Three questions to ask yourself before retirement

Three questions to ask yourself before retirement.


Image by David Mark from Pixabay


Recent discussions on boredom in retirement, early or otherwise, have prompted me to revisit an old post in the drafts folder and finish it up.

Over a year ago now, I was listening to an episode of the FT Money Show.

They had a guest, Don Ezra, who talked about “retiring the word ‘retirement.'” He said that entering the post-work phase of your life is something to be celebrated rather than dreaded, and gave some advice on how one should go about preparing for “life-2.0.”

There are obviously many different things to consider, but the gist of the podcast is that you can prepare for retirement by answering the following three questions:


1. You have all the money you need. How would you live your life?

I arguably began to answer this question when responding to one of Saving Ninja’s thought experiments – What would you do if you won a million pounds?, but didn’t go all the way.

If I had no need to work for money, I think I would continue doing what I’m doing right now.

First, I would finish my contract, seeing as it only has a few months left anyway.

Second, I would continue my studies to retrain to be a financial planner. I think most people need to do some sort of meaningful work for as long as possible, and I think this career path would fulfil that for me.

In terms of possessions, I’d probably get out of the pokey flat we live in at the moment and buy a house. Nothing extravagant – the bigger it is, the more effort it is to clean it! But I would like to have a 2-3 bedroom house, so we have a spare bedroom for guests and a dedicated office space (essential with this current move to home working!).

In non-covid times, I would certainly travel more often. It would be great to emulate FIRE and Wide and slow travel across the world, a few months at a time. I also think it would be great to have the option to accompany family on their annual holidays without having to worry about taking time off or asking permission.

According to Ezra, this first question brings out, ‘what would you like to have?’ i.e. here is what you’d like to have more than anything else.


2. You’ve just found out you have 5-10 years to live. How will you change your life?

Interestingly, if I only had 5 years left to live, thoughts on becoming some hotshot financial planner start to fade a bit.

Faced with an entire lifetime to fill, studying and maintaining a “meaningful” life seems like an important thing to do. One cannot travel or play videogames for 50 years!

However, with only five years left, I’d become more focussed on spending time with friends and family, and making memories with them all.

Just like the previous question, Saving Ninja got there first, asking participants “what would you do if you had ten years to live.

Ezra stated that this question moves away from “what would I like to have” and towards “what would I like to do.” One quote that stuck out was:

Experiences bring memories, possessions bring repair bills.


3. You’ve just found out you have 24 hours to live. What are your regrets?

The first regret that springs to mind is not financially related at all, and is something I have been giving a lot of thought to over the last year.

But, I’m going to be annoyingly vague and not talk about that just yet. Maybe later.

Otherwise, I don’t have any huge regrets that I can think of.

I suppose I’d regret not going on that group holiday last year. At the time, I didn’t want to dip into my savings in order to pay for it, and, as ever, “there’s always next time.” But if there is no next time, then suddenly that seems rather pointless.

I’d also regret not having more adventures with Mrs FIRE, although, to be fair, covid has scuppered a lot of our plans this year, and in previous years we’ve had to be careful as we were living on one wage. That should hopefully change in the next year, as Mrs FIRE approaches the end of her PhD.

In the interview, Ezra said that this final question clarifies what is important. Who do you want to be?

Reading back over my answer, it looks like I want to be the sort of person who is able to chill out with friends and loved ones.

But not too much though. As an introvert, you can definitely have too much of a good thing.

It also brings to focus that once covid is done and travel is allowed again,  we need to make time and set aside some money to get out and see the world!


In conclusion

So, there you go, three questions to solve the retirement dilemma!

I think they’re a useful start to figuring out what you want out of life. It’s interesting that the final question highlights the old adage, “no one regrets not working enough when they’re about to die.”

I’m intrigued to hear what other people think, and how you would answer these questions.

8 replies on “Three questions to ask yourself before retirement”

Love it. Cheers for the shout out too – you are going to love slow travel I think.

Found it really interesting you would still want to become a financial planner even when you didn’t need to money-wise. I think there’s something there about having had to “try” a career first before working out if you want to give it up or not?

Nice read though – cheers!

For sure. I love the idea of essentially living in a place for 3-6 months and really getting to know it, as opposed to the usual “spend a week in a place and try to cram as many tourist sites in as possible.” That can be fun, but you when you get home you need another holiday to recover!

Perhaps you are right. The grass is always greener, etc. I admit that, if money was no issue, my tolerance for crap would be far lower than it is now. So there’s every chance that I would be less likely to stick at it if the bad outweighed the good. On the other hand, if I didn’t have to play the games and could only do what I wanted, maybe I’d like the job even more!

Thanks for reading and commenting 🙂

I’ve always seen owning a big house as a cleaning pain. I am not the type of person who would be happy to pay someone to clean my house.

The third question is thought-provoking. One of the things I would regret is to not have travelled more. I only started travelling a bit more after moving here. For instance I’ve barely visited any place in Spain. I bet many Brits know better about my country than I do!

If you don’t minf I’ll tweet about this third question. Want to know what others respond. May help me to discover something new about myself.

I get what you mean. As a renter, I’m not as inclined to keep the place in perfect condition, whereas, if I owned it, I would be much more compelled to clean constantly and keep everything spick and span. However, I still like the idea of eventually owning a house. Both, as a place I can call my own, a refuge away from the world. And because, once the mortgage is paid off, monthly outgoings will decrease by a fair amount.

I agree, travelling is a big one. Even in the UK, there are a number of places I’d like to visit. As for the rest of the world – there are entire continents that I’ve yet to visit!

Of course, tweet away. I didn’t come up with the questions, I’m merely sharing what I’ve read :). It will be interesting to see what others say.

Excellent post, Dr FIRE – not easy questions to answer with that last one being the toughest, ‘Who do I want to be?’

I think I’d like to be someone similar to what you mentioned, ie able to chill out with friends and loved ones. But I also like helping others too, in the same way you want to be a financial planner to help people, although I’m not sure how that would manifest itself in the future.

I love the idea of slow travel but I’d have to think twice about 1) the cost and 2) doing it on my own!

Thanks Weenie. The cost of slow travel is definitely something to take into consideration. I like the idea of living in a place for 2-3 months, to really get to know it, rather than trying to cram everything into a week. Unfortunately, that’s not the sort of holiday that is feasible when you have a full-time job, so something to look forward to in the future. Fair point as well about doing it by yourself. Probably not as fun (or as safe!).

Hi Dividend Power, thanks for reading and commenting. Agreed, the questions definitely get trickier as you progress!

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