Omoiyari for Travel Entrepreneurs: The Power of Deep Empathy in Your Business

More Than “Great Customer Service”

Every travel advisor says they offer “great customer service.”

It’s on websites. It’s in bios. It’s in pitches.

But clients don’t stay loyal because you answered the phone and did your job. They stay loyal because, at some point, they felt:

“This person really sees me.”

They felt:

• Understood
• Anticipated
• Cared for beyond the transaction

That’s not just customer service. That’s Omoiyari.

What Is Omoiyari?

Omoiyari (思いやり) is a Japanese concept that goes beyond simple empathy.

It’s:

• Deep consideration for others
• Anticipating needs before they’re spoken
• Acting in ways that reduce burden, stress, or discomfort for someone else

It’s the quiet thoughtfulness that says:

“How can I make this easier, kinder, and more human for you—without you having to ask?”

In a travel business, Omoiyari is the difference between:

• “I booked what you asked for,” and
• “I understood what you meant and designed something that truly fits your life.”

Why Omoiyari Is a Superpower in Travel

Travel is emotional.

Your clients come to you with:

• Dreams
• Fears
• Insecurities
• Money they worked hard for
• Time they can’t get back

They might say:

• “We just want a beach.”
• “We just want something special.”
• “We just want it to be easy.”

But underneath that, they might really be saying:

• “We’re exhausted and need to feel like ourselves again.”
• “We’re celebrating something big and we’re scared it won’t feel special enough.”
• “We’re overwhelmed and don’t want to feel stupid or taken advantage of.”

Omoiyari helps you hear that layer—and respond to it.

When you practice Omoiyari, you’re not just selling trips.
You’re stewarding people’s emotional lives.

Omoiyari in a Travel Business: Real Examples

Example 1: The Anxious First-Time Traveler

A client reaches out for their first international trip. On paper, it’s simple:

• Flights
• Hotel
• A few activities

But you notice:

• Their questions are very detailed.
• They apologize a lot for “not knowing how this works.”
• They mention being “nervous flyers.”

You could just answer their questions and send the proposal.

Or you could practice Omoiyari:

• You create a simple “What to Expect” one-pager just for them.
• You build in extra connection time on arrival day so they don’t feel rushed.
• You proactively share a few tips about the airport, transfers, and cultural basics.
• You reassure them that their questions are normal and welcome.

They don’t just remember the trip.
They remember how you made them feel safer and less alone.

Example 2: The Overwhelmed Parent

A busy parent wants a family vacation. They say:

• “We just want the kids to have fun.”
• “We don’t have time to plan anything.”

You could send a standard family package.

Or, with Omoiyari, you might:

• Ask one extra question: “How do you want to feel on this trip?”
• Notice the pause when they say, “Honestly? Rested. Reconnected. Like we’re not just managing chaos in a new location.”
• Design the trip with built-in downtime, childcare options, and one special moment just for the parents.
• Provide a simple “Here’s how to talk to your kids about the trip” note to reduce their pre-trip stress.

You didn’t just book a vacation.
You created space for a family to breathe.

The Difference Between Omoiyari and People-Pleasing

Important: Omoiyari is not:

• Saying yes to everything
• Overgiving until you burn out
• Letting clients walk all over your boundaries

Omoiyari is:

• Seeing people clearly
• Caring about their experience
• Designing your processes and communication with their humanity in mind

You can practice Omoiyari and still:

• Charge planning fees
• Enforce policies
• Say no to misaligned requests

In fact, clear boundaries are part of Omoiyari—they protect both you and your clients from chaos.

Practicing Omoiyari in Your Travel Business

Here are some practical ways to live Omoiyari, starting now.

1. Ask Better Questions Up Front

Instead of just:

• “Where do you want to go?”
• “What’s your budget?”

Add questions like:

• “Why this trip, and why now?”
• “How do you want to feel on this trip?”
• “What are you worried about when it comes to travel?”
• “What would make this feel like a win for you?”

Omoiyari starts with understanding the human, not just the itinerary.

2. Anticipate the Stress Points

Think through your client journey and ask:

• “Where do people usually get confused?”
• “Where do they tend to feel nervous?”
• “Where do they drop the ball because life is busy?”

Then build in Omoiyari:

• Clearer pre-trip instructions
• Timely reminders
• Simple checklists
• Short videos or voice notes explaining key steps

You’re not adding fluff. You’re removing friction.

3. Design for Emotional Safety

Emotional safety might look like:

• Normalizing questions: “There are no silly questions here. If you’re wondering, I want to know.”
• Being transparent about what you know and don’t know.
• Owning mistakes quickly and clearly if something goes wrong.
• Giving clients a safe way to share concerns or feedback.

When people feel emotionally safe with you, they:

• Tell you the truth
• Ask for what they really need
• Come back again and again

4. Remember the Whole Person

Your client is not just “a booking.”

They are:

• A parent
• A partner
• A caregiver
• A business owner
• Someone who’s been through things you may never know about

Omoiyari might look like:

• Checking in on a client who mentioned a tough season, even when there’s no trip on the books.
• Sending a small note on an anniversary or meaningful date you know about.
• Being gracious when life delays their decisions.

You’re not trying to be their therapist. You’re just choosing to be human.

The Business Case for Omoiyari

Let’s be clear: Omoiyari is not just “nice.” It’s strategic.

When you practice deep empathy:

• Your referrals increase—because people talk about how you made them feel. You are remarkable—literally, worth remarking about.
• Your retention improves—because clients don’t want to start over with someone who doesn’t know them.
• Your marketing gets sharper—because you understand your people at a deeper level than “they like travel.”

In a world where so much can be automated, Omoiyari is what can’t be copied.

Anyone can send an itinerary.
Not everyone can make a client feel truly seen.

That’s what makes you remarkable—and that’s what fuels real word of mouth.

You Are Allowed to Care This Much

If you’ve ever been told you’re “too sensitive” or “too emotional” for business, let me flip that for you:

Your capacity for empathy is not a liability.
It’s one of your greatest assets.

Omoiyari doesn’t mean you carry everyone’s burdens.
It means you design your business with real humans in mind—including yourself.

You are a Phenomenal Force not just because of what you know, but because of how deeply you care.

Lean into that.

Your Next Step with Omoiyari

Take a moment and ask yourself:

1. Where in my current client journey do people most often feel confused, anxious, or overwhelmed?
2. What is one small act of Omoiyari I could add this week to ease that experience?

Maybe it’s:

• A clearer welcome email
• A short “what to expect next” video
• One extra question in your consultation form
• A simple check-in message before departure

Pick one. Implement it. Watch what happens.

You don’t have to overhaul everything to practice Omoiyari.
You just have to start caring out loud in one more place.

I’d love to hear from you:

What’s one moment in your client experience where you know people feel stressed, confused, or vulnerable—and what’s one way you could ease that with a little more Omoiyari?

Share your idea in the comments below. Your small act of empathy might spark something powerful for another travel entrepreneur reading along.