’


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