PTO Approved - Managing Travel And Your Career

This year was eye-opening when it came to job stability—and what I thought living life to the fullest really meant. Big trips out of the country every other month. Even bigger boats. I had reached a full-blown flow state. I was making moves in my career while managing my time and income well enough to travel luxuriously with my friends.

And then I lost my job.

Suddenly, I had to get creative about how I experienced the world—and sometimes, that meant missing out. In this article, I’m explaining how I managed to do both: build a career and travel, and how to gracefully decline an invitation that feels almost impossible to say no to.

When it comes to planning trips, I genuinely believe the best time to start is the moment the idea pops into your head. If you’re sitting around with friends on Thanksgiving, daydreaming about how fun Cabo would be for the Fourth of July—hop on it immediately. For me, that usually looks like pulling out my phone on the subway ride home or opening a few tabs during a lunch break between work.

Start monitoring what’s available, how much it will cost, who can realistically come, and when it would make sense to lock things in. This gives you time to solidify the guest list and, ideally, have most things paid for before you even step foot in the airport—all without disrupting your daily routine or financial flow.

Figuring out the guest list will almost always be the hardest part. Life happens, and plans can change quickly. When inviting people, transparency is key. Have a destination picked, along with a few accommodation options for people to look through. If the goal is to split costs evenly, planning around a set number of people makes everything easier.

Not everyone will be able to make it, so inviting slightly more people than you expect can help stabilize the financial side of the trip. Think of it as insurance. If everyone ends up coming, even better—the more, the merrier. Be thoughtful during this process, but don’t overcomplicate it.

With that being said, some people live to work, and others work to live. If you’re passionate about your job or your pursuit but also want to enjoy the fruits of your labor, time management and communication become everything.

If you’ve just started a new job or are working toward becoming your own boss, travel might not be your top priority—and that’s okay. It’s important to communicate that and accept that you’ll miss out sometimes. One of the hardest lessons I learned in 2025 was patience. The world will still be there.

Social media makes it feel like your peers are living the dream 24/7. Comparison really is the thief of joy. Instead, focus on aspiring toward something similar at your own pace—when it actually makes sense for you and your career. A friend once reframed it for me: life moves in seasons—seasons of building, seasons of coasting, and seasons of exploring. Not every season is meant for luxury travel, and that doesn’t mean you’re doing anything wrong.

On the other end of this, being understanding when someone declines an invitation you really wanted them on is just as important. Everyone is balancing something you might not see.

Working nonstop can easily lead to burnout, which is why taking time off is crucial if you want to keep loving what you do. Now for the fun part: when to actually use your PTO.

Stacking your days off around holidays can stretch your time away from work, though holiday travel itself can be expensive. Personally, January through July offers the best balance. You can take advantage of built-in holidays without paying peak prices. New Year’s, MLK Day, Presidents Day, Good Friday, Memorial Day, Juneteenth, and the Fourth of July are all great opportunities to travel somewhere warm without draining your vacation days—or your bank account.

Holidays like Labor Day, Thanksgiving, and Christmas tend to come with premium prices. For example, using April 2–7 allows you to take just three PTO days and still enjoy a full week off thanks to Good Friday. It’s also an easier sell to friends, since many of them will already have that day off.

Of course, luxury looks different in different seasons of life. Sometimes it’s a villa abroad, and other times it’s a long weekend somewhere close that still feels like a reset. Both count. The key is being honest with yourself—and your friends—about what you can commit to without stretching yourself too thin.

That honesty also makes declining invitations easier. A simple, genuine response like “I want to be there so badly, but it’s just not the right time for me” goes a long way. You don’t owe anyone a detailed explanation. Protecting your peace, your finances, and your career is reason enough.

Working and traveling are both important parts of life, but finding the balance between the two is where the real reward is. It’s rarely about choosing one over the other—it’s about timing, planning, and going with the right people.