The wonderful variety of portfolio careers

Portfolio careers come in all shapes and sizes. Let’s dive into the careers of a few of our founding members.
The Wonderful Variety of Portfolio Careers

A portfolio career, more than any other career, is a blank page upon which you can write a wide variety of stories.

At The Portfolio Collective we have learned the back stories of hundreds of successful portfolio professionals and are yet to meet two people trying to develop their career or make money in an identical way.

A portfolio professional is not defined by a company name or job title. Our identity comes from our back stories, skills, knowledge, networks, passions and values.

This makes it more difficult to explain ourselves in one succinct sentence, but makes us far more interesting when you get to know us!

You can have a portfolio career with virtually any background too. We have members who started out as journalists, lawyers, architects, vets, graphic designers, army officers, therapists, entrepreneurs, engineers, accountants, marketers, professional athletes, analysts and much more.

Many portfolio professionals combine guaranteed money earning activities with speculative side hustles.

For instance, Steve Fleming, who describes his portfolio career below, was farming pigs whilst advising Russian oligarchs and writing press releases for tech startups – all bundled into the same portfolio career at the same time.

Many juggle their paying portfolio work with family life and unpaid community activities.

To bring this wonderful kaleidoscope of humanity to life, let’s dive into the careers of a few of our founding members.

Lara Hayward

Laura Hayward portfolio career
© Jane O'Sullivan / The Portfolio Collective 2020

Lara began her career as a lawyer, but was always drawn to side hustles that involved helping others. In her own words: “Even when I started training as a lawyer, I was volunteering in a palliative care hospice on a weekly basis. Because I was doing something very corporate, I wanted to ensure I was also doing something that mattered more.”
Throughout her professional life, Lara’s approach has revolved around having one main role, alongside other more cause-based roles filling in the gaps.

According to Lara.


All of my work is better when I'm doing more of the things that I enjoy. It’s a cliché, but I'm passionate about things where I feel like I can make a real difference.

Laura Hayward portfolio career in action

At present, she is on sabbatical from her primary role as Lead for the Creative Industries at Oxford University’s Careers Service, to undertake training in aerial and acrobatics at Circomedia Centre for Contemporary Circus whilst studying sports physiology and psychology on the side.

Sabbaticals have been a major part of Lara’s working life, which started when she was working in New Zealand. “Whilst I was in NZ, I had a main gig, but Kiwi working practices seemed much more flexible. People would take longer holidays, or be able to go on sabbatical as a family or just generally able to fit in other things. It was just a much nicer way to live and that always stuck with me.”

Given that Lara has done so much already in her portfolio career, one which spans a diverse range of areas, some may struggle to see the core thread holding them all together, however “high performance” and questions such as “how can we work better?” and “how can we learn from different environments to do that?” has connected everything so far.

Steve Fleming

Steve fleming portfolio career
© Jane O'Sullivan / The Portfolio Collective 2020

Steve Fleming has one of the most diverse and rewarding portfolio careers that we’ve come across, with his main focus simply being on challenging himself to do things that he hasn’t done before.

Steve fleming portfolio career pig farming

Steve’s portfolio career has spanned everything from farming pigs through to helping a Russian oligarch’s wife get a theatrical agent. However, it all started in sports journalism with Steve working on the sport desk for the Daily Mail and The Times.

His knowledge of sports has prepared him to adopt the right mindset for a portfolio career professional.

“There’s a story that Gary Lineker used to get irritated by journalists always saying he was just in the right place at the right time. He said, ‘Look, I’m always in the right place. I can’t affect whether the ball comes to me or not but I’m always in the right place, physically and mentally ready to do what I need to do’.”

Steve has followed suit: since he started his portfolio career he has made sure to be in the right places with an open mindset.


My mantra over the years has been when somebody asks, ‘Steve, do you do this?’ My answer is yes, whatever they ask me to do.

This “yes” approach has led to some of the most unique tasks he has undertaken, like when somebody asked him to get them membership to an exclusive private members club in London – which had a one year waiting list – in under a month, or when he had to be part of an undercover operation to find out information for one of his clients.

However, Steve’s portfolio career isn’t just doing these tasks for super high-net-worth individuals. It also consists of editing books, PR work for high-net-worth individuals, PR for companies, crisis management, helping secure startup funding and sitting on startup boards.

Paul Mather

Paul Mather portfolio career
© Jane O'Sullivan / The Portfolio Collective 2020

Paul Mather has had a portfolio career for around two years, with the main focus of his work not necessarily being on what he wanted to do, but where he wanted to be.

Paul and his fiancée had dreamt of traveling the world.

However, with his previous operations-based role at Deliveroo, traveling and working wherever he wanted was not an option for him. His fiancée retrained as a yoga instructor, which allowed her to work wherever she was based, so Paul needed to rethink his career.

Paul started his career at the Royal Military Academy Sandhurst and spent four years as an army officer, including time in Afghanistan. After leaving the army, he took his transferable operational skills to the private sector, joining the operations team at Deliveroo, a fast growing startup.

He spent another five years at Deliveroo, with ever increasing responsibilities in operations, followed by leading their global global electric vehicles programme.

While at Deliveroo, as a side hustle Paul also co-founded an educational startup with his brother. He remains a non-executive director there.

This gave him a taste of portfolio life.

In mid-2019 Paul started his portfolio career in earnest. He took on some sustainability coaching for a sustainability consultancy. He found it relatively straightforward: “I’d already been mentoring and advising a number of founders and very early stage startups for free, basically people that I knew through my network. So I started to understand how the process could work and this allowed me to use my network to start monetising and doing my consulting in a more professional way.”

Paul Mather portfolio career travel on motorcycle

Paul’s portfolio career now consists of early startup operations mentoring, advisory work with his brother on the startup and sustainability consulting. This has given him the opportunity to work wherever he wants – which is currently in Antigua, where he is also working on EV ventures to support sustainable travel.

Unsurprisingly, Paul told us

“I definitely don't see myself just doing one thing 100% of the time ever again.”

Paul’s journey to a portfolio career hasn’t been a case of simply knowing that this is what he was going to do, then doing it.

Paul says that:


It's something that I've come upon via a process of iteration rather than something where I definitely knew that I was going to have a portfolio career.

Laura Thomas

Laura Thomas portfolio career
© Jane O'Sullivan / The Portfolio Collective 2020

After five years at IBM, Laura Thomas’ portfolio career is one that she has come to through following a line of problems she was interested in.

Laura has always been passionate about a healthy lifestyle and personal development. Her first move into portfolio career work came almost accidentally when a blog she started writing in 2012, Happy Sugar Habits, grew steadily in popularity and turned into a business. This allowed her to work and live abroad as a “digital nomad” whilst coaching clients online.

As Laura went deeper into her work with clients, she discovered there were other root cause issues behind unwanted behaviours. When Laura returned back to the UK she decided to work in employee wellbeing and organisational development to understand how issues at work lead to stress or lack of fulfilment.

Laura Thomas portfolio career business consultant and coach

I’ve been very intentional with my skills and knowledge development, immersing myself in roles and industries that increase my capability to solve the problems I am interested in.

Her fascination with how we live, work and learn has continued.
More recently Laura has worked as a facilitator, a small business consultant and coach – helping others navigate their portfolio careers and all the decisions that come with them.

Think this sounds like the right path for you? Come along to our monthly Get started event for new members to find out what a portfolio career could look like and how The Portfolio Collective can help you take those first steps towards professional success – and don’t forget to connect with our community!

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