Overcoming Perfectionism

Many leaders I observe aren't failing because they make bad decisions. They're failing because they make no decisions, or not enough and not fast enough. Last week, I started coaching an executive at a large consumer goods company who told me he spent three months with his team perfecting a launch plan. Market conditions shifted. Competitors moved. His “perfect” plan launched into a world that no longer exists. Meanwhile, another leader ships something rough in three weeks, learns what breaks, fixes it, and is two iterations ahead. It´s like you're staring at a wall you need to cross. One ladder is crudely assembled, a few bolts missing, slightly wobbly. But it's finished, and it gets you over. Next to it sits another ladder, beautifully crafted, perfectly engineered. Except it's even not half-built. You can admire it all you want. It's useless. Unfinished perfection is responsible: "We're being thorough. We're mitigating risk." What you're actually doing is outsourcing decisions to an imaginary future where you'll have perfect information. That future never comes. Five practical ways I work with coachees to break the pattern: 1) Ship before you're comfortable. If you feel fully ready, you've waited too long. 2) Define "good enough" upfront. What's the minimum that tests your core assumption? Everything else is decoration. 3) Make reversible decisions fast, irreversible ones carefully. Most decisions aren't irreversible. Stop treating them like they are. 4) Reward speed of learning, not quality of first execution. If your culture punishes rough drafts, people hide behind perfectionism. 5) Kill projects that don't ship. If something has been "almost ready" for six months, either ship it quickly or kill it. Yep! Ugly action exposes you. So what? Or would you prefer that “false” perfectionism protects your ego? It only lets you maintain the illusion of competence without ever testing it against reality. On the other hand, reality rewards people who move. Who learn. Who iterate. The gap between where you are and where you need to be doesn't close through planning. It closes through motion. Let's swing into action and improve as we go. Step by step. *********************** I'm an executive coach, scholar, and sparring partner to leaders and entrepreneurs worldwide. Former senior executive at Amazon, L’Oréal, and Chewy, and board member at Tchibo.

Mistakes are inevitable. No one achieves anything meaningful without stumbling along the way. The question isn’t whether you’ll make mistakes—it’s how you respond when you do. Too often, mistakes are viewed as final—a failure that closes doors. But in reality, mistakes are rarely the end. They’re lessons in disguise, providing insight, experience, and an opportunity to grow. There are 3 steps to overcome mistakes: Own them, Analyze them, and Move On. Use them as fuel to keep going. Mistakes are a sign that you’re trying and stretching beyond your comfort zone. Making progress. I like to say: Progress, not perfection. In 1995, a Stanford professor named John Krumboltz asked his students to take two approaches to learning photography. One group would focus on creating one perfect photograph. They could spend as much time as they wanted planning, shooting, and editing a single masterpiece. The other group, however, had a different challenge: they were tasked with producing as many photos as possible—quantity over quality. At the end of the term, something surprising happened. The quantity group not only produced more photos but also created better quality work than the perfection group. Why? Because every photo they took was a chance to learn, experiment, and improve. While the perfection group spent time agonizing over their single image, the quantity group made mistakes, adjusted, and progressed. The lesson is simple: progress comes from consistent effort and learning from mistakes, not waiting for perfection. https://lnkd.in/dfn7egP4

Once upon a time, in a world not unlike our own, there was a belief. A belief so captivating, yet so misleading. It whispered of perfection. Perfectionism promises greatness. But often, it leaves you stranded in a sea of anxiety, overwhelmed, feeling like a failure. Welcome to the Perfection Paradox. Ironically, chasing perfection makes excellence an impossible dream. Where does this mindset stem from? Two beliefs: Perfection is possible and the ultimate goal. Perfection is the sole path to success and worthiness. But here's the twist. These beliefs are toxic. They create a pressure cooker of fear - fear of failure, chronic procrastination, loss of joy and perspective. So, how do we escape this paradox? Question these perfectionist beliefs. Do we really need flawlessness to succeed or feel worthy? Is perfection realistic for humans? Often, the answer is a resounding no. Consider the story of Instagram. It started as Burbn, a cluttered, over-ambitious app. Only when the founders embraced imperfection, focusing on one imperfect feature – photo sharing, did Instagram emerge. Imperfect beginnings, leading to extraordinary outcomes. Or take J.K. Rowling, rejected by 12 publishers before Harry Potter saw the light. Her imperfections in those manuscripts? They didn't define her future. Perfection is a myth. It's the mask of fear, wearing the disguise of ambition. Success isn't about being faultless. It's about being fearless in the face of your faults. It's about progress, not perfection. The key lies in adaptive perfectionism - striving for excellence, but being flexible, learning from failures, and valuing the journey. The flawed diamond is often more intriguing than the perfect pebble. Remember, the beauty of the human experience lies in imperfection. Our flaws, our stumbles, they make our stories worth telling. So, dare to be imperfect. In that imperfection, you'll find your true path to success and joy. Your legacy isn't in the flawless execution of your plans. It's in the beautifully imperfect journey you undertake. Embrace your imperfections. Therein lies your true perfection.

