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5 tough questions you need to ask yourself before retiring

By Sam Instone - March 22, 2023

One of life's most challenging financial puzzles is retirement planning.

Mainly because of the irreversible nature of many decisions...

To make things harder, the decisions are often ones we've never had to make before.

They often have higher stakes than the saving and investing decisions you had to make throughout your working years. 

What kinds of things am I talking about?

Here are 5 examples.

1. Should I downsize my main home?

Selling a house is a huge and often costly life transition. Transitioning from a single-family home to an apartment, say, can be a wise decision.

However, keep in mind that this new living situation may come with a set of rules and regulations that you may not be accustomed to. These restrictions may affect your lifestyle and personal preferences. If you're unhappy with your new home, reversing the decision can come with a significant financial burden. Weigh the pros and cons before making a final decision.

2. Should I move somewhere else?

Downsizing is one thing. Relocating is another. It's important to consider the potential impact on your social support network and the friendships you may be leaving behind.

While better weather and lower taxes can be appealing, they may not fully compensate for the loss of close relationships.

It's worth considering the possibility of regret or homesickness, especially since moving can be both costly and logistically challenging, particularly if you've already spent a significant portion of the proceeds from selling your previous, more expensive home. It's essential to weigh the potential benefits and drawbacks of such a significant move before making a final decision.

3. When should I stop working?

Determining the right time to retire is crucial.

It marks the end of your regular income and puts a stop to your savings, as you start drawing from your retirement fund. However, there's always the option of working part-time during retirement, which has many benefits.

Not only does it provide some financial stability, but it can also give a sense of purpose to retirees.

4. Who do I want to leave inheritance to?

Many successful family stewards prioritise leaving a substantial inheritance to their spouse, children, or a charitable organisation.

If this is important to you, determine what you want to leave in addition to your own needs.

When consulting with your financial planner regarding estate planning options, consider the potential use of a family trust.

5. What options do I have for accessing my pension?

If you're a UK expat, you have several options for taking money from your pension pot when you reach retirement age.

If you have an employer pension, you may be able to take your benefits as either a lump sum or regular payments. The amount you can take as a lump sum will depend on the terms of your scheme, and you may be required to purchase an annuity with the remaining funds. Alternatively, you may be able to take a regular income from the scheme, either through an annuity or through income drawdown.

If you have a private pension, you may have similar options to those with an employer pension. You can typically take up to 25% of your pension pot as a tax-free lump sum, with the remaining amount used to purchase an annuity or invested in an income drawdown plan.

It's important to note that the rules around pension withdrawals can be complex, and the amount of money you receive may be subject to tax. You would be unlikely to pay UK income tax as a non-resident, but may be taxed in the country of residency.

Additionally, the decision to take a lump sum or regular payments should be made carefully, taking into account your financial needs and long-term retirement goals


When thinking about the above, it's natural to lean towards an option that reduces the risk of short-term financial loss and regret.

However, selecting the emotionally comfortable choice now could lead to long-term financial harm.

There’s also research backing up the importance of asking these questions...

You’re more likely to make better decisions if you’re emotionally engaged to tackle potentially tough retirement choices.

Below are some more questions you might like to ponder as you approach your retirement years:

  • What would you consider to be a successful retirement?
  • What kind of lifestyle do you really want to have?
  • How can you control your costs?
  • What are your plans for your later years and covering costs for your long-term care?
  • What will happen to your business?

All the above should be factored into your financial plan - which can only be created when your planner truly understands you and your story.

Try to envision your life in retirement. Only then, will you invest the time it takes to determine how you can support the life you really want. 

Time for a second opinion