When planning your trip is a waste of time and other travel lessons

I’m excited to share the first of a series of guest posts I’m hosting about the lessons we learn from travelling. I know I have learnt a huge amount from all my trips over the years, but I wanted to get the perspective of a few other people, too! I’ve collected some wonderful stories and I look forward to sharing them with you over the next few months.

First up is a post from Kate Storm of Our Escape Clause, who began her travelling time as a very strict planner. Of course, there’s nothing wrong with planning a trip, but … well, I’ll let Kate tell the story.

Is planning your trip a waste of time and other lessons from travel

Is planning your trip a waste of time?

The first time I left the USA, I literally planned out everything.

The moment that Jeremy and I arrived at the airport for our flight to the Bahamas (exhausted and newly married – our wedding had been the previous night!), I knew exactly what hotel we would be staying at, where we would get food, what activities we would participate in, and how we would get around.

And, to ensure even further that I knew absolutely everything there was to know about my honeymoon before actually taking it, we booked this trip roughly six months in advance.

How did it go after all that careful over planning?

Pretty wonderfully, actually.

… As long as you ignore the fact that our flight was delayed three times, we weren’t sure how to fill out the customs paperwork (having never seen any before), our luggage was lost, and we at one point ended up with a drunk cab driver who treated us to a graphic monologue about her sexual exploits.

As it turns out, even an all-inclusive resort and months of planning can’t cushion you from misadventures on the road.

Now, I consistently look back on that trip and smile.

Not only because of the amazing snorkeling, or the tasty food, or how it felt to glimpse the Caribbean for the first time, or the romance of being on a honeymoon with the love of my life, and not even simply because this trip was the first domino in a sequence of events that led us from having never left the USA to being full-time travellers in less than 3 years.

Lessons from travel with Kate from Our Escape Clause

Kate and Jeremy of Our Escape Clause in Budapest

I smile because our taste of the Bahamas knocked me upside the head with a very serious travel lesson: plans are both important and useful, and also utterly worthless in the face of hang ups.

Stressing about things that go wrong, or simply change?

It gets you nowhere.

Now, the same girl who less than five years ago planned a 6-day trip with excruciating detail months before actually going on it regularly books trips to other countries on a whim and only does basic research ahead of time.

What used to cause me stress, now simply rolls off my shoulders: not sure when the bus is coming? We’ll wait. Plane delayed? We’ll get there eventually. Hotel is terrible? We’ll find another one. Not sure where to eat? Eh, I’m sure that place on the corner will work.

Travel has given me the gift of relaxation, and has caused my natural optimism to bleed over into planning most aspects of our travel–which today, makes up most aspects of our lives.

It has been a long time since I fretted over taxi rides instead of fearlessly negotiating the rate, or found traveling independently without a firm plan in place more intimidating than exhilarating.

Have I learned my trip planning lesson?

In many ways, that first trip outside the USA feels like yesterday. But in other ways, those days feel like a lifetime away.

Today, in between typing this post, I am perusing flights to two different continents, neither of which is the one I’m sitting on, that leave less than 3 weeks from today.

Trip planning and lessons from travel - climbing a volcano in Guatemala

Kate and Jeremy climbing a volcano in Guatemala (without meticulous planning required!)

I don’t know which one we’ll choose, exactly what date we’ll leave, or what we’ll need to pack.

And unlike planning my honeymoon five years ago, when I would have spent this time anxiously researching all of the things that could possibly go wrong, all I can think is: three weeks from today I’ll be exploring a brand new country– and that makes me feel so very free.

Ah yes! The ability to plan what you can and go with the flow for the rest is something that I learnt during my early travelling years and take for granted now – but it is such a valuable lesson that many people never learn! Thanks, Kate, for this great post, and I wish you many more years of that feeling of freedom.

If you’d like to read more from Kate, I love her post about getting bitten by the radioactive travel bug in Paris, and it’s a perfect read for people who are nervous about setting out on their travels. It reminded me of the podcast episode I did about first trips, where I learnt that many seasoned travels had wonky starts to their first steps into the world! Kate also has a great post about the “right” amount of time to spend in a destination … you can probably guess – there’s no one answer. 

Other lessons from travel:

As the series continues, I’ll add some other great lessons from travel here.



  1. This reminds me so much of myself. 🙂 Some countries take more planning than others, but I definitely went from micro-planning and micro-managing, and suffering the associated disappointment when all that planning goes for naught, to “whatever!” Your last sentence is spot-on.

    • Yes, I guess it’s pretty common to start relaxing about it the more travel you do – I went back to micro planning when I first started travelling with my son but it took much less time to get out of that habit again than the first time round!

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