Commentary: Rethinking the 5-year career plan and its false promises of success and happiness

SINGAPORE: “Where do you see yourself in five years?” 

Once a question reserved for job interviews, it has since wormed its way into workplace appraisals, financial planning discussions and networking events – and more horrifyingly, family reunions, first dates and catch-ups with friends.  

And with upcoming Chinese New Year gatherings, many of us may be steeling ourselves for the familiar query and perhaps an accompanying existential questioning of our life choices. 

The thing I miss most about being in my early 20s is the absurd amount of confidence I had that my career would go according to plan.

I didn’t always know I wanted to write. But once I did, I set my sights on becoming a prolific magazine journalist in media capital New York City by the time I was 30. Blame the “30 under 30” lists, but it felt like if I hadn’t “made it” by then, I would never taste success. 

But as I neared that monumental 30th birthday, half-expecting adulthood to magically fall into place, all I had was burnout and the hazy vision of a five-year plan muddied by jadedness. 

I had a budding journalism career and a job I loved. But being based in Singapore meant a specific box in my five-year plan went unticked, so it never felt good enough.

For many, burnout is due to larger systemic issues, like a culture of working overtime. My problem, however, was the belief I would only be successful when I met those aspirations and expectations – and that happiness was tied to achieving that particular definition of success. 

A LOT CAN CHANGE IN FIVE YEARS  

From picking a university course to landing our first job, society pressures us into having life thought out from a young age. There seems to be no escape from planning one’s future or discussing career plans.

To be fair, the tide seems to have shifted. While hustle culture largely defined the millennial generation, Generation Z saw the resulting burnout and became known for their need for boundaries at work – think “quiet quitting” and “tang ping” (Mandarin for “lie flat”). 

It is also increasingly common to see people share online, from LinkedIn to TikTok, that they don’t know what they want to do for a career. What may have been seen as a shameful admission in the past now resonates as a relatable sentiment. 

After all, five-year plans are often based on the hopes and dreams of our present selves. A lot can change in that time, and we might not be the same person or want the same things five years later.

RETHINKING THE FIVE-YEAR PLAN

But don’t throw out the baby with the bathwater – that is, don’t throw out the five-year plan with the fixation on achieving it. 

The beginnings of a five- or even 10-year career plan are like throwing a rock into a river and hoping the ripple effect will result in the ideal career trajectory. It can keep you motivated with milestones or outcomes, be it an organisation, job title or salary range. 

It also tends to be guided by the popular goal-setting mnemonic acronym, SMART. Making specific, measurable, achievable, relevant and time-bound goals can inform other life decisions, such as family planning or buying a house.

Yet, the best plans always plan for the possibility of things not going according to plan. Embracing, and even preparing, for unexpected circumstances cultivates an adaptable mindset and can prevent us from rooting professional success to a single desired outcome. 

Seeing waylaid plans as failure or an end to our dreams can result in perennial dissatisfaction and burnout. 

But seeing it as an opportunity to grow and understand ourselves is similar to the “growth mindset” often discussed in business psychology. Someone with a growth mindset “views intelligence, abilities, and talents as learnable and capable of improvement through effort”, according to the Harvard Business School blog.

A fixed mindset may form outcome-driven plans, which sees success – and thus failure – in black and white terms. But a growth mindset could mean creating a value-driven plan that goes beyond the technical skills or key performance indicators (KPIs) needed to succeed in a job.

Instead, it requires us to figure out what we value in a career – such as novelty, mentorship, autonomy, creativity – and why.

The last nearly-three years of the pandemic have shown that even the best-laid plans can be upended. Industries are shifting beneath our feet, from artificial intelligence to an increasing prioritisation of flexibility, leading workers to re-evaluate priorities and take a chance on alternative paths.

A non-linear career trajectory may be lamented as a “waste of time” in an outcome-driven plan, but decisions driven by our core values make the journey intentional and meaningful.  

DON’T SPRINT A MARATHON 

A five-year plan doesn’t have to come to fruition for it to serve its purpose. But it’s not easy to rewire the all-or-nothing mindset that defines success and happiness by what we accomplish rather than who we are.

I initially felt guilty for straying from my dream, even though I could objectively still achieve it sans deadline. 

But I’ve since realised that perhaps I didn’t want to achieve the dream, as much as I wanted to aim for it. What would drive me anymore if I reached the end goal?

Perhaps I preferred the idea of my dream — the pursuit of an ambition so huge it is forever a little out of reach, with just enough discomfort to force me to take a chance on myself over and over despite looming self-doubt or imposter syndrome.

After all, with five years such a short runway, I felt I had to constantly push myself to do more. I could not afford to see my career as a marathon, which requires patience and pacing.

For the longest time, I had an answer to where I saw my career in five years, only to realise it wasn’t the right question. It should have been: “Who do you want to be in five years?” 

In hindsight, the confidence I had in my early 20s about where I wanted to be was clarity about who I wanted to be. My five-year plan worked out – just not as I planned. 

Grace Yeoh is a senior journalist with CNA.