Dealing with Fear of Failure: Let’s Resolve to Be Gentle with Ourselves

In her blog, leadership coach Lolly Daskai asks, “What would happen if we didn’t run [from fear]?” She proposes we expose it, face it, dissect it, and lean into it — kind of a no pain, no gain approach.  (Read her whole blog post here….) She concludes: “When fear stops scaring us it will not stick around.” This works great, especially with the smaller anxieties that nip at our heels and hold us back.
Today, I’m going to riff on her excellent ideas — applying my Storyweaving approach to the processes she suggests to “get to know your fears.”
Where the brain feels fear. To find out more, check out "How Stuff Works..."

Where the brain feels fear. To find out more, check out “How Stuff Works…

“No pain, no gain” works for most people, at least with very specific fears we can confront, shrink and banish. The pain is almost always less than than relief after our fear passes. For example, fear of driving on a highway — facing it by practicing highway driving really does make the fear go away, because reality is almost always less more tediously stop-and-go than the horrible accidents we imagine. Or fear of public speaking, (as long as it’s not an entrenched phobia).  Practice increases comfort, 90% of the time, because we change our story and our brain chemistry in the process.

Sometimes we just need to get tough with ourselves, and push outside our comfort zones. Courageous thinking and self-motivated reflection are tools every leader should have. Developing a tough habit of confronting our fears does make us better leaders because it’s easier to cope with crisis.  And fear does cringe away when we understand and face it — after all, our fears are stories we tell ourselves about futures that might — again, might — happen.

On the other hand, getting tough about our fears means we might toughen up in ways that push our fears into the shadow. The big fears don’t entirely disappear when we stare them down or dissect them — they just change form, attach to different stories. True fearlessness means being able to live with fear until we can change the story, not just beat fear back until it pops up again, stronger than ever.

Take our recurring fear of failure, for example. In our twenties, we are afraid of failing because we’re new at the game. In our fifties, we’re afraid of failing because we’ve been at it too long, may not find a fresh or impressive solution. Different situation, same fear. Until we understand the roots of the anxiety, we can’t change the emotional plot.  Toughness isn’t necessarily the best tool for these moments.

So how do we overcome these normal, recurring, resilient fears? What tools transform the fear of failure into effective leadership practices?

Like Daskai, I encourage my clients to face, dissect and lean into fear of failure. After all, experience teaches us that risk (and healthy failure) are a learning process. When we step up, most failures are minor problems. This is a good skill to have.

But these big fears don’t just disappear. For some of us, it may seem like a paradox, but it’s most important to practice LOVE, a key leadership skill to create a sustainable strategy.

1. Love the fear. Feel it, expand it, let it have all the space it needs. Trust me, the bigger it gets, the less power it will have, and the more insight you’ll have into the story it’s attached to. (Make sure to give yourself a private time and place to do this process. You may also want to have support — a friend, a coach, a therapist — to keep you steady!)
2. When you can expand your fear, you can really figure out what kind of failure feels most like doom, and name it. (Journaling, drawing, dancing, talking — any way you can get to the heart of the matter.) This process has to be gentle. It’s not about dissection. You don’t want to kill the fear, just understand it. Your dreaded failure will not look anything like mine. And, I promise, once you see the whole story, it won’t feel so scary. It will feel like — well, a story.
3. Then, you can change the story (which reduces the fear, and prevents it from going underground in the same moment.) Say your definition of failure is “looking like a fool,” and that means being “wrong” or “getting too much attention.” Ask yourself, “Is there any time when it would be good to be “foolish?” Start practicing healthy foolishness. Speculate when the stakes are low. Dance ridiculously at a party. Whatever. The fear will soften and fade, because you’ve taken its power away by gently living a healthy version of the story that once made you scared.

For leaders and courageous followers, loving our own fear also means having more compassion for people who struggle with anxiety and fear. “No pain, no gain” may work for you, for most of your fears, but those habits can create a hard shell that gets in the way of empathy.  The more ways we know to deal with fear, the more effective we can be supporting ourselves and others.

So, resolve to face your fears — with courage, with love and with an eye to the stories they’re telling.

With thanks to Lolly Daskai, for a thought-provoking blog, very pertinent to the New Year’s Resolution season!


  1. What a fantastic article and an honor to be mentioned.



    1. Thanks, Lolly! I always enjoy your posts! Happy New Year, and thanks again.


  2. Really, really useful. Thanks.



    1. Thank you so much! Coming from someone creative and brave and so strong, that means a lot!


  3. Love that you nailed something important here: distiction between the fear to be pushed through, and the fear to be respected. For those of us with PTSD there are places that need a more unraveling approach, where JUST DO IT is counter productive.


    1. Yes! Even for people without PTSD or extreme trauma, “Just Do It” is often a very frustrating dead end. Iʻve only been able to “just do it” when Iʻm facing a small fear that I can easily break down into steps. Big stuff, visceral fears, deep anxieties — the steps we need to take have to deal with the physical/emotional anxiety, as well as changing the habitual thoughts and habits resulting from the fear. Itʻs a larger process.


  4. […] leader struggles to distinguish between ego identity and authenticity, co-dependency and compassion, failure and growth, and many other seeming paradoxes. This question about fear, its benefits and […]


  5. This is a very useful post — especially the idea that we need to “lean into” our fear, to take a good hard look at it. I also like the idea that “fears are stories we tell ourselves about futures that might or might not happen.” The real take-away is that we need to learn to live with our fears rather than running away from them.


    1. Thanks so much! We absolutely need to live with our fears as something giving us information, something useful to inform us that we’re either at the learning edge of our lives and leadership, or we’re about to move into territory that needs more than casual care and attention. It is particularly difficult for people who suffer from anxiety, PTSD, or sensitivity to learn to tolerate fear, but everyone has a challenge in this culture where we celebrate courage but create heroes who push through fear as if it were an obstacle, not something we need to pay attention to, adapt with, learn from. It’s a balance, isn’t it? We can’t let fear become the dominant guidepost of our work but we can’t ignore it as a marker of something (potentially) important….


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