Three sabbatical fears & course launch!

I write about the Big Fears that stop people from going on long-term sabbatical. I'm also launching a self-paced online journey which will help people on sabbatical navigate their time away from work.

May 21, 2023

So many people dream of taking an extended break from work, yet few people end up doing it.

I get it; it’s terrifying. I weighed pros and cons for months before deciding to take the leap. I was worried about spending money with no income, about my professional skills becoming atrophied, about my career taking a hit, and even about not knowing what to do with all the free time I would gain. .

I couldn’t resolve all those Big Fears fully before going on sabbatical, so I had to take a leap of faith. Now that I’ve experienced pondering whether to go on sabbatical, deciding to go, actually going and finally returning to work, I’ve gained a lot of perspective on the topic that I’ll share with you in this issue.

But first, some exciting news…

I am launching ‘On Sabbatical’, a self-paced online experience that helps people navigate multi-month sabbaticals.

Inside is a collection of short videos with stories and insights I’ve distilled from my 12-month sabbatical and the 40+ conversations I’ve had with fellow sabbatical-takers. It also contains invitations to explore and embed new ways of being, useful resources I’ve collected along the way, and a community where you can meet and engage fellow sabbatical-takers.

Consider it like a map. I don’t tell you where to go, because your sabbatical will be as unique as you are, but I will point out interesting directions that are worth exploring if you’re looking for a transformational experience. I’ll also point out traps and challenges that you’ll end up facing, and share ideas on how you can avoid or escape them if you get stuck.

For now, the standard price is $125, with options for lower and higher prices. I will increase the price in the future as I improve the course and as the community becomes more active, but don’t know yet when that will happen.

If you’ve been eagerly waiting for me to launch this, head over here for more details.

Now, back to those Big Fears!

First of all, it’s normal to be worried about taking a break from work for an extended period of time, particularly if you’ve never done anything like this before. Even if you’re feeling uncomfortable in your current work situation, that’s a situation that feels familiar, and it’s often easier to pick familiar discomfort over the risks of the unknown.

After all, if you’ve been following the same path in work and life for a while, you know it inside out, and you have no idea what the alternative might have in store for you. It’s easy to imagine all sorts of horror stories. Often, though, that’s just what they are: stories.

Don’t get me wrong, sometimes the stories are right and you shouldn’t be going on sabbatical. I wouldn’t recommend you take an extended sabbatical when you only have enough savings in the bank to last a couple of weeks. That’s not a sabbatical, that’s either a bucketload of stress or a fast-paced money-making adventure!

As I was talking to people who were considering going on sabbatical a few months ago, I noticed that many felt paralyzed by the same Big Fears. I’m going to name a few of them, and offer alternative perspectives to help you think about them differently.

Fear #1 - Going on sabbatical is a money sink

Yes, going on sabbatical costs money. Sometimes a lot of money.

I spent 50% more while on sabbatical than I would have spent if I had stayed in London, which felt like a *lot* of money to me. That money went on accommodation, flights, insurance, touristing, plus local and online experiences like breathwork, tantra workshops, a leadership retreat, and a few online courses like Write of Passage.

Even worse, this doesn’t account for the opportunity costs of not having saved for a year, not getting a bonus, or not adding money to my pension pot.

Sabbaticals can be an expensive affair, I’m not going to lie, but there are ways to make it less expensive.

First, you don’t have to take a whole year off, though if you do opt for a shorter sabbatical, I’d encourage you to take at least six months off. People who’ve been on sabbatical report that they’ve needed at least three months to feel deeply rested, and another two or three months to start experiencing early signs of the transformation that they were going through.

Then, you can decide to live in a place where the cost of living is low. In Indonesia, rent was a quarter of what we were paying in London. If you opt for this solution, go live in an environment that is sufficiently different from your normal living environment so that new aspects of your character will feel invited to show up. You don’t have to travel to the other side of the world to find that environment, you could also find it online.

The thing is, if you isolate this Big Money Fear and look at it from a purely financial perspective, it’s hard to make the case to go on sabbatical, because the benefits are much more intangible than the costs. You know how much money you’re putting in and how much money you’re not getting from your job, but you can’t put a value on the transformation you’ll go through.

Spending money on a sabbatical is only a ‘money sink’ if you get absolutely nothing out of your experience. Speaking from personal experience, and from the 40+ conversations I’ve had with people on the topic, there’s a very low chance that this will happen.

Paul Millerd

, author of The Pathless Path, reports: “I’ve literally talked to only one person out of close to a hundred that took some sort of sabbatical in the last five years and said, “yeah, didn’t do anything for me.” The other 99% of people? They typically report dramatic shifts.”

