Portfolio careers: pros and cons

Glenn Shoosmith

BookingBug founder, Glenn Shoosmith

If you don’t enjoy your job – as, sadly, many people don’t – the idea of having more than one career might be quite horrific.

But that is essentially what some people do. Someone with a portfolio career is essentially doing two or more different jobs for various employers, or for their own businesses.


Someone with a portfolio career, who will invariably be self-employed, will often provide services which are complementary to one another. For example, if they provided, variously, consultancy, mentoring and bookkeeping services, then it’s not too difficult for them to switch between mindsets required to inhabit those roles, and often all three services can be offered to the same customer as part of a package.

That said, you might have wildly different passions and skills. Katie Ledger, who mentors many people with portfolio careers, says she’s “interviewed an environmental lawyer who also makes and sells fancy, over-the-top cakes.”

If you fancy having a portfolio career, you first have to discover what you’re good at, and what you enjoy, then find a way for people to pay you to do it in such a way that it fits into your lifestyle.

The term ‘portfolio career’ was first popularised by management consultant Charles Handy 20 years ago – but few people had such a career. However, development of remote communication technologies since then has made multiple careers more feasible.

If you fancy having a portfolio career, you first have to discover what you’re good at, and what you enjoy, then find a way for people to pay you to do it in such a way that it fits into your lifestyle.

Ledger, who has written And what do you do? 10 steps to creating a Portfolio Career, says that setting up a single business is easier than ever before. “As long as people have a PC, broadband connection and a smart phone, they can have a business,” she says.

Thus, technology, along with the fact that people switch careers much more frequently than ever before, means people have the breadth of skills and necessary tools to have portfolio careers.

Internet entrepreneur Glen Shoosmith tapped into this growing trend and created BookingBug, a booking and reservation system for self-employed professionals to offer their time online. Explaining his website’s raison d’être, Shoosmith says: “It helps people manage their time. If you’re balancing four or five different jobs the valuable commodity you have to offer is time. It’s also useful when you’re running classes, and taking booking payments.”

Irregular income

The big, obvious downside to having a portfolio career is that income is irregular. However, the flip side here is that salaries have a natural ceiling, whereas portfolio career earnings have no limit. It’s higher risk, but potentially more lucrative, as Ledger, who also mentors people with portfolio careers, points out:

“Most people we interview earn significantly more then they had in their previous single-track careers. There’s no limit to what you can earn, if you’re prepared to work hard you can earn a lot.”

Before you embark on a portfolio career, you need to ask yourself: can you afford to have an irregular income? Are you happy not having a steady salary?

Nevertheless, there is a sense where a portfolio career is actually a more secure way of making money, especially in a recession. After all, if one of your skills is in much lower demand during a downturn, another – for example accountancy is fairly recession-proof – can fill the gap.


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