The Trips I Almost Never Took: Why You Shouldn’t Wait for the ‘Right Time’

Suppose you’ve spent time on social media lately. In that case, you’ve probably seen the viral photo of the elderly couple in Venice—cruising down the canal in a beautiful gondola, but completely asleep. It’s a heartbreaking image that teaches an important lesson: You can’t wait to take the trip.

For years, they likely dreamed of this moment. Maybe they talked about going to Italy when they retired, when they saved enough money when the kids moved out when work slowed down. But by the time they finally got there, their bodies were too tired to truly experience it. The excitement, the energy, the adventure—it had passed them by.

This picture hit home for me. It made me think of when I almost didn’t take the trip. The excuses I made, the reasons I gave myself for waiting until it was a “better time.” And it made me realize how grateful I am that, at some point, I stopped waiting.

Growing Up With ‘One Trip a Year’

Travel wasn’t something I took for granted as a kid. My dad took us on vacations every year, but they were always the same: Panama City Beach (probably 25 times), Branson, Missouri (hello, Silver Dollar City), Eureka Springs, and the occasional big trip like Hawaii. We would count down the days for months, anticipating that one vacation, because that’s just how it was—you worked all year, and then you took your trip.

And that mindset stuck with me for a long time. I thought you had to wait for the right time, for everything to align just perfectly. But what I’ve learned in my adult life—especially after losing my mom—is that if you keep waiting for the “right time,” you’ll blink, and it’ll be too late.

The First Trip That Changed It All

A few years before my mom passed, I made a decision that changed everything. I took her to Mexico.

I remember splurging on that trip—it felt like a massive financial decision at the time. I spent $1,300 per person, which was a huge deal for me then. I was brand new in real estate, still bartending one day a week at Redrock Canyon Grill to make ends meet, and only had a few thousand dollars in the bank. But I did it anyway. I surprised her with a trip to Riviera Maya, and it ended up being the best experience of our lives.

Since then, I’ve been back to Mexico probably 8 or 9 times. But more importantly, that trip ignited something in me—a passion for travel that has taken me all over the world.

Travel Became My Healing & My Joy

After my mom passed away, I knew I needed to get away. Just five days after her funeral, I booked a trip to Costa Rica with my boyfriend at the time. We found cheap flights and an affordable resort, and for the first time, I planned something just for me.

That trip was a reset. A time to heal, to reflect, to step into this new chapter of life without my mom. And from that point on, I never stopped traveling.

Since 2015, I’ve traveled to:
✈️ Iceland
✈️ Ireland
✈️ London
✈️ Bora Bora
✈️ The Caribbean Islands
✈️ The Virgin Islands
✈️ Countless places across the United States

And what I’ve learned is that travel isn’t just about seeing new places—it changes you.

In America, we’re trained to work, work, work. To keep up with the Joneses. To chase the next big purchase, the newest car, and the latest trend. But when you travel, especially to other countries, you realize… none of that matters.

You slow down. You learn patience. You wake up excited to explore rather than just get through the day. You start looking at the world with new eyes. And for me, travel became more than just vacations—it became my joy.

Work Hard, Play Hard—Traveling While Running a Business

One of the biggest misconceptions about travel is that you have to put your life on pause to do it. That couldn’t be further from the truth.

There was one year where I traveled a whopping 19 times—all while maintaining my real estate business. The best part? Most people had no idea I was even gone.

I learned how to work from anywhere, how to stay connected, and how to balance hustling hard with living fully. I was taking calls from tropical beaches, answering emails between excursions, and negotiating deals while sitting in an airport lounge.

It was the best of both worlds. So, if you’re waiting for the “perfect time” to travel because you’re busy with work—let me tell you, you can do both. You don’t have to sacrifice success to see the world. I’d argue that traveling actually helps you succeed. It gives you fresh perspectives, new energy, and a level of motivation that sitting in an office all day just can’t give you

The Art of Planning the Perfect Trip

Now that I’ve traveled so much, I’ve also become that person in my friend group—the one who does all the research. My friends love to just “show up,” and I love making sure that every dollar we spend is worth it.

A lot of people think planning a trip is overwhelming, but for me, it’s part of the fun.

Here’s how I do it:

1️⃣ Make a List of Dream Destination

• Write down all the places you want to go.
• Rank them by priority—where do you really want to go first?

2️⃣ Book in Advance

• You’ll get better prices and better choices.
• Waiting last minute means you get the leftovers.

3️⃣ Use Trusted Travel Sites

• My favorites: TripAdvisor, Expedia, Wikitravel, Viator, and Pinterest for travel blogs.
• Read reviews. Check multiple sources. Make sure it’s worth your money.

4️⃣ Take Notes & Compare Options

• I use Google Sheets & Notes on my phone to track everything.
• I compare hotels, excursions, and flight prices before booking.

5️⃣ Balance Planning with Spontaneity

• I love having a plan, but I also leave room for adventure.
• Some of the best moments happen when you just go with the flow.

Stop Waiting—Take the Trip

If there’s one thing I hope you take away from this, it’s this: Stop waiting for the “perfect time” to travel. It will never come.

Life is unpredictable. One day you’re healthy, the next day you’re sitting in a doctor’s office getting news that flips your world upside down.

Take the trip.

If you have kids, show them the world while they’re young.
If you have parents, take them somewhere while they can still enjoy it.
If you have dreams of seeing new places, go now.

You don’t want to be the couple in that gondola in Venice, finally making it to your dream destination, but too exhausted to enjoy it.

I’m grateful I took that trip with my mom. I’m grateful I didn’t wait until it was “more convenient.” Because if I had, we never would have gone.

So, where’s your dream destination? What’s stopping you from going? Let’s change that. Let’s make it happen.

Because time isn’t promised—but adventure is waiting.

Love,

Tiffany