Solving the Housesitting Puzzle

Housesitting Puzzle

Individual housesits aren’t puzzling of course, they are very straightforward. There are start and end dates, a location, and pet responsibilities. What could be puzzling about that? Well it’s not the individual housesits that I’m referring to here, it’s the process of organising those bookings into a schedule that works. Not always as easy as it may seem.

What makes it a puzzle?

We’ve been doing a couple of puzzles on our current housesit here in Essex and it was whilst we were agonising over which bits of sea went where that we realised it was a really good metaphor for our travelling lives at present.

Housesitting Puzzle
“The troublesome puzzle in question”

Just imagine that your calendar is your puzzle frame and each housesit an individual piece that has to be placed in that frame to fit neatly with all of the subsequent pieces. Add to that the fact that you start the puzzle with only a couple of pieces and have absolutely no idea how the complete picture will end up and it’s a bit harder than imagined.

Obviously this issue is the same for all housesitters, even more so for those full-time sitters out there, or it may just be the way that we choose to live our lives that makes it so tricky. Not sure. We spend just under 50% of our time housesitting so the puzzle is even more complicated with our travelling plans and personal trips included.

Applying for housesits

We are always on the look out for new sits on TrustedHouseSitters and scan the daily emails and search the website on a regular basis. And although we do have a rough idea of future available dates the sits never quite pop up in such an organised way. We may see one for five months time that we like and another for two months, and apply for both. If we get both then that puts two pieces in the puzzle and starts to give us a structure of sorts. Now we need to look at dates that fit in with those booked sits.

Housesits or Travelling? Which comes first?

That’s the million pound question isn’t it? There is no definitive answer here as it all depends on how we feel and what we have been discussing. Sometimes we decide on a big trip or week away and that gets booked and added to the puzzle first, other times we wait and see what gaps occur. I’ll come on to ‘gaps’ later. First though it’s probably a good idea to give you an example of how our puzzles develop.

Example of JWalking Housesitting Puzzling

Housesitting Puzzle

You can see above that we have a trip to Snowdonia in North Wales booked followed by a stay in the South of France working with Helpx.

Housesitting Puzzle

A week after returning from France we’ve organised a get-together with our sons and daughter-in-law leaving us a short one week gap to sort out.

Housesitting Puzzle

Our Helpx stay is cancelled due to issues with accommodation. Luckily we manage to get a housesit in Hertfordshire for the first week but that now leaves a huge gap.

Housesitting Puzzle

We apply for another couple of housesits and get one in Wiltshire whilst waiting on another. Some take longer than others to arrange.

Housesitting Puzzle

The second sit in Devon is confirmed and we manage to secure a third in Hampshire. We decide to book a weekend in Cardiff after Devon as it’s so close but that still leaves us a couple of gaps to fill.

These changes to our puzzle continue constantly and we often have to book one night or two night stays in Travelodges or Premier Inns just to plug gaps between longer stays. A almost completed section of our puzzle could look like this…….

Housesitting Puzzle

Transport and Travel

Once we have a section of the puzzle sorted out and confirmed we then need to look at transport. How do we get from one housesit to our sons house, or from a weekend away to a sit down in Devon? This is where we look at trains and start booking our tickets in advance to try and save as much as we possibly can (How to save money on train travel). In truth the process of organising transport happens at the same time as booking, another part of the puzzle.

Housesitting Puzzle

Anything else?

Are you kidding? Add a few more tasks to the planning list for other things that need adding to the puzzle.

  • Planning when we wash our clothes
  • Visits to the doctor and dentist
  • Shopping for food
  • Occasional meals out with family and friends if we are nearby
  • Dropping our bigger bags in storage if we plan to fly
  • Putting winter coats and boots in storage for the summer
  • Family birthdays
  • Getting coats and boots our for the winter

So as you see it isn’t just a housesitting puzzle is it? It’s our JWalking life planner but a lot of the arrangements do actually depend on the housesits that we book as they determine our location and a rough structure to our weeks. And I haven’t even started on our trips and travels and all of the planning that entails ……..

Sounds like a nightmare doesn’t it? Well it’s not. We actually love the planning and organising and are never happier than when we are researching new places to go and new housesits to apply for. We do need to be ultra-organised and really on top of our arrangements but to be honest we’ve both always been really good at that sort of thing.

Please be patient

So when we suggest a day to get together that’s four months in the future or ask you what time exactly you want us to arrive it’s because we have to know. We’re not being awkward, it’s just our life.


Pinterest SOlving the Housesitting Puzzle


  1. I’m book marking this!! Thanks for posting – one day we will be house-sitting – one day. You all have too much fun together. Sean and I are big puzzle fans – we’ve been averaging at least one a month. We have some friends we trade with. Makes it fun!

    Liked by 2 people

    • Glad you liked the whole puzzle analogy, I thought it described our life really well. Actually doing a few puzzles where we are at the moment, local charity shops are great for picking them up cheaply.

