Best Year Ever: Fail Well, Fail Often

A road from driver's perspective with blue sky and  clouds
The fastest way to succeed is to double your failure rate.
— Thomas Watson Sr.

Years ago I worked at a lively startup where one of the younger executives loved to run around proclaiming, "Failure is not an option."

At the time I was impressionable enough to wonder: "Is he right?" Was he right to hold such a narrow margin for failure? Because I thought failure was TOTALLY an option, and I was also OK with the chance that the company I was working for might possible NOT take off. That's the risk of start-ups. Still, I was hopeful and working hard and excited about the opportunity the job gave me to manage a team and be an executive decision-maker for the first time in my life. That's HUGE. Was there something wrong with me that I was OK with failure? In the end, the company did fail, but I considered the experience a huge success because the challenge invited me to learn and grow more than I could have imagined.

Can you imagine if Thomas Edison didn't allow himself 1,000 failures to get him to the light bulb? (Edison called it "1,000 steps to create the light bulb.").  We could list endless famous failures here that turned into world transforming triumphs.

So how can you fail well and often this year to achieve your big bold beautiful goals?

1. Choose failures that you learn from and move you forward.

2. When you fail--i.e., the outcome doesn't meet your expectation--have your own back. Be kind to yourself, be your biggest fan and move on. 


What is "choosing a failure"? It's choosing an action, approach, experiment, connection or creation that represents you putting yourself out in the field of what you want to achieve for yourself. You might start with a list of everything you plan to do over a period of time--a month, six weeks, a quarter, half a year, your call. Make a list. If you're starting a business it could be a list of businesses or people you will reach out to. An online class you'll offer. A talk you'll offer. If you work at a company and would like to move into management, it could be a list of actions that bring you closer to a leadership position: a conversation with your boss; taking initiative on a project; organizing a brown bag.

Lean forward into these actions, and ALLOW YOURSELF TO FAIL. Maybe you reach out to businesses and the first ten don't give you the return you hoped for. Find another tactic for the next ten. If that doesn't pan out quite the same, keep refining the way you reach out. What's important is that you DON'T GIVE UP. If you're the one looking for a promotion into a management position, and the boss turns you down, keep trying new approaches. Take on a fresh project, approach it from a new POV, see how you can continue to make a difference.

This is important: Failing well is NOT self sabotaging. For example, showing up for a presentation poorly prepared and ten minutes late. Self-sabotaging failures in which you don't take action or go immediately to failure is you swimming in place, indulging in "can't do." Assigning yourself an activity you then don't show up for is passive failing. These are not advancing failures.

Only those who dare to fail greatly can achieve greatly.
— Robert F. Kennedy


Remember what a failure is: Activity that falls short of an expectation. An unrealized goal. Don't make it mean more than it is. Failure is not personal. The falling-short didn't happen TO you or AT you. It just happened. Keep your mind moving forward and filled with curiosity. Have a look at this so-called "failure" (remember, Thomas Edison called each failure a "step"); learn from each failure and then keep going. Tweak. Take a jump to the left, shake a tail to the right. Don't give up. Don't rip yourself a new a**hole. Keep going, keep experimenting, keep PLAYING.


One of the worst things we do when we fail, is we become real jerks to ourselves. I do it, do you? The inner dialogue, OMG it's fiery and vicious. It's enough to make a person never set out on a bold creative path again. But then life would be boring--and stagnation is not a good option. So when you're setting out on your path, and you have a list of activities that you are willing to complete to success OR failure, and then you have a failure--or a step--then be kind to yourself. Give yourself a pep talk, or at least cut out the mean language. Don't indulge in feeling bad or sorry or embarrassed. And keep going!

There's only one thing to say to yourself when you're going through your list of possible advancing failures. When you do strike out, sit back, reflect, see the next opportunity for refinement and then simply say:



You have bold soulful visions for your life. You have the best intentions to manifest them . . . but then, life gets in the way. Is it life, or something else? The Crazy Good Coaching mastermind is a full-hearted adventure into creating exciting shifts so that this year—yes, THIS YEAR—is when those long-held desires become a reality.

Recognize the power of thought and how to use it to transform relationships, love your work and create the best year of your life.

Have the best year of your life, and do it in the supportive community of like-minded women.