Serial Entrepreneur and host of one of Europe's top business podcasts, Secret Leaders with over 50M downloads & angel investor in 85+ startups - here to share stories and studies breaking down the science of success - turning it from probability to predictability.
The Value of Being Sh*t
This Might Piss You Off.Read time: 6 minutes Hey, welcome back. Last week, I talked about how we as a collective need to put a stop into immediently comparing your actual wins to an imaginary one. In other words, stop turning wins into losses. You can read that (and all past issues, here). Before you read on: It’s not motivational fluff, just a quiet, structured way to think clearly. You can download it here → Your Best Year Ever Guide Today I want to go deeper on that same idea, but from a different angle. There's real strategic value in being shit at something. And most people miss it entirely. The Counterintuitive Edge of Terrible We've all heard the conventional wisdom: "Your first attempts will be bad, but you have to start somewhere." But that framing misses something crucial. When you're terrible at something in a deliberate way, you access advantages that become inaccessible once you're good. Let me explain. The Beginner's X-Ray Vision When I started my first company, I was painfully naive about business fundamentals. But that very naivety led me to question industry assumptions that experienced entrepreneurs accepted without thought. "Why do subscription boxes need to be monthly? Why can't customers choose their frequency?" This seemingly obvious question, which came from my complete ignorance of industry norms, ended up becoming our key differentiator and competitive advantage. There's a phenomenon psychologists call "beginner's mind": the ability to see possibilities that expertise blinds you to. But I've come to believe something more specific happens: beginners can see the structural gaps in systems that experts have learned to work around. It's like having temporary X-ray vision that vanishes once you become proficient. The Strategic Exploitation of Low Expectations When we started Secret Leaders, we were entering a crowded podcast market. Instead of trying to compete with polished business shows, we leaned into authenticity and vulnerability. I remember telling our first guests, "We're building this as we go. We want to have the conversations no one else is having." This approach, born partly from necessity as I learned the ropes, became our defining feature. Founders opened up about failures and struggles they hadn't shared elsewhere precisely because our show wasn't trying to present a glossy, edited version of entrepreneurship. What started as a limitation became our unique selling proposition. Now with over 50 million downloads, the authenticity that came from our early "learning in public" approach remains central to our identity. The Data Collection Opportunity Most people see the "being terrible" phase as something to endure. But this fundamentally misunderstands its value. When you're terrible at something, you generate exponentially more data about what works and what doesn't than someone who's already good. Your failure rate is your learning rate. At Heights, our earliest product formulations were, frankly, terrible. However, each iteration generated customer feedback that would have been impossible to collect otherwise. Those early, terrible versions created the data ecosystem that eventually led to our breakthrough formulation. The terrible versions weren't just stepping stones to the good version. They were the essential research lab that made the good version possible. The Authenticity Arbitrage There's another advantage to strategic terribleness that few discuss: the authenticity premium. In a world where polished content saturates every channel, deliberate imperfection creates a pattern interrupt. It signals authenticity in a way that perfection cannot. When I shared my struggles with insomnia and burnout openly, our engagement at Heights skyrocketed. Not because failure is inherently interesting, but because visible imperfection creates trust in a way that curated perfection cannot. This isn't about romanticising incompetence. It's about recognising that there's a market advantage to strategic vulnerability that disappears once you've mastered something. The Humility Compound Effect Perhaps the most valuable asset of being terrible is what it does to your relationships. When you're learning something new, you must ask questions. You must seek help. You must position yourself as the student rather than the expert. This creates relationship dynamics that become nearly impossible to initiate once you're established. The connections I made while fumbling through my first fundraising attempts have become my most valuable professional relationships, precisely because they were formed during my period of maximum vulnerability. Terrible creates relationship opportunities that good cannot access. Beyond the Comfort Narrative The standard narrative around being "bad before you're good" is primarily about emotional management: getting comfortable with discomfort. But this frames terribleness as merely something to endure rather than something to strategically exploit. What if instead of just accepting that you'll be terrible, you deliberately leverage your terrible phase for the unique advantages it offers? The Terrible Strategy Here's what this looks like in practice: Document your terrible insights. What questions are you asking now that you might stop asking once you know better? These beginner questions often contain breakthrough insights. Leverage your terrible publicly. Don't just admit you're new. Use it as a strategic opening. "I'm new to this field, which is why I'm approaching it differently..." Collect terrible data obsessively. Your early attempts generate more valuable feedback than any other phase. Treat this as the primary value, not just the outcome. Build relationships through terrible. Use your learning phase to connect with people in ways that will become inaccessible once you're established. Bank your terrible advantages. Identify the unique perspectives your inexperience gives you, and preserve them even as you develop expertise. To strategic terribleness, Dan P.S. I'd love to hear about a time when being new at something gave you an insight or advantage that experience might have prevented. These stories remind us that terribleness isn't just a phase to endure. It's a strategic asset with an expiration date. It helps you:
If you want to give 2026 a real foundation, you can download the guide here → Your Best Year Planning Guide And if you want the Word doc of the guide, you can get it here → Word doc of Best Year Ever Guide (No pressure. Just a tool, use it if it feels right.) |
Dan Murray
Serial Entrepreneur and host of one of Europe's top business podcasts, Secret Leaders with over 50M downloads & angel investor in 85+ startups - here to share stories and studies breaking down the science of success - turning it from probability to predictability.
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