      Liked by 1 person

  2. Good thing you enjoy organising, Jonno. I would like the research and new areas to explore but booking transport can be a pain. Most things have a down side, don’t they, but you seem pretty happy with the lifestyle. 🙂 🙂

    Liked by 1 person

  3. What an interesting post!! It’s a good job you both have good organisational skills. You really have to be on top of your house sitting game. Great idea using the jigsaw to demonstrate and explain😊

    Liked by 2 people

    • Thanks Liz, thought the puzzle example worked pretty well. Seems to sum up our life at the moment. We’re both organised so it works perfectly. Currently sitting till March then not again till almost July so lots to sort out.


  4. I am now spending around 70-80 % of the year house sitting, so I am very familiar with those organizational challenges.

    My main trick is to look for longer house sits (a month or longer). For those, even a long trip is worth it. Or several house sits in one country/area. Last summer, for example, I had three house sits in Belgium, with just a few days in between. That was perfect and gave me a good overview of different regions in Belgium. But it only works in countries with lots of offers (and maybe only in the summer or winter holidays.)

    And if there is an interesting offer in between the longer sits, I only accept it if the transport is reasonably possible. Even if it’s a fantastic place, I won’t travel three days one-way for a one-week house sit. (Especially as I try to fly as little as possible.)

    Looking into the future for more than 6 months, I usually won’t apply for a short house sit, but rather hope that a long one will come up. If it won’t, I will always find short ones on short notice, if I want to.

    Liked by 2 people

    • Interesting life isn’t it and you are so right about travel expenses being a major consideration. No point in going anywhere for a week if it’s expensive to get there. Belgium must have been good, lovely country. Where are you sitting at the moment?


      • Belgium was really interesting, especially as I saw in Flanders, in Brussels and in Wallonia, getting to know the different regions.

        At the moment, I am “home”, which means my parents’ place because I don’t really have a place of my own, getting ready for a university field trip – to Flanders again (I am studying history and it’s about World War I).

        And then I have two long house sits coming up: 3 months on the island of Faial in the Azores (which is surprisingly affordable to get to from Lisbon) and 2 months in Kyiv in Ukraine (for the same cats that I took care of this winter).

        Liked by 1 person

  5. It’s actually pretty cool, it’s almost like you have a full time job of admin to organize your adventures and house-sits! I quite like puzzling things like this out. I wonder if when we retire we could do something similar. It sounds like a lot of hard work, but way more exciting than sitting in one spot.

    This also makes me think we should sign up to trusted house-sitters, and get you to stay with our cat next time we plan a long holiday. 😀

    Liked by 2 people

  6. A fascinating insight into your lives Jonno, and yes, you are both super organised. As you’re probably aware I’m frequently away and think of myself as being well organised but it’s easier for me as I have a home to return to. Sometimes I wonder how I manage to get everything done as I’m always busy but like you, I wouldn’t have it any other way !

    Liked by 2 people

  7. Using tbe jigsaw pieces as a visual aid is a great idea. I too love the planning and organising nearly as much add the actual sits. I am trying to be much more organised this year, mainly to cut down on flights. I am aiming to be in one particular country for at least 7 or 8 weeks. I have a 3 month sit later in the year in Bulgaria so that’s a big chunk of the year taken care of.

    Liked by 2 people

  8. Hi Jono reading your puzzle story was like reading about our life! The puzzle analogy is perfect! We love the planning too and looking at “where to next” and “is that even possible?” “Does that fit?” Thanks for the insightful read! Donna

    Liked by 2 people

    • Those are the constant questions aren’t they Donna? The ‘does that fit’ one is a daily issue but like you we love all the planning. Are you sitting somewhere at the moment?


  9. Interesting insight. There’s much more ‘back end’ planning to it all than I might have thought. I’d never considered issues like storing seasonal items. All worth it when it comes together though, plenty of adventures and exploring!

    Liked by 2 people

    • Quite a lot of planning for absolutely everything so always a lot to organise. But like you said it’s totally worth it. Lots of adventures still to come hopefully.


  10. I’m glad you finished by saying you love planning because I know that you do and it saved me having to say it! Like you I think the planning is half the fun. It builds the excitement but for you it’s become vital now.

    Liked by 2 people

    • It can be a bit of a nightmare at times but I think we actually enjoy the challenge of sorting things out and any cancellations or issues just make it more interesting. Been doing it a while now so I guess we have a fair bit of experience.

      Liked by 1 person

  11. What a head spin. I can understand why you need to be super organised and look so far ahead. But I’m sure it’s worth it. We’re hoping to fit Housesitting into our lifestyle when we retire so I was really interested to read your post. Sharing

    Liked by 2 people

    • It is a bit head-spinning at times Jennifer but like I said we really enjoy the planning and organising so it’s just part of our lives now. I would thoroughly recommend housesitting when you have some time as it’s a wonderful way to explore and see more of the world. We love it. If you need any advice …….


  12. This is so incredibly interesting – genuinely one of the loveliest posts I’ve read in a while 🙂 it sounds such a fascinating lifestyle. Just planning my next 3 months of trips around work/school is exciting enough, let alone living it every day. Keep doing what you’re doing and thank you for sharing 🙂

    Liked by 2 people

    • Thanks for such a lovely comment Kaz, it really is a great lifestyle for us. Not sure it would suit everyone but we love the nomadic life we’re leading. The planning can be as exciting as the actual trip sometimes can’t it?


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