Career Coaching

Unlocking your potential with portfolio careers

By: Dale Simpson


Portfolio careers have been around for decades, though without that particular title, gaining momentum and attention in recent years due to the rise of the gig economy and remote work. Google the term ‘Portfolio Careers’ and you will get 840, 000, 000, 000 results.

Human beings are multi-faceted – why shouldn’t our ways of earning income be multi-faceted too? 

"The Age of Unreason" by Irish philosopher and organisational consultant Charles Handy, starts with a prophetic declaration – the demise of the all-powerful career ladder.  Handy's narrative introduces us to organisations that resemble shamrocks and doughnuts, concepts that may have seemed outlandish at the time but now unfurl as models for modern, outsourced, and lean corporate structures. He prophesied that individuals would become free agents, their careers no longer beholden to organisations, in a world increasingly characterised by flux and unpredictability.

Handy's predictions in 1989 have, indeed, come to pass. Today, more professionals are bypassing traditional career paths to forge independent careers or join the gig economy. This shift represents a definitive departure from the security and predictability of the past, as individuals are now more inclined to pursue their passion, purpose, and self-fulfillment. Handy's insights extend beyond the age-old dichotomy of seeking 'work-life' balance, suggesting instead a concept of life balance, where work is interwoven with the fabric of our lives in a manner that fosters holistic fulfillment, a mantra to which  I can only respond ‘Bravo’. 

This new way of working is changing the traditional idea of a career as a linear progression within a single field or company. Instead, many individuals I work with are now happily and actively seeking out multiple income streams and exploring diverse interests and skills throughout their professional lives.

However, societal expectations of career can be a major hindrance when it comes to pursuing a portfolio career. From a young age, we are often conditioned to believe that success means having one stable job in a specific field and climbing up the corporate ladder, and having a singular profession.  It can raise the spectre of the term “Jack of all trades, master of none”. Yet this narrow view limits our thinking and prevents us from exploring other opportunities or interests, often waiting until retirement to explore different facets of ourselves through our hobbies, interests and non-professional skills. 

Why a Portfolio Career?

The societal expectations around “success” and the cult of status fed by ambition leaves many individuals wanting more - and the economic transformations that have played a critical role in shaping current career perspectives have sharpened this need. This is driven by a notion that we will be happy only if we are successful in terms of specific societal standards. Ask any parent what they want for their child and they would turn that equation on its head.

Widespread layoffs, the rise of outsourcing, and the precarious nature of employment have made job security an artifact rather than a given. The rise of the 'gig economy', fuelled by platforms like Uber and Upwork, offers a stark contrast to the secure job tenure once enjoyed by many Boomers. Technological advancements, globalisation, and digitalisation have drastically altered how and where we work. The maturation of the internet and the coronavirus pandemic have accelerated the take-up of remote working, and careers now often blend personal passions with professional pursuits.

Resonating in particular with Millennials and Gen Z, employment is no longer just about economic necessity but is seen as a platform to express individuality and achieve personal growth, and they look to pursue careers that promise a sense of purpose and social impact. But this approach is not just for younger people who want to fully inhabit the diversity of their lives, it applies to those of us who may be wanting something more from our lives. Essentially it is about simply living more fully, in and through what we do.


What is a portfolio career?

In The Portfolio Life: Future-Proof Your Career and Craft a Life Worthy of You, Harvard Professor Christina Wallace speaks of:

“people building the vivid multidimensional lives they dreamed of rather than the linear ones they had permission to build”.

Why do we need permission to live the life we want? A friend of mine with no interest whatsoever in law, enrolled in a Law Degree simply to please her father. She was almost relieved when her parent's divorce a year later gave her the imprimatur to leave Law for Arts, but she had also missed an opportunity to accept a TAFE place to do Graphic design, which was not considered in her family a worthy career. Another friend’s son was studying Oncology – when I asked why he chose it, he replied matter of factly and without shame “for the money”. 

Sometimes we allow ourselves to fall into careers for all the wrong reasons. Why don’t we have the courage to pursue our passions, even if they are diverse and unconventional? Why not be the polymath of our time? 

No one in history has embodied this idea better than Leonardo Da Vinci, described as a “polymath” – artist, inventor, architect, poet, mathematician, cartographer etc etc. Modern-day polymaths may be those that are fondly called ‘slashers’ - such as writer/marketer, graphic designer/stylist/yoga instructor. 

Like a financial portfolio, says Christina Wallace, a portfolio approach means not putting all your eggs in one basket, but rather ‘crafting a diverse mix of opportunities to address your current needs’, while building in opportunities to adjust when those needs change.

It is predicated on:

1.You are more than any one role or opportunity

2. Diversification will help you navigate change and mitigate uncertainty

3. When your needs change you can and should rebalance your portfolio. 

A portfolio career is not just about holding down multiple jobs; it's about curating a suite of professional roles that are aligned with one's skills, interests, and life goals. Each role is a piece – or a 'portfolio item' – contributing to a greater whole. From freelance gigs and part-time positions to consultancies and entrepreneurial ventures, a portfolio career is typified by variety, autonomy, and personal fulfillment.  Again, and it is worth repeating “living more fully, in and through what we do”.

Why Consider a Portfolio Career?

For many, the appeal of a portfolio career lies in its versatility. It offers a blend of stability and risk, allowing individuals to explore new sectors while relying on steady streams of income. Here are a few reasons why a portfolio career might be right for you:




How does it all work? 


Perhaps you started your career with an English major and ended up working as a content writer for various online publications. You however also have a passion, curiosity or motivation for marketing and social media. As you gain skills in writing online and digital marketing, you might start taking on freelance social media management projects for small businesses.

Or perhaps you trained as a teacher, and moved into corporate learning as an instructional designer, becoming a learning and development consultant, manager or facilitator.  You could also include tutoring or online teaching as another stream of income. This way, you have a blend of traditional and modern education methods, providing diverse learning opportunities for students and keeping your skills up to date.

Or you may be a software developer who also offers project management services – a combination that allows for the creation of custom software solutions while also managing the development process and ensuring timely delivery to clients. You provide a unique perspective on both roles, allowing for continuous learning and improvement in both areas. 

Or perhaps you have project management skills that can be applied to any industry, allowing for even more diverse career opportunities.  So, whether you have a combination of skills or are open to learning new ones, exploring portfolio careers can offer a fulfilling and dynamic professional path. The possibilities are endless and it's up to you to create your unique blend of work that aligns with your passions and goals.

Other examples may be less "coherent" but are equally fulfilling for people with a kaleidoscope of interests. You may, for example be a graphic designer by day, a yoga instructor by evening, and a weekend pop-up cafe owner. Or perhaps you are an IT consultant who writes travel guides and tutors high school students in computer science.

If you can successfully blend your skills and passions into a fulfilling series of income streams there are many benefits.

In closing


For those who want to live more fully in and through what they do, be more flexible in times of economic instability, and able to optimise their level of income, portfolio careers can offer an exciting alternative to traditional career paths. 

They open up avenues for creativity, innovation, and adaptability – qualities crucial in today's dynamic job market. If you're contemplating a move toward a portfolio career, start with introspection, plan strategically, and prepare to diversify your professional life in ways you've never imagined.

Remember, the objective is not just to work more, but to work smarter by creating a career that is as unique and multifaceted as you are. 


If you found this piece insightful do like, comment and please repost. We also invite disagreement as it helps improve our thinking.

If you are looking for more ways to develop your career path, stay tuned for our upcoming posts designed to help you thrive in a portfolio career.


Handy, Charles, The Age of Unreason 1990

Wallace, Christina, The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build a Life Bigger than Your Business Card, 2023