The Rise of Portfolio Careers: Could this be the era of the new Renaissance Man?

Christopher Jackson

I’ve been lucky enough to go often to Florence, more than any other the city of the Renaissance man. Each summer the crowds gather outside the copy of the Michelangelo David beside the Palazzo Vecchio, and I wonder how many people there know that its creator also wrote poetry, and designed the stairs to the Laurentian Library about half a mile away. They queue around the block for the Ufizzi galleries, and when they’re inside they long to see Leonardo’s Annunciation. But it isn’t widely known that Leonardo was also a fine musician and for his time, a mean palaeontologist. People often feel they are dreaming when they come to Italy, because the past has such a strong pull. But we must also ask ourselves why they have that pull. It’s because these figures have a reach and potential that, however clever we might think we are, demonstrably exceeds our own: they were the Renaissance Men.

For myself, sometimes I’ve taken a moment to sit on the benches in the square Santa Maria Novella, the façade of which was produced by the man who is sometimes said to have started it all Leon Battista Alberti (1404-1472). Alberti might be better known if one were better able to pinpoint who he was – but that’s just the point, he was the original owner of what today we call the portfolio career. However he seems to have gone out of his way to make his identity as difficult to define as possible. He was by turns an author, artist, architect, poet, priest, linguist, philosopher, and cryptographer. Alberti is probably now a little in the shadow of Leonardo Da Vinci and Michelangelo, both of whom could do almost anything, and perhaps you might say, could do all those things a little better than Alberti. But there is a daring about Alberti which is part of the Florentine spirit. Perhaps he is more fitting emblem of the Renaissance that Michelangelo and Leonardo, those superb outliers. Alberti embodies the opportunities of doing lots of little things, but perhaps in a way some of the drawbacks.

It is sometimes said that Goethe, who died in 1832, was the last person alive to know the entire state of human knowledge as it was at that time. Nobody who has studied him can ignore that for Germany’s most famous poet he knew an awful lot about physics – and architecture, art, plants, geology and everything else. Others have observed that Joyce’s Ulysses, that massive work published in 1922, showed that its author had arrived at something close to a complete knowledge of the world as he found it at the start of the 21st century.

Received wisdom is that this is no longer possible. The story goes like this. In the 21st century it became quite impossible to arrive at any overall view of things, because everything from poetry to mathematics became almost outrageously specialised. You might just about get your head around Nils Bohr’s physics, but it would come at the cost of not being able to understand The Wasteland. I must admit that I have rather tended to dislike this reductive and unambitious way of living. It was Saul Bellow who in The Adventures of Augie March (1953) had its hero say: “This is an age of specialisation and I am not a specialist.” In my own life, I’ve found myself writing books about figures as disparate as Theresa May and Roger Federer – and also had a stab at a long book on American democracy, and fiction and poetry too. I’ve also wanted to mentor, start magazines, edit, paint, and play piano. It is a moot point as to whether I have ever done these things well: but I know this tendency within myself to lie so deep as to amount to a fact of my life.

This restlessness, you might say, or perhaps inquisitiveness, can be punished by the world. It doesn’t make one easily categorizable. It was something which the late Clive James, who insisted on his write to appear on television, while also translating Dante and learning the tango (and speaking about ten languages), used to complain about. Today it can still look rather peculiar on CVs to have wheeled about continually: he speaks of lack of staying power, and can raise doubts (often justified ones) about the extent of one’s commitment to any one thing.

One such person is Anushka Sharma, the founder of the London Space Network, who tells me of her own portfolio career. “I worked in politics but then left in 2012 to work in the Olympics,” she recalls. “I then went into self-employment and began working in the start-up ecosystem, before realising my passion was space. I was building up a network, doing a lot in the space sector, and people would say: ‘You’re doing so much in space but not telling anyone.”

Life for Anushka was somewhat unpredictable. She recalls: “I was straddling one six-month contract with one and then another, getting a break in between, getting access to the space community. I was network mapping and looking at the opportunities. I’ve definitely had a portfolio background.”

But this, she says, has brought both huge benefits and certain costs. “I’ve followed what I love and what I’m passionate about. My CV was rejected by so many jobs. Prospective employers would assume I’d get bored, or they’d say they didn’t understand my story. It’s only now in retrospect that all this makes sense.”

Finito mentor Sophia Petrides has seen this regularly with her candidates: “I see this a lot in my work as a coach. Clients who are feeling burned out and stuck often come to me for help in navigating this difficult time and figuring out their next career move. In many cases, a portfolio career can be a good solution. It allows them to leverage their skills and experience in a way that is more fulfilling and sustainable.”

She attributes the trend to a range of factors. The first is a desire for flexibility. “Many individuals seek greater flexibility in their work lives to pursue multiple interests and accommodate personal commitments,” Petrides explains. “A portfolio career allows them to design a work schedule that fits their lifestyle.” This, she continues, carries with it possible financial benefits, in particular diversification of income: “With the rise of the gig economy and freelance opportunities, individuals may choose a portfolio career to diversify their sources of income. This can provide greater financial stability and resilience against economic downturns or job loss.”

