The Pros and Cons of a Portfolio Career

All of our reviews and recommendations are completely impartial but some posts may include affiliate links that can earn us a commission. Click here for details.

How do you like the idea of having not just one career, but several at once?

Would you enjoy a working life that’s full of variety? One where you never have to do one thing for so long that it becomes a grind?

If those thoughts appeal, perhaps a freelance portfolio career is for you?

In this article, we’ll cover the following:

  • What IS a portfolio career?
  • How realistic is it to have a portfolio career?
  • What are the downsides?
  • Why there’s a certain stigma around people choosing to work in this way.

Let’s begin!

What IS a Portfolio Career?

It didn’t really occur to me that I have a “portfolio career” until a HomeWorkingClub member emailed me asking me to write about it!

However, “portfolio career” describes my working life perfectly.

Here are some of the things I do to earn my living:

  • I own and run this website, as well as a couple of others.
  • I have a series of regular freelance writing gigs with a number of different clients, mainly in the IT and cybersecurity industries. (You can see some examples of my writing work in my Contently portfolio).
  • I earn royalties from a book I published about life in Portugal, and have two more underway.
  • I do one-off writing jobs for websites and magazines.
  • I build and maintain websites for clients.
  • I do IT consultancy work for UK businesses.

On top of these things, I do various little side gigs, both to review them for this site and to earn extra money to pay for holidays and treats. (Read this article to see how quickly this income adds up!

Essentially, having a portfolio career is about using the skills you have at your disposal to make a freelance living, and doing it in a way that’s rewarding and provides you with variety. It doesn’t have to mirror the things I detail above – somebody could have a portfolio career by doing a mix of freelance writing, selling crafts and baking cupcakes.

Similarly, and as another example, my wife works as a PR Consultant and a freelance writer, and also takes on project management contracts.

A portfolio career can, quite literally, be anything you want it to be. Such careers have even been described on Forbes as “the future of work.” Yet despite how appealing this kind of working life can be, there are disadvantages, not least the attitude some people have towards those who’ve chosen to build their career this way. And we’ll discuss all that in a moment.

How Realistic is it to Have a Portfolio Career?

I’m perhaps slightly biased on this issue, given my own working life, but I think that building a portfolio career is a very realistic thing to aim for. In fact, I think it’s sometimes more realistic than having one specific freelance career goal.

I aim to be very frank when providing advice on this (as you’ll see if you read my freelance writing jobs for beginners article). Despite what the people selling writing courses and gig-finding services may have you believe, it’s incredibly hard to make a good living as a freelance writer, especially as a beginner. There’s a steep learning curve and an abundance of experienced competition out there. All but the most determined novices fall away before making a career of it.

But how about considering the possibility of building that writing career a couple of days a week, maintaining a part-time job for another two days, and building a little eBay business to work on over the weekend?

Equally, say you’re currently in a high-powered career but secretly want to spend your life designing and making fashion items? Well, why not consider looking into doing your existing job for x days per month on a consultancy basis, using most of the rest of your time to set up a Shopify Store, and designing some print-on-demand items so you can generate some income from Society6 on the side?

(You’ll see plenty of links above, because there’s loads of content on the site demonstrating how people are doing many of these things successfully right now!)

Building up a portfolio career and establishing several different streams of income makes an awful lot of sense. In fact, it’s arguably safer than having just one job that you could lose! However, there ARE downsides, and there IS some stigma – so let’s move on to that now.

What are the Downsides of a Portfolio Career?

1. A loss of identity

It seems a little ridiculous that people take so much of their sense of identity from the job they do, but it’s a reality proved with statistics, and therefore something it’s unwise to ignore.

When you have a portfolio career, and someone asks that dinner-party favourite, “what do you do?” The answer gets complicated.

You can’t really answer with, “I have a portfolio career,” because you’re gonna sound like a douche. At the other end of the scale, you can’t really say “a bit of this, a bit of that,” because people will then assume you’re either unemployed or unemployable.

So you’re left with the options of just choosing to mention one of the things you do, or running off a laundry list of all the different things until the listener’s eyes start to glaze over.

As I say, it does seem daft that – in the modern world – it’s so hard for people to understand that it’s possible and desirable to do more than one thing for a living, but even The Financial Times discusses the “identity crisis” that can come with portfolio careers.

