I dont like such statements so much. Because you can "do" different things.

Often it is not just the decision for doing an longterm trip. It is more an tradeoff between severall options in your life.

I am disappointed in 20 years:

- that I dont buy a flat/house
- I didnt do more out of my career
- I dont had kids
- I dont did a longterm trip
- I dont have good financial reserves

No, a longterm trip dont avaid that you buy a house. But 60`000$ more or less can do the difference at the end at example.

Correct is - you will regret when you did nothing

Surfy

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About Overlanding, Travelogues, Equipment
Trans-Africa over the west coast

During a couple of years

* I had done 2 surgeries for Arthritis,. Both heaps. => 3-4 years in total as invalid. Sick, waiting for operation, Operation 1,operation 2, recovery... Time passed

* I survived a heart attack. 25% does not survive the type of incident that I had

* I was totally exhausted from the combination of work and bad health => Almost ended up with a mental collapse

* My wife decide to leave and look for something fresher.....

* Constant redundancy and reorganization at work. At the ago of 61, I got an "offer" for lay off including a "package"

* My father got Parkinson's disease and never got any useful retirement. Died at 69

=> I made a 3 year plan to prepare for travelling (The redundancy contract and other stuff had requirements so I could not just leave). But I did a trip to Nepal during these years. And a lot of smaller trips. The plan was to start with a 4-5 month trip in South America 2020. And to do smaller trips i Europe during the summer periods.

But. When it was time to leave.... Covid 19....
+ The knee stopped working. More arthritis ?. No, only a cracked meniscus. But.... queues to hospitals for "none urgent issues" during Covid19 times....
But surgery has been done and I am recovering again.

I feel like Sisyfos.....

But. Decision is made, Plans are done. Just waiting for opportunity. Hopefully next winter => Argentina and Chile. Or Vietnam, if it opens. Or Tibet ???

Time is running. I hope it opens while I still can travel.

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So no long term trip so far. But I have during the last half year done:
* Pilgrimage to Trondheim in Norway
* Part of the Swedish TET
* Touring the French and Italian alps
* Riding N2 in Portugal
* Touring Douro Valley in Portugal

And done a huge amount of one day trips.
=> No RTW trip. But there is a lot to do and see anyhow.

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My plan for Argentina is to buy a small local bike. No preparation needed to arrange shipping and stuff..
For Vietnam: rent for 4 weeks (30 days Visa was easy to get, pre Covid 19 times)
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Travel requires

* Money
* Time
* Health
* That the borders are open..

I hope that all conditions will happen at the same time

Being on the other side of fifty, my only suggestion is if you have the ability, is to buy a piece of property before you go OS.

Doesn’t matter what it is or its size, get it and get it rented out so it pays for itself.

you are locked into the market for later.

But each to their own of course.

I'm 65 and planning to ride to Magadan and back by various routes next year. Actually I planned to do it in 2020 but, y'know.... Keeping an eye on the virus spread and border closures I'm not very optimistic of even that date, but we'll see. I left my travelling late because I did the career and house and kids thing. In some ways it's not ideal because it can be a tough trip for an old bloke, but at least I know I have something nice to come back to. No way could I have been one of the young guys who has a great time for years on the road then comes back to no home, no family and no job. The main thing is to always keep your dreams alive, hope for the best but plan for the worst. You're never too old until your body tells you so... your mind never will

Same start but different end. But my wife left. The house is sold, kids are spread over the world...
I have nothing left there to come home to.
Total freedom. If not lock downs and state of emergencies due to Covid19.

I also hope that the body will keep healthy enough until Covid19 is under control.

Do you have a plan for after the trip ?

Do you own your house and have a pension that you can retire on ?

Throwing in a good job and coming back skint and having to start fresh in your late 50's may not be the wisest move.

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Did some trips.
Rode some bikes.
Fix them for a living.
Can't say anymore.

We are planning to buy a place in France, somewhere with a couple of gites we can rent out. I have a HGV license (although I’m not working as a driver anymore) and lose plan when we return is to semi retire letting the gite and drive agency 3/4 days a week. Obviously won’t be able to cash the pension in until I get to that age.
I just don’t want to wait until I’m 65(ish) and then go travelling as I may be too old/unable/unfit etc….

Thanks for all the comments guys, really appreciate the input.

