Who Told Us We Need a Five-Year Plan?

“Plans are of little importance, but planning is essential.” - Dwight D. Eisenhower

"Where do you see yourself in five years?"

I have asked people this question and I've been asked this question. I've probably asked myself this question more times than I care to admit. All in equal measure.

It used to be a reasonable question. Now I'm not so sure.

The world changes too quickly. Jobs change. Technology changes. Companies disappear. Entire professions get reshaped. And yet we still expect a 25-year-old to tell us exactly what they want to become by 2031.

Maybe we need to start asking the right questions.

I used to think careers were ladders

Ofcourse, our parents' generation propagated that belief - You joined a company. You became good at something. You got promoted. Then promoted again and again, until you retired.

The ladder was always visible. So you could plan your climb.

Fast forward to post pandemic world, careers don't resemble ladders anymore. They look like roads.

Sometimes you move forward. Sometimes sideways.

Sometimes you take a completely different road.

Sometimes you stop. And sometimes you discover that the road you were on no longer exists.

Recent workforce data reflects this change. India's Gen Z and millennials are placing greater emphasis on stability, skills, sustainable workloads and realistic pathways rather than simply following traditional career timelines. Deloitte's 2026 India survey found that 54% of Gen Z respondents had delayed major life decisions because of finances, while 60% or more said housing affordability affects career decisions.

That's not a generation lacking ambition. It may simply be a generation becoming more realistic about uncertainty.

The right question

One of my mentor manager would often ask his team members this question "What do you want to become capable of?" instead of "What's the next role you want?".

Subtle, but the impact it made on his team was enormous. A title is something an organisation gives you.

Capability is something you carry with you.

You can lose the title yet still keep the capability.

That's why I like individualization so much as a leadership principle.

One person may want to become a better strategist. Another may want to become a stronger facilitator.

Another may want to learn how to influence senior stakeholders. Another may want to become a better coach.

Growing and going up the ladder should not look the same - It isn't the manager's job isn't to push everyone up the same ladder. It is to understand which road each person wants to explore.

This is where coaching matters

The GROW model is useful here.

Goal: What do you want?

Reality: Where are you today?

Options: What could you try?

Way forward: What will you actually do?

Notice what isn't in that list.

My answer.

That's intentional.

Good coaching doesn't replace someone's thinking with yours. It helps them think better.

I've become increasingly wary of managers who build careers for their employees.

You can build a roadmap. You cannot walk the road for them.

In the next 5 years:

• Build skills.

• Build relationships.

• Build character.

• Learn how to communicate.

• Learn how to handle disappointment.

• Learn how to disagree without becoming disagreeable.

• Learn how to sit with uncertainty.

• Learn how to recover when something doesn't work.

These things don't become obsolete every time LinkedIn announces a new job title.

What's this got to do with UX?!

UX taught me something useful here. We often design for the happy path.

The user completes the journey exactly as expected. But real people don't behave that way.

They change their minds, get distracted, go back and forth, and sometimes just abandon the journey only to come back six months later.

Careers are the same. A good career isn't necessarily one with a perfectly designed journey.

It is one that gives you enough capability to handle the unexpected turns.

So what should managers ask?

Instead of "Where do you see yourself in five years?" try asking "What do you want to be better at a year from now?". Then ask "What experience would help you get there?" and follow it up with "How can I help you get that experience?"

That's a much better management conversation, and a ruthlessly honest one.