Category Archives: Experience

16. Rejecting The Patriarchy With Vanessa Osage

Vanessa Osage is a journeywoman. On a voyage of remediation to mend a loophole in the schooling system. One that has concealed the historic sexual exploitation of children. And a governance model – that unfortunately – still fails to adequately protect and serve our most treasured assets. Our children.

Vanessa is a sexuality educator, president of the Amends Project and founder of the Justice CORPS. 

As a sexuality educator, she operates on the fringes of sexual health. Her personal mandate is to pull this conversation out of the perimeter and into the mainstream. She does so by honouring this topic with the honesty and reverence it really deserves.

Her work has drawn criticism. Vanessa, however, is no stranger to critique.

As a child, Vanessa was condemned by her school leadership team for speaking up about an incident of sexual overreach that occurred on school grounds.

Vanessa was in attendance at a prestigious private boarding school in Massachusetts – New England. The perpetrator was the school groundskeeper. When she approached the school leadership team for support and guidance. She was muted. Her story invalidated. Her funding revoked.

The groundskeeper stayed in role until Vanessa returned as an adult. She insisted on speaking at a school graduation event. She hit the podium and valorously delivered a speech that uncloaked the entire cover up.

The aftermath. The resignation of the headmaster. The instigation of a restorative justice programme. Surely the beginning of a journey into remediation? 

Not exactly.

However this journeywoman was not to be deterred.

This conversation explores Vanessa’s story through the lens of a failing patriarchal system of governance and self protection. We delve deep into the social and fragile construct of masculinity. And remind ourselves of why the systematic and – what can feel like – innocent humiliation of boys is the source of these offences. 

We discuss why boys should be taught to embrace and nurture both masculine and feminine energies. And to deny men the benefits of emotional intelligence is a disservice to men as much as those who are harmed by men. Our societal norm however has delegated emotional responsibility to women.

Men by far are the perpetrators and concealers in each and every one of these stories. Traditional masculine values – ones that seem revocable – are now starting to harm us.

This is a conversation – not of sexual abuse, but betrayal. In her own words, Vanessa reminds us that the undertone was sexual, but the overtone was an abuse of power.

We need more conversations that support what it means to be a sexual being, at the time when sexual maturity is happening. And boys should be taught to respect and honour that right.

Vanessa is the embodiment of her story. A seeker. And a journeywoman who in the face of adversity ran towards the sunrise. She journeyed from coast-to-coast with the barebones of an automobile, a few clothes and some basic rations. This revealed to her an America, honest people and an opportunity to heal.

On her travels. Those painfully seasoned eyes were able to see the real gritty honest heart of America. It revealed its tragedy, its triumph and its kindness. Vanessa’s words. Not mine.

This conversation will echo in its eternity based on those three words alone. Tragedy. Triumph and Kindness. For me, that is Vanessa Osage.

Warning: This episode contains explicit language and a topic of discussion that some may find distressing.


Vanessa Osage: Website | Instagram | LinkedIn | Twitter | Bookography
Book: Can’t Stop the Sunrise: Adventures in Healing, Confronting Corruption & the Journey to Institutional Reform
The Amends Project: Justice CORPS Initiative
The Amends Project: Support the Movement
Thrive Global: Vanessa Osage: “Be authentic and imperfect”
Knkx: Boston Globe’s Investigation Into Widespread Sex Abuse In New England Private Schools
Boston Globe: Private schools, painful secrets
Michigan Daily: In defence of the female gamer
CBS News: 11 former New Hampshire prep school staffers accused of abuse
BBC News Feature: The boarding school ‘monster’ who always walked free
The Needle Blog: Brookside School, nr Ludlow, Shropshire
White Collar Week Podcast: Ep. 17: #TruthHeals: Systemic Abuse & Institutional Reform with Vanessa Osage, feat. Guest Co-Host Chloe Coppola


Episode #10: Correcting Reality with Craig Stanland
Episode #15: The Invalidation of Experience with Candice Mama


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4. Skillz from the Vault

This episode is a continuation of the blog post – Mastery of craft. Where I alluded to a lost year, an experience and set of skills that are one of my best-kept secrets. 


  • A lost year of education and a teenage ambition, that has now been resurfaced, reshaped and fused into my current career path
  • A valuable leadership lesson in allowing individuals to make their own mistakes
  • Why any experience, no matter how small or historic is never wasted


“We all have old experiences and skills that can be dusted off to create something new, and that’s exactly how good ideas begin.” – Bobby


Blog post: Mastery of craft
Instagram: My new podcasting studio
Web link: An introduction to Indian classical music – What is a raag?
Web link: What is computational musicology?


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My eBook is scheduled for release on 1st Sept. All PRE-ORDER’S before this date will receive a series of BONUS material, where I will share two decades of hard learnt contract negotiation techniques and strategy.


