The Transformative Leader's Guide to The Art of Failing

Photo by  Jason Wong  on  Unsplash

Photo by Jason Wong on Unsplash

There is no doubt that for every successful endeavor ever achieved, there were many, many more attempts that resulted in failure. This isn’t something that is immediately obvious, because of the fact that only successes stand the test of time, while failures, being nothing more than successes that never came about, are more or less invisible in the eyes of history. Although in hindsight, it seems clear what would work and what wouldn’t, nothing and no one has ever been instantly successful; every success was preceded by a series of slightly less catastrophic failures. Ultimately, success belonged to those who persevered despite those failures. Those of us who don’t seem to give failure a second thought—the Branson’s, Musk’s, and Blakely’s of the world—appear to focus only on what they are out to achieve, and relentlessly deal with whatever comes their way until they achieve it. Like Transformative Leaders, they refuse to use failure as an excuse to give up.

So, since we know that failing is essential to achieving success, I’d like to offer 12 tips to plan for and deal with failures, based on the principles in my book, The Transformative Leader. My intention is to empower you to not only endure the pain of failure along your journey, but to use it as a springboard to bolster your efforts and accelerate your progress toward your goal.

You will never achieve any breakthroughs if you avoid breakdowns at all cost.

1.       Predict your failures to proactively identify and prevent the drama associated with them. One of the problems that exacerbates the negative effect of failures is that we are all hoping nothing bad happens, which is kind of like hoping that we will never have to pay taxes or that we will live forever.  When something bad inevitably does happen, we negatively overreact to it, and in doing so, impair our ability to do what it takes to actually solve the problem. Then, on top of that, we try to make sense of things and put the pieces back together in the heat of the moment, which rarely works out. That’s kind of like never paying any attention to the possibility that there may be a fire in any given building, acting surprised when it happens, and then trying to figure out what needs to be done as the fire rages. What if we predicted some of the possible worst-case scenarios, before they happened, and discussed how we would deal with them as a team? There’s no need to go overboard with the risk management though. You will never be able to predict every scenario. But if you only predict a few and begin to make some plans, you will likely end up with the habit of applying the principles you develop through the process to other scenarios as well.

2.       Set a target for the number of times you are prepared to fail before you get started on any transformative endeavor. If you are going for something big, you won’t necessarily know how to achieve it. That means that any transformation will necessarily involve failure. Rather than hoping you don’t experience any setbacks, ask yourself how many times you are willing to fail before you decide to take a different approach or create a new initiative. Set a target and then, every time you consider yourself to have failed, say “one down, X more to go!”

3.       Bake failures into your success criteria. One of the major inhibitors of innovation is that, although companies always have the right slogans on the walls that say things like, “Be bold! Try new things!” the only thing that people see and hear are the subtle yet powerful signals from leadership that imply, “Be bold…but don’t screw up!” If you are in the business of developing the next generation of a concept, material, or process that is going to be a game changer, this fear of failure can kill innovation. The solution is to put it in the project criteria that you will have X number of promising ideas that simply may not work, and when a failure happens, celebrate it just like any other milestone. By baking failures into the success criteria, you give people license to go for something big, knowing that they could either hit the mark and have a winning idea, or hit the mark by “thinning the herd” of possible ideas and making it easier to find a winning one in the future.

4.       Identify the people, or the community, that will help you get back in the saddle after a setback. Part of preparing yourself for failures is setting up a structure for restoring integrity when you are out of it. Be deliberate about picking the people you are going to go to for counsel when failure happens. Pick them wisely and ahead of time, and exercise the discipline to seek them out. If you don’t do this, you will end up talking to anyone who is willing to listen and you might even gravitate toward people who will only commiserate with you, rather than those who might encourage you to get back in action to remedy the situation.