I've uploaded 800+ YouTube videos since 2017. But it took me 7 years to upload my first video. I thought I needed the perfect plan - that if I waited and prepared for long enough, I'd feel ready. Perfect content strategy. Perfect production quality. Perfect camera confidence. So when I read about the pottery class paradox, it hit home. A ceramics teacher split his class into two groups. Group A had to make one perfect pot in 30 days. Group B had to make as many pots in 30 days. At the end of the month, the teacher judged the quality of the pots. Without exception, every one of the most beautiful and well-made pots came from Group B - the quantity group. For me too, the moment I shifted to just making one video every week no matter what, everything changed. My writing started flowing better.  My editing got better through repetition. I developed better instincts for what worked. 800+ uploads later, I still fall into perfectionist habits sometimes. But I try to trick my brain into starting. I ask "What would this look like if it were fun?" I tell myself, "Just record - no need to publish." I focus on serving others, not protecting my ego. And once I hit record and start talking, the creative spirit moves within me, even when the process feels messy. P.S. If you want more insights on productivity and overcoming perfectionism, I share my best thinking here 👉 https://lnkd.in/e5cMJJ5k

I once coached a rep who spent 45 minutes writing a single prospecting email. It never got opened. This is what perfectionism looks like in sales. It feels like diligence. But it's actually fear in disguise. It’s the #1 silent killer of productivity I see in top performers. And it’s keeping thousands of reps from greatness. When I ask my clients why they procrastinate on key actions—emails, calls, exec meetings—it's rarely because they’re lazy. It’s because they’re scared it won’t be “good enough.” They believe if it’s not perfect, it’s not worth doing. So they delay. They overthink. They rewrite the email 9 times. They wait until they “feel more prepared” to meet the VP. They avoid risk… and call it professionalism. But here’s the truth: Perfectionism is just fear—dressed up as high standards. And it’s costing you pipeline, confidence, and growth. The irony? You only become “good enough” by doing the reps. You don’t become a world-class presenter by sitting in Google Docs. You become one by presenting. Over and over. You don’t write powerful emails by waiting for inspiration. You get there by writing 100 bad ones first. Mastery doesn’t come from waiting until you're ready. It comes from acting before you are. The best salespeople I know are not perfectionists. They are consistent executors. They ship when it’s 80% ready. They call the VP even when they’re nervous. They send the message before second-guessing every word. They understand that competence is built through action. Not before it. Perfectionism isn’t a high standard. It’s fear of failure in a nice suit. You don’t beat it by thinking. You beat it by acting. Every single day. Done now Beats perfect never. Always.

I stared at the blank screen, desperate.  Nothing but a blinking cursor.  Every sentence I typed, I deleted. I had no post I could create.  Every idea felt stale. And the longer I sat there, the worse it got.  Maybe I’ve said everything worth saying.   Maybe I’m just not in the right mind.   Maybe I should just skip this one.  And then it hit me.  Writer’s block isn’t a lack of ideas.   It’s a lack of permission.  The person who started writing the post?   He was trying to be perfect before being real.  He was over-editing instead of digesting.   Ideas were deleted before they could breathe.  Great posts don't come from thinking harder.   They come from writing messier.  Want better ideas?  Say the bad ones out loud.    Want to grow your business?  Launch before you feel ready.    Want to improve at anything?  Let yourself be bad at it first.  Perfection doesn’t create progress. Momentum does. 

