How To Plan A Sabbatical: A Real-Life 21 Step Guide

This post guides you step-by-step through how to plan a sabbatical.

This is a real-life example, which documents all the actions we took in planning three months in Southeast Asia, including our exact spend, how we dealt with our property, organising the break with work and how we planned our route.

I (along with Mrs TSG) have great experience in planning these long breaks, having taken multiple sabbaticals and also planned our emigration from the UK to Australia. We have become experts in ‘project managing’ these big life events, and hope the practical examples in this guide will help you do the same.

For reference, this sabbatical took place in 2018, so some costs may have changed in a post-Covid world, but the sabbatical planning tips are no less relevant now.

Why Did We Take This Sabbatical?

Before we start talking practical sabbatical planning tips, I thought it was important to start with why we took this sabbatical, as this will be something many of you can relate to.

It came on the back of a tough few years. Work had burned us both out (I had to make over 50 people redundant on my 30th birthday), my Dad had recently been involved in a serious accident which made me reflect on the fragility of life, and my wife and I were planning on starting a family, which meant our time to travel as just a couple was running down. I’d also recently been overlooked for a promotion, despite feeling I’d put in the work to get the role.

Becca and I both love to travel and, sitting on a beach in Seychelles as a treat for her birthday, we both realised we needed to see more of the world.

man looking out to sea under palm tree in sunset seychelles
Pondering the future on a beach in Seychelles

I was reading Tim Ferriss’ book The Four Hour Work Week and read about the concept of building ‘mini-retirements’ into a career. He wrote passionately about how too many people save up life experiences until they are too old to enjoy them.

I was sold.

The idea of our sabbatical, and The Sabbatical Guide website were born.

How To Plan a Sabbatical (The Early Stages)

Our Routine For Planning the Sabbatical (Don’t Try Eating An Elephant Whole!)

Things to do before Travelling Abroad

Once we knew we wanted to take a sabbatical, we started to deal with the practicalities of how to plan it. We needed to research policies with work, look at when and where we should go and deal with everything from what to do with our cat to what gear to buy.

We decided we needed a routine, which for us was an hour every Sunday morning.

We set up a joint to-do list (the app doesn’t matter, you can do this on everything from a shared Apple note to a fully-blown to-do list program) and ‘brain-dumped’ everything we thought of into a single place.

Every Sunday we would then sit together and work through the tasks.

  • Each task would be assigned to one of us to deal with
  • We put tasks in a logical order. For example, no point booking flights until we had the time signed off with work. We couldn’t book travel insurance until we’d agreed a destination

This meant we were each focused on a few things at a time.

There is an old phrase I learned growing up in Africa ‘you can’t eat an elephant in one bite’. Thinking about the enormity of planning a sabbatical as a whole can be overwhelming. Storing everything in a single location and working through it systematically makes it achievable.

Research Work Policies (Without This, Nothing Matters)

office clerk searching files in the filing cabinet

We started here, as we felt that without it, the rest didn’t matter at all.

If we research sabbatical policies with our employers and found there wasn’t one, or we hadn’t been at the business long enough to qualify, then the whole plan would have to change radically.

It would either involve quitting, postponing or (horror of all horrors) not taking a break at all.

We felt the key here was subtlety. Wandering in and asking our bosses, or even someone locally who worked in HR, could easily get rumours going that we didn’t need. Not that we were worried about the prospect, more that we wanted to professionally talk to our business at a time that was right for us.

We found most of the information was easy to access on company intranet pages. We both worked for big retailers in the UK who have modern systems, so we could find the sabbatical policies without too many issues. Mine needed some clarification, as there were some restrictions based on time worked for the company, so I phoned up the confidential employee relations lines, and claimed I was making enquiries for one of my team to get the answers I needed.

Both of our companies had similar policies.

We could take up to three months off, unpaid, without it being seen as a break in service. Longer than this and it would be seen as leaving the company and re-joining, meaning any long service benefits would reset. The businesses should also guarantee us the same role on return, though this would be a key part of how we communicated out plans to our bosses, which I go into later in this post.

Deciding What To Do On Sabbatical (The Fun Bit!)

This bit was fairly easy.

We knew we wanted to travel, it was just a case of where. We also now knew we could travel for up to three months, so this opened up lots of possibilities that we could never manage through two-week vacations.

