A Lifetime of Hope and Regret

A black and white photo of a man walking alone on a beach
Posted: 2/12/18 | February 12th, 2018

It’s easy to get lost. To look around and suddenly find yourself wondering how you got here — and why it seems so far from where you thought you’d be. What wrong turn did you take? Is there still time to go back and start again? To be the person you wanted to be? To do the things you want to do?

One day becomes a year, which quickly turns into a decade. Before you know it, you’re miles from the life you imagined.

“Tomorrow,” you say to yourself. “Tomorrow, I’ll fix things.”

But tomorrow comes and goes and you continue down the same path, caught up in the surging river that is life.

Reading entries for my round-the-world trip contest brought regret to the forefront of my mind. I saw so much of it from the strangers who entered; strangers who poured their heart out to me about loss, pain, suffering, snuffed-out dreams, and second chances.

Yet beneath all the worry, regret, and sadness, there was hope.

The desire for a new beginning. A chance to be the person they wanted to be; to find purpose in their life; to escape a future they didn’t want — but one that felt so inevitable.

As writer and blogger Cory Doctorow said, “You live your own blooper reel and experience everyone else’s highlight reel.”

When you ask people why they want to travel the world, and 2,000 people come back with stories that all end with a version of “to start fresh,” it brings this obvious but forgotten realization back into your mind.

My own life is a minefield of regret — both big and small: Regret at not traveling sooner, partying too much, never becoming fluent in a foreign language, never studying abroad, letting a certain relationship slip away, not staying in touch with friends, not saving more, not moving slower, and not following my gut.

Then there are the day-to-day regrets — things like not closing my computer 30 minutes earlier or reading more or laying off those french fries more. There are countless regrets.

In thinking about our own issues, we often forget that everyone around us is fighting their own inner battles. That the grass is never truly greener.

That when someone is snappy at you in the grocery store, short with you at the office, or sends you a nasty, trolling email, they, like you, are dealing with their own inner demons.

They, like you, think of second chances, missed opportunity, and unfulfilled dreams.

We’re taught by society to avoid “a lifetime of regret.” “Have no regrets!” is our mantra. But I think regret is a powerful motivator. It is a teacher, a manual to a better life.

Regret teaches us where we went wrong and what mistakes to avoid again.

Reading these entries initially weighed me down. I couldn’t help but think, “There’s a lot of unhappy people out there.”

But, the more I thought about it, the more I realized they weren’t unhappy.

Yes, there was regret, pain, and sadness in those contest entries — but there was also a lot of hope, determination, and energy. These entrants were not going to wallow in regret. They were looking for a way to move forward. They felt inspired, motivated. Many promised that no matter the outcome of their entry, they were determined to make a change.

Two thousand people said, “Not again!”

A “lifetime of regret” means you actually have lived.

Regret, it turns out, is life’s best motivator.

Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

Want to Travel for Free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.

Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.