Traveling jobs that pay well

I may be living the freelance life now (which includes lots of travel since I can take my laptop anywhere), but I worked at traditional 9-5 jobs for most of my 20s and early 30s. Even while holding down sometimes demanding positions, I did plenty of hitting the road, from 12 days in Egypt to a dozen long weekends in Vermont and one in North Carolina, from six-day trips to the Dominican Republic, Canada, and Costa Rica to eight-day jaunts to Maine and Morocco — and on a limited budget too.

I made it work through a combination of tactics, including these:

First, get more time off

Negotiate: Just because a job only offers you a paltry 10 days of vacation a year doesn't mean you have to accept. At two jobs in a row, I didn't haggle over salary during my negotiations, but I did ask for extra vacation days, since more time off was worth more to me than money. Once I was successful in my request, and once I wasn't, but it's definitely worth asking — and it's usually easier for your boss to OK more vacation than more money anyway. You can also ask for more time off after you've been hired. A great time to ask is just after you've scored one for your team or otherwise proven yourself to be a valuable employee.

Take unpaid vacation: I did this successfully at two separate jobs, both times giving my bosses plenty of notice so they could get the paperwork and approvals through fairly easily. In both cases I was simply docked a week of pay from my normal check, and it was totally worth it to me to have that extra five days to travel. Of course I made sure I could cover my bills for that cycle in advance. One of these weeks was used for my trip to Egypt, for which I took five paid vacation days and five unpaid ones. Frankly I don't even remember my coworker's names from that job, but I'll never forget flying over Cairo and seeing the pyramids for the first time, or cruising down the Nile River and seeing the stars twinkle over the distant dunes.