The world feels more uncertain than it was before. Yet I’ve never felt more sure about the kind of career I want. 

That’s not to say I know exactly what role I’ll land in five years or which skills I’ll need to master next. Job titles and roles matter—they help you understand required capabilities and map stepping stones forward. I’ve used this approach many times, and it’s served me well.

But I’m entering a new phase of career thinking. Rather than chase the next job with its narrow definitions and built-in limitations, I want to cultivate my own unique suite of skills and expertise that leads to interesting, challenging opportunities.

Enter the portfolio career.

The Era of Portfolio Careers Has Arrived

We’ve long thought of careers as ladders to climb—promotions, better pay, prestigious titles. That paradigm is all but outdated.

The OECD confirms what many already know: 21st-century career paths have become increasingly fluid. Workers change jobs, employers, and entire careers more frequently than past generations. Average job tenure has declined across OECD countries. U.S. data shows baby boomers held nearly 13 jobs over their working lives, with surveys suggesting half of all workers undergo a complete career change during their lifetime.

“The successful career of the future is not a ladder to climb. It’s a portfolio to curate.” — April Rinne, futurist

Rapid technological change and labour market disruption mean we must adapt continuously, develop new skills, and sometimes change careers entirely. Unlike a job that can be lost, your portfolio career—the collection of skills, experiences, and capabilities you’ve built—is yours forever.

Portfolio careers are especially relevant for international professionals who have crossed borders, rebuilt careers in new countries, learnt whole new cultures, and navigated challenges of visas, identity, and belonging.

This isn’t a trendy concept. It describes what we’ve been doing all along—whether for advancement or survival—even when we didn’t have language to name it.

So how can we better appreciate our own portfolio careers?

Taking inspiration from Agile methodology, I suggest doing a career retrospective: a structured reflection on your journey to date, examining all your roles (paid and unpaid, including volunteering), and discovering themes and threads.

My Career Retrospective: 25 Roles in 25 Years

When I list everything I’ve done from my first gig out of high school to now, I count 25+ roles spanning 25+ years.

My laundry list includes: piano teacher, lifestyle writer, dance company manager, English teacher, conflict management trainer, business communications lecturer, researcher, student association president, business development manager, principal advisor to a deputy secretary, social media manager, board member, worship leader, and university career consultant.

One could call it chaotic. To a recruiter, it might seem like a bewildering collection of disparate roles, leaving them wondering what kind of career chameleon they’re dealing with.

But how about poetic? From a young age, I’ve been driven by curiosity and purpose, following personal interests rather than conventional pathways. Each role represents a desire to pursue passion, help people, or contribute to something bigger than myself.

The Early Years: Passion vs. Pragmatism

The coolest role I had at university was arts and film reviewer for an e-zine set up by enterprising students starting their web hosting business. The gig didn’t pay, but spending evenings watching theatre, dance productions, and countless films for free was payment enough. Critiquing performances and narratives was the highest form of self-actualisation for an arts student majoring in English.

After graduation, I worked in the dot-com sector as it was about to bubble-burst, moved to arts management, then teaching. I constantly felt tension between passion and pragmatism in my home country of Singapore. My peers were well ahead in their established careers while I worried about my CV, which screamed “job-hopper” from day one.

The Settling Down Phase: Getting “Real”

When I was ready to settle down and start a family, I was determined to hang up my footloose approach and get serious about a “real job.” I interviewed for a conflict management trainer role that felt very much in my element. I was video recorded doing a mock training session which felt natural, thanks to past teaching gigs and high school drama productions.

Then came the chat with the big boss. She was concerned about my CV: “Can you actually stay in this job?” I played my adulting card—all truth, no fluff. She later told me: “If it wasn’t for your video, we wouldn’t have given your CV a second look.”

Life stage and family responsibilities changed everything. I was looking for stability and professional growth, which I found in training and education roles. I spent 10 years sharpening my trainer’s toolkit, honing my teaching craft, delving into pedagogies, and completing my Master of Arts in Teaching. There was great satisfaction doing meaningful work through my skills and talents, yet a restlessness tugged at my sensibilities.

The Big Leap: PhD and Migration

That restlessness led to another life-changing transition. Inspired by theories and research I’d spent long hours writing about for my Master’s, I wanted to go further. I decided I wanted to do a PhD in Education with dreams of becoming an academic. I also wanted my family to experience something new, for my children to enjoy their childhood, and to take this calculated risk before we got too comfortable.

We moved to New Zealand where I started a new role as a PhD candidate and threw myself wholeheartedly into academia and research.

Making Sense of the Pattern

How could I make sense of all these roles?

