He Lost It All… And Found Everything He Was Looking For



Simon Berkley lived a high octane life, selling investment property for a firm in London. Inspired by the example of his high achieving stepfather, an entrepreneur whose business thrived on risk-taking, Simon pursued a pressurised career in sales. He earned a lot and spent a lot.


Like his clients, Simon invested in property, building up a £1 million portfolio. But, when the economic downturn hit Simon found himself facing crippling debt. His life began to spiral out of control as he fought to earn enough to cover his massive outgoings.


Simon did not know it, then, but in losing it all he would find the very thing he had been looking for all along…


Simon Berkley was born into a Jewish family with a strong ethos of academic and career achievement. When his parents divorced at the age of 9, his mother remarried a successful businessman who founded one of the first UK telesales companies. There was an expectation in the family that Simon would follow a similarly conventional career path and he never really questioned this. He learned from an early age that it was important to have wealth and material success in order to experience security and peace of mind


An impulse to help children

In 1981, when Simon was 11, East Barnet Lower School, where he was a pupil, began a fundraising campaign to pay for two deprived children in India to go to school. Simon can clearly recall thinking “if the school can do this for two children, I can do it myself for one child.” He began his own separate fundraising campaign, organising a sponsored swim to raise money. Simon succeeded in raising £80 and was able to fulfil his wish of sponsoring an Indian child to go to school. For the next six years, he did a sponsored swim every year to raise money to educate deprived children.

“My impulse was always to help children, even when I was a child myself.”

Simon swimming as a child

At the age of 14, Simon stepped up his fundraising activities, pledging to raise as much money as he possibly could for Save The Children. “I walked every street in Hatfield and Totteridge, knocking on doors and asking for people to sponsor me swimming. I did the same thing all over again when it came to collecting the sponsorship money. I also contacted the local paper and got them to run articles about what I was doing. I managed to raise £1,000 and presented a cheque to Lord and Lady Salisbury at Hatfield House.”


A Future in Business

Despite his clear affinity with children and the sense of fulfilment he got from giving something back to the world, Simon remained convinced that his future lay in business. “At 18, I began working as a trainee chartered surveyor in London. I hated that job and soon quit to work as a cocktail barman, before heading off to Greece to work in a bar.”


When he returned to the UK in 1991, Simon took a degree in European Business Studies at Hatfield Polytechnic. The final year of his degree was spent in Paris. It was while he was there, aged 23, that he learned of the suicide of his best friend, Corin, on 10 February 1994. This tragic event had a profound impact on Simon.


“I was left with lots of questions and I did something that no-one in my family had ever done before. In 1995, I signed up for a personal development course called Outlook (http://www.anewoutlook.com/), which is all about helping people to change their perspectives and attitudes and live more fulfilling lives.”


Children from Chernobyl

The seeds of Simon’s future life were planted during the Outlook course. “It felt like being part of a family. We examined how we saw the world and how we saw ourselves. The feeling I’d had since I was a child, of wanting to give something back to children, came back to me very strongly.”


There was talk about setting up an Outlook children’s charity and Simon put himself forward as a trustee. It was here that he met his future wife, Anna, who was also keen to be involved with the charity. Unfortunately, the Outlook charity didn’t get off the ground but the team that was trying to set it up organised a holiday to the UK for 80 children affected by the Chernobyl disaster[1].


“The children were 13, although many of them were the size and stature of 8-year olds and in poor health, with a reduced life expectancy,” says Simon. “We took them to different places, bought them new clothes and did everything we could to make sure they had a lovely time. I went with them to a farm in Wales. I can remember carrying one young girl’s wheelchair through woods to make sure she was able to meet Father Christmas with all the other children.

Simon pics,_0003

“It was the most incredible thing I’d ever been involved with. I can still remember the raw pain of parting from these beautiful children.”


A Choice Between Heart and Head

In 1995 at the age of 25, Simon had begun working for his stepfather’s business as Sales Manager and then, later, Sales Director. He took three weeks off work to organise the trip for the Chernobyl children. “I had found something that I loved to do,” says Simon, “but I felt scared. There was still a big part of me that needed to earn money, to follow a conventional career, so I stuck with the job.”


Simon helped to grow the business from a £250,000 turnover with 18 staff, to £3 million with more than 200 staff. By 1999, however, he was beginning to feel the strain of his high pressure job. “I was stressed about work most of the time. I quit my job with dreams of becoming a life coach but it didn’t work out and nine months later I was back.”



Simon and Anna had married on 17 September 2000. Their first child, Jade, was born in March 2002. Financially, Simon felt trapped. “We had a nice house a nice car, a growing family… all of the responsibilities that come with working in a well-paid job.”


“Inside, I was constantly afraid of “being found out” and I used to spend money to compensate for the unhappiness I felt inside.”


Managing Director

In 2001, Simon was made Managing Director of his stepfather’s company but after only a few weeks in the role, he realised he was out of his depth. “I didn’t know how to run a business and, to compound things, I wasn’t being allowed to make the decisions an MD needs to make.” The stress of the situation was exacerbated with the loss of a £650,000 client.


Six months after the birth of his second child, Samuel, in August 2003, things came to a head. “My stepfather wanted to make me co-Managing Director with a colleague. It felt like he had lost confidence in me. I left the job for the second time, with no income, or idea of what I would do next and a young family to support. In hindsight, it was not a great decision but it seemed the right thing to do at the time.”


