The Art Of Screwing Up


I was enjoying breakfast with my good friend, Danny O’Brien, recently, when our conversation moved to the topic of screwing up, making mistakes and the steps we take thereafter.  Danny said, “The quality of our lives is not determined by whether or not we screw up—because we all will.”

“No, the quality of our lives is determined by what happens next.  Will we hide or come clean?  Will we make excuses and search for justification or take responsibility, even if it means receiving consequences?”

Whether in our families, businesses or financial management, mistakes are a given.  So as long as screwing up is a part of all of our lives, why not make it an art form, transforming it from a curse to a blessing?  Here are three steps to doing so:

1)     OWN – Our first instinct is always to deny and defend.  Our self-preservative nature fights to keep our better judgment at bay, but in the face of a clear but yet un-owned error, we have an opportunity to claim full or partial responsibility.  And while family, friends and employers don’t love our mistakes, they hate buck-passing even more.  However, owning our failure isn’t easy, because owning also means accepting the natural consequences of our actions.  Claiming bankruptcy might eliminate your debts, but you’re also not likely to procure credit for another seven years or more.  Demeaning your children still weakens their resolve that you’re their biggest fan, blowing up at your employer can still get you fired, and calling your spouse a choice word could leave an impression that lasts for years, even decades.

2)     APOLOGIZE – John Wayne famously said, “Don’t apologize, Mister, it’s a sign of weakness.”  Hogwash!  (As someone from Wayne’s generation might say.)  A willingness to apologize is a sign of strength—an unwillingness to do so is a sure sign of both delusion and weakness.  Do you avoid apologizing to perpetuate a façade that people might perceive is impenetrably perfect?  Do you think people are more likely to trust, love, respect or follow you if you can (apparently) do no wrong?  The opposite is true.   If you try to prolong the ruse, the best case scenario is that people will fear you—if you’ve succeeded in fooling them—but it’s impossible to truly trust, love, respect or follow someone (in a healthy way) if we believe them to possess the inherent infallibility we know to be present in our own lives.

3)      REFORM – “Only the penitent man shall pass.”  Do you remember that classic line from Indiana Jones and the Last Crusade?  As Indie mumbled the cryptic phrase written in his father’s journal on his quest to retrieve the Holy Grail, he properly (and in this instance, necessarily) infers aloud that, “The penitent man is humble…kneels before God…KNEELS!”  And right as he drops to his knees, he narrowly averts sure decapitation.  Penitence, repentance, humility—whatever you want to call it—might be seen as only the first step of reform, followed by a second step, an action of a more preferable sort.  But true penitence quite naturally results in different (better) behavior; if it doesn’t, the humility itself is merely superficial.  Indeed, the root meaning of the verb “repent” actually implies a fluid continuum: contrition, followed by action that is the stark inverse of the errant behavior.

If you have followed this path before, then you know that the satisfaction of recovering from a mistake is often proportionately greater than the pain suffered in being humbled by our own fallibility.  You also likely know that when our misdeeds cause others pain, we can somehow mysteriously surpass the strength of our pre-mistake relationship after owning, apologizing and reforming.  Although it’s no guarantee, practicing the art of screwing up is often endearing to family, friends and even clients.  But let’s not forget that if we’re genuine in our penitence, we shouldn’t be screwing up quite so much in the first place.

As published on http://www.forbes.com/sites/timmaurer/2013/05/16/the-art-of-screwing-up/

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About Shailendra Nair

AI Generalist & Executive Tech Leader in Insurance & Benefits Tech. Driving growth, trust, and resilience from AIG to Marsh McLennan. I am an AI Generalist and Executive Technology Leader with a career dedicated to reimagining how insurance and benefits ecosystems work in a digital first world. My expertise spans Insurance & Benefits Tech, digital transformation, and cybersecurity, with a proven ability to turn technology into both a growth engine and a resilience enabler. I have worked with global leaders such as PepsiCo, Allianz, AIG, and Marsh McLennan, experiences that gave me a rare mix of perspectives across insurance carriers, broking, and benefits advisory. This combination allows me to design solutions that balance global standards, local compliance, and client expectations while driving measurable business value. My strength lies in full stack insurance technology leadership, covering Property & Casualty, Life, and Benefits. I bring hands-on expertise in infrastructure, cloud, security, and enterprise architecture, combined with data platforms, AI automation, and digital ecosystems. Having led across this spectrum, I can translate complex technology into practical outcomes that deliver trust, scale, and innovation. As an AI Generalist, I focus on impact: • Building automation first operations that scale efficiently. • Designing chatbots and intelligent assistants to empower employees and clients. • Deploying AI-driven QA frameworks to improve speed and accuracy. • Exploring agentic AI roles to support compliance and transformation. My philosophy is simple: technology should reduce friction, inspire confidence, and accelerate growth. I design platforms that enhance sales, revenue, and client stickiness, proving that tech can directly enable business outcomes. At the same time, I remain deeply client centric a solution enabler who thinks out of the box to solve real challenges and deliver measurable ROI. 🌍 What excites me most is reimagining benefits ecosystems for the future of work. Employees demand seamless digital first experiences, organizations need efficiency, and regulators require trust and security. My mission is to build ecosystems that are secure, resilient, innovative, and human focused.
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