Analysing them using Holland Codes (RIASEC personality types) revealed this: I have a Social-Enterprising-Artistic (SEA) profile. Social is clearly dominant, Enterprising a strong secondary, and Artistic significant. Conventional and Investigative are moderate, while Realistic is non-existent.

Whilst people usually take the profile test to explore related jobs, this reverse analysis helped me appreciate something profound: The SEA profile isn’t just about job preferences or job fit. It reveals my desire to combine social, enterprising, and artistic elements in my work. Or put another way: to be someone who influences and develops people, spearheads projects, and offers creative and original insights.

The portfolio I built was invisible to me for years because I measured it against conventional markers of progress and prestige, even whilst trying to explore alternative directions.

Seven Years of Change, Challenge, and Completion

This realisation emerged recently whilst reflecting on my original migration plans and PhD dreams. Serendipitously, it’s been seven years since completing my PhD.

Seven years. That’s how long it took from completing my PhD in Education at the University of Waikato to finding my way back to a university setting, but in a role I never imagined when I submitted my thesis.

Seven years often represents a period of completion, transformation, and cycles. When I walked across that graduation stage, I carried dreams of an academic career: publications, teaching positions, research grants. That was the primary motivator for moving countries and uprooting my family. The academic career seemed like a natural progression from teaching in higher education, and a worthy, family-proud career I would add.

The pathway I envisioned was clear and conventional. What I got instead was seven years of non-academic roles where I swapped my academic identity for a professional one that felt strange at first but grew in skills, knowledge, and networks over time. It was difficult to admit I’d “failed” to become an academic. I used to joke that I was a “recovering academic” when I first started my professional role.

But looking at those seven years through an emotional lens, I also recall the roller coaster: rejection and reinvention, success and shattered plans. The search for academic jobs felt hopeful but grew hopeless through successive rejections. Then came a career consultant role for new migrants that was supposed to be temporary but led to pragmatic considerations of stable income. A pivot into government work took me further from my academic identity, yet the professional environment was exciting and rewarding. Just when I thought I’d made impressive strides, involuntary redundancy forced me to consider returning to Singapore, questioning whether migration itself had been a mistake.

The roller coaster graph of those seven years ends on a high with my current role as university career consultant. Climbing from rock bottom to this high point was no magic wand, quick career hack, or pure dumb luck. I was forced to consider all options, dig deep, and get uncomfortable with worst-case scenarios. The Social-Enterprising-Artistic aspects of my career personality jostled for attention. I felt drawn to roles that gave me the most energy and hope.

At any point during those seven years, if you’d asked about my career, I would have simply answered with facts, stating the job I had or that I was looking for one.

But here’s what hindsight reveals: I was building a portfolio career all along. I just couldn’t see it because it’s very hard to avoid measuring yourself against conventional markers of progress and prestige, even when you’re consciously trying to explore alternative directions.

When Your PhD Feels Like a Cruel Joke

PhD students often indulge in cruel optimism – the doctoral aspiration for academic life despite depressing realities of limited opportunities and precarious pathways. I was truly an optimist, feeling ultra-motivated to publish, attend conferences, and do everything possible to increase my academic capital and beat the odds.

My PhD research focused on peer brokering practices amongst international learners, specifically how students navigate culturally relevant connections and networks to succeed in unfamiliar academic environments. I understood, intellectually and personally, what it meant to be an outsider trying to find my way. I’d lived it as a Singaporean Chinese in New Zealand: trying to explain who I was culturally and ethnically to a largely disinterested audience, working hard and speaking out to prove naysayers wrong, always seeking connections and networks that understood my work and identity.

Cruel optimism ran its course. Urgent pragmatism loomed large in the rearview mirror.

The cruel part wasn’t just the reality of the academic job market and short-term contracts, but that being migrant, Asian, Chinese, unconventional, and assertive was a mixed bag of traits that didn’t quite fit the people, place, and perspective where I was situated.

With my PhD degree done and dusted, it was a full-time paid job that would keep my migrant dreams alive, not a half-baked notion of someday getting an academic position. Because that’s what migration demands. You can’t afford idealism when you need to prove economic value whilst still establishing your foothold in a new country.

The Invisible Portfolio I Was Actually Building

They say hindsight is 20/20. Commenting on the past seems easy when you know the outcome. But that clarity is only useful if it’s meaningful and teaches lessons for the future.

What do my aha moments tell me about myself, my career, and my future?

Phase 1: Getting a Foot in the Door (The Accidental Job)

When I took the career consultant role working with new migrants, it felt like survival mode. Ditching the academic dream for a job. A foot in the door to the public sector. Something to pay bills whilst figuring out what came next.

What it looked like then: A compromise. Moving away from academia and research. Leaving behind the identity I’d worked so hard to build.