We were initially thinking about a road-trip through Europe or maybe the west coast of the USA.

We abandoned those ideas for two reasons:

  1. They didn’t feel culturally too different to the UK
  2. The cost!

We ended up researching the cheapest places in the world to travel and settled on Southeast Asia. This would be the perfect place to immerse ourselves in cultures very different to ours, but also keep costs at a more reasonable level.

The location was set!

Choosing a Time For The Sabbatical (Considering All the Factors)

The next part to decide was when to take the sabbatical.

At this point it was around October.

There were a number of factors we considered:

  • When was the best time to travel in Southeast Asia. We wanted to be outside of peak crowds, but also avoid most of the rainy season
  • When was the right time for our workplaces. Retail is very busy at Christmas and Easter so we wanted to avoid these times as we didn’t want to burn bridges with our employers
  • How much notice we should give. Technically the policies said one month notice was enough, but out of respect for our employers we wanted to give them much more time than this, again to be respectful to them and help them with cover,

So with all this considered, we decided late April would tick all those boxes.

Working Our How Much It Would Cost ($$$ Talk)

Before we took the last step and of telling our bosses, we wanted to make sure we’d actually be able to afford our dream plans.

I have a complete guide to calculating sabbatical costs here, but very simply we:

  • Calculated ongoing costs we couldn’t cancel while we were away (such as house insurance)
  • Calculated any big one-off costs associated with the sabbatical (flights, tours etc)
  • We used websites to work out what we thought would be the daily cost of living in the countries we were visiting (food, accommodation, travel etc)

This gave us a rough cost for the trip (around the 12,000GBP mark full costs are included later in this article).

We’d been building up savings for a number of years, so we were happy we could afford this, but also knew some of the costs would come whilst we were still working. Expenses such as flights could be paid for while we were still working, so wouldn’t be paid at a time when we had no income. This would spread out the cost and make it more manageable.

Telling Our Bosses (The Scary Bit)

This was the natural next step.

We decided not to plan any itineraries or start dreaming about the possibilities until this practical step was out of the way.

In early December we decided to tell our bosses our plans.

I will describe my experience here, as I can tell the story first-hand.

It’s important to understand when reading the below, that at the time I had responsibility for 25 stores and around 1,250 people. It was very unusual for people in my position to take time off like this, so I knew this would be a risk and, that given I had been overlooked for a recent promotion, they may think I was being difficult.

I felt had to be clear about my commitment to the business and help them find solutions for my cover for this to be signed off. The sabbatical program in my business was there in policy, but it also said it was a benefit not a right, and that it was down to an individual line manager to decide if it suited the needs of the business. The way I went about this process was going to be key.

Firstly, I booked an appointment with my boss. It was at the end of a full-team meeting, where I knew we would be together anyway, but I made it clear to him I needed some closed-door time and it was really important to me. He knew something big was coming (I think he thought I was going to resign) so this straight away set the scene for the meeting. He wasn’t distracted and I had his full attention.

In the meeting I came straight out and described what I wanted to do. I said we wanted to take a three-month unpaid break from the end of April, and told him the story of why I felt I needed it (all the points from the ‘Why Did We Take This Sabbatical?’ at the top of this page). I also described to him I was still completely committed to the company and wanted to return at the end of the break, which was why I was taking the sabbatical at a time which didn’t conflict with key trading periods.

I then went on to say (and this was I think the key in getting sign off) that I also felt that there could be some huge benefits to the business of my break. I made clear that I was giving significantly more than the required notice, and I was doing this out of respect for him, but also I wanted to be part of the solution to covering my absence (which would have been his biggest fear). I said I had identified two future leaders in my team, and that we could split my role in two whilst I was away and I could spend the next few months readying them for my break. On my return it would then mean the business had two additional people to add to its pipeline.

He was great. Really open to the idea and thanked me for coming with solutions too. As expected, he said he would need to run it past his boss. He even went on to say he wished he’d been as brave as me earlier in his career and taken time off.

Within a week they’d got back to me.

It was on…

READ NEXT: How To Ask Your Boss For A Sabbatical

Sabbatical Planning (The Nitty Gritty Stuff)

In this section I will talk through the practical and most difficult decisions you’ll need to make when planning a sabbatical.

This is the tough stuff and where our weekly Sunday catch ups became really crucial in making sure we had every base covered.

