A few months after leaving my full-time job that left me burned out at my NYC office, I kicked my legs up and logged into work from my laptop. I was in the Canary Islands, an archipelago off the coast of Morocco. I had been traveling for three months by that point, and I was a digital nomad.

How did I get to that point, though? The truth is that months before, I had convinced my boss’s boss to rehire me as a part-time remote employee. My goal was to work remotely and travel the world.

This wasn’t as easy as it looks, and in this list of tips, I can show you what I did to convince my higher-ups to let me be a remote worker. Here is what to know.

You may have to “quit” your job

In May of the year I aimed to “go remote” and “travel the world,” I got the courage to quit my job.

Yes, I was going to QUIT! I had my savings built up, I had my escape plan ready. Dan and I were both going to quit our jobs (or see if they asked us back, after quitting) and we had booked one-way flights to Amsterdam for June 2.

So in mid-May, I put in notice with my boss’s boss, because my boss had recently quit as well. This put me in a place of a bit of unexpected leverage, because our team was disappearing one by one and it didn’t look great for the department.

I called a meeting with my boss’s boss, who I guess at that point was actually my boss, and said, with my biggest calming breath, “I am putting in notice. My last day is June 2.”

He was a bit shocked, because he noted that I had just gotten the promotion and raise I’d been working toward, but I said yes, this is happening and I’m leaving.

He said, “Can I keep you longer?” and I said, in one of my most famous professional episodes, “Nope, because I have a flight to Amsterdam in early June.”

So, while my plan was actually not to get re-hired as a remote employee, my specific situation made it that way because of this point in time and the scenario at my employer. Maybe you’re in a similar spot. Read on!

If you had to quit, try to get re-hired as a remote employee

A few days later, I came up with an offer to my nearly-former employer. I called another meeting with my manager and said, “If the company would like, I can make myself available to work part-time for the department, remotely.”

I was even more nervous this time while my manager mulled over this offer with his higher-ups. I was nervous for a few days, mostly because the prospect of leaving to travel but also having income (yay) was valuable.

A few days later, I was presented with an offer letter of a “new job” that was a part-time role, nearly identical to my former role but without managerial aspects, and an hourly rate based off my NYC salary. I would be remote, and I could travel anywhere in the world I wanted to.

Was this the dream? Maybe! I was going to find out. For the moment, it sounded like the best catch-all solution to my desires of seeing more of the world on an open-ended remote “workation,” and I also would be escaping the 9 to 5.

Even if you don’t have to “quit” first like I did, see if you can come up with a win-win offer for your employer or your company to leave your role, and then come back to a NEW role — one that is part-time and remote (if this fits your needs).

Show a remote work success story

The team I was working on already had a remote employee. Unfortunately for him, he was the only remote employee on the team, and the rest of us were in NYC. It kind of created a disconnect, yet at the end of the day, he was working remotely (from Hawaii!) and did his job really well.

So, in trying to prove myself as a person worthy of becoming a remote employee who’d be romping around the world looking for WiFi, I was able to show that remote work was already a part of our department. Our current remote employee was dedicated, loyal and smart, and luckily for me, my “ask” of wanting to essentially become our first digital nomad employee wasn’t so ridiculous.

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Photo of Becca Siegel and Dan Gold

Tell your boss how dependable you are

My boss knew I was dependable and highly communicative. I was always in the office, working extra hours when needed, and I was trusted by our clients and external parties that worked with me. Plus, I’d been at the company for almost six years, with a longer tenure than 95% of my coworkers.

If you can show your manager how dedicated and trustworthy you are, you’re more likely to win the battle of negotiating a remote work and travel setup for yourself. One of the scariest things for bosses is to think that one of their employees is out in the middle of Asia or Africa, caring less and less about their work and productivity.

If you can squash these fears, you’ll be in the clear.

Demonstrate the value of yourself as a remote worker

If you want to work remotely and travel, a great way to do this is to show your boss the incredible value of you being a remote worker around the world, while traveling.

For me, I got lucky again: I was already working with companies in East Asia, Latin America, Western and Eastern Europe and even some parts of Africa. I had a very special job at the time, and had formed relationships with heads of companies around the globe.

I demonstrated my value as being able to meet up in person with the heads or points of contact in the countries I’d travel to. My big proposition was that I was going to travel so much that I could see a lot of them and make stronger connections for our business.

Do you know what? I was RIGHT.

I had business lunches in Mexico City and in Latvia, and I visited with the presidents of our suppliers in Hanoi, Vietnam, and in Taipei, Taiwan. Every time, I would send a report (or even a photo?) to my team so that my managers could see the success.

