Which Hat Should I Wear? – Whats, Whys & Tips for Starting a Portfolio Career

Written by Kate Windebank

Kate runs, Kate & Co, an online career coaching company that helps people to find work they truly love doing. With over 15 years experience in corporate Britain and Australia in a variety of marketing and communication roles - she has never been a rule follower, nor followed a standard career path. She is unashamedly authentic, enjoys a cheeky glass of vino and loves nothing better than travelling to a new culture.

While at University I worked three jobs to pay for my tuition and living expenses. By day, I worked casually for a catering company, with a side hustle baking cookies and selling them to local cafes. By night,  I worked behind the bar at a local pub. Little did I know, I was ahead of my time and getting my first taste of a portfolio career. Looking back (perhaps with rose-tinted glasses) these were some of the happiest times in my working life – I loved the variety, working with a diverse bunch of people and doing so from different locations.

So what IS a portfolio career, and do I want one?

Well, instead of one full-time job, a portfolio career allows you to do several part-time/contract jobs within one or more professions. A portfolio career means that you get to combine your education, skills, experience, interests, hobbies – everything that you know and like – and use them in different part-time roles.

Not surprisingly, a portfolio career gives you heaps more freedom and flexibility than a traditional 9 to 5.

Why choose a portfolio career?

There are quite a few reasons why you might opt to go down the portfolio career route. Firstly, your work/life balance will be more harmonious.

When working a portfolio career, it’s you who’s in charge of managing and organising your time. This independence will certainly improve your work/life balance – a bonus if you’re currently stretched. One of your new roles might allow you to work from home. As you can imagine, there are several perks to home working, not least less time spent travelling which equates to more work and money!

You don’t have a boss anymore. A portfolio career puts you firmly in the driving seat.  Sounds bloody good, doesn’t it? Realistically, you will work for a few individuals or clients, but at least you get more freedom when it comes to picking and choosing.

Speaking of control, you control what kind of work you do and where you do it from. You could, for example, work from home, in a co-working office or at a different location every day. If this sounds interesting, here are my 8 tips to get you started on a “portfolio career”.

8 tips for starting your portfolio career

  1. Assess your hobbies and interests: spend time reflecting on the types of activities that bring you the most satisfaction and joy. When you’re not working, what kind of activities do you enjoy doing? How do you fill your weekends? What do you do on holidays? Make a list of these activities and consider whether any of them could translate into cash-producing work.
  2. Look at your educational background: besides the credentials received from your education, make a list of your favourite courses, any professional development or workshops you’ve undertaken. See if there are any jobs where you can apply this knowledge.
  3. Review your work history: look for common threads that bind all your past jobs together. Most of us follow a traditional career path, intentional or not, and that path is not always straight and narrow.
  4. Deconstruct experience into skill sets: for all your past experiences – work, volunteering and educational – develop a list of the skills you’ve mastered. Don’t focus solely on technical skills, look beyond them for ones such as communication, leadership and management!
  5. Weigh-up the pros and cons: there are risks involved in all activities but managing a portfolio career carries additional risks. Produce a detailed list of the pros ( better work/life balance, being your own boss) as well as the cons (financial instability, reduced company benefits, an uncertain future).
  6. Develop a plan: the best way to handle the common problems of a fledgling portfolio career is to create a plan of action. Your plan should include a list of possible jobs and prospective clients/employers, a weekly or monthly schedule, plans for home office or co-working space and detailed financial budget.
  7. Get organised financially: understand your financial situation and work out how much money you need to feel secure. Try to have a financial buffer in place for times when your income drops. Remember, part-time workers’ hours can often change with little notice and if you’re freelancing or consulting you need to identify and actively pursue new projects and income sources.
  8. Have a support system: it’s crucial, especially in the early phases, to have the support of family and friends. Surround yourself with people who wholeheartedly support your career choices. (This could mean steering clear of the naysayers in your life).


Finally, above all, remain positive. A portfolio career could be just the career change you’ve been looking for…


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