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The Story of a Reluctant Entrepreneur

The Story of a Reluctant Entrepreneur

I am motivated by imposter syndrome. I don't feel anything I do is innately great. Or reflective of a special talent. Feeling I don't ever quite belong or have ever quite proved myself drives me. It's a weird type of motivation. I know I have done things that few others have achieved. At least one of which is pretty unique. It's also twice led me to starting my own company. Reluctantly so, despite my ongoing passion for what I do. 

But I can't throw it off. So I've learnt to embrace it. Despite the difficulties it brings. Here's my story. 

A Reluctant Entrepreneur: The Early Years

Having drifted around the world as a freelance artist and language teacher, I started my own company in my late 20s. At the behest of IBM, who wanted me to run their soft communications training in Scandinavia. But were under a hiring freeze. So they asked me to set up a company to run the courses as an external contractor. Which I did. For six years. 

I didn't set out to be an entrepreneur in this space. But I became one. With pretty much the biggest training contract in Scandinavia underpinning me. Word of mouth marketing enabled me to pick up other high profile clients. Just when the company was becoming a serious concern, I canned it.

Why? Because I felt like a fraud. I was running communications training for a mega-multinational with only a Fine Art degree to my name. So I took a year off to get a Masters in Cross-Cultural Communication and International Management. At a good red-brick university. My intention was to get the piece of paper that proved what I was doing was worthwhile. Then go back to it. And do it better. 

I came first in my Masters, getting a distinction for every module I took. Plus the highest mark ever awarded for the professional communications module. While doing it, I fell in love with the International Management side of my degree. Why? Because having worked for years in the field, the communications stuff was too easy. I felt anybody could do it. It was nothing special. Imposter syndrome again. 

The management stuff drove me. It was complex. It was difficult. It was fascinating. So I wanted more. My intention of getting back into communications fell by the wayside. I craved more knowledge about organisations, management and leadership. I wanted to make a difference in that space. So I looked for opportunities to achieve that.

Ultimately, I was granted MGSM's first ever international scholarship in organisational behaviour and change. Which seemed the right move. A way to make a difference. Which is why I'm in Sydney.

A Reluctant Entrepreneur: The Research Years

Again, imposter syndrome struck. I wasn't comfortable doing a bog-standard Ph.D. I had access to the data from the biggest research project into organisational behaviour in Australian history. But I found the empirical methodologies too lightweight. I didn't see how using them added anything worthwhile or interesting. And if I don't find it worthwhile or interesting, I'm convinced nobody else will. 

So, I decided to do a synthetic theoretical analysis. This means that I was producing a helicopter-level theory explaining why certain things happened in the contemporary organisational environment. And what they meant. 

I examined managerial efforts to produce loyalty, commitment and enthusiasm through organisational culture.  And found that the data consistently showed something else happening. Irony, sarcasm, cynicism, mockery and ridicule appeared everywhere. The opposite to expectations. I tried to work out why.  So I researched irony. Across multiple disciplines. Management, organisation, philosophy, sociology, psychology, literature, cultural theory, history, media. And synthesised them into a meaningful whole. I can now predict and explain this phenomenon. 

Nobody does synthetic theoretical analytical Ph.Ds. Why? Because they take too long. You should finish your Ph.D. in 3.5 years. That's achievable if you follow the standard pattern. That's why scholarships give you four years of funds*. Synthetic theory takes far, far longer. 

*Albeit $28k a year. And visa restrictions preventing you from working more than 10 hours a week. A 700% pay drop from my reluctant entrepreneurial endeavours. But that's another story. 

So. 6.5 years. 2.5 of which with no scholarship to support me. But I ended up with something worthwhile. A theoretical overview of a common organisational phenomenon that everyone observes but nobody understands. That demonstrably predicts and explains it.  

But it's still not enough. Imposter syndrome again. My opinion of its worth is not valid. I wanted to be examined by the best of the best. Intellectual heavyweights in the management field. That way, I would know my work had value. 

My supervisor advised me against it. In his 30+ years of supervising Ph.Ds, he'd never had a single Ph.D candidate try for three big names. It's too risky. They do not let substandard work get through. Far too big a chance that you add a year plus to the research through forced rewrites. But I was insistent. And I got them.

Another thing my supervisor had never experienced. Having a candidate get the highest possible pass marks from all three examiners. Well, he has now.Getting those marks was the moment I finally felt I might belong. That I might have something special to offer. And so to part three. 

A Reluctant Entrepreneur Today

I then, for the first and hopefully only time in my life, took a role purely for the money. Two years in a mining company, working on communications, operations and change. Totally and completely necessary when you examined my end of Ph.D. finances.