I've been reflecting on something fundamental: the mythology of perfection that permeates our profession. Three uncomfortable truths I've confronted in my practice: 1.    Legal brilliance isn't about perfection. It is about judgment under constraints. The greatest lawyers I've known weren't people who made zero mistakes, but people who recognized which imperfections mattered and which didn't. 2.    The lawyer value proposition is multidimensional. When a client praises exceptional legal work, they're rarely evaluating it on technical accuracy alone, but on how it navigated competing pressures within their specific context to achieve a desired outcome. 3.    The most powerful advances in our field have come not from isolation but from integration. By integration, I am referring to bringing together perspectives, approaches, and knowledge systems that challenge our default thinking. What troubles me is how our professional culture celebrates a form of perfectionism that doesn't reflect the reality of excellent legal work. Our mentorship often fails to communicate that mastery comes from navigating complexity, not eliminating it. Maybe it's time we revised our professional narrative. What if we stopped pretending that impeccable legal work means error-free work, and instead acknowledged that it means thoughtful, context-aware navigation of inevitable limitations? #legaltech #innovation #law #business #learning

I need to get better at being worse at my job. Here’s why: I hate making mistakes. I have unreasonably high standards. And (I cringe to type this) I just want to be the best at everything I do. If reading that made you tired, you’re right: perfectionism is exhausting. Maintaining constant high standards takes time and emotional commitment and causes stress. Just as bad is that perfectionism interferes with my relationships. I tend to hold those around me to the same high standards (MY standards, not THEIRS). So when they (reasonably) fail to meet the standards, I can get resentful and impatient. My creativity suffers too. When I’m focused on being the best, I get way too “heads down” and miss what’s happening around me. I know this perfectionist habit will not be easy to break, but I’m determined to start the process by asking myself these five questions: 1. How can I make this task less stressful? ➡️ Rather than “how can I do this perfectly?” I’m asking, “what could I do to make this easier?” For example, I’ve started giving myself time limits for how long I’ll work on a project, or outsourcing parts of it to others. 2. Is that mistake the end of the world? ➡️ I guarantee it’s not. So stop pretending it is (Amy!). 3. Are you being nice to yourself? ➡️ When it’s time to review work I remind myself that I’m not perfect and that’s OK. 4. Can I lower my standard and still be satisfied with the outcome? ➡️ Chances are yes. What would the end result look like if I dialed it back 10 or 20%? 5. Am I ruminating or problem solving? ➡️ Sometimes when I overthink something I convince myself that it’s helpful. Now I ask myself if I’m solving a problem or just spinning. 🌟 On avoiding “compound perfectionism”: The sneaky thing about perfectionism is that it makes me want to be perfect at not being perfect. (A gift that keeps on giving!) So while these questions are meant to help me change my habits, I do NOT want them to become another unreasonably high standard. So if (just kidding, when) I forget to ask myself these questions, I have to let it go. I have to say: “It’s okay, Amy. You’re doing really well. You’re learning new habits, and it takes time to change. I’m proud of you for trying something new and challenging.” Here’s to being worse at my job(s), from writing to parenting and everything in between. Are you with me? (And for more on this, see the link in the comments.)

When a junior associate made a critical error on a seven-figure case, I had two choices: fire them or mentor them. It reminded me of two mistakes that shaped how I lead my firm today. In one firm, when I made a mistake, a partner tore into me. And I didn't become better - I became unnecessarily afraid. As a result: - my growth stalled. - my confidence collapsed. - my respect for leadership vanished. Later, when I made a mistake, a different partner coached me instead of criticized: As a result, I flourished, gained confidence, and developed a profound respect for the leader who saw my error as an opportunity rather than a failure. This contrast directly shaped our firm's core philosophy: Always assume positive intent. When someone on your team makes a mistake, resist the easy assumptions: - They were careless - They didn't care enough - They're incompetent Instead, lead with curiosity: - "Walk me through your thought process" - "Let's retrace the steps together" - "Help me understand how you reached this conclusion" You'll be shocked how often you discover: - Their reasoning was sound but they missed one key factor - They were working with incomplete information - Their approach was different but still valid - You misunderstood their presentation The strongest legal teams aren't those that make the fewest mistakes. They're the ones that respond to mistakes in ways that build rather than break confidence. You see, great leadership isn't about finding perfect people. It's about creating an environment where imperfect people can do exceptional work.