5.       Don’t keep your failure to yourself. Publicize it so it won’t be your little secret. Keeping your failures secret is what causes them to morph into shame, and then that shame holds power over you from that point forward. Being ashamed of our failures, by thinking that they mean something is wrong with us, rather than accepting them as necessary stepping stones to success, is the main reason why most of us fear failure so much. However, the only ones of us who will never fail are those who never aim for anything big, and never end up accomplishing anything worthwhile. There is no shame then, in admitting that you fell off the wagon and making a commitment to get back on track. Hold your head up high and demonstrate your courage to publicly admit that you had a setback and you are still committed to your cause. That way you can let go of the pretense that everything is perfect, and actually focus on doing what you need to do. This will also liberate others in your community to give up their fear of failure and go for something big!

6.       Reflect on past failures and dwell on the lessons you learned that may not have been obvious at the time. Don’t start with the most recent failures you have had because you may not have had enough time to let the emotions of the experience subside to be able to clearly see the benefits and lessons you got from them. Think back to failures or setbacks in your past and think about the growth you experienced as a result, or the doors that were ultimately opened because one door was closed. Dwell on the positive outcomes and condition yourself to look for the positive effects of any failure or setbacks that may occur in the future.

Unless you learn to fail, you will fail to learn.

7.       Practice taking responsibility without self-condemnation. There is a sweet spot that you need to find, where you can be fully responsible for learning what to do differently to avoid this same failure in the future, and also, not condemn yourself not knowing what you didn’t know in the past. Realize that, if you had known better, you wouldn’t have made the mistake, and if you hadn’t made the mistake, then you wouldn’t know any better right now. You aren’t responsible for what you didn’t know, but you are responsible for putting what you now know into practice. Condemning yourself for past mistakes does not help you prevent future ones, so give it up because it isn’t necessary. The more you practice this, the more likely you are to powerfully take responsibility and harvest learnings for the future without making yourself and others wrong for what happened, which will supercharge your ability to effectively deal with setbacks without baggage or drama.

8.       Learn to separate fact from fiction. Bring the learnings from your failures with you, but leave behind the stories you made up about them in the heat of the moment. The best way to do this is to say and do what you need to in order to truly be okay with what happened and put it behind you. A helpful way to remember the difference between fact and fiction in your personal experience is this: whatever happened is what’s real, most of what you tell yourself about what happened is a story.

9.       Deliberately choose whether you are going to be in the passion zone or the drama zone. Passion and drama are both fueled by our strong desire for a desired future, but the thoughts, emotions, and the behaviors we experience and exhibit are completely different when we are expressing our passion or experiencing drama. Choose deliberately to keep the passion and ditch the drama. For more on this, read One Point Lesson #11 on page 139 of my book.

10.   Be grateful for what’s going right. Gratitude is the best way to shift your focus toward a positive outcome. While the thoughts in your head may be all about what went wrong, open your mouth and speak out loud (to yourself or a friend) about what is going well and what you are grateful for. Always keep in mind that things could be worse, sometimes in ways we can’t even appreciate, because of how lucky we have been in life.

11.   Get centered on the greater purpose behind the cause that you are committed to.  Shift your focus from the immediate situation at hand to the big picture. What inspires you about achieving what you are committed to? Why is it important that it be achieved? Who would it benefit for it to be achieved successfully? Consider these questions and their answers, and then, get in action on the very next step you should take to make the desired outcome a reality.

12.   Take failure as a sign that you’re up to something big. Those who never fail are not trying to achieve anything worthwhile. Acknowledge that you are pushing the limits of your comfort and abilities, and celebrate that because that’s the only way you will ever grow!

My hope for you is that you go over this list and identify 1-2 items at a time and focus on them until you master them, rather than relating to this list as a bunch of theory that doesn't apply to you because your situation is unique. Everybody's situation is different but in all those different circumstances, what is the same is that those who learn to capitalize on their failures, tend to succeed.

Further Reading: Richard Branson's Top 10 Quotes on Failure

I have failed over and over, and that’s why I succeed.
— Michael Jordan

As always, have a great week! May you Boldly Declare, Courageously Pursue, and Abundantly Achieve the Extraordinary! I would love to hear about your victories and/or challenges. Please leave your comments below or send me an email at

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