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Mastery of craft

We rarely, if ever – use the term “craft” to reference any form of discipline in the field of IT. 

The term is largely associated with a carpenter, an artist, a musician or even a brewer of fine ales. By defintion – a craft is a skill mastered by creating something by hand, obtained by a high degree of both practical and theoretical knowledge of a trade.

As professionals – technology or otherwise, from senior leadership to programmers, aren’t we inevitably trying to master our own craft? 

Bobby at 7

I started my craft at the age of 7. Seriously – I did! 

Programming BASIC on a Commodore Vic-20, all 8 bits and 1Mhz of compute. I suspect my parents’ motivations at that time, were the games to keep me entertained with their high bitrate graphics. But the real magic was buried inside the user manual.

Chapter 7 to be precise – “Introduction to Programming”.

At the time, I don’t think my parents fully appreciated the magnitude of their investment. I suspect not many parents did.

I had no clue what I was really doing, what the syntax meant or even what a program was. But it was the fact that I, with my own hands crafted syntax, which made the computer come alive and respond to my commands. I influenced and created an outcome.

Naturally, this fascination only grew, and it wasn’t long before I was upgraded to the breadbin Commodore-C64. An extra 59KB of RAM to support my coding endeavours.

Though I must admit, 10 PRINT “HELLO WORLD” didn’t demand much compute.

Bobby the elder

We don’t always need an arena to master or nurture our craft. When we don’t have that – we have training courses, books, webinars and personal coding projects. But there is one crucial component that influences our ability to execute and deploy our craft. The 7-year-old me or even the 21-year-old me, fresh out of university, would never have appreciated its influence… the art of workplace politics.

When black and white becomes grey

There is an irony here. Coding is about logic, a 1 or 0. Children see things in black and white, right or wrong – clear as day. But the world of business is far from logical, it’s quite the opposite, it can be very grey.

Our success in the workplace can be largely driven by our ability to navigate the political spectrum. As with all youngsters, I was idealistic and for years I fought what at times felt illogical. However once I learnt to accept this and nurtured it alongside my craft, this opened up a wealth of opportunity.

Politics, is not something you can learn in books or be taught on a training course. Many people, just like I did – could never really contemplate how influential this skill is in the mastery of our craft. Some may argue that it’s on the periphery, but as I said, for me it’s integral.

Politics in the workplace is seldomly viewed as a positive vehicle. This is largely down to motives. But if the intentions are good – to drive a successful outcome for an activity or a project – then mastering the art of politics; is an immensely powerful tool.

An outcome of a project or your credibility can be highly dependent, on not only how well you respond to political moves but how you shape your own field of play.

Interestingly, it’s the one aspect of our craft that is ancient in its origin. The advent of agriculture in 7000-8000 BC saw human societies transition into tribal forms of organisation. Politics went beyond survival; it provided a framework for the growth of humankind. Enabling tribes to work together to compromise, negotiate and make decisions. 

This extends into every aspect of our lives; 

  • At some point, our children stop listening to us and we soon learn how to navigate that political spectrum. We provide them with tools, means and support to empower them. Hoping they will making their own informed decisions and learn from their mistakes. 
  • In the workplace, we may have the answer to a problem. But sometimes people aren’t receptive to our answers, so we lead, steer and provide insight to enable them to carve out the right answer. 

There is a fine line between teamwork and politics. Sometimes it’s not easy to distinguish. However, in both examples, managing personality conflicts and personal agendas can not only provide a better-quality outcome but is more likely to promote ownership. For which it’s ownership that drives real change.

In contrast, it’s also true that underlying political motives can also drive a sub-optimal output.

If I could go back in time

Look at your job or role through the lens of mastering a craft. Being the best at what you do, mastering the practical and educating yourself on the theoretical. All the traditional aspects of growth – be that climbing the rungs of the corporate ladder, or the size of your remuneration package would naturally come together themselves.

If I could go back in time, and advise 7-year-old Bobby on anything – it would be…

Master your craft, for which you don’t need to be gifted or talented. Pay attention to the process and invest time in improvement. Small gains every day have a compound impact – just like interest on a savings account. If you invest in experiences that in themselves can pay dividends. Don’t be afraid to make mistakes, it’s ok to deviate off your path to explore new avenues – no experience is ever wasted. 

In the next episode of my podcast I let you into a secret, something not many people know about me. For the last 20 years I looked upon a particular experience as a lost year. But when viewed through a lens that is now transforming my life, it’s enabled me to create something new.

I suspect many of you in the field of technology have a similar story. When that first computer landed on your desk or dinner table – all those parents would never have imagined the influence of that moment. Is this unique to technology?

How many other professionals were given the tools to start mastering their craft from an early age?

A writer inspired by a book; a painter inspired by their crayons…

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