Why a journey of a thousand miles begins with a dream

Nick Lockey
5 min readMar 1, 2021

The battle for your hard-earned holiday money has never been more fierce. The winners are going to be the brands that help you dream big and plan smart.

[Originally published on 06/12/2018 on the 383 blog https://383project.com/blog/why-a-journey-of-a-thousand-miles-begins-with-a-dream/]

Photo by Simon Migaj on Unsplash

The first frosty beer in that secret beach bar; the feeling of sand between your toes; that shimmering sunset above a rugged mountain peak; all these perfect moments exist in your mind long before you reach for your passport — or at least they should if your travel booking site is doing things right.

In an age where friction-free eCommerce has become the norm rather than the exception, customers have come to expect nothing less than a fantastic travel booking experience. From buying a flight or choosing a hire car to booking a hotel room or arranging a tour, anything less than Amazon-level perfection just won’t cut it. Any travel brand failing to nail the basics is simply going to struggle to compete.

So, in a world where amazing, joyful shopping experiences are a given, where can travel and leisure brands really make their mark? The answer lies further up the funnel.

The five phases

From our work with clients within the travel sector over the last few years, we separate the end-to-end holiday booking journey into five key phases. As defined by Google’s insights team, these are: Dreaming, Planning, Booking, Experiencing and Sharing.

These represent all the typical steps a user would go through from choosing a destination and finding the activities they want to engage with, to booking their trip, jetting off and documenting what they’ve experienced.

From the products we’ve built and the trends we’ve been observing, we firmly believe the biggest opportunities lie in the ‘Dreaming and Planning’ space at the start of the booking journey. This is the part where we must first inspire our customers with all of the amazing things they can do on their trip before helping them to turn those dreams into a concrete reality. This is by no means a simple task as these two parts of the journey are, in essence, completely antagonistic.

Dream a little dream

In the Dreaming phase, our goal is to grab the user’s attention by stimulating both their senses and their imagination. We need to open their eyes to a world of possibilities that lie before them and help them to project themselves into those experiences. Whether it’s hedonism or relaxation, culture or adventure, our job is to transport would-be travellers out of their day-to-day lives and into a vision of what their perfect trip could be.

Photo by Drew Dau on Unsplash

This stage is all about emotion, curiosity and empathy.

It should be rich with tantalising content that brings these worlds to life and makes you long to be part of them: eye-popping images, evocative videos, gripping stories that spring from the screen. Ideally, these should be told from both the everyman and the expert perspective, mixing insider secrets with the experiences and testimonies of other travellers just like you.

The key to a great Dreaming experience is to not ask too much much of the user in terms of interaction or input. Instead, we should simply provide compelling, easily navigable content that makes it easy to discover new ideas and connect the dots between them.

Bringing the plan together

Next comes the tricky bit: How do we help our customer turn these ethereal, idealised travel plans into actual, bookable experiences? How do we turn the fun into functional?

The Planning phase is actually all about compromise. It’s where our flights of fantasy are grounded by the cold hard reality of travel schedules, budgets, airport transfers and shared itineraries.

This is often the bit where your globe-trotting dreams of adventure get curtailed by your paltry two weeks of annual leave, your meagre holiday savings and the fact that that you’ll have to spend 8 hours in some backwater airport waiting for a connecting flight to paradise.

But this process doesn’t have to be a downer. A great Planning experience can be as exciting and satisfying as the dreaming part, if it’s executed properly. There is immense satisfaction to be found in distilling all of the myriad possibilities for your trip into the absolute must-do elements, especially when you feel like you’re wringing every drop of value from it. This can be amplified even further when you feel like you’re creating something perfectly tailored to you — a unique travel experience that’s a world away from the cookie-cutter package deals that anyone could buy on the high street.

Photo by Simon Migaj on Unsplash

Unlike the giddy rush of the Dreaming phase, Planning requires thought, focus and structure.

This necessitates simple and effective tools such as itinerary builders, trip comparisons and budget planners that help users to craft a trip that suits both their desires and their constraints. Best-in-class experiences also add in a social layer here, enabling co-travellers to create shared travel plans or to curate ideas together.

The customer expectations in this phase are very different too. Where the Dreaming phase is ethereal, emotive and full of ‘what ifs’, nobody wants their travel plans to be ambiguous. This is the point where you need to emerge with your i’s dotted, your t’s crossed and all of the need-to-know questions definitively answered. You should be ready, willing and able to hit that ‘book now’ button with full confidence in what you’re going to get.

Knowing how to build the right Dreaming and Planning experiences and then how to navigate customers between them requires a thorough understanding of what your users are trying to achieve.

By interrogating the ‘jobs’ they’re trying to fulfil through the trips they plan and by understanding the frictions they typically encounter along the way, you can begin to build a truly inspirational holiday booking experience.

The real challenge for travel operators is in marrying up these two very different parts of the experience. How do you take the infinite possibilities of the Dreaming process and channel them into a Planning experience that shapes the best possible trip for your users? This task is difficult but by no means impossible. Get it right and you’ll be surprising and delighting your customers long before they get those well-earned holiday cocktails in their hands.

Originally published at https://383project.com.

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Nick Lockey

I’m a digital creative with a passion for product strategy and UX research. 👋