What I can see now: This role built new knowledge structures of the public sector and provided the very foundation of my career practice today. I was developing:

• Deep empathy through shared experience: I wasn’t just helping migrants; I was one. I understood the disorientation, the pressure to prove yourself, the exhaustion of constant cultural translation.
• The art of brokering in practice: My research had been about peer brokering. Now I was doing it professionally by connecting people to resources, translating between cultural contexts, helping others navigate unfamiliar systems.
• Client-centred coaching skills: Every conversation required listening beneath the surface, understanding what people weren’t saying, recognising cultural dimensions of career aspirations.
• Knowledge of settlement systems: I was learning the landscape of migration support, policy, and barriers—knowledge that grew my systems thinking and analysis skills.

This wasn’t just a job. It was an apprenticeship in policy implementation and cross-cultural career development that no academic position could have provided.

Phase 2: Embracing a New Professional Mindset (Switching Track)

The pathway into government jobs took me even further from what I thought I wanted. Policy. Stakeholder management. Bureaucratic processes. This wasn’t education. This wasn’t research. This was a completely different professional culture.

What it looked like then: I was losing my academic identity. Becoming someone else. Forced in a different direction.

What I can see now: I was gaining dual citizenship in academic and professional cultures—an attribute I didn’t think much of before but has provided unique credibility to different audiences. I developed:

• Policy thinking: Understanding how systems work, how decisions get made, how to navigate institutional structures
• Stakeholder management across differences: Working with diverse groups, building consensus, translating between organisational languages
• Public sector networks: Connections across government agencies, exposure to how settlement and education policy machinery actually operates
• Institutional navigation skills: The patience to work within complex systems, the strategic thinking to influence them

I was learning my identity didn’t have to be either/or. I could hold both academic researcher and government professional. I could maintain my “north star” of international education whilst being pragmatic about where I worked. In fact, that north star helped me land a job at Education New Zealand as business development manager.

However, holding two identities also taught me that working in government was less about asserting personal authoritative expertise and more about implementing policies of the government of the day, regardless of opinion or perspective.

Phase 3: Contributing to Causes and Networks (Keeping My Passion Alive)

Throughout my government years, I never stopped watching for opportunities related to my research interests: international students, migration, cross-cultural engagement, supporting ethnic communities. 

I initiated Lunar New Year celebrations at my workplace. I was an active member of the Pan-Asian Public Sector Network. I applied successfully to be a board member of English Language Partners (New Zealand’s largest provider of English language training to migrants and former refugees). I maintained connections with academic friends and professional associations, and wrote about my passion topics on my blog.

What it looked like then: Scattered focus. Trying to be someone I couldn’t really be anymore. Not knowing where passion projects were leading—maybe a dead end.

What I can see now: This was planned happenstance in action, the career theory by John Krumboltz about creating and transforming unplanned events into opportunities. I was engaging in:

• Strategic networking: Building bridges between sectors, creating weak ties that Mark Granovetter’s research showed would be more valuable than strong ties
• Domain expertise maintenance: Supporting and advocating for cross-cultural engagement and inclusion even whilst working in completely different areas, ensuring I could speak both languages when opportunities arose
• Persistence without rigidity: Having direction without being so attached to specific outcomes that I missed other possibilities

I also wonder if keeping passion alive with these extracurricular activities was the extra fuel that kept me motivated in my day job, especially when work demands zapped all optimistic energy from my tank.

Career transitions aren’t just about skills and opportunities. They’re about identity, belonging, and the courage to rebuild yourself when your plans fall apart.

Phase 4: Losing My Job and Feeling Like a Loser (Hitting Rock Bottom)

When the notice of redundancy came, I felt I was free-falling. No government job. Few alternatives. A good track record and previous connections seemed to count for little when everyone else had those things too.

It felt like reliving the cruel optimism of pursuing a PhD but worse. I had overcome, I had succeeded, and now I’d fallen off what looked like the highest rung, with no substitute in sight. Was someone punishing me for thinking I could make it this far?

Urgent pragmatism reared its fat, ugly head. Should I stay or should I go? Should I return to Singapore? Had my PhD and all these years establishing my New Zealand career been for nothing?

What it looked like then: Failure. Career stagnation. The end of my New Zealand story.

What I can see now: This forced pause helped me pull together my portfolio career elements. Now both content and process are key components of my training and coaching practice. I gained:

• Clarity about values: When considering leaving a country, you discover what actually matters. I had to articulate why I wanted to stay, what New Zealand meant to me, what kind of work would be meaningful.
• Resilience through radical uncertainty: I learnt to sit with not knowing. To hold multiple possibilities without immediately needing resolution. To be reminded that man proposes, but God disposes, and that God ultimately directs my steps and determines my outcomes.
• Introspection as a practice: The ability to examine my assumptions, challenge my own narratives, and ask hard questions became a skill I could offer others.
• Normalising ‘return’ without shame: Many international professionals face this crossroads. I learnt that considering all options, including returning home, isn’t failure. Despite the social stigma of a failed migration story (common in many Asian cultures), I consider it a blessing to be able to have the option of returning home when others may not have such a choice. It’s a choice worthy of consideration that holds potential benefit.

