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  • Writer's pictureFleur Brown

Why (multiple) side hustles are the new main hustle

At four years old, my daughter said she was planning to be a Vet, have babies and surf professionally. She insisted she would be doing all three things at once.

I admired the diversity of her ambition. But, struggling with the conflicting demands of parenthood and running a business at that time, I suggested she might like to focus on one or two things at once.

“Why?” she said.

“You’ll enjoy it more,” I said.

“Like you do Mummy?” she asked.

Generation Alpha — two of my daughter’s career roles have a marine focus.

At six and ¾, my daughter has added a new area of focus — becoming an ocean environmental manager. She’s said she’s going to be spending a lot of time at the beach.

I’ve stopped handing out career advice to my daughter. In fact, I’ve taken some of her work-life perspective on board.
This year. I’m dividing my time across four gigs including my main business. It’s more due to opportunity than design. But I’m curiously happier. Somehow adding more dimension has bought energy and perspective back to all my activities. It’s also made me question why we let ourselves become so tightly defined by one role

I’m not alone.

One of my ‘side hustles’ is teaching professionals how to grow their personal brand, To my surprise, most of the people I meet in the workshops are actively working on at least two, often three, occupational roles.

If you think that’s a bias sample, read on…

I also produce a TV series, EntrepreneursTV. Amongst the hundreds of successful entrepreneurs I’ve chatted to in making the Show, most are running multiple ventures. It’s a struggle to choose between which company brand to feature in their title on the screen. This dramatically contradicts the old rules for anyone building a business — requiring 200% focused commitment from the founders. Which may still be true in very early stage, but it’s certainly no longer true once established.

Even the most tightly buttoned suits are loosening up their career plans.


I noticed the trend towards, what I call a ‘portfolio career’ a few years ago when I was helping a CEO exit a high profile corporate role. I was often called on to help C-suites seamlessly transition from one power role into another — with their pride and profile in-tact (and little pause for thought in-between.)

Being perceived as “under-employed” even for a fleeting second used to feel like the kiss of death for upper management. It had been bred into them that you hang onto you corporate career for life — working your way up the ranks and then keep progressing until you reach board status, then you remain on multiple boards until you retire or die.

This gentleman didn’t fit the mould. He was incredibly ambitious and hard-working, but he was fed up with the demands of CEO life — a role which required his mind, body and soul to be poured into a business suit with little gratitude or loyalty and little left for anything else. In a disrupted workforce, he knew these demands would only intensify.

He told me: “I want to exit well, and improve my personal brand.”

That request threw me. Personal brands are traditionally tethered to company brands and titles — the bigger the company the more you can cash in on your title. How would he improve his brand unless he took another, bigger CEO role?

What he did next surprised many people — including himself. He didn’t take the first round of offers that turned up with seven figure sums attached — providing him with guaranteed corporate relevance.

He sat with the question of what he really wanted to do. And then he started, slowly, testing out some ideas one at a time. Until eventually, rather than settling for one thing, he found he had assembled a portfolio of interests wonderfully tailored to his skills and passions.

A few years on, he can’t imagine returning to a full-time corporate role. And his profile remains strong — only now it is diversified across a number of his interests.

What he did seemed pioneering, but I now know countless executives in this position. Few would ever contemplate going back into full-time management roles.

Which brings me to millennials (or Gen Y and Gen Z — whichever you prefer).

It will surprise nobody if I say that millennials are pushing hard at the edges of our professional boundaries and helping us redefine what work-life looks like.

Check out this post by millennial boss Nathan Tesler of Wildcard Money for a glimpse of the argument.This is a generation who refuse to check their identity at the door — and employers have to let them run their side projects or risk losing them.

This change may have felt like torture for those fixed within corporate infrastructure. And it’s been inconvenient at best for the rest.

But I am going to argue this shift away from doing “one thing” is good for us and we will be happier, and more liberated in the long-term.



A great new flexible working campaign by CBA

Most of the conflict I felt three years ago centered more around the guilt than the reality of my juggling act. Even though I had built a business to be the master of my career destiny, I felt judged by others — clients, staff, anyone really, when I took time out from the business to be a devoted parent. That didn’t stop me. I spent maximum time with my daughter and I worked hard after hours to compensate. But I occupied a kind of hell where I kept both worlds secret from the other — I fiercely protected my time with my daughter from any business encroachment. I kept the realities of being a parent hidden from my work life.

In 2018, I can tell my clients or staff I need to take time out to be with my daughter without the cringe. And I see visible examples of others, including men, doing the same.

When attitudes shift. it prevents the torture of guilty working and guilty parenting. I know as a parent and an employer of parents, that productivity has little to do with a time-clock. Quite the opposite. If we can cut the judgement, we will not only be happier we will have more energy to get stuff done.


The obvious thing that’s changed and changing the workforce is the gig economy. Uber and Airbnb income is not just helping people generate extra income, many people are using it as the opportunity to career transition and build a new employment opportunity whilst maintaining steady income.


In the next few years, well over 50% of the workforce is expected to be freelance, a contractor or self-employed. Unlike the drive towards entrepreneurship amongst the self-actualised employee, this trend is not something people are signing up for necessarily. It’s a flow on-effect from job shifts and job losses due to tech changes, the fact business no longer wishes to maintain large corporate overheads and the drive towards new ways of flexible working. This will only increase.


Not so long ago, parents and career counselors were the most likely means for a young person to determine their career path. The corporate guardians then took over this role once someone commenced their career and saw to it that individuals need not check in with their feelings much at all whilst climbing the career ladder. They merely needed to follow the directions.

This saw generations of young people uncomfortably shoved into professions like accounting, only to feel trapped by the choices others had made for them. It is fair to say that young people not only want more freedom of choice than their parents around their career, they want the freedom to experience as much as possible — often at the same time. The quest towards startups and entrepreneurship is a natural flow-on of this shift in ambition.


One of the most exciting and positively progressive trends I’ve observed is the gradual emergence of freedom of identity. It started with freedom of speech, shifted to diversity policy in the workplace and is now more fully expressed by the expression ‘bring your whole self to work.’ But ‘which whole self?’ is becoming the question — for all humans are naturally multi-dimensional, or should be.

For more on developing your personal brand — my book The Business of Being YOU is available on Amazon and in all bookstores.

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