But that's over. I now have to work out how to translate my knowledge.  Which is cutting-edge and world-class (I have pieces of paper telling me so!). Rework it so it speaks to the practical realm of organisation, management and leadership. Which is why I have rebooted my company. And blog on LinkedIn.

But reluctantly so. I have a passion for making organisations better. But to do so, it seems I have to be an entrepreneur. Once again. Despite having made decision after decision that should make me ultra-valuable to an organisation. Only to find out that the gap between management academia and actual management is enormous. So my knowledge isn't trusted. Irony at its finest. 

Ultimately, I have to trust my talent. That the opinion of world-leading academics in power, leadership and resistance is meaningful. That I am one of the most original management and organisational thinkers about. That leaders and companies crave the knowledge I possess. That I can use this to propel my career forward. To translate it into something meaningful in the practical realm. To help make a difference to organisations. Because that's my passion. 

And you're supposed to follow your passions. Whenever I've done it, I've been pretty successful.

The Happy Entrepreneur

Because of my visa, I wasn't allowed to work more than ten hours per week when I was doing my research. But I did manage to get a few other bits and bobs done. All pretty entrepreneurial in nature. All driven by genuine passion. 

Football Manager: Have you played the PC game Football Manager? It's a bit of a religion for those that do. Well, I have. A lot. So much so, I once wrote a guide on how to play it. Its final iteration was 17,000 words! Which has been downloaded and read well over a million times at the last count. 

If you've played it since 2010, you are actually playing my design. Thanks to my guide, I was asked by the game's creators, Paul and Ov Collyer, to redesign the tactical module. If you've played the game and ever picked a Poacher to play up front? Or a Deep-Lying Playmaker screening the back four? Or a Complete Wing-Back to get up and down the flanks? Then you've used my design. That a few million people have played a game I helped design is one of the things I'm most proud of. 

Tennis: I've also a bit of a passion for tennis. And am distraught by the loss of playing numbers in Australia and the UK. It's a dying sport, with crumbling facilities. So, I've done something about it. Created a model for playing tennis that bucks the trend. And supposed best practice. 

As a result, my tennis club has gone from struggling to survive to having the highest court occupancy in Sydney. If not Australia! The national average is circa 23%. Our courts have 65%+ occupancy. We have doubled senior membership. Tripled junior membership. We have waiting lists. Our coaches have more work than they can cope with. Revenue has increased by almost 400%. We are the most successful club in the Sydney tennis leagues. All because we didn't listen to the way things are 'always' done. And created a unique experience.

Scratching the Ever-Present Imposter Syndrome Itch: I've also taught myself to build PCs from scratch. To design websites from scratch. To administer servers. To design training courses. To read at 2,000 words per minute. All because I didn't feel I could do my work well without knowing this stuff. 

With Thanks

My LinkedIn and blogging adventure has been extremely useful in helping me deal with my imposter syndrome. I've expanded my connections from 360 to 950 in four months. Hopefully, soon to hit that magic thousand. This suggests that people are at least interested in what I write. That it resonates. Which helps. 

I've met some very interesting people. Some other critical thinkers trying to make a difference to the world. Many of whom have opened their arms out wide, shown interest and offered to help. So thanks go out to Stefan NorrvallTrent Selbrede,Kim Chandler McDonaldTracy MellorGavin GerRob JonesDr Ross WirthDr David VikZiern LiewRex StockChristopher Hughes, Rod BarnettPaul DruryBill HoveyAdi GaskellMarcel JB TardifKeith WrightMichael Cardus,Brian Field and Paul Donaldson. Most of whom I've now either met or had extended email conversations with. Plus the many others who've provided feedback and comments to my blogs. 

If you are as passionate and serious about rethinking organisations as I am, please connect with me on LinkedIn. Thanks.

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The Ironic Manager seriously rethinks how organisations work at the most fundamental level and offers a variety of solutions for businesses struggling to cope with the ambiguity and stresses inherent to contemporary organisational conditions of constant change.

Richard has been helping businesses and people deal with leadership, management, communication, technology and change for over twenty years through his training, coaching, speaking and consulting services. 

His innovative research is highly regarded by world-leaders in management and leadership. 

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Over twenty years helping people managing change understand why resistance happens and develop quality vital communication skills that aid successful business transformation.


Research recognised as exceptional by world-leaders in the fields of power, leadership and organisational change, receiving considerable praise for its originality, depth and rigour.


Extensive training, coaching and mentoring experience in professional development in well-known organisations, governments and business schools across the world.


Consulting on change, transformation, culture, organisational narrative, innovation and creativity, and communications to private and public sector organizations and entities.

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