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What if I hadn't retired early?

Updated: Mar 21, 2023


A recent blog post, You don't have to be brave to retire early, but it can help, discussed how being a little bit brave helped me make my early retirement decision and is now helping me make the most of my early retirement life.


Following that post, I received a question in the comments:

What if I hadn't retired? What might life have looked like if I'd stayed working?

It's a good question. Of course, I can't know for sure what would have happened, but it is interesting to wonder.


When I think about what if I hadn't retired, the first things that come to mind are not what I would be doing but, rather, what I wouldn't be doing, what I'd be missing out on.


What if I hadn't retired? I'd be missing out on...

If I hadn't retired early, I wouldn't:

  1. be living in France.

  2. have travelled to many new places, including backpacking in hostels (making up for the experiences I didn't have when I was younger).

  3. have bought a campervan.

  4. be blogging, and doing some newspaper, podcast and radio interviews (I couldn't imagine doing any of these things).

  5. be living in a ski resort and trying to get the hang of off piste skiing, even if I'm currently largely failing!

  6. have cycled the Route des Grandes Alpes from Lake Geneva to Nice on the Mediterranean coast, and I wouldn't be doing it again this year.

  7. be planning to hike the Tour du Mont Blanc trail.

  8. have run my marathon personal best time when I was 52, then improved it aged 53. At least, I'm pretty sure I wouldn't have done this.

Some of these might not seem attractive or exciting to everyone, but they are making my life fuller and more interesting. One day, perhaps sitting in a rocking chair, I'll look back and think my life has been the better for having these experiences, as well as the things I'll do in the years to come.


Plus, if I hadn't retired early, I wouldn't have the flexibility that I now enjoy. Some friends said they were cycling this morning (Monday) at 10am - no problems, I can do that. Sally is flying back from a short trip on Wednesday, that's fine, I can collect her from the airport. What I do with my time is my choice, not the choice of an employer.


What if I hadn't retired? I'd still be working...Version 1

A reader, Matthew, replied to the "what if I hadn't retired" comment, suggesting that the answer was obvious. Not retiring would mean continuing with 40+ hours a week at work (I was definitely in the plus range), an unchanged social circle and the occasional holiday, with this on repeat year after year.


I suspect Matthew is right. Humans are creatures of habit and routine, and we don't easily shift away from our current course. Society tells us that it's normal to work a job, and society therefore thinks it's a little odd and confusing when we do something different.


Mostly, we tend to comply with the societal norms, so what might my life look like if I'd done just that, and therefore hadn't retired when I was 47? I guess there's a good chance that life would have continued to look much the same as it had in years before:

  1. I'd have carried on working for another 20 years until I hit the "normal" retirement age of 67! While I mostly enjoyed my career, thinking that I might have done another 20 years does not sound appealing.

  2. I'd have more money because I'd be earning for 20 more years. On the face of it, more money sounds good, but that extra money probably wouldn't lead to me doing much different. Firstly, because instead of having time in which to spend this extra money, I'd be busy working. And secondly, because having more money only really matters if I need more money or if more money would make me happier. While it may instinctively seem good to have more money, I don't think it would have changed my life materially or put a bigger smile on my face.

  3. I'd be more stressed. I remember the first day of early retirement, it was like someone had taken a weight off my shoulders. It was wonderful. Now I'm generally not stressed at all, but on the occasions where I do feel a little worry or stress, it's because I've chosen to be out of my comfort zone, I've done it on purpose and it's therefore a good stress.

  4. Of that list of eight things that being a little bit brave and retiring early has let me do, if I'd continued working, I suspect I'd have done either none or possibly one of those things. My life would be poorer for that.


What if I hadn't retired? I'd still be working...Version 2

This involves quite a bit more guesswork. Since I retired, the company I worked for decided to close it's Middle East operations where I worked, so I assume I'd have lost my job. If you're working in your home town, you generally get a new job in that same town. But I was an expatriate worker, and that can make things a little different.


My version 2 could have headed in a few different directions:

  1. I could have looked for another job in Dubai, which is where we were living at the time. If I found one, then life would have continued pretty much the same as my pre-retirement life i.e. busy working, somewhat stressed, and not having the flexibility I value nor doing the things I now enjoy as part of my early retirement.

  2. It's possible we'd have returned to our "home" country, the UK, and found jobs there. I guess it would have been OK but, at least for now, the UK doesn't excite me. Once settled back in the UK, it would be business as usual i.e. busy working, somewhat stressed, and not having the flexibility I value nor doing the things I now enjoy as part of my early retirement.

  3. Alternatively, maybe we'd have found jobs somewhere completely different. Who knows where, perhaps somewhere in Asia, Africa or another place I'd never thought of. Maybe Sally would have found a job first, and we'd have headed to wherever that was. Historically, I was the main earner, but perhaps those roles could be reversed? If that were the case, perhaps my new job might be in a different field, and maybe it would come with less pressure? Settling into a new country isn't easy, but it would have been interesting and exciting. I'm not saying I'd rather have done this compared to retiring early, but it's probably would have been my second choice.

