The Career Pitfall Gen Z Hesitates to Admit: Overlooking Middle Management

When my parents were my age, middle management was something to aspire to. A promotion meant stability, respect, and recognition. Loftier titles were markers of achievement — proof that you had “made it.”

The corporate ladder was simple and structured: climb a rung, get a raise, take on a team, rinse and repeat.

That made sense in their world. Stability wasn’t guaranteed. Facing recessions, economic upheaval, and the pressure of being the primary breadwinner, climbing the ladder was less an option and more a matter of survival.

Today, however, the allure of middle management has faded for many millennial and Gen Z workers.

I’m in my mid-twenties, yet already, fewer of my peers dream of becoming “assistant vice-president” or “senior manager.”
Some want to specialise in their craft — design, engineering, writing — rather than juggle people, emotions, and office politics. Others treat work purely as a means to fund life outside the office, prioritising mental space and personal time over titles.

For many, that trade-off feels worth it: earning a little less, living a little more.

I’ve felt torn too. Should I keep climbing the corporate ladder the way my parents did? Or step away from the traditional path entirely?

The Corporate Sandwich Nobody Ordered

Being in the middle is tricky — and increasingly unappealing.

Middle managers today are squeezed between employee expectations and leadership demands. Their roles extend far beyond supervision and KPIs. They’re asked to be culture builders, therapists, conflict diffusers, and unofficial firefighters dealing with the problems neither top management nor staff want to touch.

In my first job, I was fortunate to have an exceptional mentor who could defuse tension, build trust, and steer difficult conversations. He taught me accountability, attention to detail, and ownership — skills I carry both professionally and personally. Because of him, middle management looked noble, even fulfilling.

But not everyone gets a role model like that.

I’ve seen friends step into middle management eager to make a difference, only to become overwhelmed. They received teams without proper mentoring, projects without clarity, and responsibilities without direction. Many eventually grew resentful.

One friend told me that the “emotional labour” of keeping her own boss calm often overshadowed managing her team. Another declined a promotion altogether after watching her manager burn out.

And then there’s title inflation — promotions that come with more stress but almost no meaningful pay increase. In a time where many Singaporeans are starting families later, middle-management roles often collide with caregiving responsibilities, amplifying stress.

It’s no wonder my generation is questioning whether climbing the ladder is worth it.

The Rise of the Portfolio Career

Success is no longer defined solely by reaching the top.

More young adults are building “portfolio careers” — branching into diverse skills, industries, and income streams.

My own day job as a communications strategist comes with a managerial title. But outside work, I take on projects across different fields. The extra income helps, but what I value more is staying adaptable, curious, and creatively fulfilled.

Many of my peers share the same mindset.
Some choose flexible schedules to prioritise time with family. Others take on freelance roles or part-time work that offers financial breathing room without the emotional toll of managing a team.

But the portfolio path brings its own challenges.

Without a big corporate title, you become your own brand. Your value depends on the work you produce, the network you nurture, and the reputation you build. That level of self-reliance can be both empowering and exhausting.

Finding Meaning in the Middle

Despite its declining appeal, middle management remains critical in any organisation.

Strategy still needs to be translated into action. Teams still need guidance. Leaders still need support. Workplaces still need cohesion.

So how can the role become more attractive?

A lot of this responsibility lies with employers:

• Provide proper training, not just KPI sheets.

• Give middle managers authority, not just accountability.

• Offer mentorship, both upward and downward.

• Protect work-life balance, with flexible arrangements or project-based workloads.

But middle managers themselves can also reclaim the role.

I’ve seen colleagues set boundaries early, say no when necessary, and prioritise meaningful work over busywork. Peer support networks have helped me tremendously — having colleagues-turned-friends who understand the grind makes the load feel lighter.n of ambition fits my life and my values.

As the definition of a “good” career shifts, perhaps it’s time success stops being measured only by how high we climb. Instead, let it be measured by balance, curiosity, and growth — even if that growth doesn’t always go upwards.