The Possibility Club

Don’t call me an expert – a life of restless curiosity

This is the transcript of a talk given by always possible CEO, Richard Freeman to the Brighton Chamber of Commerce on Friday 22nd June, 2018.

Last night gave a PechaKucha talk in Bexhill about how our understanding of anthropology has changed thinking in business and social networks

On Monday, I ran a workshop with college principals and careers advisers about why they could tell the story about their geographical area completely differently.

Next week I’m helping a tech entrepreneur and his team change the way they consult with their customers and recruit their staff.

I spent a lot of this week shaping a programme of events that helps retiring engineers in Hastings to become teachers.

I am not an expert in anthropology, in teaching, careers advice, engineering or emerging technologies – but that is why people hire me and my team. I’m not really an expert in anything, but that is absolutely crucial for what I do. And I’ll do my best to explain why.

Two months after Margaret Thatcher won her second term was a good time for Paul Young fans and yuppies, not such a good time for working class teen mums.

My mum was 17 when I was born in Poole in Dorset, and she had already got a higher level of education than anyone else in the history of her family.

The expectations, locally (she was kicked out of her church) and from the state (the original ‘project fear‘), were not very high. But when I was still not quite six, she made a decision that certainly kickstarted a chain reaction that affects the decisions I make today.

My mum decided that she hadn’t finished learning.

She managed to get enrolled on a degree at the only university, and on the only course, she could find that would consider taking on a single mum – which was philosophy at the University of Essex. I would often get picked up from school and then rushed back to lecture halls, and it was a common site to find me reading a comic under a bench whilst Kant’s Critique of Pure Reason was being dissected by an enthusiastic professor over my head.

After Colchester we moved to Cambridge where my mum went on to do a PGCE and then an MA, in our evenings we would do pottery classes together and go swimming – and partly out of her own restless thirst for new experiences, but also because she just needed me out of the bloody way so she could do what 20-somethings at university need to do – I would attend every single possible club or activity going. Judo club, afterschool club, jazz dance, youth club, drama, brass band, piano lessons, German club, science club, film club, tennis club, Woodcraft folk (left wing Scouts, for those not familiar). When I was ten I was allowed to leave school five minutes early every Thursday because I had to rush across town to read the news on the community radio station.

Between the ages of six and 12, I lived in six houses – many sharing with other families – and attended four schools.

Because we moved around so much, and I was never in a school for more than two academic years, I learned four fundamental things that at the time I just assumed everyone else knew, but I have come to realise in later years that perhaps they didn’t –

  1. being involved in lots of things, means you end up knowing lots of people

  2. if you’re always the new kid, you need to know how to build a network quickly

  3. if people know you have a network, you become potentially useful

  4. being useful to other people not only feels like a good thing, it can give you some influence

I moved to Brighton when I was 12 and a very different life began. It became home rather than just a place to live. I finished school and college without interruptions. It was the 1997 watershed, when Tony Blair brought some youth and ambition to government and I was just hitting my teenage years at the coolest time to be a teenager in the coolest city in the world.

So music happened, and girls and Barcardi Breezers and books and black eyeliner, velvet jackets and B&H menthols. But I still had this need to be busy, to show up for things, to infiltrate tribes. I didn’t know how to be anything other than a fixer, determined to have a route into any circle of people and to know what everyone was doing. I’d be at every gig, every party, at the back of the bus. An irritating dickhead, no doubt, but it was the only way I knew how to get on. Even though more settled, my status as a perpetual outsider was confirmed very young, so having some sort of dialogue with everyone was actually a way to stop me getting bullied.

At 16, I set up a theatre company for young people to do grown-up plays (Stoppard, Pinter, Fo) because I was arrogant enough to think that would work. In Brighton though, things like that did work. A few of us did it for three years, selling out the old Akademia (now Latest Music Bar), Marlborough, Komedia – we blagged sponsorship deals, grant funding, press coverage. There was no real fringe festival at the time but we were part of a wave of serious youth-led arts coming out of Brighton with a cocky sense of winging it; The Electric Soft Parade were up for the Mercury Music Prize while they were still doing GCSEs at Hove Park School. Cult films like New Year’s Day and The Big Finish were being cast and shot in the local FE and sixth form colleges. Pubs like The Free Butt and The Pedestrian Arms (God rest their souls) were the epicentre – not a single person in there of legal age, but a hell of a lot of creativity, writing, music and intense relationship-building.