Of course there’s risk attached too in that one’s roots across different sectors may somehow be shallower than is the case with somebody who becomes highly expert in a single, durable career. People with portfolio careers are best advised to make sure that they are following their passion – or passions – otherwise the risks of this path may not seem worth it. Petrides continues: “A portfolio career allows individuals to pursue multiple interests and passions simultaneously, leading to a more fulfilling and varied work life. This can lead to greater job satisfaction and a sense of purpose. Furthermore, some people have a diverse set of skills and interests that may not be fully utilized in a traditional career path. A portfolio career allows them to leverage all their talents and expertise across different roles or industries.” We’re also, she points out, at a point in time where all this is possible and so why not give it a try? “The nature of work is evolving rapidly with technological advancements and globalization,” she explains. “A portfolio career offers individuals the opportunity to adapt to these changes by continuously learning new skills and exploring different opportunities.”

However, while these benefits are real, they will likely fit a particular sort of person – and even that sort of person might want to be aware of certain potential drawbacks. “On the downside of a portfolio career, juggling multiple roles or projects can be challenging and may lead to income variability as you constantly chase the next job,” Petrides adds. “Balancing different commitments can also be overwhelming, potentially leading to stress and burnout if not managed effectively. Additionally, you may lack benefits such as health insurance or retirement plans.” All in all, like everything in life, it’s a choice: “In today’s uncertain times, having a portfolio career can offer advantages by making individuals more agile, resilient, and adaptable to change. It allows them to find joy in life by pursuing diverse interests and maintaining a flexible work-life balance.”

But how to know whether this path is for you? Petrides outlines certain personality types who might be particularly suited to a portfolio career. Her first category are those who are curious and creative, adding that “those who enjoy finding new solutions and exploring different ideas are likely to thrive in a portfolio career. The variety of work can help them stay engaged and motivated.” But she’s also keen to point out that this is no walk in the park. She adds that you’ve got to be self-disciplined (“managing multiple projects and clients requires strong time management and organisational skill” as well as adaptable (“the ability to learn new skills and adjust to changing markets demands is essential for success in a portfolio career”). It’s also important to work on your networking skills.

So are we perhaps evolving in this direction? Dr Paul Hokemeyer, an admired psychologist who has built up an impressive practice and client base, thinks that’s possible.  “Human beings are born to evolve,” he tells me. “In 1859, Darwin noted that it wasn’t the strongest species that survived, but rather the ones who could adapt to changing circumstances. Over a half a century later, Sartre wrote eloquently about how existence precedes essence. In our modern world, this applies to one’s professional successes and fulfilment in life as well. In my experience in working with young adults and nascent professionals, I’ve found in our rapidly changing world, people are best served by developing a well-diversified set of professional credentials that change over time.”

So are we therefore in the era of Renaissance Man 2.0?  Hokemeyer is enthused by the idea. “I love the promise of Renaissance Man 2.0. In it, we recognize that life is meant to be lived, relationships nurtured and our earth, honoured.  One of the central features of the original Renaissance Man was that it was grounded in an ethos of abundance, a recognition that the world contains more than enough resources to provide a safe and equitable place for everyone. Given that today science has turned its attention to issues relating to longevity and reversing the aging process, I welcome a renewed focus on issues relating to an embrace of all knowledge and an intentional focus on developing one’s capacity to their full potential.”

However, as exciting as all this is, I’ve also sometimes wondered whether my own tendency to do lots of different kinds of things might perhaps open up onto fear of failure. It was Sir John Mortimer who was amusingly open about this. As both a barrister and a writer – and a writer across many genres – he only have jokily observed that having lots of projects on the go was a useful wager against failure. Hokemeyer finds this plausible: “There is of course the potential that adopting a scatter shot approach to life is grounded in unhealthy personality and mental health issues. Typically, these include things like imposter syndrome, commitment issues related to poor self-concept and low self-esteem, and issues such as ADHD, bipolar disorder, depression, anxiety and addiction issues. For people who suffer from these aforementioned conditions, their ability to attain success in or mastery over a professional area will be compromised due to their reactive rather than intentional nature.”

So perhaps it can really be a sort of ‘covert laziness’? “I think there is something to it for sure but I don’t really see the archetypical ‘layabout’ trying different things. They tend more towards the victim mentality. They lay about bemoaning the ills of the world rather than doing anything to change them.”

Sophia Petrides is not so sure that the motivations for the portfolio career are usually bad. “While restlessness might play a part for some, the core of a portfolio career lies is taking control of your work and shaping it to fit your goals and aspirations.” However, she does concede that there is ‘a danger in not specialising.” Why is this? Petrides explains: “Specialisation allows you to develop a deep understanding and expertise in a particular area. This can make you more valuable to employers and can help you to advance your career. However, there is also a danger of overspecialising. The world is constantly changing, and the skills that are in demand today may not be in demand tomorrow. If you are too specialised, you may find it difficult to adapt to these changes.”

All of which means there’s a necessary balance to be struck. We no longer expect to spend our lives at the same firm or even in the same profession for our entire working lives. We now have the ability to move about and try different things, and as curious creatures, we are naturally inclined to explore these now opportunities [1]. However, as the world develops swiftly in this new direction, we must also be aware of the need to pursue a portfolio career with a certain measured caution, and be sure above all that we’ve embarked upon it for the right reasons.