The way things are going with HGV drivers at the moment you could take on a job for a month and that'll finance your travel

Retiring to France certainly seems like the way to go although the path isn't as easy post Brexit for Brits as it used to be. There's a lot more paperwork hoops to jump through. We bought a place in the mountains there about fifteen years ago and that's rented out (through a local agency) for about six months of the year (ski rental in the winter and cycling fanatics in the summer). The rental income just about pays the bills. The up side is that it hasn't cost us anything (except during Covid) and the place has risen in value through house prices going up and the pound going down. The down side is that even with a captive market for rental clients the yearly income hasn't been fantastic. That may be easier if you're living above the shop so to speak but if you're doing it yourself marketing costs and time are going to be considerable.

Don't write off life post 65 quite yet I know people vary in how age treats them and you can be unlucky with your share of the gene pool, but with a bit of care - diet / exercise/ not smoking etc, 65 is rapidly becoming the new 50. Not good news for the pensions industry as they have to pay out for longer but post retirement motorcycle gap years are perfectly feasible. My plans are based on it.

I totally understand not wanting to wait. It only ever gets harder the older you get. And I think you should definitely do it whilst you can.

I threw away many careers and spent all my savings throughout my 20's and 30s for travel. I Saved for 1-2 years then travelled for six months etc. On and on...

Coming home from those trips penniless was almost suicidal. And incredibly difficult to adapt to, even though I had the benefit of youth, ignorance and boundless energy. The older I got the harder it became. To the point in my early 30's when I had to stop. The travel didn't justify the fallout. It ruined travel for me somewhat. And I had to start planning for my future and retirement.

I've been static for ten years now and I'm close to being able to travel again without having to come back to nothing.

I would never long term travel now without a surefooted exit strategy and return plan. Borrowing money is a huge stress. Looking for work is a huge stress.

Will you be able to enjoy your trip if you're constantly worried about it ending ?

Plan your return before you plan your trip. Have everything (almost) in place for your return. And then it can all be a great success.

__________________
Did some trips.
Rode some bikes.
Fix them for a living.
Can't say anymore.

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That is what I did.I sold my house with garden and garage.
Good to have for a family. But a lot of maintenance.
And something you can't just leave.
And bought an apartment in Portugal/Algarve. Very low monthly cost. That I can easily get covered by rented out. Just lock and leave...(A lot of apartments here are empty all winter)
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Finding decissions which will fill up the last chapters of your life with satisfaction and happiness is the game we are all in.

Some who start longterm travel travelling are running away from something; some are looking for something. Some will find something which gives their life a new direction; some will loose more and will have a big problem to return to "after travel life".

Think it`s quite normal if you look back to your life that you will detect some wrong and right decissions you made.

Your past will always be your lesson. Your motivation and your discipline will be your future.

So why should I worry or regret about my past if I can`t change it anymore?
I learned to live with my decissions equal if they later showed off as right or wrongs ones.

__________________

That is what we pray for at every AA meeting.
But is equal important for everyone.
Sober alcoholic or not.

But much easier said than done

Vaya con Dios

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Buying a place in a foreign land other than your own may sound like a good idea But if you dont know the language or customs sounds like a bad idea only if you like to rub shoulders with other property owners Its costly but may have benefits for your family that want to go on vacations.
I was in Cape Town a couple years ago my flight was the non stop from Amsterdam Packed to the brim of mostly Dutch for there January vacation. I was surprised when I rented a moto and went cruising along the coast the local beach towns.They were full of Dutch Nationals partying and having a good time , I thought family runs deep in this part of the world the Dutch had a strong hold in this place for many generations. Good for them what way to escape if you are living in Holland one of the most densely populated places on earth
My thinking is if you want to retire or are close to retiring in a foreign place why not rent or lease this is what I do at 61 and have full privileges as a temporary foreigner pensioner in Colombia, I pay300 bucks a month for a modern apartment and 300 for all the food I could possible eat plus 300 a year for my moto to be legal the rest is a adventure

I think it depends on what someone wants from retiring to another country - both me and my sister moved from the UK into Europe (her to Bavaria, me to Catalunya) while still "young" because we felt more comfortable fitting into these places; all but one of the English people I've met who live here are not about learning the language or customs ... it doesn't hold them back from life, though I couldn't live like that.