Flying High

Simon spent the next two years in a succession of jobs, trying to make ends meet. Just as their savings were starting to run out, he landed on his feet, securing a sales job with a property investment company. “It was commission only but I quickly became the best salesperson in the company. I was selling between 15 and 20 properties a month. I never took a hard sell approach, I had empathy and honesty. People liked this.”


Within months, the family had bought its dream home. The children attended the private Steiner School in Kings Langley and Simon built up his own investment portfolio to eight properties.


The Start of the Nightmare

It was 2008 and the economic downturn was just starting to bite. Simon was headhunted to another property investment business but the move didn’t work out and he quickly became disenchanted with his new job. At the same time, the family started to experience significant cash flow problems.


“Rents on the properties I owned were starting to fall and the cheap mortgage deals were disappearing. I needed to clear £6,000 per month just to cover our basic outgoings. I was unhappy at work and feeling hugely pressurised. It was the start of the nightmare.”


Anna had worked since the children were small, building up a successful pre and post-natal yoga business. However, the economic downturn also hit her business and the income from it all but dried up.


The family rented out their home and moved into a rental property to try and reduce their outgoings. However, the end of their mortgage deal saw their mortgage jump by over £500 in one go. Simon left his job at the investment property company with dreams of setting up a life coaching business with Anna. However, the reality of their situation meant that he needed to earn as much money as possible just to try and manage their spiralling debts.


Working All Hours

“I’ve never been afraid of hard work and I was prepared to do anything I could to keep things together. I started working as a private hire taxi driver, working all hours to bring in money.  I worked for a friend making cold calls, selling sales training. In March 2009, another friend who worked for Ocado, the grocery delivery company, got me a job as a delivery driver. Within three months I was promoted to the marketing department.”


It felt like the family’s troubles were at an end. However, their huge outgoings meant that they could no longer afford to pay the fees for their children’s private education and they were forced to take their children out of the Steiner School and send them to the local state school.


“This felt like a real failure. I was facing the fact that, despite all the work I’d put in, we risked losing everything. We’d had to take our children out of Steiner education, which we loved and believed in.”


Retraining As a Teacher

Simon moved from the marketing department at Ocado to the employee engagement team. Around the same time, he made the decision to retrain as a Steiner School teacher.


“In the midst of this darkness, I started to remember who I really was and what I loved to do. I knew I wanted to work with children, but the question was whether I would work for a charity, raising money for children, or take on a more hands on role. I opted for the latter.”


Simon and his wife were both deeply committed to the principles of Steiner education. “It is education for the whole child,” explains Simon. “The children learn to read, write and do maths, but the job of the Steiner teacher is more than that. It is about helping the children to connect with who they really are. We lived within a few feet of the Kings Langley Steiner School. I thought that I could, perhaps, get a job there and, in the meantime, continue working for Ocado.”


A Black Hole

However, fate intervened once again. All of Simon’s investment properties had been remortgaged to the fullest extent and many were in negative equity. He was maxed out on his credit card to the tune of £24,000 and, when he reached the end of his interest free period, he found himself unable to refinance the debt. “It was like staring into a black hole,” says Simon. “Every month, the properties I’d bought as an investment were costing us around £500, on top of all our other outgoings. The debts we were carrying were increasing month on month. I knew if we went bankrupt we would lose our home, but there seemed to be no other choice.”


In January 2011, following extensive discussions with Anna, Simon declared himself bankrupt.


“It was the worst time in my life. I felt that it was my job to provide an income and stability for my family and I’d messed everything up. Yet, despite everything, Anna and I stayed together and our relationship grew stronger.”


Putting Happiness Ahead of Money

“I’m sure many marriages would have crumbled under this pressure, but we worked together at everything.”


Although there was a temptation to rush back into a sales job, or to become a state school teacher, with far more earning potential than a Steiner teacher, Simon felt that he had learned his lesson the hard way:


“I now decided to put happiness ahead of money. I had always believed that the money would lead to happiness and it didn’t, so I realised it was time to change.”


In May 2011, the family’s fortunes began to turn around. Simon applied for a job as Class One teacher at the South Devon Steiner School near Totnes. He was invited for interview and offered the job.


Connected to God

“We packed up our lives outside London and moved to this beautiful part of the world. I have now completed my first two years as a Steiner teacher and I have never been happier.

“I lost everything of a material nature, yet I have gained all I have ever wanted. I now have a career that touches me so deeply that I feel I am connected to God.”


“We have enough money to live on. We live without debt. My children attend the same school that I teach at and I see them at break times. We live in a rented flat without many possessions. I am part of the most amazingly supportive community and I get so much back from the children in my class.”


It’s All About Happiness

“When I weigh all this against my previous life striving to survive and make money, I realise it was not a life at all. At last I am being me and I have found something that I am really good at and that allows me to express who I am. It is all about being happy. I can find happiness in the most chaotic painting lesson with my class or in swimming in the Dart river with my family. We may not have much money but we have love and quality of life and that counts for all.”


[1] Chernobyl was the worst nuclear disaster in history. An area of 1,000 square miles was evacuated following the blast in April 1986. The long-term effects of the disaster include cancer and deformities. Experts estimate the area will not be habitable for another 20,000 years.


2 Comments to He Lost It All… And Found Everything He Was Looking For

  1. upliftingstories says:

    Simon and Anna, yours is an inspirational story of spiritual growth and letting go of material things in pursuit of a higher goal. Thank you for having the courage to tell it. I’m sure it will bring hope and consolation to anyone facing similar life pressures.

  2. Zoe says:

    Wow! What a story!
    Losing the trash and gaining treasure!

    With God all things are possible!

    “A man’s life does not consist in the abandance of things he possesses” -- Jesus Christ

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