The Annual Leave Conundrum

Annual Leave - Why It Matters More Than You Think (and Why It Can Feel So Hard to Use)

Let’s start with the obvious truth that often gets lost in the day-to-day grind: annual leave isn’t a benefit or a perk - it’s essential.

Time off plays a huge role in protecting your mental health, physical wellbeing and long-term ability to perform at work. Yet despite this, many people still struggle to take the leave they’re entitled to - not because they don’t want a holiday, but because finding the 'right time' in a busy schedule, fitting in around school holidays, working round workplace principles for staff numbers who can be off at any given time or the process around booking leave itself can feel…well... restrictive.

Sound familiar?

The policy paradox many employees face

Most annual leave policies are very clear on one thing: don’t book a holiday until your leave has been approved.

Perfectly reasonable from the side of the employer - they want to ensure they can do without you before you make firm decisions and commit money.

At the same time, many organisations will only allow you to request or book leave within the current leave year.

Also potentially reasonable - they don't know what workloads will look like further ahead but realistically this is more often than not a system thing, rather than a planning thing.

But put those two rules together and suddenly you’re in a strange grey area - especially if you’re the kind of person who likes to plan ahead, secure good prices or spread the cost of a trip.

On paper, the rules make sense.
In real life, they can quietly work against you.

The internal debate to tackle

If you’ve ever found yourself hesitating over making a booking, you’re not alone. Many employees end up wrestling with the same internal debate:

❓Do you book the holiday anyway and hope approval follows?

❓Do you book the holiday and try to force the hand of your company, saying you've already booked it?

❓Do you wait - even if that risks prices rise and availability disappearing?

None of these options feel ideal, and all of them add friction to something that’s supposed to support your wellbeing.

Is it fair that your company policies unintentionally stop you from benefiting from early booking deals or instalment plans?

Why this isn't just about holidays

This isn’t just about travel logistics — it’s about rest.

Research consistently shows that a large number of UK employees don’t use all their annual leave. By mid-year, around two-thirds of workers have taken less than half of their entitlement, and many finish the year with unused days. That matters, because when people don’t take regular breaks, levels of burnout, exhaustion and poor mental health rise noticeably.

On the flip side, employees who spread their leave across the year report feeling happier, less run-down and more productive. Not exactly a shocking result - but an important one.

And more interestingly, even when people do take time off, switching off can be surprisingly difficult. More than half of professionals admit to checking emails while on holiday, and many feel anxious about what they’ll return to. That constant mental connection to work limits the real benefits of time away.

This isn’t just a “you” problem

Not getting round to booking your next holiday sometimes feels like a personal failing - that you should be better at planning, better at switching off, better at advocating for your time.

But this isn’t just a you thing. It’s often a workplace culture issue.

Studies show that properly detaching from work during holidays helps reduce sickness absence, supports mental health and improves performance over time. When rest is delayed, rushed or disrupted, both employees and organisations pay the price.

It should be a no-brainer that when annual leave is treated as a productivity tool rather than an inconvenience, everyone benefits...but do cultural practices and booking policies bear this out?

So where does that leave you?

If you’ve ever felt caught between policy and practicality, you’re not alone - and you’re not wrong for finding it frustrating.

Wanting to be able to secure a price and have time to save towards a holiday makes sense. It allows you to financially plan, it allows you to book a better holiday, it gives you something to look forward to. 6-8 months in advance, used to be the sweet spot for booking holidays but for many options, especially escorted tours, cruises and longer haul destinations, that's no longer the case. The emerging ability to book packages with out of date range (ODR) flights, and suppliers offering guranteed prices for a year even two years in advance makes 6 months a late booking nowadays. Not having the ability to take advantage of this availability can be tough to swallow.

Raising these frustrations is worth doing, both within your organisation and at home. Starting the conversation about how annual leave policies and booking processes can become more congruent with managing wellbeing and alongside that, work hand in hand with modern travel planning and pricing, allowing you to benefit from truly rejuvenating experiences, quality time with family and friends and disconnection from work is important.

Because people who rest well don’t just feel better - they do better work - so shouldn't it be easier?

If you'd like to have a chat about your next holiday, you can contact me via WhatsApp on 07726286903, email me at [email protected] or book a time to chat via my calendar HERE.

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