What Should We Do With Our Property (& Our Feline Lodger)?

What to do with pets on a career break
Smudge helping us with planning our route through Thailand

The first big conundrum was what to do with out house.

This was from two aspects.

Firstly, we were homeowners with some big monthly mortgage payments. We needed to find a solution as we weren’t going to be able to keep this paid with no income.

We looked through a number of options, including a short-term rental, but decided the best solution was to take a mortgage holiday. Thankfully we’d had a mortgage with our company for a number of years and been consistent with out payments, so they would allow us to stop paying the mortgage for up to six months, and these payments would be added to the end.

Whilst this meant our mortgage would be extended, we felt this was the best solution.

Secondly, our insurance had a clause in it (as most do) that if the house was left vacant for more than eight weeks then the insurance would become invalid. Whilst the chances of something happening to the house were low, this was a risk we needed to mitigate.

Our first thought here was to find someone to move into the house. This would also deal with a third problem, what to do with our little cat Smudge, as the cost for 13 weeks in a cattery was huge.

We looked at housesitting sites, but quickly came on a better solution. Our neighbour’s daughter had just turned 18, so we thought it might be a great experience for her and her boyfriend to move in and live together for a while (five years later they are now engaged and have a baby on the way so it clearly worked!). I chatted with my neighbour and he thought it was a great idea (of course he would!), and agreed to keep an eye on them while they were here.

In return, she would look after the cat and we’d leave all the services on (internet etc) so she could have full use of the house. Much cheaper than the cattery for us!

It was an absolute dream solution. We met up with her a couple of times and set a couple of rules (no parties for one!), and left her money to feed the cat but honestly, she was just super-excited (as I would have been at that age). She was also amazingly respectful, and when we got home the house was as clean and tidy as we left it.

READ NEXT: What To Do With Pets When You Take a Sabbatical

Planning the Route (the Special Spreadsheet!)

We wanted to make sure the sabbatical wasn’t planned with military precision, as we wanted space to adapt as we went, but also knew we needed a general timescale, so we could understand if our plans were actually possible and also for more practical reasons such most countries only offering a four-week tourist visa.

a spreadsheet showing route planning for 3 months in southeast asia

So we built a spreadsheet with all the dates on it, first putting in the immovable objects (such as when we were back at work, when we were meeting my Dad in Cambodia and the earliest we could be in Vietnam without going over our visa limit) and then adding in the smaller elements.

You can see on the above, that we planned out the first month, but this didn’t actually end up turning out this way. We didn’t go to Sukhothai, opting to go and spend some time up in Chiang Rai (which we’re glad we did as it was the best place we visited), and also missing out on Pai.

As you can see, building a framework like this is more a compass than a map, it gives a general sense of direction rather than an exact route.

What Gear Did We Buy?

Southeast Asia Packing List

You can see our complete packing lists here, but here is an abridged list of things we bought specifically for the trip (most clothes etc we already had):

Full list of things to do before travel (Any other bits?

We discovered during our planning sessions that are a staggering number of things to do before you go travelling long-term.

I’ve mentioned earlier in the article about the big things – someone to look after the house, the cat etc – but the list of smaller jobs is significantly bigger.

From getting vaccinations to extending our passports (some visas needed at least a year post-leaving the country), buying travel insurance to unlocking our phones so we could get local sim cards where needed.

I documented everything as I went and turned it into a list you can use – 35 Things To Do Before Long Term Travel.

The Last Few Weeks of Work (The Dive For The Line)

The last few weeks of work were tough, but that was mostly self-imposed.

On one hand, there was a lot of last-minute bits to deal with, from packing to saying goodbye to people, but on the other hand I wanted everyone at work to know that I was serious about my commitment to the business.

If anything, I worked harder, training the two people replacing me and trying to show the world that I wasn’t winding down early.

It was a weird sensation on the final day, getting the train back from London knowing I wouldn’t be heading back to work for three months. I’d had that sensation once before, but that was unplanned when I was put on gardening leave by a previous company. This time we’d got it all planned out, it was time to get on the plane to Thailand!

Three Months in Southeast Asia

7 Best Tourist Attractions in Northern Vietnam

How Much Did Three-Months in Southeast Asia Cost? (Complete breakdown)

I can answer this question exactly.

