The death of the ‘job for life’

Since I started my sabbatical and moved back to Lisbon, I’ve been lucky enough to meet lots of different people, many of whom don’t do the typical, salaried 9-5 thing. Over the last few weeks, I’ve found myself, for the first time, starting to… tentatively… just slightly… consider what an alternative approach to work could look like for me.

Lisbon is a bit of an unusual case. The concentration of remote workers/expats/people with non-traditional careers is denser than anywhere else I’ve lived. So it may not be an accurate reflection of what the majority of millennials today are doing, but nonetheless, I’ve met a lot of people here who have their hands in a lot of pies. I’ve met people who are consulting, teaching, writing a book, making content, running workshops and, somehow, doing it all at the same time.

It seems to me that these pies are things at align, at least generally, with their interests. Instead of viewing one job as a means to an end, what they have is a very intentional, identity-driven, ‘bespoke’ version of a career. This concept is intriguing to me.

The death of the ‘job for life’

My parents have stayed in the same job pretty much all their lives. These jobs never fulfilled them, I suspect, but my parents never expected them to. What these jobs gave them was a comfortable salary that funded a nice house, education for their kids and the occasional holiday. It represented stability. And for them, that was enough.

In recent years, I’ve found myself on the same path of a ‘job for life’. The job I left behind is pretty great on paper - it’s well paid, low stress, good benefits and comes with a bit of status. But it’s also not particularly challenging or aligned with my interests. It’s something I wish I could overlook. But yet, that misalignment has chipped away at me over the years.

For better or worse, newer generations expect a lot more from our careers. We want novelty. We want progression. We want money. We want agency. We want fulfilment. We want it all.

Nowadays, we expect to move jobs every few years. Add to that a horrible job market and you have a recipe for long-term languishing and dissatisfaction without any clear answers. Because I’m fairly sure a career that ticks every single one of the above boxes doesn’t exist.

But damn it if we won’t try to find it anyway.

Cue: the rise of the portfolio career

The job market is tight right now. Things are unstable. The economy is changing at a rapid pace, the cost of living is becoming untenable for many, and our expectations for our careers (and lives generally) continue to be high.

In the face of uncertainty and drudgery, people want to take back control.

A portfolio career involves balancing multiple income streams—such as part-time roles, freelance projects, or consulting—rather than holding a single, full-time position.

I’ve noticed that, at least in Lisbon, many people are turning to a more agentic approach to work. People love the idea of being their own boss and being in charge of their own time. What better way to do that than intentionally building your career, piece by piece?

The benefits of a portfolio career

I always said I didn’t want to work for myself.

I’ve struggled with uncertainty and my stress tolerance is, admittedly, pretty low (working on it!). I like showing up at my office every day, talking to my colleagues, doing my work and clocking out. I make the most of my free time by spending it with friends/family and pouring into my hobbies. I like seeing my pay packet hit my account predictably every month. It’s easy. It’s comfortable.

But this sabbatical has already made me realise that there are other ways to go about things. While comfortable, it’s also paradoxically draining to do a job that doesn’t interest you, especially if you’re someone who values growth and impact. After all, you still have to spend 40 hours a week - most of your waking hours - actually doing the job. That’s a lot of time.

Alignment and identity

I’ve found that taking a risk - and betting on yourself - increases confidence. Even if things don’t pan out the way you want, it’s the recovery and the carrying on that builds self-trust. A portfolio career is a great way to challenge yourself, to create a work identity that’s reflective of your interests, values and who you are as a person. This in itself can be very energising, expansive and fulfilling.

You could visualise your portfolio career like a pie chart - a model that keeps you flexible, that evolves along with your interests, needs and circumstances at each point in life.

Example of an evolving portfolio career by Anna Mack’s Stack (a good read)

My perfect ‘pie’ would probably look like part-time office work to pay the bills, plus an impact-led part-time/volunteer role, therapy practice, writing and taking part in community projects.

Sometimes I like to imagine myself clocking in for a policy job in the morning, then hopping off to teach a class, lead a coaching session or write in a coffee shop in the afternoon, before going home to my cosy apartment and spending stress-free weekends with my friends and family.

