Three Key Retirement Questions

Throughout our lives, we will experience numerous significant shifts.

The shift from our working lives to retirement is arguably the most essential of them.

We go from being busy, successful, and respected to waking up one day with a blank page and having to rethink our function and purpose in life. We progress from saving to spending. We go from building wealth to spending wealth.

Many successful and happy people go on to unsuccessful and unhappy retirements. For those who saved diligently, this is a sad outcome. The key to making a successful transition is to be clear about what you are leaving behind and moving towards.

The Three Key Retirement Questions

I've developed three critical questions to help you move into a successful retirement after helping many people manage this once-in-a-lifetime change from work to retirement.

With increased longevity resulting in lengthier retirements, this is not a decision to be made hastily. Consider these three questions carefully to ensure you have the successful and joyful retirement you deserve.

Question 1: Have you had enough of work?

Although you may not have the same drive as before, you may still have the energy and enthusiasm to continue contributing to your work. It may be possible that you can continue to enjoy the mental stimulation of remaining economically active, without the pressure and commitment.

The modern work environment has created more flexible and accommodating work options. Remote work, hybrid office structures, part-time consulting, or even mentoring could be a way to remain economically active and fulfilled in your work.

Before deciding whether to retire, it's essential that you are emotionally ready to transition away from work as you knew it. Do not underestimate the magnitude of your work’s contribution to your well-being and identity.

In summary, question one is purpose-driven.

Question 2: Do you have enough?

It is important to understand what lifestyle your savings are realistically able to sustain. Be mindful of day-to-day expenses, irregular expenses, and possible surprises.

Be prudent when estimating future investment returns, and be sensible when projecting your life expectancy and inflation. It's better to under-estimate and be pleasantly surprised, than the other way around.

A robust financial planning process is designed to help you make sense of the complexities behind this simple question: Will I run out of money?

If an initial analysis gives an unexpected answer, consider that even an extra year or two of saving can make a significant difference in these projections.

Ensure that you have received a detailed opinion from an expert before you make any irreversible decisions.

In summary, question two is money-driven.

Question 3: Do you have enough to do?

This is often the most challenging question to answer, particularly if you have achieved success in your work over the last several decades. How will you fill your time?

When you are accustomed to working full days, an empty calendar can be difficult to navigate. Sadly, a two-week holiday is not a reflection of what you may want to fill your days with.

Those around you may still be in their everyday routines, leaving you with more time than you know what to do with. There are only so many rounds of golf you can play or TV series you can watch before you get bored.

It's important to think carefully about what your ideal week will look like.

Be sure to build in time for family, hobbies, and travel. If there’s too much time unaccounted for, it’s worth reflecting on whether you are ready for this big decision.

Lastly, if you and your partner are not used to being around each other all day, it’s important that you agree on what you will be spending your time on and how you will each retain some independence. As the joke goes, retirement is twice the spouse and half the income.

In summary, question three is lifestyle-driven.

A Happy Retirement is Hard Work

A successful retirement transition requires being intentional about what you are leaving behind, what you are retiring to, and how it will be funded.

Consider your answers to the preceding questions carefully, and you will ensure that you embark on this new adventure with enough money and purpose to make a successful shift.

While financial planning is focused on ensuring that you have enough money to sustain an independent life, I am just as committed to assisting you in making a happy and successful transition.

Amyr Rocha Lima, CFP® is a financial planner who specialises in working with successful professionals age 50+ to help them reduce taxes, invest smarter and retire on their terms.

Amyr has provided me with objective and impartial advice when reviewing my financial plan and objectives. Amyr has excellent technical knowledge and, more importantly, he delivers his advice clearly and in a way that helps you decide your next steps."

Paul Dawson
(Senior Risk and Compliance Officer - Metlife)


”I appreciated Amyr's friendly, relaxed and helpful manner and, even more, his highly professional approach. He soon understood my financial situation and what I was looking for. The financial plan he proposed met my requirements. I have every confidence we will have a good working relationship in the years ahead.

Louise Anstead
(London Stock Exchange)


”After trying several IFAs who did not 'cut the mustard' I was lucky enough to find Amyr. He has been exemplary in his dealings with me. He is very professional, knowledgeable, honest, friendly, and (most important to me) someone I know that I can trust with my financial affairs.”

Dominic Cortizo
(Certification Specialist - Civil Aviation Authority)


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Amyr Rocha-Lima MSc FPFS CFP Chartered Financial Planner Kingston upon Thames
Amyr Rocha-Lima MSc FPFS CFP Chartered Financial Planner Kingston upon Thames