Don’t Wait for the Right Time: How Loss Taught Us to Travel Now

There’s a saying that goes, “Tomorrow is never promised.” We all know it, but how often do we actually live by it? We put off experiences, waiting for the “right time” to travel, to chase dreams, or to make memories. But life has a way of reminding us that time isn’t guaranteed.

For Jake and me, that wake-up call came in 2021 when his dad passed away from COVID. It was sudden. It was heartbreaking. And it changed everything.

We had always loved travel. We had taken amazing trips together before, but like so many people, COVID put everything on hold. It had been a few years since we had traveled anywhere significant, and even as the world started opening up, we kept delaying it—waiting for a better time, when life felt more settled. But losing Jake’s dad made us realize that waiting wasn’t an option anymore. If we kept putting it off, we might never go.

So in 2022, we made a choice: We were going to start living our lives now—not later.

Losing Jake’s dad was devastating. They had so many plans—talks of future dirt biking trips, adventures they were saving for “someday.” But that someday never came. The realization that they would never get to take those rides together, never share those moments they had always envisioned, was heartbreaking. It made us stop and question everything—why were we waiting to do the things we dreamed about? We had always assumed there would be more time, but suddenly, we understood just how fragile and unpredictable life really is.

For years, we had talked about traveling, about seeing the world together. But there was always a reason to wait—work schedules, finances, responsibilities. And then, the pandemic happened. It took away years that we thought we would have for adventure and put everything on hold.

Even in 2022, traveling still wasn’t easy. COVID was still lingering, restrictions were constantly changing, and we had to be more careful. But instead of letting that stop us, we adapted. We took extra precautions, followed health guidelines, and made adjustments as needed. It wasn’t always convenient, but it was absolutely worth it. The joy of experiencing new places and making those memories far outweighed any of the challenges.

Instead of pushing travel to “someday,” we booked the flights and went.

That year, we explored Egypt and Italy, two bucket-list destinations that had felt out of reach before. We stood in awe before the pyramids, sailed the Nile, and walked through ancient temples that had stood for thousands of years. In Italy, we indulged in pasta, strolled through Rome’s historic streets, and soaked in the coastal beauty of the Amalfi Coast.

And in a moment of personal adventure, I visited Paris alone to see a dear friend—something I might have hesitated to do before, but now felt like an essential part of my journey.

But it wasn’t just about big international trips. We also made time for small trips to visit family, prioritizing connections that felt more important than ever.

Then in 2023, we continued that mindset, making family visits a priority. We traveled to Pennsylvania to visit my grandparents, spending time with them while we still had the opportunity. And in a long-awaited adventure, Jake, my brother James, and I finally made our dream trip to New York City—something James and I had talked about for years but had never made happen. That trip, the three of us exploring the city together, was one of the most memorable experiences of the year.

How We Made Travel Happen Despite Busy Schedules & Budgets

One of the biggest myths about travel is that it requires unlimited time and money. The truth is, we made these trips happen by being strategic—with points, PTO, and smart planning.

✈️ We used points and miles to cover flights whenever possible. For our big 2022 trip, we used a combination of Alaska Airlines miles and Capital One points to bring down our flight costs significantly. Earning points through everyday spending on credit cards made a huge difference, and I highly recommend learning the basics of travel hackingif you want to travel more often without breaking the bank.

📅 We planned travel around weekends and holidays to maximize PTO. Instead of taking long stretches off, we scheduled trips around existing long weekends and took just a few extra days off. For example, we used Thanksgiving weekend to visit family in Pennsylvania, allowing us to take fewer PTO days while still getting a meaningful trip.

🏨 We stayed in budget-friendly accommodations when needed. In New York City, we opted for an Airbnb instead of an expensive hotel, splitting costs between the three of us. In Italy, we stayed in a mix of hotels and guesthouses, prioritizing experience over luxury.

🚆 We used trains and buses to save money on transit. In Italy, taking trains instead of flights between cities helped cut costs, and in New York, we relied entirely on public transport.

These small decisions made travel possible without sacrificing our long-term financial goals. If you want to travel more, don’t wait for unlimited time and money—start planning smarter.

Your Kids Are Only This Age Once—Your Parents Are Only This Young Once

One of the biggest realizations we had was that time doesn’t wait for us.

Our kids only get one childhood. Our parents only have so many years of good health. The people we love won’t always be here.

So why wait to make those memories?

If there’s something you’ve been putting off—a trip, a goal, a dream—this is your reminder to stop waiting.

You don’t have to travel across the world. Start small. Prioritize experiences over “someday” plans. Make the effort to visit family, take the road trip, or explore a new place nearby.

Because in the end, the only thing we regret is the time we didn’t use well.

Final Thoughts

Jake’s dad’s passing was a heartbreaking reminder that time is our most valuable resource. We can’t get it back, and we don’t know how much we have. But what we can do is use it wisely, invest in experiences, and create memories with the people we love.

So take the trip. Chase the dream. Live fully—because tomorrow is never promised, but today is yours.