Helpful Tip

Even if your job isn’t remotely (pun intended) anything like mine was, there are creative ways in which you can demonstrate your value as a remote worker. Maybe it’s by being inspired by new surroundings, or picking up another language and immersing yourself in a culture that will propel the business forward.

Bring up times in the past when you worked remotely

Here is where I personally got lucky for yet another time: I had already taken a two-week trip to Argentina, the previous year, to visit Dan while he was traveling on a program with Remote Year and we were dating long-distance.

That trip was two weeks, and I wanted so badly to take a two-week trip, but posed it to my boss at the time as being part business, part leisure. I guess I invented “bleisure” travel for myself at the time.

I went to Argentina and spent one week in Cordoba, and one week in Buenos Aires. I was able to spend several days of each week sightseeing with Dan, and the other few days in each city working remotely from his cohort’s coworking space. I would sign into work, answer my emails and attend a meeting or two, and then I would also meet up in person with the suppliers we worked with in each city.

I got to see one or two of their headquarter offices, and I also went out to lunch or dinner with the heads of companies in each city. I was making the short-term remote work and travel dream WORK!

Even though the boss I had when I put in my final notice to quit my job was NOT my boss during that Argentina trip, I was able to bring it up as a case study and as evidence that I provided value in doing this type of thing.

Helpful Tip

If your job doesn’t afford you any of these unique things I did, bring up times when you worked remotely from a hotel, or a sick day from home, or even from another part of the city you’re working in. It can help your boss to visualize that it isn’t so radical.

Offer a glimpse into your plans

I had a unique situation in that I sort of had the upper hand in what I was offering my company. After all, I wanted to leave the country in two weeks on a one-way ticket, and having a remote job (albeit part-time) was just a bonus at this point. And they wanted to keep me around, as an employee of six years who knew a lot of “stuff” about the business and the company’s history.

I didn’t really have to offer a glimpse into what I had planned. I actually didn’t have many plans past the upcoming 30 days, which was going to be spending time in the Netherlands, Portugal and the Czech Republic — all during which I’d be doing a lot of traveling and seeing some old friends who lived abroad.

The best glimpse into my remote work plans that I could give was that I was going to offer to be available during NYC working hours. In Western Europe, this meant working from mid-afternoon to later in the afternoon. 9am in NYC would be 3pm in Prague, and 12pm in NYC would be 6pm in Prague.

I also was going to work under the assumption that my 15 hours a week would be split into three hours a day, five days a week. We had an agreement that if I planned to take a day off (shhh — like if I wanted to go on a long weekend somewhere like hiking in Ireland! That would come later), I would communicate this, and would make up the hours by tacking them on to make “longer” workdays earlier in the week.

Helpful Tip

If you’ll be joining a remote work and travel program, these companies often have resources that can be shared with your higher-ups, like a “day in the life of a participant” and things like this.

Give your boss confidence that it’s a good move

Maybe this means telling your boss that you’ll be back after 5 months, or maybe this means showing your boss receipts of coworking space memberships you’ve already booked in Barcelona.

Either way, show your boss that you will have the support you need to be productive and maybe even out-perform your previous performance.

By instilling confidence that you will still be “you” even if you’re working remotely and traveling, far away from the confines of the office, you can get this negotiation to go your way.

Show the financial benefit

Everything at a company, no matter how big or small, comes down to the finances. And your boss is responsible for you, and your productivity, because that translates into MONEY.

Show the financial benefit of you being away for some time while you work remotely. Maybe it means that the company can actually save money by giving your desk to someone else. Maybe it means the company won’t have to pay for a certain benefit of yours, because you won’t be able to use it while abroad.

Whichever the case, think of all the ways the company will save money by you not being physically around the office anymore, and if the company has been looking for ways to save, this could help.

Try to put yourself in your boss’s shoes

This is something I should’ve done a bit more when I was being all up into my own situation and my desires. If you’re working for a company at which no one has asked to work remotely and travel before, it may sound daring, and absolutely crazy.

Consider that if you were in your boss’s position, would you be shocked? Worried about having your boss approve this individual’s request to leave the office and go work in Thailand?

I can see now how this was going for my boss while it was happening, and why it required probably more than just one approval for me to shake things up and ask about doing the digital nomad thing.

Say thanks, and leave some parting remarks

If you do come out on top with your negotiation of asking your boss about working remotely and traveling, make sure to thank him or her.

Leave some final words of promises like how you’ll always be present for the team meeting, or you’ll send the team a postcard every month from somewhere new.