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I would like to share some of my experiences in Failing Upward, my personal philosophy. It is defined by a relentless positivity and continually making lemonade out of lemons. If I am going to fail or lose or get hurt or even get fired from a job I will do so while ending up with personal gain. I do not need to lose entirely or even at all when I lose.

I ask myself “if I lose a competition did I really lose? If I came in last place, but had a fantastic experience and gained many positives from the experience did I truly lose?”

One of my favorite examples of Failing Upward is the times in my life when I left my jobs. Each time I was stuck or at best content at jobs that were dead-end and I received no personal enrichment from. They did not afford a good work-life balance, the pay was mediocre for the time investment, and I did not feel supported or fulfilled any longer if at all. I got to a point where I knew I should find something else, but I was too tired from working unhappily for so many hours and too burnt out when I was off to go find something else.

Then I quit or got fired and had time to reconnect with my wife who I had brought my stresses home to for too long. Although she worried that we may not make our bills or that I would not find work she supported me. I relaxed and thought about the skills I had acquired and my experiences and tried to find work I wanted to do at places that sounded interesting.

At interviews I improved with practice. I would assess how I did and whether it went well or awful. I would take a look at the positive and brought that to the next interview. As for the negatives I did my best to not repeat the same mistakes twice.

When the offers came in I got better each time at negotiating pay. Each time I ended up at higher paying and better quality jobs. I never settled for lateral or less. This was not just to be a statement of compensation. I would look for work where I would learn valuable life skills. I also put energy into looking for something I really wanted to do. Ironically I did get paid better each time. Now I am at a job where it’s not perfect, but I am happy and I am blessed with a better balance of work and family time then I have ever enjoyed before.

I failed at those old jobs by becoming complacent. I failed by not setting appropriate boundaries. In the end I just failed. Not strangely I always ended up better off and heading upward.

Another place I employ my Failing Upwards is my martial arts school in Boulder Colorado. It is a full contact Chinese Kung Fu academy where we punch and kick and block with martial intent. One of the goals is if we are ever in a situation where we need to defend ourselves that we we will end the conflict as quickly as possible. We do partner exercises where we condition or arms and legs while learning precision and speed striking and blocks. Often it hurts and very often I get punched in the face.

When I started out sparring in the school I had had minimal prior combat experience in my life. When working out with my fellow students I would become quickly exposed by my lack of defense. I held an uncertainty and unwillingness to enter an opponent’s striking range. I would duck and leave my head exposed. I would back down and away instead of moving forward. Sometimes I would just drop my guard and get punched in the lip or the cheek. I was afraid to get hit because it hurt and I was soft. The punches stunned and sometimes bloodied me. There was no way I would win a fight for my life if I couldn’t even penetrate my training partners’ guards or take a punch.

I kept at it. I practiced and found opportunities to drill my weaknesses. I learned to move forward. I learned that I would have to take damage sometimes to gain an opportunity to land my own strike. I learned to be confident and relaxed. Most importantly I learned that getting hit didn’t hurt that bad. I could tolerate it and I could probably take a lot more hits than I thought I could.

Today I still get my tail whipped in almost every sparring and drill session, but I have improved and feel like I will be more prepared if I ever need to defend myself or my family or friends from a physical attack. The months of failure and exhaustion and embarrassment have laid the foundation for the structure I have built in my physical capability. This reminds me of so many ways that I have failed or I have seen failures lead to more, and to greatness.

It is common cliche that practice makes perfect and although my kung fu teacher, Shifu Howie would have a lesson for anyone who says that, there is definitely a semblance of wisdom in the statement. Practice definitively makes us better because we fail repeatedly and then learn from our mistakes to become more proficient in whatever skill or activity we have been practicing.

Think about anything you do regularly. When you start running usually you just need to strengthen and rest your muscles and joints and learn to breath with your pace and breath enough that you are actually taking oxygen into your lungs. Even a half or full mile may be difficult to run through when just stating out. When I started running to aid in becoming fit you may have seen me huffing and grabbing my knees after even a short run. After becoming proficient in these tasks they become automatic. You can graduate to deeper breathing and adjusting your footwork and how your hold your arms. Then you can monitor your pace and heart rate to look for additional gains. The early failures are necessary to teach us and to build up the running habit. These failures allow you to run distances and extended lengths of time later. Without those sore legs there is no gain in the end.

Making a sale is similar. I have an ice pop business. At first I bring a box of ice pops and stand on the corner near where you hang out. You come up to me and ask to buy an ice pop. I tell you it’s fifty dollars. You politely ask me if there are gold flakes in the ice pop and laugh and begin to walk on. I prevent you from leaving yet by telling you I was just kidding and that my pops are made with organic strawberries and mountain spring water. I made them all myself with love. I ask for five dollars and although you know that’s a lot for an ice pop it sure is hot outside and an organic strawberry spring water ice pop sure sounds good right now. I take your five dollars and hand you the ice pop in wrapper. You tear into the wrapper and all this pink juice pours out and all that’s left is the popsicle stick and the spilled juice all over your sneakers. I sure hope we all learned something to be better business owners and consumers after this incident.

The thing about creating strength from failure is you have to become stronger from weakness and failure. It is possible that you will develop scar tissue and not want to hit those huge snowboard jumps or talk to members of the opposite sex after you’ve failed. However if you learn something from failing on a jump or striking out with a hottie you will improve your odds of success on the next attempt. Primally just practicing will make you better. Moreover insight toward what went wrong and preparing for your next opportunity with planning may produce better results. It may produce another failure as well, but hopefully a better failure.

Even right now as I prepare this blog post I recognize it may not get views or worse yet it may just be truly bad writing. So what? I’m bettering my writing ability and exercising my creativity. If this post is horrible I can only go up from here.

It’s in the attitude and the actions. Fake it and fake it and fake it and eventually you’ll get it and make it. Fail and fail and fail in epic proportions and learn something and experience other things. You may not even achieve the originally intended results, but you will grow and make yourself more valuable and more skilled and hopefully and all around better person.


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  • […] habits and introduced new more positive ones (see: The Dichotomy of Habits). We have learned to use defeat to find strength. We have reduced wasted time in our personal lives to improve the quality of our free non-work time […]