Summary

Sabbatical policies can benefit both employers and employees. But these extended leave arrangements need careful design and inspection.

• If they take too long to be eligible for, they cease to be motivating.

• Adding too much fine-print to availing such leave can sour the deal in the employees’ minds.

• Leaders must set the right example by taking their sabbaticals and designing the organisation to deal with such prolonged absences.

• Taking a sabbatical shouldn’t have an adverse effect on anyone’s career at a company.

I’ve been reflecting on my career recently, and I realise I’ve led a charmed existence thus far. I come from a rather average background, and when Thoughtworks hired me in 2007, I felt I’d lucked out. And in the first few months of my time in the company, I felt that I’d pushed my luck too far. There I was, a nobody in the company of some absolute legends. 

17 years on, and that impostor syndrome hasn’t gone away yet. I continue to meet people who intimidate me through their sheer intelligence and make me wonder if I even belong here. To a great extent that impostor syndrome keeps me alert. I can’t ever take anything for granted. It also helps me be grateful for the work-life I’ve had so far.

One of the important things I’ve been lucky with is to have found an employer where I could have a passion outside work. As I’ve admitted on this site, my work funds my true passion; which is to explore the great outdoors. One policy that’s helped me pursue this passion is Thoughtworks’ sabbatical policy. Thoughtworks offers a 3-month sabbatical when employees complete 10 years of service. After that, employees are eligible for 6 weeks of sabbatical leave for every 5 years of service they complete. Thoughtworks India also used to offer a one-month sabbatical after you completed your first four years of service. The company discontinued this policy for people who joined after 2011, but I was lucky to have joined in 2007, so I got that sabbatical too. Until now, I’ve been eligible for three such extended breaks. Amazing, right?

These sabbaticals have enriched my life in ways I could only have dreamed of. During my first sabbatical, I went on a big cat trail, covering many of India’s tiger reserves and its only lion sanctuary. On my second sabbatical, I visited the high Himalayas and toured Ladakh and Spiti Valley. I followed that up with a circuit around Africa. We drove around Namibia, experiencing the world’s tallest dunes, the Southern African coastline, the massive Etosha National Park and the darkest skies you can imagine. I visited my favourite place in the world - the Maasai Mara, for the great migration. We then tracked gorillas and chimpanzees in Uganda. I joined my best friend to explore Madagascar. And finally, I joined my then-girlfriend, now wife, to visit the Himalayan kingdom of Bhutan. My third sabbatical is coming up soon and it’ll be the first time I’ll spend an entire summer vacation with my family, touring Central India, Bali and Borneo, with no work strings attached. I can’t wait!

Sabbatical policies aren’t uncommon these days. I found a list of 70-odd companies that offer extended breaks from work. The venerable HBR recently published research in favour of such policies. I’m sure you noticed - I’m a big supporter of these policies. But I also think there are ways to do this right, which we don’t talk about often. After all, sabbaticals are usually rewards for long tenures. And long tenures are like rarefied air in the tech industry. Only a few people get the benefit of sabbaticals, so there isn’t much conversation about them. So let me share some of my reflections about them.

There’s a sweet spot where they make the most sense

As I mentioned earlier, sabbaticals are tenure-based. Here’s the deal with tenure-based rewards. Most people see them as a reward only if they can visualise a long enough tenure with the company. If it’s too far beyond the time horizons people can plan for, it’s not a realistic reward. If the company gives it away too early, it doesn’t serve the purpose of encouraging people to stay. 

This is where my luck makes a repeat appearance. You see, I got my first sabbatical after four years of service. But people who joined my employers four years after me weren’t as lucky. I haven’t verified this, but I can imagine that looking forward to a month’s extra leave after four years seems more realistic than looking forward to three months off after 10. The first time off seems like a proper reward, the latter is a fantasy. The sweet spot is somewhere in the middle. 

I don’t know if there’s a magic number of years that qualifies as a sweet spot though. It depends on the company you’re in. For example, big-tech companies have a rather short shelf-life for employees. The average tenure is less than two years for most of them. That’s in contrast to the industry average of four years. Sabbaticals make sense when they're longer than the median tenure at the company but not several years longer. In 2024, it feels like four to six years could be the right interval at which companies could give out sabbaticals. In my case, I get them every five years now, which feels OK. I could do with a shorter frequency, but I don’t mind five years either. But I envy 37Signals’ policy of a six-week sabbatical every three years. Boy, aren’t they spoiled!

The fewer strings attached, the better 

Imagine a company that gives you a 30-day sabbatical after four years of service. Pretty damn good, right? But then you examine the fine print. You notice that while you’re on sabbatical; you don’t accrue any of your other employment benefits. You find that taking a four-week sabbatical means that you also don’t accrue leaves during that time. This means that instead of 22 days off, you’ve only got 20 days off because the rest came from your unaccrued annual leave. It’s not horrid, but it doesn’t feel nice either.