I fell in love with one of my theatre company co-founders aged 16. I often wonder where she is right now.

*Looks at watch* I’m guessing she has just dropped our two children off before she goes to work. Boom boom. Our 18th anniversary this year.

I’m telling you all this because what I learned between the ages of six and 16 about who I was and how I remain motivated has shaped any decisions I have made in business since then.

I left Brighton to go to university when I was 19 and then didn’t meaningfully come home for about six years. I was considered to be part of the widening participation programme at university – something like “decent A Levels but his family have no money” – stamped on my UCAS form. I blagged a press office job at the university – not one meant for students – because I could put together a decent press release from the theatre company days. I was put in charge of getting positive student stories into local papers around the UK, which immediately gave me a tool to build a network with the bigwigs in the Students’ Union (two of whom are now shareholders in my business).

I needed more income though, so I trained as a private special needs tutor for a wealthy family in Ascot alongside studying and the press office job. I’m still in touch with my bosses and colleagues from then.

I did a Master’s at Oxford to see what the academic theme park ride was like, and this was the first time that I came across the sort of networks that I didn’t enjoy. I’d only before ever known them to be open and driven by creative spirit. I was naively alarmed to see just how much access people at Oxford got to influencers and opportunities most other people would only dream of – and very rarely was it on merit. I had a difficult year out of my comfort zone, but it confirmed that if I was to remain useful to other people, then that was not the place to do it.

I moved to London and got a job with a charity, training marginalised people in digital skills – and I was thrown in the deep-end with a crash-course in business coaching and how to assess what training people need. I also had the opportunity to work with young offenders and excluded teenagers on film-making and creative leadership projects and something woke me up.

I devoured this work. I became a youth worker on the challenging South Kilburn estate and given cart-blanche to develop a programme of creative enterprise projects – there was money around back then – so worked with groups of 11-19 year olds to found a youth film festival, oral history projects, a professional street dance company and one of the best things I have ever done – to work with a hip-hop producer, a West End set designer and 100 kids from the estate to create a full-length musical about Jungian dream theory, black culture and teenage exceptionalism. One of the girls in the show has now just finished her MA at Sussex Uni and is one of my business associates (you can see a pattern emerging here…).


In London I lapped it all up again, became a Trustee of Samaritans and ran some of their high profile comedy benefit nights. I sat on the board of a couple of small tech start-ups and became a freelance fundraiser for arts and health charities. I was getting to the heart of quite a few organisations – especially in local government, voluntary sector, entrepreneurs, scaling creative industries businesses and the media. I was actually getting a good education in inefficiency. Some brilliant work and astonishing people, and networks I was proud to build, but I could sense that a lot of time and money was being chucked away. I didn’t know how or why, but I knew that the culture of ‘every idea is a good idea’ is not a healthy one.

Then 2008 – the crash happened. All the money and projects started to disappear. London was a difficult place to be. And coming up to our tenth anniversary together, my fiancee and I were suddenly expecting our first child.

So we came home, to Brighton. I had to commute to north London for six months with a new born baby at home – 20 hours per week just traveling – until I found a job at a peculiar little music and fashion training provider for disadvantaged teenagers called Dv8. They had just bought a double-decker bus and needed someone to run it like a mobile studio and classroom. What the hell, I thought.

I soon became the Operations Manager and over the next six years I worked with the owner, Dan, to turn it from a staff team to 7 to 32 by the time I left. And from a small informal workshop provider to a structured college and apprenticeship provider for 14-25 year olds, with two big training centres and direct government contracts worth nearly a million quid.

That’s enough of the life story, I promise, but I wanted to illustrate some of the things that have led me to where I am now.

I quit my job at Dv8 because I was becoming an expert, and that scared me.