$7,235.20 (excluding the flights to and from the UK as we paid these a long way in advance)

That is made up of:

  • $798 in flights
  • $1,146 in accommodation
  • $1,039 in big one-off costs
  • $4,251 in other day-to-day costs

This works out at just under $80 a day for 91 days for two people.

This information was taken directly from our credit card statement (we used one with zero fees so all sabbatical spending was in one place).

You can see a full breakdown below.

spreadsheet showing full costs of 3 months in southeast asia

There is no doubt it could have been done cheaper than this, as we had some big expenses such as learning to dive and meeting my Dad for his 60th at the temples of Angkor. We also didn’t stay in cheap places all the time, mixing up our time between cheap accommodation and then a bit more luxury when we felt we needed it.

What Route Did We Take? (Map & Day-By-Day Guide)

Here is the map of the exact route we took over three months in Southeast Asia.

We used an app called Tripline to keep a journal for our family to see daily, and you can now do the same if you’re interested in planning a similar trip.

It broadly worked out to:

  • 4 weeks in Thailand
  • 3 weeks in Laos
  • 2 weeks in Cambodia
  • 4 weeks in Vietnam
The White Temple in Chiang Rai

The more detailed route was:

What Were the Highlights? (Did a three-month Southeast Asia Sabbatical Deliver?)

In short, yes, the sabbatical did deliver!

So what were the most memorable parts?

Firstly, it was breaking our normal routine. For me this is what a sabbatical is all about, you quickly start to notice more about the world around you when every day is so different to what you’re used to. When this is amplified by being in new countries, with new people and new cultures it is a real blast to the senses.

Secondly, it was spending time together. We had so much time, so many conversations that I felt we got to know each other on a whole new level. Whilst it didn’t turn our live upside down completely, we definitely became a closer couple and built a bank of memories and stories we’ll be telling for generations.

Specifically on Southeast Asia, we’ve already written a post detailing our top places, countries, foods and experiences in Southeast Asia, but here are some of the main things that we enjoyed about the trip:

Taking a break this long was unlike anything we’ve ever experienced. It was much more than a long holiday. When the day-to-day responsibilities are gone, you’re free to think, experience and just live.

This, for me, was being human in a very pure sense, and I loved it.

Post Sabbatical

What Was It Like Returning To Work?

Honestly, it was tough.

What you realise after packing three months full of the most memorable experiences, is that life for most people doesn’t really change over a three-month period.

I was very conscious not to brag, but for people who seemed genuinely interested I shared some of my favourite stories, but I was also determined not to become a distraction. In the same way I put my foot on the gas on the run-up to leaving, I quickly got back into the swing of things. I knew that if I ever wanted to ask for a break again (or, given I had set a precedent, if anyone else wanted to), I needed to show that I could reintegrate quickly and get back on with business.

On the inside though, I was missing both Becca and travel like hell. When every day has felt so vastly different to the usual routine for a while, getting back to the usual routine is like jumping into an icy lake.

I wrote about my thoughts a few months later, reflecting on how little had actually changed, and how easy it is to slip back into the life that was waiting.

“I definitely learned that whilst on sabbatical. Not because I had some kind of epiphany, in fact entirely the opposite. I was expecting thirteen weeks of travel around Asia to be life changing.

Memory creating, yes.

Enjoyable, yes.

Spending more time with Becca than ever before, yes.

Life changing. No.

I came back fundamentally the same person I was before. The anticipation was huge, the experience fantastic, but (save for a few tweaks around the edges), I came back the same guy who’d taken off.”

If there’s one thing I wish I could do differently, it would have been to get a coach to help me work through all the unprocessed thoughts that were still rattling around my head.

But I didn’t, and I ended up just fine. But it certainly wasn’t going to be the last sabbatical I ever took…

Finishing Up

I hope you’ve found this guide on how to plan a sabbatical useful.

It’s something I wish I’d had when I was trying to work my way through the tangled web of questions and actions, so I’m so pleased to be able to pass on some of that knowledge to other people.

If you have any other questions, reach out on my contact page, and I’ll get back to you. I’d also suggest joining the newsletter which comes with over 90 days of sabbatical tips and stories to help.

the reeves family picture


Reeves Roam, is a first-hand travel blog. The Reeves have lived in the UK, South Africa and Australia and have travelled extensively in Europe and Southeast Asia.

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Thanks – Ben, Becca and Gracie