Planning ahead feels like the responsible thing to do. But after leaving the UK, Ben and Claire discovered that too much planning was quietly limiting the freedom they’d set out to create.

Why We Planned Everything Before We Left

Before we left the UK, Claire planned the first ten to twelve weeks of this trip in real detail, where we’d be, roughly what accommodation would cost, which areas we’d stay in. She’s the more organised, structured one of the two of us; Ben is more free-spirited, more comfortable living in the moment. That planning was hers to need, and neither of us regrets doing it. It gave her something solid to hold onto in the run-up to a decision that otherwise felt enormous.

We assumed, going in, that having things booked was the same thing as having security. It’s a fairly natural assumption, most of us are taught that planning ahead is simply the responsible way to do things, whatever the context. We carried that belief straight into this trip without ever really questioning it.

Where the assumption started to crack

Once we were actually moving, the plan didn’t hold up the way we expected. We’ve changed and cancelled flights. We’ve altered bookings more times than we can count. Slowly, that pattern led us to a decision we hadn’t anticipated making: we stopped booking anything beyond the end of our time in each location..

The clearest example of why is Montenegro. We’d booked a week there in advance, and when we arrived, it just didn’t feel right, the location wasn’t what we’d normally choose, it didn’t align with how we usually like to stay somewhere. Because we’d already committed to a full week, we stayed the full week. If we hadn’t pre-booked it, we’d almost certainly have moved on within a couple of days.

What we actually learned

Having things booked too far in advance doesn’t protect you from changing your mind, it just removes your ability to act on it. You might arrive somewhere and fall in love with it, and want to stay five nights instead of the two you’d planned. Or you might arrive and know within a day that it’s time to move on. Advance bookings answer a question you haven’t been asked yet. Real life often gives you a different question altogether.

Since buying a car in Albania, we’ve had the freedom to make these calls in real time, and it’s changed the entire feel of the trip. We can pull into a location and simply decide, based on how it actually feels to be there, rather than how we imagined it would feel from a screen months earlier.

The bigger, more useful question

We think this is one of those inherited assumptions worth naming out loud: the idea that planning ahead is automatically the safer, more responsible choice. For a family living a fairly settled, conventional life, that’s probably true. But the moment your life is built around flexibility, forward planning can quietly become the thing working against you.

We’re not suggesting nobody should plan. The first month of structure mattered to us, and it’s not nothing to walk into the unknown without any shape at all. But we’d encourage any family considering something like this to ask, honestly: is this plan giving me security, or is it just giving me the feeling of security, while quietly taking away my ability to change my mind?

What else is possible, when you stop assuming that planning ahead and being safe are always the same thing?

Related reading: Beyond the Postcard: The Weeks Nobody Documents · The Stranger Who Helped Us Buy a Car in Albania · The Cost of Different: What We Actually Gave Up

Frequently Asked Questions

How far ahead should you plan long-term travel?

We found planning our first month gave us confidence to leave the UK, but after that we became much more flexible as our travel style evolved.

Is it better to book accommodation in advance?

It depends on how you like to travel. We discovered that booking too far ahead often made it harder to change our plans when somewhere felt different to what we’d expected.

Why did you stop planning so far ahead?

As we travelled, we realised flexibility had become more valuable than certainty. We wanted to make decisions based on our real experience of a place rather than assumptions made months earlier.

Has travelling by car made a difference?

Yes. Buying a car has given us the freedom to extend our stay somewhere we love or leave sooner if a place isn’t right for our family.

Would you still recommend planning before you leave?

Absolutely. Planning our first few weeks gave us a reassuring structure. We’d simply avoid feeling the need to plan every step of the journey months in advance.