And what about availing the leave? How easy is it? How many approvals do you need? Can your bosses exercise their discretion to disallow it, even if you give them sufficient notice? Difficulty in availing sabbaticals can sour the deal in a big way.

Most importantly, it helps to examine if the sabbatical seems like an entitlement or a favour. To be fair, if a company institutes such a policy, it should look at those days off as an entitlement. This means that if an employee eligible for a sabbatical leaves the company without taking the time off, they should be able to encash those leaves for a monetary equivalent. Of course, this could seem “too employee-centric” to accountants who run many firms. But I argue that there’s a lot of intangible value associated with a no-strings-attached, employee-centric sabbatical policy. Especially if you want the policy to encourage long tenures and to foster a positive sentiment towards the employer. 

The right examples matter

If your company or prospective employer has a sabbatical policy, it’s worth checking who recently took a sabbatical and what they did during that time. I mentioned 37signals earlier for their exceptional policy, but guess what? Jason Fried, one founder, didn’t take a sabbatical for 23 years! To his credit, he admitted, “It’s sort of embarrassing and irresponsible, frankly. I mean, for everybody. Like you gotta set a good example…”

And that’s the point. The people who’ll be eligible for a sabbatical are the people who see a long-term career in a company. These people will inevitably look up to leaders as role models. When leaders don’t take sabbaticals, or worse, take the sabbatical only to check into work every few days, they are sending a message about what the company expects other employees to do. Soon, not taking a sabbatical becomes a badge of honour.

The way a company implements its sabbatical policy is also important. Some teams and companies don’t design themselves for resilience. Certain people become indispensable to their day-to-day functioning. Invariably, it’s leaders and people with long tenures who fall into this position. So when these people become eligible for their sabbaticals, there’s no practical way for them to step away for extended leave. What happens next? Well, the sabbatical leave becomes a quasi-annual leave, that the individual takes in fits and bursts. But four one-week breaks are not the same as one four-week break, are they?

People with long tenures want the company to value them. When these people see “important” employees convert their sabbaticals to annual leave supplements, it’s natural for them to adopt the same behaviour. Before long, no one takes extended time off. The sabbatical loses its rejuvenating potential, and the company does nothing to build its resilience. 

Like with everything else, leaders must set the right examples. Regardless of how important they are, they must take their sabbaticals and tell their sabbatical stories loudly, so they set the right example. Plus, sabbaticals should be all-or-nothing. You either take the full duration or don’t take it at all. Every exception you make to split someone’s sabbatical justifies the next time someone asks for a similar arrangement. Encourage people to unplug from their jobs. It’s not enough to write up a policy. If a company believes in a sabbatical’s benefits, it must coach its employees to use this time off effectively.

By the way, “important people” can’t step away for a few weeks if there’s no slack in the system. This is a serious organisation and team design flaw. As DHH says,

“Regardless of what you do, if you are not replaceable for at least six months, something is not right. The organisation is actually misconfigured.”

Sabbaticals shouldn’t be career limiting

Last but not least, not all tech companies are the same. Some companies build products and have long-lived teams. Other companies build stuff for clients in teams that aren't as long-lived. Employees in this second type of company operate in an internal gig economy, moving from team to team during their tenure. In both kinds of companies, but more so with the second company, sabbaticals shouldn’t become career-limiting.

Imagine that you apply to take a sabbatical in a few months and your manager approves you to take that time off. But you also wrap up the gig you’re on, soon after getting the approval. The next thing you discover is that no team wants to take you on because you have a sabbatical planned. Welcome to professional pariah hood! 

A similar situation can occur when you’re on a small product team. What if you’re a soloist - the only QA, the only designer or the only product manager on this team? If you want to take a sabbatical will people think you’re leaving the team in the lurch? 

Some situations are easier to remedy than others, but the point I’m trying to make is that companies and teams that have a sabbatical policy must ensure that people don’t perceive an impact on their careers and status in the company when they take such extended time off. Such effects make the sabbatical policy feel disingenuous. The policy itself makes for great marketing, but the company seems to dis-incentivise extended time off. Why even have a sabbatical policy then?

In the universe of employment, companies that offer sabbaticals are still a minority. We must congratulate them for their initiative. That said, creating a sabbatical policy and reaping its benefits are two separate things. If being eligible for a sabbatical feels impossible, it’s not a motivator. Sabbaticals that come with fine print attached feel dodgy, even if they’re better than no sabbatical at all. When sabbaticals become difficult to avail, there’s little incentive to take them or even serve for as long as to be eligible for them. And most importantly, if key people avoid sabbaticals, then few others will feel comfortable taking such time off. 

If you’re considering a job offer from a company that offers a seductive sabbatical policy, I encourage you to study how they implement it. The benefit may not seem as attractive on closer inspection. Conversely, if you’re involved in crafting a sabbatical policy, consider how you can design it to reap the most benefit from it. Or if you own the sabbatical policy for your company, consider how effective it’s been thus far. Will your employees think of themselves as lucky to have such a benefit? I think that’s a fine scent test for most policies, isn’t it?