It’s not a money sink. It’s a transformational investment in yourself and your future.

Fear #2 - I have no idea what I’ll do with all this free time

Yes, it’s likely that you’ll get bored.

When you stop working, 40-60 hours of time are suddenly handed back to you, or 80 if you’ve been working like a maniac. Your best hours. The high-energy, high-creativity hours that you usually spend on your job.

You might know how to fill this extra time the first week, maybe the second week, and even the third if you’re lucky, but at some point you’re likely to start feeling agitated. It turns out that dozens of hours a week is a lot to fill, particularly if you’re used to working intensely and not used to thinking about how you want to use your time meaningfully.

Four months in, I started realising that there was such a thing as having too much free time. I only knew how to put 15-20 of those extra hours to good use and got incredibly bored. I also got anxious about not putting this time I’d gifted myself to good use, whatever that meant.

"All of humanity's problems stem from man's inability to sit quietly in a room alone" wrote the French philosopher Blaise Pascal.

I’d known that quote for 20 years, but I’d never quite understood what Pascal meant until that moment in Mérida, Mexico, when hours and minutes were going by at a painfully slow speed.

I felt tempted to schedule a bunch of activities to fill the void. I found myself scrolling through websites offering hikes in the mountains and visits to pre-hispanic sites. I could have easily signed up for all those activities but deep-down I knew that those activities were distractions from my main quest. They weren’t the solution.

The truth is, to start thinking and being in a different way, you have to stop doing things all the time. If you keep moving at the same pace that you used to work and live at before you go on sabbatical, you won’t know how it feels to experience life at a different pace. Your nervous system will feel just as activated by constant travelling, day trips and site visits as it used to feel from working hard day after day.

Unsurprisingly, the only way out of boredom is through. Feel what it feels like to be stuck.

But sitting on your sofa for days (or weeks) won’t make creativity and novelty descend upon you, so once you’ve had enough feeling stuck, start moving both your body and mind. You don’t need to know where to go, you just need to move so you ‘unstick’ yourself both physically and psychologically. The two are linked anyway. You can walk, stretch, run, journal, tweet, or do all of it at the same time—whatever you feel drawn to.

Fear #3 - My career will take a hit

Maybe.

Probably, if you try and go back to the exact same career as the one that you left behind.

But if you’re thinking about taking an extended break from that career, it’s probably because your priorities have shifted and that career doesn’t feel right for you any more.

Why would you want to go back to something that isn’t working for you?

Your priorities are likely to shift even more while you’re on sabbatical, and the chances of you wanting to return to the same kind of work in the same industry may not be that high.

Even if you’re taking a sabbatical not because you hate your job, but because you want to dedicate a period of time to a specific project or people (for example to spend a whole year with your newborn child), you’re bound to be quite a different person in a year’s time.

Trust that your future self will be able to sort itself out.

Steve Schlafman stepped away from his career after making partner at a multi-billion dollar VC firm to become a professional transition coach. He writes a newsletter ( I’m sure you would love) called

Where the Road Bends

and he nails it in this tweet:

You won’t lose the skills that you built over years of hard work. They’ll simply go into hibernation for as long as you don’t need them, and for 90% of knowledge workers it won’t take more than a month for them to awaken again. To be honest, the only skill that I totally lost was my ability to tolerate bullshit tasks and projects—and I’ve decided that’s probably a good thing.

If you end up wanting to return to some form of employed work, you’ll have to figure out a way to distil your experience into a few talking points that the professional networks you want to join will understand. Maybe you’ve learned new skills, or you’ve built a network of useful contacts, or maybe you’re simply deeply rested and truly ready to bring energy to a new work challenge. Whatever it is, demonstrate that the experience was valuable to you and hence valuable to them as a potential employer.

Despite that, you’ll sometimes stumble upon employers that still don’t understand the value of sabbaticals. Some of them might see ‘twelve-month sabbatical’ on your resume and decide not to call you in for an interview. This is a good thing. If a hiring manager doesn’t appreciate the transformational value that comes from experiencing that, you probably wouldn’t want to work for them anyway.

For those among you who will not want to return to any form of employed work, the Big Fear of whether your career will take a hit becomes irrelevant. That career belongs to a past version of you. The current version of you can use that career to set itself up for a new phase of work and life.

To be honest, if you leave your job to go on an extended break from work, there’s a high chance you won’t go back to the working world you left behind. A high chance that you’ll end up doing something completely different instead. If you’ve read this far, isn’t that what you’re looking for?

What do you think? How tempted are you by taking a leap of faith?