It’s a fantasy where everything is in balance, where I am the embodiment of my values and interests, where I am the person I want to be.

And now: the drawbacks

Of course, in this fantasy there is no friction, no teething problems, no annoying practicalities to consider. Because there does seem to be a downside - if not multiple downsides - to a so-called portfolio career.

Instability

Firstly, it’s inherently unstable. Sure, you could end up earning more than if you had a salaried job. But depending on your field of work, you also could end up earning significantly less, with the amount varying month to month.

You’re your own boss, so you’re responsible for your own wins. When it’s going well, that must feel great! But you’re also responsible for continuously finding your own work and under the cosh when things go wrong. That’s stressful. Also, selling yourself is hard, especially when it doesn’t come naturally.

I’ve heard people say that the self-employed, freelance or portfolio career life can be very intense and uncertain, especially at the beginning. And even more so when life gets real with bills, health, dependents or whatever responsibilities you have. Plus, you don’t have the benefits (like sick pay) that an employer would provide.

Some people swear by the freedom and flexibility of the portfolio career life, touting it as a way to stay agile and resilient in an ever-changing job market. I know others say it affected their mental health and ultimately ended up returning to the stability of a 9-5. I can totally see both sides.

Isolation

Remote consulting/fractional work comes up a lot when talking about portfolio careers as something that offers a lot of flexibility and pays the bills. But the trade-off of remote work is often isolation.

I’ve done bouts of remote work with my policy job, the longest being for 2 months. That was enough to tell me that being constantly at home with my laptop isn’t healthy for me long-term. Though I am starting to wonder if it was more about that job than it was about the remote working…

Either way, the impact of remote working is something to be aware of, especially if you know your tolerance for solitary working is low.

Beware turning your hobbies into a job

I’ve learnt that putting the pressure of your livelihood onto things that you enjoy can sap the passion out of them faster than you’d expect.

I encountered this when I first started getting art commissions a few years ago, and also when I started coaching as a volunteer in 2024. As soon as other people’s expectations were placed upon these things I was doing for fun, the internal pressure of doing them well made me balk and retreat.

But to caveat this, I wasn’t quite ready to take the step with art commissions at the time. Meanwhile the volunteering obviously wasn’t paid, so I was starting to feel like I was putting in more than I was getting back. The conditions weren’t quite right for these things to be sustainable.

So I’m not saying don’t turn your hobbies into a job. If you have the right mindset (being open to rejection, having self-trust) and are being compensated, the conditions might actually be right for you to monetise your hobby in a sustainable way. So far, at least for me, it just hasn’t quite worked out.

Is a portfolio career worth the punt?

Like everything, there are pros and cons.

I can’t really weigh in on whether it’s worth it overall, because I haven’t tried it. But I’m a big believer in trying stuff to see what works.

I have to be honest - I actually like the 9-5. I like the regular hours, having colleagues, and not having to graft to find my next project or worry about income. It frees up my mental energy for other things in my life. But I also don’t like how restrictive and narrow-scope it is, especially if you attach a bit of your identity to work. I’m learning to separate my identity from the job I do, but it’s hard - especially if you spend 8 hours a day doing that one job.

Maybe there’s a middle ground to start with. Maybe it looks like asking to go part-time at your current job to provide a steady (if significantly reduced) salary. Maybe you could use the freed-up time to volunteer, pursue your side hustle, or take another part-time job in an area you’re interested in. It’s still taking a risk, but perhaps a more calculated one than an all-in leap of faith.

All that to say, present circumstances will largely dictate what you can do here. How much time you have, your savings, work history, appetite for risk, stress tolerance and whether you have other responsibilities (like kids or ailing family members) will play a part in whether a portfolio career is even a viable option for you.

I’m not saying I’ll definitely go down this route, but it’s interesting to think about. I’m glad that this sabbatical has given me the time and headspace to explore these ideas and really consider what’s important before making the next step.

If you have a ‘portfolio career’, I’d love to hear about your experience!

Until next time,

Rose :)