Why Travel Is a Fun Job but a Brutal Business

You’re helping people escape their routines, reconnect with friends, see the Eiffel Tower, eat a pretzel on a train in Switzerland, take a picture with a llama in Peru. There’s emotional resonance, shared memory-making, and a vague sense that you’re not just slinging software but doing something more meaningful.

Which makes it all the more perplexing that travel, as a consumer tech category, has chewed up and spat out a long list of otherwise smart people.

It’s not that travel companies don’t make money – they do. Booking.com, Expedia, Airbnb: multi-billion-dollar platforms, all doing fine. But for anyone trying to innovate in the consumer layer – particularly around trip planning – the road is littered with the remains of great intentions and elegant slide decks.

So Much Interest, So Little Retention

The demand side is real. Travel is a $9 trillion global industry. Americans alone spent over $1.3 trillion on travel in 2023. But while that may sound massive, frequency is the killer.

The average American takes about 1.4 trips per year. Even generous numbers put it under three. That means your product – if it’s centered around pre-trip planning – is going to be used maybe a few times a year. Once, if you're lucky.

And usage frequency, it turns out, is destiny. Most consumer internet products that work at scale exhibit some kind of daily or at least weekly use case. Retention curves flatten around 20% daily usage for breakout consumer products. Trip planning? It's often sub-1%. People use it once, then forget it exists. Even if it was good.

Trip Planning as a Hobby… and a Trap

In theory, this is a fun UX problem. Everyone wants to travel. Everyone complains about how hard it is to coordinate dates, flights, hotels, and activities across friends, partners, or families. There are spreadsheets. There are long email threads. There is one poor “dictator” trying to get everyone to commit to a weekend and vote on which Airbnb to book.

In practice, the problem is overdetermined:

• Planning is not a daily activity.

• Most people like the planning itself – or at least certain parts. It's aspirational. A fantasy exercise.

• Others hate planning and just want someone else to do it.

• Group consensus is hard.

• Actual travel is deeply constrained (time, money, kids, visa rules, school schedules).

• And the moment you get even slightly outside the bounds of what a tool anticipated – it breaks. Computers are bad at ambiguity. Travel is full of ambiguity.

So the real issue isn’t that no one wants to solve travel planning. The issue is that they want different things, at different levels of fidelity, at different points in time. Some want control, some want magic. Some want spreadsheets, some want vibes. All of them are right, and the product needs to accommodate that.

Why People Keep Trying Anyway

Despite all this, people love building travel software. One of Yahoo’s best recruiting tricks was apparently letting new hires build Yahoo Trip Planner (*head nod to Garry Tan*) not because it was a good business, but because it was a great idea. Engineers and designers loved the problem. And then, a few months in, they were reassigned to something else.

This happens over and over. Because travel is one of the few product categories that everyone can relate to. It’s like dating apps or personal finance tools – the total addressable market is "everyone alive," the pain points are familiar, and the emotional upside feels huge. It’s fun to work on. It just doesn’t work very well as a business.

A Better Way to Think About It

The best-performing consumer travel products – Google Maps, Airbnb, TripIt, even Instagram – succeed not by organizing travel in advance, but by being useful during or around travel. Maps works because it’s great when you're actually in a city. Airbnb solves the accommodation problem. Instagram is what you use to share (or inspire) travel. These tools are not specific to trip planning, and they are used frequently enough outside of travel to stay top-of-mind.

The real opportunities lie adjacent to planning:

• Collaboration tools (like Splitwise, but integrated with calendars and payments)

• Discovery layers (Pinterest, but for real-world locations)

• Flexible logistics (tools that adapt to uncertainty: such as a GPT-powered concierge)

• Memory and content (journaling, trip recaps, photo maps)

The actual planning becomes a side effect – not the point.

The Most Fun You’ll Have Losing Money

The conclusion, unfortunately, is not that this is impossible. It’s that it’s hard. There are segments where travel works: B2B travel management, luxury travel agents, tour booking, influencer-driven itineraries. But for the general case – a slick, collaborative planning app that millions of people use to organize their trips – it’s an uphill battle.

Still, for a founder or a team looking to work on something beautiful and meaningful, it’s hard to beat travel. Just go in knowing that the product might be a joy to use, and a joy to build… but not necessarily a joy to monetize