It's been fun to imagine what might have happened if I hadn't retired, to try to envisage what life might have looked like. My early retirement wasn't a result of a long held plan, it was more some events that lead me to question whether I was enjoying my job and wanted to continue with it - in particular, there was a "do I have to put up with this $#!T" moment which resulted in me reflecting on things and discovering that no, I didn't have to put up with it if I didn't want to. It was only at that point that retiring early entered my mind in a serious way.


If that "do I have to put up with this $#!T" moment hadn't happened, maybe I wouldn't have retired early. It's almost a scary thought. If I were having my time again, I hope I would be more proactive, and not just relying on a $#!T moment to create an action. During job interviews or annual appraisals, it's common to be asked where we see ourselves in five year's time, and I'd have an answer for that. But one thing I never asked myself was:

Where do I see myself, in terms of my personal life, in five year's time?

Where do I see myself, in terms of my personal life, in five year's time is something I should have been asking myself and, if I had, I like to think that I'd have asked whether retiring early was something that I might like to do.

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Thanks for another excellent article. This sort of analysis and your stories of life ‘on the other side’ of retirement are very useful and inspiring. I am hopefully 3 and a half years away from pulling the plug and expend a considerable amount of mental energy worrying about what amount of money will be sufficient, whether I will regret giving up a well paid professional career and whether early retirement will be worthwhile. Your blog is very helpful in answering these questions in a positive way. As you say, there is only so much money you need and I feel that as in many aspects of life, it’s a case of finding the sweet spot that provides enough money for…

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David @iRetiredYoung
David @iRetiredYoung
25. März 2023
Antwort an

Hi Matthew, I'm glad that my experience with early retirement is giving you an idea of what it can be like. Having worried about the finances ahead of time, that has been one thing that really hasn't been an issue - I was definitely worrying without cause.


I completely agree with your game changers, freedom, health and travel - I also went straight into work (aged 18 for me), so I enjoyed doing my backpacking later in life. A bonus that I have found is that, in addition to those things that I was looking forward to, there have been many other things, some small, some larger, that I hadn't expected and really have added to my early retirement life.…

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woodyacat
woodyacat
22. März 2023

Very thought provoking. I am retiring in a couple months but this is making me think back - what if I did it a couple years ago? Who knows how things would look now for my wife and I. I am looking forward to the flexibility and options that just don't work when we are tied down to a 9-5 job. I've just found your site and enjoying digging into your posts.

Mike @ GORetire

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David @iRetiredYoung
David @iRetiredYoung
23. März 2023
Antwort an

Different but perhaps related to the looking back theme, something I focus on now is trying to be better at looking at the decisions or options open to me now, and trying to make the choice that means I won't look back at some future point and say I wish I'd tried that/why didn't I do it? It doesn't always come easily to me as I think I'm naturally a more conversative/safer personality, but I think I've moved in the right direction.


It's exciting that your retirement is so close. I love the flexibility that I now have and, as to options, you're right, there are those that just didn't work when tied to a 9-5 job but, in addition,…

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Interesting post, and an interesting analysis of your situation. Having to move or change jobs would certainly have been stressful, and you might have decided to retire at that point!


My first thought was that if I hadn't retired I'd have more money, but I'd be having less fun too. From where I am now, I certainly wouldn't make that trade. Then I started thinking about that new boss I didn't get along with who got promoted just as I was leaving, the new computer system I didn't have to learn, more new laws in the industry etc. That might be confirmation bias though. Who knows. It's fun to think about!

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David @iRetiredYoung
David @iRetiredYoung
22. März 2023
Antwort an

One thing that I'm relieved about it that I didn't have to deal with Covid as part of a management team - if I'd still been in the Middle East, I suspect that may have been a massive challenge and not a lot of fun!


Whether or not you have some confirmation bias, as you say, who knows. But like me, it seems that you are fortunate to have had enjoyed your career and now your new early retired life. We aren't having to choose between the two, we're having both...happy days!

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Good article Dave. I'm approaching 55 when I have an option to go part time (3 days / week) and work until I'm 62 or work full time until I'm 59. You are lucky that you have been able to make the transition so have the opportunity to go away for weeks at a time. How would version 3 have been for you if you had taken part time? Would you have hung on for a few more years full time or dropped to part time and worked longer?

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David @iRetiredYoung
David @iRetiredYoung
22. März 2023
Antwort an

Hi Andy, it does indeed sound like you've answered your own question and, from a distance, your conclusion seems to make a lot of sense. Exciting times for you, I;m sure you're going to love it.

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Maybe as a society we would be 'richer' if we were encouraged to think outside the box and not just be stove piped into working for as long as possible for material gain. There does seem to be a view from our current leaders, aimed at those 50+ that we should be working until age 70, although I do wonder to what extent this is as a result of the younger generations pushing back and refusing to comply with a 9-5, 5 days a week working lifestyle!


Thought provoking blog as usual David.

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David @iRetiredYoung
David @iRetiredYoung
20. März 2023
Antwort an

Hi Peter, some of these things are far beyond any expertise that I have, but I do question how the economics of our societies are governed. It seems to me that countries need to produce and grow in order to pay for infrastructure, services and pensions of the growing population. So those same countries need people to carry on working which I can just about understand from a mathmatical, adding up the numbers perspective. These same countries also need to encourage the growth of the younger population, more babies need to be born in order to become the future workers who will then pay for the older population etc. But isn't this a spiral that doesn't have an end, that…

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