It’s not until you start to work on multiple things at once that you notice how often the question of “what you do?” comes up, and how much your identity relies on the answer you give. Moving away from the ease of simply being able to say “IT Manager,” “Nurse” or “Events Organiser” can prove surprisingly uncomfortable.

(And – just in case you think you’re one of those rare people who’s mastered the art of “not caring what people think” – the neuroscience behind this suggests you’re probably kidding yourself. There’s an interesting explanation of that in this book.)

Personally, my usual approach is just to pick one of the things I do and focus on that, unless I’ve been given an indication the person I’m speaking to actually cares, or if I’m moving in similarly entrepreneurial circles! Still, it’s undeniably frustrating that portfolio careers are so hard to explain.

2. Finding a balance

Maintaining a portfolio career isn’t particularly easy, and ironically it gets harder as you become more successful.

I could happily work 60 hours per week on HomeWorkingClub alone, but income from a site like this is unpredictable and irregular. Or, I could take on every offer of writing work that came my way, and find myself with no time at all to work on personal projects.

It’s a constant balance, and one you never have complete control over. Sometimes, for example, I may have a big IT or website project to do for someone else – lasting a week or a month – which means I have to back off from my own projects and only do writing work for my regular core clients.

There’s a constant need to juggle the different priorities, at the same time as making sure there’s always enough money at the end of the month to pay the bills. (Add in two children and a wife who works in the same way, and you’ll probably understand how this can prove stressful!)

This doesn’t mean that having a portfolio career means your life must be financially precarious (beyond the inevitable “feast or famine” nature of freelancing in general.) However, it’s unavoidably complex, and one month rarely resembles the previous one in terms of the work you actually end up doing.

It’s therefore fair to point out that this disadvantage alone is one that will probably put some people off aiming for a portfolio career. If you’re the kind of person who likes a fixed monthly paycheck, the jump to freelancing itself is probably quite enough to take on without the complication of a portfolio career!

3. Ticking boxes

There are various ways in which the world isn’t truly ready to handle people who’ve chosen the path of a portfolio career.

For example, it’s a struggle to create a very focused LinkedIn portfolio when you do a bunch of things. (Mine says “IT Consultant, Freelance Writer, Digital Marketer!”)

Worse can be dealing with banks and other financial institutions. If, for example, you’re trying to get a mortgage, banks like to see a nice, traditional and steady job. If you’ve chosen this more modern path, you can find a lot more hurdles in your way.

One potential way around this is to set up a company, flow all of your income through it, and pay yourself a wage. Of course the simplicity of this will depend a lot on what types of work your portfolio career involves, and the way things operate in your specific country – but it’s something to think about.

Self-employment has always made things like obtaining credit and mortgages rather more difficult. But throwing in the complication of a portfolio career certainly isn’t making this part of life any easier for yourself – and there’s no getting away from that.

Why is there a Stigma around Portfolio Careers?

The issues discussed above go a long way to explaining why some people shy away from portfolio careers, and why some others may look upon those taking this freelancing path with a certain disapproval.

The world of work has changed dramatically in recent years. Only a couple of decades ago, plenty of people were still accustomed to “jobs for life” and “final salary” pensions. Things have changed, and they’re going to change a lot more.

However, that doesn’t mean that there aren’t plenty of people (who may, perhaps, be our parents or grandparents) who don’t understand why we can’t all just get a job and stick with it until retirement. I believe most of the stigma originates here.

Some people have no desire to work for themselves; They want to get up every morning, do their work, and know they’re going to get paid. Others perhaps have a vague idea of something they’d really love to do, but for whatever reason – lack of drive, fear of judgement, parental expectation – decide to remain on the “safe” path anyway.

The reality is that the “safe path” is an option for fewer and fewer people nowadays, with numerous studies suggesting it’s only a couple of years until 50% of people will be self-employed.

There’s therefore a strong argument that the people who are already making the jump to freelancing will be one step ahead. Those diversified into portfolio careers could, arguably, be those in the strongest position of all.

Whether you choose to believe that and do something about it is your decision alone.

Want to know more? Check out “Portfolio Careers: How to Work for Passion, Pleasure & Profit” on Amazon here.

Leave a comment