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Here’s to the crazy ones

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Written by roundPegz fellow: Richard Claydon

Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules, and they have no respect for the status quo. You can quote them, disagree with them, glorify and vilify them. About the only thing you can’t do is ignore them because they change things. They push the human race forward. And while some may see them as crazy, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.

Apple’s Think Different Commercial

In a volatile, uncertain, complex and ambiguous (VUCA) world of black swans and predictable surprises, the one thing we can’t do is think the same way as we did in the past. But we can’t risk organisational oddballs taking us in completely inappropriate directions. What are we to do?  

Apple’s 1997 Think Different campaign blatantly attacked the past, specifically the Think IBM campaign.  It suggested an excitingly plausible future fueled by imagination and drive. 

Apple’s subsequent success is the stuff of legend. But is it something that can only happen in The Valley?  The CVs of the crazy ones, misfits, rebels and troublemakers are catnip to Californian technology companies. 

Not so much elsewhere in the world. In most places, more traditional industries dominate and fitting in is paramount. 

However, as even traditional industries begin to struggle with the VUCA world and its turbulences, they are increasingly trying to digitally transform and become future-ready. 

This is why we set up roundPegz

Many of the rebel talents hired to do innovative work in traditional corporations are square pegs in round holes.  Try as you might, you can’t fit them in. The jagged sides always get in the way. Too often, hiring such people leads to culture clashes, increased toxicity and sunk costs.

But if you hire those that do perfectly fit, you don’t get the think different that drives future-readiness. You risk being disrupted out of existence. 

You need round pegs in square holes. While round pegs don’t fit, they don’t have abrasive jagged edges and hard corners. They operate in the space between business-as-usual and oddball craziness. 

Round pegs have experienced the perils and pitfalls of organisational life. Many of them become sole consultants, trying to pitch their deep learnings to organisations that could massively benefit from their impact.  

They struggle. How they struggle. 

On one hand, they are competing with established consulting brands that nobody ever gets fired for hiring. On the other hand, they end up spending nearly all their time looking for gigs rather than delivering value. And as their personal IP is difficult to scale, they won’t find any investment to grow their business. 

For those operating in highly conservative business environments, that struggle will define the rest of their working life. 

This is where we come in. 

roundPegz operates in a collaborative partnership with theDesk, one of Hong Kong’s premier coworking brands. In combination, we do the following:

1: We collect cutting-edge consultants and thinkers. We make sure they are think different value creators rather than oddballs or snake-oil salesmen.  They provide us with services that support our wider membership – the smaller companies that make up the vast majority of all businesses. Our members have direct access to this cutting-edge thinking simply by being part of theDesk’s community. 

2: We generate trust. By combining the roundPegz expertise into a greater whole, we can help them attract the larger organisations who would benefit from their insights but baulk at the idea of working with boutiques. 

3: We give them a home. This allows the roundPegz to try out experimental workshops and develop them into great events without the risk of the process bankrupting them in venue costs. 

4: We expand their network further. Most of our roundPegz have great contacts elsewhere in the world.  By tapping into the various roundPegz networks and running online events linking them together, we become a major “futurework” hub in APAC. 

5: We amplify their ideas and voice. By sharing their content across our membership network, we make sure they get heard. 

6: We build the future of coworking. For us, the community spirit and personal growth that underpinned the origins of the coworking movement still lie at its core. The roundPegz cultivate them both.


roundPegz – a community of disruptive thinkers working with theDesk to try and help community members develop excellent work practices, deep industry knowledge and meaningful relationships in today’s complex and competitive world. 


Guilds – Now more than ever, the business community needs to work together to overcome the challenges it faces in the short and long term. At theDesk, we believe in the power of collaborative communities. Using different collaborative practices Guilds is designed to expand your knowledge, improve your performance, and increase your network of industry peers. Find out more >

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