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Three Ways I Hope to Fail in 2020

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To fail is distressing - Woman distressed from failure (black and white)

Most people avoid failure for a variety of reasons, but in this coming year, I hope to fail in a few big ways.

Failure #1: Not Playing It Safe

Take a poll of your professional circle and ask how many people are willing to go to the limits and beyond in their professional careers. Chances are you’ll find most people unwilling to push the limits. Most of your colleagues are content to keep the status quo; to not make waves; to not find and exceed their professional boundaries.

I am not content in that safe place. No one ever changed the world by staying within the boundaries set by the women and men before them. I hope to fail at what many others work so hard to avoid: staying safe.

A safe is for your jewels and important papers, not your career.

I get a lot of advice that to be successful, I need to play it safe. That is an easy definition of “winning” for most people. Safe might work in the early stages of one’s career. Learn the game. Follow the “rules.” Walk the path and follow the advice of the accomplished colleagues in my industry.

This year, however, I hope to fail in playing it safe. I want to take risks. I want to push boundaries. I want to explore the far-out edges of the known universe of our (professional) world. I want to find out for myself just exactly how capable I am and what the real boundaries are. Until you really push yourself, how do you really know you can’t go further?

Failure #2: Set Unrealistic Goals

Go out there and read any personal productivity blog or self-improvement book that deals with goals. Every one of them says to set realistic goals. “What is the purpose of setting a goal that is not achievable?” they say. Setting unrealistic goals is literally setting yourself up for failure.

Have you ever heard about S.M.A.R.T. goals? Specific, Measurable, ATTAINABLE, Relevant, and Time-bound. If you’re setting S.M.A.R.T. goals, it is built into the model that you reduce your goals to something that is actually attainable within the frame of possibility and time constraints.

And yet… S.M.A.R.T. goals are reduced. Limited. Held back. Minimized. S.M.A.R.T. goals are great— in a certain framed mindset. But for me, for this year ahead… I plan to set H.A.R.D. goals.

Easy races don’t prove your strength or endurance, just as easy goals don’t show the limits of your capability.

For the uninitiated, H.A.R.D. is another acronym for goals that stands for Heartfelt, Animated, Required, and Difficult. I won’t break down the definitions of each of these items (you can read up on a great explanation here), but I will say that the one I will focus on is Difficult.

“Attainable” is lowering the difficulty, which might be fine for some who need or want the win. But I want to fail. I want to set a difficult goal and push myself to try to get there, but still have the goal so difficult and just out of reach that I still fail. Why? Because the growth and exploration of my real boundaries are in that space between where I fall short and the finish line. If you set an “Attainable” goal, you’ll never know where that last ounce of energy you have will place you because you moved the goalpost back to a zone you know you could win with.

Failure #3: Missing Opportunities

Oprah’s definition of luck is preparation meeting the moment of opportunity. It is certainly an inspirational quote and one I find very motivating to continuously push myself to learn more and hone my skills and experience. One day, if I am prepared enough, I will be ready for a moment of opportunity— something many might call a lucky chance.

But in 2020, I’m going to fail at some of those opportunities. I want to fail— to miss some opportunities (maybe a few or heck, maybe many). For this year, I want to be fixated intensely on the preparation part of Oprah’s formula. I want so much focus on leveling up my expertise that I miss early opportunities that may match a lower level of skill. 

Opportunities come-a-plenty, if you’re paying attention. Most are minor improvements matched with low skill levels, meaning you can be slightly lucky a lot of the time. For me, for this year— I want that end-of-the-rainbow, just-hit-the-jackpot kind of “luck”. I want to put my head down, focus on the Deep Work (as described by Cal Newport in his 2016 book), and really sharpen my skills to be ready for the not often occurring high-level opportunity that comes along.

The F-Word Isn’t That Bad

Many times and for many people, the idea of failure is terrifying and demotivating. Fear of failure holds a lot of people back because of the fear of long term or permanent damage. I contend that it also holds people back from iterative levels of success.

I’ve shared a few ways I actually hope to fail this year— which is quite a liberating exercise. True, the ways I hope to fail aren’t as devastating as making an honest mistake with large financial ramifications or anything self-destructive. Instead, I have reframed a few commonly accepted “safe zones” that many professionals find themselves in— warm and cozy and safe… and rarely finding satisfying success.

If you have begun to think a little differently on this topic, tell me— what ways might you consider failing this year? Which parts of your professional life are you staying in a “safe zone” that may not serve you as well as you might assume?

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