What Kind Of Retiree Are You?

By Bhuvanaa Shreeram

Why knowing the answer to what kind of retiree you are could make a difference to the next 25 years of your life? A few years ago, while speaking to a senior corporate executive who was approaching retirement, he informed that he had spent nearly three decades with his organisation, had built a comfortable investment portfolio and, by most financial measures, was well prepared to retire.

When I asked him what he planned to do after retirement, he smiled and said, “Oh, I am not going to sit at home. I will probably do some consulting. Maybe join a few boards. There is always something to do.”

That’s fair enough, but what if the consulting opportunities didn’t come through? What would he do on an ordinary Tuesday morning when there were no meetings to attend, no colleagues to call and nobody waiting for his decisions? He had not really thought about that.

Over the years, in many such conversations with clients, I have found that some people eagerly count the days until retirement, while others worry about whether their money will last. Still others are convinced they will never really retire, even when their employers have already announced their retirement dates!

And then there are those who have spent so much time preparing financially for retirement that they have barely thought about the life they are preparing to live.

It makes me wonder whether we have been asking the wrong question.

We spend years asking, “Do I have enough money to retire?” Perhaps we should also be asking, “Am I ready for the life that comes after?”

Five Different Ways People Approach Retirement

Research into retirement transitions suggests that people approach this phase of life with very different levels of financial and psychological preparedness. I find it useful to think of retirees in five broad categories.

The Planner: Someone who has thought about retirement beyond the money. They have a reasonable idea of how they would like to spend their time, the activities they want to pursue, and the relationships they want to nurture. They may not have everything figured out, but they have begun imagining the next phase of life.

The Gradual Stepper: This person enjoys working and would like to continue contributing professionally, perhaps through consulting, mentoring, teaching, or part-time work. They are consciously preparing for a gradual transition rather than assuming that their professional life will continue as before.

The Financially Prepared: I suspect many successful corporate executives would recognise themselves here. They have saved diligently, invested reasonably well, and accumulated a comfortable retirement corpus. Yet, when asked what retirement will look like, their answers are surprisingly vague.

“I will travel.”

“I will spend time with family.”

“I will pursue my hobbies.”

All are perfectly good intentions, but when retirement could last another 25 or 30 years, there is probably room for a little more thought.

The Reluctant Retiree: For some people, retirement arrives before they are ready. Organisational restructuring, health issues, or unexpected circumstances bring their careers to an end. Apart from the financial implications, they must deal with the disappointment of having a significant life decision made for them.

The One Who Cannot Stop: And then some would dearly love to retire but cannot afford to. Financial setbacks, delayed savings, or responsibilities that stretch their resources mean that continuing to work is a necessity.

Of course, these are not permanent labels. Circumstances change, and people can move between categories. What matters is recognising where you are today.

Why Financial Readiness Is Only Part Of The Picture

A 2024 retirement happiness study by MassMutual revealed an interesting gap between expectations and reality.

While 77 per cent of people approaching retirement expected to be happier after retiring, only 67 per cent of retirees reported being happier. Similarly, 61 per cent expected greater excitement, while only 41 per cent of retirees experienced it. Nearly a third reported experiencing loneliness at some point.

These findings remind us that retirement may feel quite different from what we imagine while we are still working.

A 2025 PGIM India retirement readiness study also suggested that only about a quarter of those approaching retirement had a clear vision of what their retired life would look like.

Think about that for a moment. We may spend 30 or 35 years working towards financial independence, yet arrive at retirement without a clear idea of what we would like to do with that independence. I find that rather ironic.

Why Successful Professionals May Find Retirement Difficult

Imagine being a senior executive in a large organisation. For years, your calendar has been full. People seek your opinion, ask for your approval, and depend on your decisions. Your designation and organisation are part of how people recognise you. And then, one day, you retire.

The organisation continues. Someone else occupies your cabin. Your colleagues gradually stop calling you about work. The decisions that once required your approval are made by somebody else. Your financial position may be perfectly comfortable, but your relationship with time, responsibility and identity has changed dramatically.

Sociologist Michelle Pannor Silver explored this experience in her book Retirement and Its Discontents, examining why retirement can be particularly challenging for accomplished professionals whose careers have been central to their identity.

This resonates with what I see in my work. People who have enjoyed meaningful careers do not necessarily want to stop being useful, relevant, or engaged simply because they have reached a particular age.

And Why Should They? So, the challenge is to discover how those needs can be fulfilled in a different phase of life.

Try Retirement Before You Retire

I believe the final two or three years before retirement offer a valuable opportunity to experiment with the life you imagine. If you hope to travel extensively, try taking a longer holiday and see how you enjoy being away from your routine. If you plan to become a consultant, explore whether there is genuine demand for your expertise and whether you enjoy working independently.

If you dream of spending your days reading, gardening or pursuing a hobby, begin making time for it now. You may discover that something you enjoy for two hours on a Sunday is not necessarily something you want to do every day! And if you imagine spending more time with your spouse, perhaps start by spending more time together now.

That last point is particularly important. I have seen couples approach retirement with very different expectations. One imagines travelling extensively while the other looks forward to a quiet life at home. One wants to relocate closer to the children while the other prefers familiar surroundings. Neither is unreasonable, but it is better to have these conversations before retirement.

Your Retirement Plan Needs A Calendar

Financial planning should begin with a calendar rather than a calculator. I believe this is especially true for retirement. Before deciding how much money you need, imagine how you want to live. Where would you like to stay? How would you spend your days? What experiences would you like to have? What responsibilities would you continue to fulfill?

Once you begin answering these questions, financial planning becomes much more meaningful. Travel plans can be budgeted for, a second career can be evaluated, relocation decisions can be explored, and the trade-offs involved can be understood.

The financial plan then becomes a way of helping you live the retired life you have imagined.

So, What Kind Of Retiree Are You?

If retirement is a few years away, think about which of these five categories best describes you today.

You may be financially prepared but not certain about how to spend your time. You may love your work and want to continue contributing. Or you may be looking forward to retirement but worrying about whether your savings will be sufficient.

Wherever you find yourself, there is value in recognising it early.

We spend much of our working lives looking forward to the freedom retirement promises. Yet, when that freedom finally arrives, we may discover that we need to learn how to use it. After all, if you have worked hard for 30 years to earn the freedom to live life on your terms, surely it is worth spending a little time deciding what those terms should be.

Retire into something, not merely from something.

The author is a certified financial planner and certified financial transitionist and co-founder of House of Alpha Investment Advisors Private Limited.

This article is for informational purposes only and does not constitute investment advice. All figures used are illustrative. Tax laws are subject to change; please consult a qualified tax advisor for personalised guidance.

(Disclaimer: Views expressed are the author’s own, and Outlook Money does not necessarily subscribe to them. Outlook Money shall not be responsible for any damage caused to any person/organisation directly or indirectly.)