How to Win at Failing | Handel Group

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How to Win at Failing

There are lots of things in my life at which I am winning. But lately I’ve been re-assessing a bunch of business practices that haven’t been working. I’ve had to face failure in a way I never have before. In the past, I’ve been really good at avoiding situations where I might fail by bailing out before I actually failed. In many ways, I’ve also altogether avoided things I could fail at. I now see that this has been unwise, because the people who make the biggest dreams come true, and the people I find to be the happiest, are people who have failed in big ways. Recently, I’ve been reminded of organizations that are 50M in the red, universities that sent out accidental acceptance letters to the people they meant to reject, and countless other examples of “temporary defeat” experienced by the people I most admire. These people pick themselves up and continue to be willing to try again and fail again. They treat failure with respect.

But for some reason, I think I should be different. I shouldn’t have to deal with failure. I should be above that. Ha!

My ego has not wanted to accept failure as a natural part of growing, learning and facing what doesn’t work about me. I have wanted the lessons without having to do the work. The problem is, there is no other way to get my next spiritual lesson. This reminds me of the process of child birth. You need to go through an intense process to get the results you want. And you can either choose to relax and trust that it will all turn out fine, or choose to be afraid and anxious.

In my times of intense challenge and failure, I have sometimes been the enlightened visionary, and sometimes been scared and anxious. I am going to share with you the pitfalls I’ve run into so hopefully you can avoid your own.


When you are failing, it is natural to want to avoid admitting it. It’s embarrassing. Usually, whatever it looks like on the surface is only the first of many layers and if you dig deeper, you may find that you were lying, hiding, or blowing off something for a long time. The sooner you can understand and tell the truth about all of the layers, the better you will feel. I recommend that you actually actively hunt for things that aren’t working, and tell the truth about them, so you find them before they bite you on their own.


Often what freaks us out so much about failure is the impact we imagine it will have on another person. The thing is, we often are wrong about the impact it will have on that person. Truly, we don’t know what the person has up their own sleeve. I can’t even count the amount of times clients have thought they were going to disappoint someone, only to find that their “news” was exactly what the other person wanted to hear. Don’t underestimate people’s ability to handle what you are up against, and help and support you.


A shift in attitude and vibe makes all the difference. It may seem crazy to ask you to be happy when dealing with your failures, but I am. Why not? That’s what you’d want for your friends and family, isn’t it? You are going to deal either way, you might as well enjoy the ride. Beware if you go into manic mode: most likely you need a good cry and to remember why you care about the goal to begin with. Ahhh, now there’s your heart again.


There is always a spiritual lesson to be learned through failure. Failure means you did not align yourself fully with your dream. Something was obstructing your ability to believe. Most likely it’s a set of beliefs or a character trait you have. If you don’t understand that beast and how it plays out in you, you may have to keep learning the same lesson over and over. So take a chance to reflect and ask what this situation might be able to teach you? You can eliminate these answers:

  • My goal was wrong.
  • I should stop trying.
  • It’s not possible.
  • There is something wrong with me.

The right lessons usually have to do with digging deeper into designing who you want to be and how you want to be. What sacred work that is.

Most of us are failing at something. What’s yours? Which pitfall above have you been falling into? If there are others I didn’t think of, let us know.


P.S.- Want more help avoiding these pitfalls and others, register for one of our Design Your Life Weekends.