The last year of my job was spent obsessing over data, financial forecasts, HR and contracts. I was the data guy. Rich will have all the stats, they would say. My network was shrinking, because I was talking to the same people everyday and my decision-making was getting influenced by fewer and fewer things. I was becoming entrenched. So badly, that I could no longer fix problems because I was losing the ability to see them unless they looked a certain way.

Jonah Sachs, the American designer and storyteller, published a book a few weeks ago about Unsafe Thinking. And the bastard has written the book that I have wanted to write for a while, but it really sums up where I was at. Expertise is great, he says, but it makes you a Safe Thinker. Experts are needed in the context of the rules, but when the rules are changing around you, too much reliance on received wisdom will not respond to the new context of the problem. I was working in education and business and creative technologies and the rules in these sectors were practically, visibly tumbling down. But I was not able to respond quick enough.

And I started to look around at other businesses in these sectors that I understood and they were full of incredible people who – like me – were getting stuck in the way they were thinking.

So I wrote a strategy for unsticking some of our thinking, which involved a restructure of the senior leadership – and I presented it to my boss and he said, but you’re not in it. No. I had written myself out of a job and the budget. I phased out and created my own thing – I called it ‘always possible’ because it sounded intrinsically optimistic, but not unpragmatic – but I didn’t really know what it was. I started to get out again, to find and build a network in Brighton – the greatest city in the world, and what a time to be an adult! I took risks, and collaborated on new ideas. I had over 15 years of work history now, unlike the first time I was doing this as a teenager.

I took on clients in the arts and media, but also sport and retail, education, local government, scaling business – because they didn’t want an expert in their products they wanted a critical friend who could help them create a strategy that unlocked the safe thinking. Someone who could be objective and ask difficult questions, sometimes the obvious questions that experts no longer think about.

I started getting a reputation – the “strategic steward”, someone said. I didn’t know what it meant but it sounded good. I looked up the true definition of steward – ‘a person employed to safeguard the assets of others’. Yes! And from a strategic perspective, this is about the bigger picture. What is good in the long-term – and what is good for the community and stakeholders? I was getting successful at helping people avoid unnecessary mistakes and to think outside of their little silo. What if? and then So, how do we?

I have been described as the hardest working man in Brighton. Of course I am not. There are people out there like my mum was, single parents who are juggling study and jobs and doing the best for their children. That’s hard f****** work. What I think people mean, is that I am everywhere. I could now follow my nose, and be useful. I got invited to be a part of things. I could pop up and pop out.

Remember what I learned as a child:

  1. being involved in lots of things, means you end up knowing lots of people

  2. if you’re always the new kid, you need to know how to build a network quickly

  3. if people know you have a network, you become potentially useful

  4. being useful to other people not only feels like a good thing to be, it can give you some influence

And so here I am. Working with breadth and variety with a growing team, and doing everything I can to avoid being an expert. I thrive on spinning plates. Not because I am determined to be busy, but because I get to spend time with really brilliant people – teachers, entrepreneurs, inventors, artists, policy-makers. I get to facilitate a group of farmers in the morning, and then planning with an opera house in the evening. I’m lucky enough to get invited into policy and decision-making meetings because I can advocate for common sense and the common language between sectors.

I have a podcast that publishes a weekly interview with someone changing the world – it is so enjoyable. I get to chat with economists, children’s authors, activists, aid workers, corporate leaders, scientists – they are the experts, so my job is to connect their ideas together and weave between them – helping them scale ideas and rethink old problems. What can teachers learn from artists about engaging the disengaged? What can business owners learn from teachers about communicating ideas? What can artists learn from business owners about sustainability and sales

I have started a network called The Possibility Club to help people break out of their bubbles and start sharing and learning. I now know that not every idea is a good idea until it is critically tested, so my team create ways to help people test assumptions, use processes to make better decisions and to allow for some unsafe thinking.

We’ve developed a range of workshops that are blowing people’s minds a bit, but quickly getting inside the heads of business owners so that we can help boost clarity and confidence on the challenges that are keeping them awake at night.

It’s not hard work, it is genuinely the best job in the world.

Thank you so much for reading.

Tell me your story:

Richard Freeman is CEO of always possible

always possible

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