Retiring or retired? Here’s the 15 most important questions to ask yourself.

The better the preparation the better the outcome. Isn’t that our perceived wisdom – from travel to DIY? And it equally applies to the major transition from fulltime work to the new era of retirement.

That’s why asking yourself the right questions – and then finding the best answers – can transform the possibly 20 years or so of active life that will follow.

There’s much more to it than ‘will I have enough money’ or ‘where can we travel to’. Much more. And the following 15 questions give you the opportunity to steer your way to a rewarding new era.

Please don’t thrash through them in one sitting. It will blow your brains. And don’t just pick the ones you like. As some are intended to get under your skin a little to provoke the richest outcomes.

One way is to face them in batches of five at intervals – weekly, monthly or whatever. And you can make your own choice on which to tackle first if you see some as a priority. However you do it, don’t rush but give yourself time for some deep reflection.

You might also find it helpful and rewarding to do some of this thinking in the company of others. Perhaps with your nearest and dearest or with others making the same exciting transition.

It’s your call and your future. So here we go.


1.How and where will I find the space to reflect on what this new season can offer?

Investing quality time and thinking now will pay dividends over the years to come. Simply trying to make it up as you go along is like arriving at a country you have never visited without making the right preparations.

To explore the issues check out The 5 key transition steps.

2.What is my number 1 goal?

Above all else, what big thing do you want to achieve in this next season of your life with all its opportunities? It may take courage to name it and own it. But it will be worth it.

3.What do I believe God is calling me to do with my retirement?

It’s been said ‘God loves you and everyone else has a plan for your life’. And the danger is of letting ‘everyone else’ drive the agenda. This may be one of the hardest questions but it is by far the most important.

You might like to see God designed old age on purpose.

4.How will I meet my financial and practical responsibilities to those who depend on me?

If you need professional advice over money then be sure to get it. And check on what reasonable expectations others may have of your support.

There’s on this at Your money – 4 top tips.

5.What legacy do I want to leave and what will it take to make it happen?

There is one absolute certainty – it’s that our lives will not go on for ever. So what will it take over the next decade or so to leave something valuable behind for others?


1.How will I replace the two key losses that come when fulltime work ends – being needed and enjoying relationships?

Don’t underestimate the ‘bereavement’ the end of fulltime work can bring. For a fulfilling retirement you’ll need situations where you matter and where lost relationships can be replaced.

For more see What 1,000 retirees said about life after work. And also Surprising community opportunities.

2.What do I need to put in place for my retirement to be the best it can be? 

The best will not happen all by itself. Some positive planning and action is going to be needed to make it so.

For more on this see The 10 planning commandments for retiring.

3.How will I deepen my relationship with God now there’s more time to do so?

Here’s one of the great opportunities that comes when the daily commute has gone. And it points to the danger of filling the new time available with ‘stuff’ rather than the delight of knowing God even better.

4.What of my skills, knowledge, talents and relationships should I let flourish in this new season?

Nail down what is special and valuable about you that can enrich others – and in turn be rewarding for you.

There’s more about this issue at Don’t waste your life-skills and experience.

5.What new experiences do I want to have and what new skills do I want to learn?

As part of making the rest of your life the best of your life, be specific as to what you want to embrace.

For some inspiration see the AfterWorkNet web page on Opportunities.


1.What is my biggest fear as I look into the future and how will I confront it?

It’s tempting just to bury our fears – or even to pretend we have none. But transition into a whole new way of living can, quite reasonably, generate anxiety. It’s wise to name yours and how you will deal with it.

To understand the challenges ahead see Retirement is a foreign country.

2.Who are the three people I should contact who I neglected when I was working?

It can happen when a driven life pushes us away from what could be productive relationships. So don’t just make a list but reach out.

3.Who do I know who have lived well in their retirement and serve as role models?

Sometimes it can be valuable to see what has worked for others and how this might inform your own plans and decisions.

4.How will I create a balance so my mind, body, and spirit are all engaged?

Indeed, ‘balance’ is the name of the game. And it is not enough to hope it will happen naturally. If only. Rather, careful plans and more than a little discipline will be needed.

5.What would I say to myself in 20 years’ time about the decisions I’m making right now?

Listen to your inner voice. You’ll only get one shot at this. So aim to make decisions you’ll be proud of in the years to come.

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Peter Meadows

Peter is AfterWorkNet’s Programme Director. He’s using his retirement to help churches, resource inter-church initiatives, enjoy his grandchildren, escape to Spain and to spend his kids’ inheritance.

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The word retirement is not even in the Bible. What is taught in scripture is transition. There is nothing that says you work most of your life and then get to be selfish for the next 20 years"

Rick Warren, PurposeDrivenLife