How to Create More Freedom With a Portfolio Career

If you want to explore options like consulting, freelancing or self-employment and gain more control over how you spend your time, you might want to consider an alternative to the “career path” norm – a portfolio career. It doesn’t matter if you still work full-time or are semi-retired. Building a portfolio career is an interesting lifestyle design option for people in different stages of the journey to financial independence.

The FIRE community is all about freedom and choices. For many of us, FIRE is not about retiring but about flexibility and control over our time. This is often at odds with the way standard corporate jobs work. Many of us want to work and explore different paths, but without the constraints of a full-time job and the pressure to “climb the ladder”. A possible solution? A portfolio career.

What Is a Portfolio Career?

Designing a portfolio career is really not much different from creating an investment portfolio. It’s a way to combine different jobs, self-employment, volunteer and freelance roles. So instead of following one inflexible career path, you create a career portfolio. What this looks like in practice will be different for every person. This approach makes you less dependent on an employer and gives you a great amount of control over how much, when and how you work.

This is a very self-directed, flexible working style and a great option for people who have many different interests and areas they want to explore. The big theme here is intentionality – a portfolio career is not just a random collection of part-time jobs. It’s also not just a combination of a full-time job and a side hustle (although it could be, of course). It’s a way to actively curate your working life and design it in a way that works best for you.

Here are some examples:

  • Part-time bookkeeper / wedding photographer / skiing instructor (seasonal)
  • FIFO truck driver / freelance translator
  • Nanny / weekend market stall operator / opera singer
  • Op Shop Volunteer / self-employed software engineer
  • Part-time driving instructor / part-time property manager

You get the idea.

I have to say that I don’t really like the “career” part of the term portfolio career. We usually associate the word “career” with “getting ahead”, which is not the point of designing a portfolio career. But for lack of a better term, we’ll run with it.

An example portfolio career

Should You Consider a Portfolio Career?

I had never heard of the portfolio career concept until a friend who is an HR consultant told me I had one. I looked up the term and went down the rabbit hole for a few days. My conclusion is that this is an excellent option for the FIRE community. I ended up with a portfolio career by accident – more on this below. All I can say is that I am very happy with the balance and variety this working style provides.

So what are some reasons you might consider a portfolio career?

  • You are still on the path to Financial Independence, but you are over the 9 to 5 grind
  • You want more flexibility and control over your time
  • You are semi-retired but still want to do some enjoyable work in a way that works for you
  • You want to explore a new field of work or start a business without having to go “all in”
  • You want to experiment with work options you might want to pursue after you reach FI (or a version of FI)
  • You have a wide variety of interests and get bored easily

Many people, myself included, fall into a portfolio career by accident for one reason or another. However, I think it is completely possible to design a portfolio career based on your interests and values.

I think this is also a great option for people who want to prepare for the transition from the full-time race to FI to a slower lifestyle. You could then just give up the elements of your portfolio career you like the least when the time is right.

There is an alternative to the “career path” approach!

How to Build a Portfolio Career

If I were to re-design my accidental portfolio career from scratch, I would first do some self-reflection and life planning. Here are the steps I think you should take if you are considering a portfolio career:

  1. Make a list of your values as they relate to working. Which values do you want your work to meet?
  2. Think about how much you actually want to work. This will, of course, greatly depend on your stage of life and where you are at on your FIRE journey.
  3. What are you good at? Which existing skills can you use in your portfolio career? Do you want to keep your current career as part of your portfolio?
  4. Which skills do you want to learn? Is there a working style (like freelancing, for instance) you’d like to add to the portfolio? Are there any particular fields of work you’d like to explore?
  5. How much do you want and need to earn? Again, this will be influenced by your stage of life, financial plans and your answers to question 4 – the less you want to work, the more you’ll have to earn.

I think it is important to consider all the different factors described above when you design your portfolio career. Different elements of your work mix will meet different values and use different skills, so like with most things, balance is key here.

Once you’ve explored these questions, you can get creative and start thinking about what your portfolio career could look like. Then you could reduce your working hours (if you have a full-time job) and add an element like freelance work to your mix. Just like with an investment portfolio, you can use a core-satellite approach when you build your portfolio career. With this approach, you pick one main source of income (like your part-time job or established business) and then add satellite projects like freelancing, consulting or a new venture.

Remember, nothing is set and stone, you can change things up as needed. Creating a portfolio career is a bit like making a recipe, trying different ingredients and swapping things out until it’s just right.

What are the ingredients of your ideal portfolio career?

Mrs. Flamingo’s Portfolio Career

As I mentioned above, I somehow ended up with a portfolio career. It was completely unplanned, but in retrospect, it makes perfect sense. I’ve actually changed careers twice over the course of my professional working life and have many different interests. I get bored of anything that I have to do too often or for too long, no matter what it is. The whole point of reaching Flamingo FI and semi-retiring was to create more balance in my life and work on the things I love. My portfolio career lets me do exactly that.

I spent a lot of time and energy figuring out my values in the past. Here are some of the values that are important to me as far as work is concerned: connection, contribution, security, making a difference, growth, variety and lifelong learning.