This period taught me something important about career transition: 

It’s not just about transferrable skills and opportunities. It’s about identity, belonging, and the courage to rebuild when plans fall apart.

During this time, I took steps to explore what I’d been interested in for ages, what was part and parcel of an academic’s job, what I’d done professionally as corporate trainer and lecturer, and engaged in when mentoring junior staff and organising onboarding programmes: training and coaching.

I started looking into professional development programmes, getting credentialled for past experience and skills, volunteering my training and coaching services to not-for-profits. The more I did it, the more alive I felt. I was once again in my element!

Attaining professional membership with the Career Development Association of New Zealand was a milestone of gigantic proportions. It validated this: that my PhD in Education and previous teaching, coaching, and career development experience had not been in vain. In fact, all of it was highly valuable for the work of a careers practitioner.

Phase 5: University Career Consultant (Full Circle Integration)

After more than 20 job applications and rejections, whilst exploring and experimenting with training and coaching, a job ad caught my attention: Career Consultant, Victoria University of Wellington. This was a role I’d been practising for months, work I’d done before, in an environment I was highly attracted to. I interviewed successfully for the role, and when I started, it felt absolutely right from day one.

It wasn’t the academic role I’d once clamoured for, but I was working in an educational and intellectual environment promoting student success and supporting equity groups like international and refugee-background students. Not only was I doing meaningful work with direct impact, I genuinely felt welcomed, included, and valued for my knowledge and contributions. Turns out my PhD and all those publications and conferences had built a reputation I didn’t know existed!

What it looked like then: Finally arriving. Coming home.

What I can see now: This role was only possible because of everything that came before. I didn’t return to the university. I arrived as someone completely different.

I brought:

• Lived experience of migration that allows me to truly understand international students
• Government systems knowledge that helps me navigate institutional contexts
• Cross-cultural coaching expertise developed through working in multicultural Singapore and with new migrants in New Zealand
• Research credentials that give me credibility in an academic environment
• Brokering skills I can now teach explicitly, drawing on both my PhD research and professional practice

The portfolio I built wasn’t the one I planned. It was more meaningful, more multifaceted, and more transferable than I could have imagined.

Hindsight is 20/20, but only if you’re willing to look back and name what you’ve built. Only if you’re willing to let go of the portfolio you planned and embrace the one you actually have.

The Portfolio Career You Have Is Often Not the One You Planned

When I look back at those seven years between PhD and university career consultant, I don’t see wasted time anymore. I see a portfolio that emerged through lived experience, adaptive responses, and willingness to learn from unexpected places.

The portfolio I built was invisible to me for years because I only saw what was important for my current job and immediate future. I thought success meant getting the job you trained for, getting promoted, getting more money.

But the career retrospective helped me see that where I am today isn’t just a result of accumulated skills, knowledge, and experience. My career personality profile of Social-Enterprising-Artistic was seeded during university, evolved over different life stages, and very much fuelled the career choices and life decisions I’ve made.

Here’s the paradox I’ve come to understand: even as I consciously tried to chart a different course, I found myself unconsciously measuring progress against traditional markers like job titles, seniority levels, institutional prestige. It’s incredibly difficult to fully let go of these ingrained metrics, even when intellectually you know they don’t capture the full picture of career growth. The tension between exploring new directions and seeking validation through conventional markers was constant. Only in retrospect can I see that the real progress was happening in the very moments I thought I was “falling behind.”

Hindsight is 20/20, but only if you’re willing to look back and name what you’ve built. Only if you’re willing to let go of the portfolio you planned and embrace the one you actually have.

An Invitation to Be Intentional

What hidden portfolio have you been building?

Look back at your career path, especially the parts that felt like failures or detours.

• What were you actually learning?
• What skills were you developing that you’ve never named?
• What connections were you making that seemed peripheral but turned out essential?

The career you have is often different from the one you planned. But different doesn’t mean lesser. It may be richer than you thought, more resilient than you realise, and truly unique and yours to own.

Dr Sherrie Lee is a career coach for cross-cultural and mid-career transitions. She helps international professionals build networks and thrive in new work cultures. Her lived experience as a migrant, research on knowledge brokering, and active professional networks give her a unique perspective on staying resilient and future-ready amid career uncertainty and disruption. Connect with her at thediasporicacademic.com