7 ways to fit more travel into your busy life + career

Work is one of the biggest obstacles that keeps people from traveling, especially in the U.S. Here, two weeks of paid vacation is considered the norm - if we’re lucky enough to be in the kind of salaried, full-time positions that offer any vacation at all.

So, if we want to fulfill our dreams of seeing the world, we have to get a little creative.

Here are some ways I’ve been able to fit more travel days into my life, demanding career and all:


1. Negotiate for more vacation time before you take the job.

Being recruited for a new job? Lucky you! But remember: this is your moment to negotiate for what you really want, and that includes vacation time. 

Now, I have found that most negotiation happens before an offer is even made - before the topic of salary is even discussed. However, I wouldn’t mention vacation time until an actual job offer is in hand. You don’t want to give the impression that you’re overly concerned about time off. 

Once you have an offer, though, don’t be afraid to push back on the vacation time if it’s not enough for you. They’ve already spent time and resources recruiting you, and if you have an offer, it means they really want you. They don’t want to lose you over something as trivial as paid time off. 

In some cases, you can begin by asking for more pay. If they push back, you can ask for an extra week of vacation instead. In most cases, that’s going to be an easier yes than more money.


2. Take unpaid leave.

If you’re unable to get more vacation time out of an employer, consider taking unpaid time off. Most companies will have no problem with this arrangement, for obvious reasons, assuming it’s not for an extended period. 

If you tried the negotiation advice above but your potential new employer has a very strict vacation policy, with no exceptions for anyone, taking higher pay with the understanding that you’ll have to eat some of that in unpaid time off is another strategy to consider.

Before taking a job at a big advertising agency, I attempted to negotiate for three weeks of vacation, because I’d had that at my previous employer. But rules were rules, and there were a lot of them at this particular agency. After it became clear they weren’t budging, I asked about unpaid time, and they said this wouldn’t be an issue.

It’s not ideal financially, but it still gives you the freedom to take a trip that extends a few days further than your paid vacation allows. To make sure it doesn’t feel too painful, save up in advance. Calculate your daily pay rate from your salary, and put aside that amount times the number of days you’ll take unpaid, in addition to the amount you’re already saving for emergencies.


3. Roll over your vacation and take longer trips less frequently.

If your employer allows you to roll over unused vacation days to the next year, this gives you an opportunity to take even longer trips. 

Let’s say you get 2 weeks of vacation per year. You could take one week this year, doing just a short trip, and then three weeks the year after. 

If you get three weeks, you could then potentially take four weeks off at once in year two (assuming your employer is cool with it, naturally) like you’re, what? Some kind of European escaping to the French Riviera? Get out of here with that golden tan and single-payer healthcare.

I didn’t actually ever need to take unpaid leave at that ad agency job, because the rollover policy worked in my favor. I was still able to travel each year, but I was strategic about the length of each trip to ensure I could max out my days for my destination wedding and extended honeymoon.

7 ways to fit more travel in your busy life and career


4. Take time off between jobs. 

There’s a magical window of opportunity between leaving a job and taking a new one that too often goes ignored. Many hop straight into the new job, either because they don’t have the savings to afford any kind of gap in income, they’re too eager to look like a hard worker to their new boss (ugh), or (worse) because they simple hadn’t considered it. 

When negotiating a start date at a new job, take a moment to consider if you really have to start as soon as you thought. Could you push your start date out a week or two and go on a quick jaunt to South America? Probably so. 

And if your new job involves moving to a new city, well I shouldn’t have to tell you that this is your moment. Sure, moving is time consuming and hectic, but you only get so many travel opportunities like this. Take them when they come. The stacks of boxes to unpack will still be there when you return.

While moving from Austin to Dallas with my then-boyfriend (now husband), we took a week off to visit Colombia, including several days in Cartagena. We ended up loving it so much we got married there 5 years later.

In either case, it never hurts to ask for the start date you want; you don’t have to say why. They’re the ones who want you, and they don’t want to lose you as a candidate - they’ve already spent too many resources hunting you down and wooing you. Once you have an offer, you’re the one in power. Use it.


5. Take all of your vacation in one shot.

It’s way too easy to fall into the trap of letting your vacation days get consumed with shorter, less fulfilling trips: a long weekend here, a family obligation there. Too often, even among child-free twenty-somethings, we Americans think of vacation as an allotment of days that is too short to actually be meaningful - so we default to using them in a piecemeal fashion. 

One of the main reasons I was able to travel as much as I did (and to as many cool destinations as I did) early in my career, while I enjoyed just two measly weeks of vacation per year, is because I took them all at once. In fact, cushioned by those three weekends before, during, and after, I could squeeze a 16 or 17 day vacation out of 10 paid days off. 

Exploring Luxor, Egypt over a 2+ week mini escape from cubicle nation.

Exploring Luxor, Egypt over a 2+ week mini escape from cubicle nation.

If you need to travel to visit family during the holidays, consider finding other ways to take the time you need to go see them. Maybe you can use personal days or floating holidays. Just don’t assume you need to spend your vacation days on trips that aren’t actually a vacation.

Americans get so few vacation days to begin with anyway. Make the damn most of them!


6. Take a job at that requires you to travel. 

But don’t get narrow-minded here. Many, many types of jobs require frequent travel.

Maybe for you this looks like a big global corporation with offices around the world, and a job that involves regularly visiting those offices. 

Or, maybe you're in a sales or account management role, responsible for keeping your clients happy across an entire region of the world. 

7 ways to fit more travel into your busy life and career

At any rate, don’t assume that the only way to have a travel-heavy job is to take a job in the travel industry. Your best bet is to work your way into a global company, but there are many companies that could use (and would pay handsomely for) someone who’s willing to practically live out of a suitcase for the job - because there are lots of people who aren’t.


7. Start your own (LOCATION-INDEPENDENT) business.

This one is easier said than done, and as someone who’s recently done it, I can tell you it’s not the glamorous endeavor some would have you believe. 

I was only able to successfully pivot into self-employment as a social media consultant following my 2018 layoff because I already had a strong network here in my home city and a solid reputation as an expert in my field.

I had marketable skills, specific in-demand expertise, experience managing client relationships from my agency days, and the right set of personality traits for the role: self-motivated, driven, organized, and able to sell myself despite being introverted. And I’d chosen a specialization that meant I could work from anywhere once I broke free from employers afflicted with butt-in-chair-itis.

If you’re just starting your career but think this might be the path you want to eventually follow, find ways now to lay a foundation. Optimize for learning. Constantly seek new challenges and educational experiences, even within traditional employment. Immerse yourself in the worlds of those you eventually want to serve when you strike out on your own. And only do so after you’ve built that baseline of knowledge and trial and error, and proven yourself in the meantime. 

You don’t have to wait forever, but unless you’re already replacing your full-time salary with your self-employment income, I wouldn’t take the leap into self-employment until you have at least 5-7 years (ideally more) in a specific specialty under your belt, a rock-solid reputation in your field, and a robust network of relevant professional contacts.


If none of these situations are likely to happen to you this year, you’ll need to just pick a place, choose some dates, and commit to making it happen. Or, be very watchful of good flight deals to a variety of destinations that appeal to you and ready to pounce when the moment strikes.

That’s the thing about priorities: once you declare them and act on them, everything else tends to fall into place. Whatever you think is holding you back from taking a trip may actually take care of itself - or prove not to be such an obstacle after all. 


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    7 ways to fit more travel into your busy life and career