The first step for me was to move from working full-time to part-time when we hit Flamingo FI. This alone was a massive shift and made a big difference, but after a short time, I felt that I had mental space and energy for a bit more. Now, two years on, my work life looks a bit more varied and has really evolved into a career portfolio.

I now only work a couple of days a week in my “career” job and love it. It provides me with a certain level of security as it provides a stable income that covers all of our expenses (combined with Mr. Flamingo’s income). I also enjoy the social factor the job provides – “having to go somewhere” and going for lunch/coffee/after-work drinks.

Then, sometime in 2020, a reader approached me to see if I could coach him through some of the mental challenges he faced during his transition to semi-retirement. I had worked in exec coaching and consulting in the business environment previously, but this was definitely a new experience for me. It turns out that I love this kind of work, making a difference in someone’s life and witnessing their transformation is very fulfilling. However, it’s not something I would want to do for more than the equivalent of one day per week. It would become a less valuable experience for both parties, and I definitely don’t want that.

Earlier this year, I also started a small consulting business with a former colleague. It’s still early days, but we’ve already started working on a small project with a client. I am not sure where this will go, but it’s really exciting to try out something new. This business could potentially replace my job one day, especially if it becomes more time-consuming, but we’ll see what happens.

Together, these three elements of my portfolio career satisfy all of my work values and offer plenty of opportunities to upskill and learn. I think it would be extremely difficult to find a single job or career that could give me the same balance, variety and satisfaction. This setup also allows me to work the equivalent of about 3-4 days per week, which feels ideal to me. Eventually (probably when my kids are both in primary school), I would like to add a regular volunteer position to the mix.

Benefits and Potential Downsides

While I think this portfolio approach could work for many people, especially in the FI community, it’s not right for everyone. Here are the main benefits of a portfolio career:

  • Freedom and control: You get greater control over your time and get to decide what you want to work on.
  • Flexibility: You can change things up, explore new options and experiment. Not being confined by a full-time job makes it much easier to re-design your work life over and over.
  • Variety: Doing anything for 40 hours a week becomes monotonous over time. A portfolio career can provide variety and excitement.
  • Security: Having multiple streams of income from your work makes you much less dependent on any one employer or customer.
  • Diverse skills: If your portfolio career comprises positions in different fields, you’ll automatically grow and maintain a diverse skill set that can make it easier to find a job or start yet another career, even in tough economic times.

As with everything in life, a portfolio career also comes with risks and potential downsides:

  • It is harder to increase your income: Part of the standard corporate career path are regular pay increases and promotions. With a portfolio career, it is harder to increase your income, especially if you have several part-time jobs. If a rising income is important to you, a standard corporate job might be a better choice.
  • Work-life-balance traps: There is always a risk of taking on too much, especially if freelancing or self-employment is part of your portfolio career.
  • Social Status: There is a certain stigma attached to not climbing the career ladder. You might be seen as someone who just floats around and doesn’t know what they want.
  • Fewer benefits: A cushy corporate job usually comes with some perks – private health insurance, employer shares, a free phone plan, compulsory superannuation contributions, you name it. You will likely give some of this up if you opt for a portfolio career.


A portfolio career is in many respects the opposite of the corporate “career path” mentality. It is a creative way to combine different interests, roles and ways to work into a mix that is perfect for you. This approach offers more control over your time, freedom to explore new options and the ability to create your perfect work-life blend. It’s an interesting option for anyone on the way to Financial Independence who wants an alternative to the standard 9 to 5 grind. A portfolio career is also a great way to prepare for semi-retirement or start a business without too much risk.

Have you considered a portfolio career? Or did you maybe fall into one by accident (like me)? Share your thoughts in the comments below!

10 thoughts on “How to Create More Freedom With a Portfolio Career”

    • All the work I do is really flexible, even the job, so it works quite well. I still see being a mum as my number one job, so everything else comes second or third. It’s definitely a balancing act!

  1. This really resonated with me. I’ll spend some time going through the work values exercise, I doubt my current role is a good match for most of my values other than security. Would love to explore this more, have also sent you a PM via your contact form. Cheers.

  2. Very well written article and thank you for giving a name to what I’ve been doing for 18 years! When I started down this road I was married with 3 young sons and worked 5 jobs, teaching assistant, school bus driver, landlady and had 2 contracts doing behavioural intervention. I loved the flexibility and I didn’t require much child care because of it. Now I’m just working the first 3 jobs, happily single, empty nester, who loves to travel on my 14 weeks off a year and I’m FI.

    • Thanks Stephanie! Wow, 5 jobs, that’s a lot. But I agree, if it comes with a good amount of flexibility it’s doable and much nicer than just one full-time job. It’s also great that you were able to just drop two of the jobs when you were ready instead of having to look for a new “retirement job”. Congrats on reaching FI, 14 weeks of travel per year sounds fantastic!

  3. Currently FlamingFI and would prefer to work than not to work. Currently running my own small business part time which has been great from a flexibility/enjoyment perspective. My two young kids will be starting school soon so was thinking to pick up some additional work. Something along the lines of working 2 days as a teaching assistant although I haven’t quite fleshed this out yet.

    Keen to hear if you’ve got any further portfolio career ideas.


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