The Value of Being Sh*t

Read time: 6 minutes

Hey, welcome back.

Last week, we explored the warning signs of leadership failure and how to address them before it's too late.

​You can read that (and all past issues, here).

By the way, if you're finding these insights helpful, I've started collecting all these tools, resources, and one-sheets in the ever-growing 'Science of Success' vault. Check it out here for additional materials on today's topic and more.

Today, I want to challenge our collective understanding of what it means to be "bad" at something:

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 romanticizing incompetence – it's about recognizing 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:

1. 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.
2. 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..."
3. 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.
4. Build relationships through terrible. Use your learning phase to connect with people in ways that will become inaccessible once you're established.
5. Bank your terrible advantages. Identify the unique perspectives your inexperience gives you, and preserve them even as you develop expertise.

A Question to Carry Forward

As you move into your week, I invite you to consider:

What unique advantages does your current terribleness at something give you that you'll lose once you're good at it?

And how might you strategically leverage those advantages before they disappear?

Until Thursday,

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.

SOS (Science of Success) Curated:

LinkedIn of the week: 7 Mental models Everyone Must Download Into Their Brain​

Podcast of the week: Imagine How Successful You'd Be If You Weren't Anxious All The Time​

My Tweet of the week: Time Management Is A Myth​

The "Curse of Knowledge" Effect

Stanford graduate student Elizabeth Newton's famous "tappers and listeners" experiment perfectly illustrates why beginners often see opportunities that experts miss. When participants tapped out familiar melodies with their fingers, they predicted listeners would recognize about 50% of the songs. The actual recognition rate? Just 2.5%.

The tappers couldn't help but hear the melody in their heads while tapping. This made it impossible for them to experience the taps as listeners did—as meaningless noise without context.

This cognitive bias, termed "the curse of knowledge," explains why experts struggle to communicate effectively or see innovative approaches. Once we know something, we find it extraordinarily difficult to imagine what it's like not knowing it.

The implications extend beyond communication. In economic settings, researchers Colin Camerer, George Loewenstein, and Martin Weber found that better-informed individuals consistently overestimate what others know, even when it would benefit them to accurately assess others' knowledge gaps.

For entrepreneurs and leaders, this presents both challenges and opportunities. While expertise is valuable, it can create blind spots that prevent us from seeing novel approaches or effectively teaching others. The most innovative thinking often comes from maintaining a beginner's mindset alongside deep knowledge.

The strategic value of being terrible at something isn't just that you'll eventually improve—it's that your fresh perspective might reveal insights that expertise has rendered invisible to others.

​Source: https://thedecisionlab.com/reference-guide/management/curse-of-knowledge​

Discover how Tom Kerridge‬ went from washing dishes to building a $50M hospitality empire. In this episode of Secret Leaders, we dive into the raw truth behind restaurant success (and failure), why most places don’t make it, and how Tom hustled his way to the top—without any business background, investors, or MBA. What we cover:

• The real economics behind restaurant pricing and margins
• How Tom built the world’s first 2 Michelin-starred pub, The Hand & Flowers
• Secrets to turning passion into profit in the hospitality industry
• Leadership lessons from the heat of the kitchen
• Why most restaurants fail—even when the food is great

​Listen now​

Until next week - smash your success,

Dan

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1-1 Coaching with Dan

In my goal to help more entrepreneurs/people who are looking to level up their careers, I've just started taking 1-1 consulting calls (only 1 a week)

Why book a call? Some of my expertise/success:

I've built 5 startups. 1 win, 1 fail, and 3 still going.

E-Commerce: Heights — with revenue over $15M a year.

Community: Foundrs, one of the UK's top founder communities

Podcasting: Leaders Media - bootstrapped media company that makes the UK's top business podcasts, Secret Leaders, with over 50M downloads.

Health/Mental Health: Managed to overcome burnout, insomnia, depression & anxiety in pursuit of success as I talk about in my interview with Steven Bartlett on Diary of a CEO​

Angel Investing: I've invested in over 90 startups

Coached & Mentored: Certified coach & done lots of mentoring

Personal Brand: Have grown to 178k on LinkedIn and X (Twitter) in the past 12 months

So if you're interested in booking a session with me to talk all things business or building a personal brand, book for 30-minutes or 45-minutes. (limited spots).

Science of Success Vault

I'm building a vault of valuable tools, resources, and one sheets that I hope help you succeed.

These will be stored in the ever-growing 'Science of Success' vault — you can always access that here

Want to take your success (even more) seriously? 👇​
🧠 Fuel your brain and feed your gut, try Heights here (use code 'SOSDMS' for 15% off your first month of any subscription

🎧 Check out my podcast Secret Leaders here​

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