Why I am building a portfolio career instead of returning to traditional work.

WTF is a portfolio career? Read on.

Hi, I’m Jess. A Mother of two beautiful girls and 2 x founder who has built over $1b worth of consumer brands. Now I write about life, productivity and happiness and how discovering your true values to build a life you love is priceless.

You can learn more about my work here.

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I first learned of the term Portfolio Career from Anna Mackenzie’s substack, it would be remiss of me not to open this newsletter without citing the woman who brought the idea into my orbit.

The concept is pretty straight forward: rather than have our work schedule filled by a singular project or full time job, we diversify like an investment fund, with varied interests and income from multiple streams. A portfolio career is about never ending growth, discovery and fulfilment; which is music to my ears and exactly the terminology to explain the work life I was already cultivating for myself when I stumbled across the term “portfolio career.”

A portfolio career is appealing to me because with diversification of work comes a type of freedom I crave where I am not beholden to any one thing; financially, emotionally or professionally. As someone who highly values flexibility and freedom, I feel as though I was born to pursue a career like this. Ironically, it’s what I set out to do when I started my businesses which (excitingly) grew to be rather successful and all consuming. It allows me to live in alignment with my two other greatest values: home and creativity - giving me more time with my family to make memories and more time to follow creative pursuits.

I have always been a Bowerbird, collecting creative ideas, product ideas & business ideas with the same excitement as my 3 year old collecting flowers on our family bike rides. Like her flowers though, a lot of my ideas have died, hidden away in the dark due to a lack of love, water and sunlight. I have notebook after notebook full of things I’d love to do but seldom have the time. I have over a dozen half written manuscripts, fiction and non fiction. I have dreams, goals and aspirations that have been parked on the sidelines for years. The desire to achieve these long lost goals, and ironically to do less work in the traditional sense in order to do more in the portfolio sense, was a driving force behind my recent life overhaul.

Isn’t this just going freelance you say? Absolutely not. The concept of being freelance implies that we specialise in one trade and build a roster of clients who need that service.

A portfolio career is its own complex beast. It’s varied, with multiple pursuits on the go at one time, often in different industries with different skills, that draw down on the multitude of experience you have.

What skills make a successful portfolio career?

Resilience: Building a portfolio career won’t necessarily be a walk in the park, you’ll need to spend a lot of time meeting, greeting and networking to build a contact list and interest in your offering. Things won’t happen overnight, a lot of people will take your time and then never respond to your emails. You get up and keep going.

Self awareness: Knowing your strengths and weaknesses is crucial to getting things right, both for yourself and your partners or clients. If you know you don’t balance multiple deadlines well, don’t take them on. If you know you get sucked into busy work like emails easily, set boundaries.

Honesty: Don’t say yes to things you can’t do. Nothing will destroy a portfolio career quicker than delivering sub par work.

Creativity: Not in the traditional sense of writing or painting. To me creativity is a way of being, it’s a person that sees opportunity where others don’t and tackles problems in an original way.

Openness: The concept of a portfolio career eschews everything we were taught growing up. We were read books and told tales about the careers we could have - nurse, teacher, firefighter - and were embedded with the notion that we would choose one job and do it until we die. For some people, this is exactly what they want and they thrive in this working style. However, it is simply not for me. I have always pushed the boundaries of traditional working styles.

Self Accountability: If you can’t call yourself on your own BS, don’t bother. Harsh but fair.

Is a portfolio career for you?

In my opinion, a portfolio career best suits someone who laughs in the face of risk, has a relatively strong sense of self and values freedom and flexibility. To take on a portfolio career and all of it’s glorious benefits, you must wave goodbye to the version of stability you’ve known for a long time and in it’s place settles a different type of security - knowing that if one things falls off, there are multiple other things left standing.

Do I think everyone is cut out for this type of work? Probably not. At least, not yet. I would not have been ready for a portfolio career until now; it’s my almost 20 years of work experience and a deep understanding of self that only comes with time that has allowed me to gather the varied skill sets, beliefs and values I have which makes this possible (and somewhat easy rather than stressful).

The time I spent building a personal network on LinkedIn in the 18 months prior to maternity leave has been a huge contributor to my ability to take this leap - I’ve created a self paced course on how to do this for yourself.

What are the cons of a portfolio career?

For some people these will be cons based on fear of being seen and failing, for others they are large financial hurdles to overcome in todays economic climate. For me these problems are simply part of the reality of building a life I love. I’ve been overcoming them since I was 22 and launched my first business with no savings and no safety net.

No sick pay.

No annual leave.

No long service leave.

No work, no money - unless you create a passive income stream.

What does my portfolio career look like?

My portfolio career reflects my experience, my interests and my personality. Think of it as a platter or pick n’ mix from a Hoyts cinema circa 1998. I’ve been mapping out what my return to work in 2025 looks like (I recently had my second baby), plotting the days of the week on a calendar each littered with potential projects from a variety of industries, each one so very different to the next but linked by the invisible thread that is me.

Founder. Writer. Author. Investor. Consultant. Advisor. Non Exec Board Member. Speaker. Volunteer. Mother.

The exact details are still rough, but it may look something like this:

One day a week dedicated to my agency Willow & Blake, where I will return in a new role as Head of Product.

One day a week dedicated to consulting and mentoring work. I work with founders and businesses to help them navigate growth stagnation, strategic product positioning and general business planning. You can enquire to work together by emailing me.

One day a week dedicated to a selection of things: from writing my books, to reviewing investment opportunities and launching two exciting new projects that I will announce in the coming weeks/months.

Two days a week dedicated to my children. Naps are utilised for writing, drinking a hot coffee and life admin. Or mental breakdowns. IYKYK.

Weekends for family and friends. Not an email in sight. Bliss.