26 Oct 2026

How Can I Be Ready to Retire on My Own Terms?

Being ready to retire on your own terms is a simple question with a complicated answer. Recently I helped Owen and Andrea* (not their real names) with how to approach this, in order to give them a clear idea of what they need to do, and peace of mind on how to get there.

In simplest terms, a holistic retirement plan considers:

• What do we already know?
• What are we expecting from the future?
• How about the unexpected?
• What actions should we take?

The process starts with what we already know:

• How much do you have saved and invested?
• Will you have any continuing income streams in retirement such as State Pension or Final Salary pensions?
• How old are you now, and when would you like to retire?
• What is your current typical expenditure? Is this relevant for your retirement needs?

The last of these items often involves a bit of probing and interrogation because one of the luxuries of a reasonably comfortable lifestyle is not having to measure every penny leaving your account, but that often means that people find themselves a little bit surprised when they add up all of their costs (positively or negatively surprised!)

Then we move onto what we expect in the future:

• What are your ‘terms’ for retirement – what does a comfortable lifestyle mean to you and what do you plan to do with your time? This takes some deeper thought.
  • I’ve spoken elsewhere about how retirement isn’t just a financial change, but a lifestyle shift that needs some clear thought and planning in order to be a successful transition (https://lnkd.in/p/ekKHn7Yy)
  • This lifestyle plan then needs to be put into actual costs anticipated in retirement (factoring in that our ability to travel and be adventurous diminishes later in retirement, but then very late in life there may be added care costs to be paid).
    Sometimes we forget to include irregular but likely costs – such as replacing our car, or maintaining the house – the sort of things that rising income and savings in working age can help us to address
• Are there any retirement milestones or celebrations planned? Part of the point of saving up for all those years is to do the things you promised yourself.
• How long do you anticipate living? This is a really hard question because none of us knows the answer, but looking at life expectancy statistics at each age, along with current lifestyle and health can give us some clues.
  Often the age that our parents survived to is a poor guide to our own life expectancy, given how much medical care has improved, and a retirement in your 60s may well mean planning to fund your lifestyle for at least 25 if not more than 30 years.

What about the unexpected?

• A serious or enduring illness that disrupts working life, for either yourself or your partner, can throw a wrecking ball into a solid retirement savings plan – the earlier you get insurance to cover this, the more cost-effective it will be, allowing you to make adjustments to your future plans and investment strategies
• For staff who are more senior, and therefore more expensive to the company, there is a real possibility that they may be made redundant and need to reinvent themselves as contractors for their last few years of work. This can be quite lucrative, but also puts a lot more uncertainty and responsibility on your shoulders and needs careful planning if it is to be done in a tax-effective way that continues to prepare you for retirement on your terms
• Changes outside your control in the world around us can challenge your existing plans:
  • we use ‘what-if’ scenarios in our cashflow modelling to consider how much your retirement might be impacted by a downturn in investment markets, or changes in inflation, interest rates, or similar variables;
  • changes in legislation or taxation can also affect your expected retirement (for example property investment has become increasingly challenging and less reliable as a source of income).
    Part of my ongoing work with clients approaching and in retirement is helping them to adapt their plans as circumstances change.

• Unexpected complexity – are you beginning to be out of your depth?
  Many people who have been happy to DIY their investments or leave them in the hands of a standard employee retirement plan while they were simply keeping their head down and working, may come to realise that it’s becoming too much responsibility and the consequences of bad decisions are too severe to continue sailing alone towards retirement. Paying for support with your financial planning may seem expensive compared to DIY investing (although not by comparison with any other skilled professional advice with a lasting impact on your life), but if you make mistakes with your life-savings when they are worth at least a few hundred thousand, and potentially a few million, it is likely to cost you a great deal more than the advice will.

Finally, we take action together to implement a solid retirement plan.

• What does your retirement cashflow plan look like right now?
  Usually you either have one of three outlooks:
  • Not enough, in which case your retirement savings need to be accelerated and the variables each considered (e.g. delaying retirement, cutting expenses, releasing capital from fixed assets such as a family home)
  • Just about enough, in which case we look at ways to optimise and manage risk, or adjust a variable (as above), to make your retirement plan more likely to succeed
  • Enough to retire – although it can be really difficult to recognise this by yourself, and it can be a huge relief when a solid financial plan shows you that you can be in control of your own destiny – often this changes your relationship to your work
• Strategic Decisions – Are you currently saving and investing for retirement in the best possible way:
  • Minimising income taxes paid?
  • Investing at the right level of risk or with the right mix of different buckets of risk to cover your whole retirement, not just up to the day you retire?
  • With a comprehensive overview of your pensions and other investments to ensure they follow a coherent strategy? (A “navy rather than a flotilla of boats” – https://hoebridgewealth.co.uk/sailing-to-retirement-flotilla-or-navy/), and,
  • Ensuring that costs you’re paying are all reasonable and represent value for money – and that you’re getting personalised advice and support not just investment brokering?
    For a great many clients of private banks, high street banks, and famous listed advice firms or large firms owned by private equity investors, the answer to this is unfortunately “no”.
• Ongoing adaptations – do you know how you’ll deal with any unexpected events, and do you have a relationship with a skilled financial planner who can support you and help you to adapt your plans to changes in the future?
  • One example is that pension providers may contact you with an offer as you approach retirement. Should you preserve any older pensions that could be unusually generous in their terms?
    Most often the answer is yes, but the devil can be in the detail of how to do this. For example when an annuity is offered with several different mixtures of cash lump sum and regular annual income.

How many of these key steps have you been through and carefully considered? Who is your sounding board to sense-check the plan?

Are you clear on your personal financial plans for retirement on your own terms? Do you have the right support to get you there?  

Get in touch if you would like to have a chat or would like to set up a no-obligation conversation with me for someone you care about.

NOTE: The value of your investment can go down as well as up. Past performance is not a reliable indicator of future results. None of the above is financial or investment advice and you should speak to me or someone else professionally qualified to give you advice specifically tailored to your circumstances. All information is correct at the date of publication. There can be no guarantee that such information is accurate as of the date it is received or that it will continue to be accurate in the future.