6 Tips To Help Convince Your In-house Job To Let You Work Remote So You Can Travel The World

6 Tips To Help Convince Your In-house Job To Let You Work Remote So You Can Travel The World

Who wants to sit in a stuffy office anymore when you could take your job with you to explore and see the world all while earning an income? It seems a lot of millennials are catching on to this extremely awesome way of living and have found their way to do it whether they are travel blogging, teaching English, freelancing or content creating. That’s nice and all, but there are even more millennials (like me in the past) who are dreaming to be able to do it – but they have no idea how. Maybe they have a few ideas, but can’t seem to pull the plug on their current life to make it happen. I’ll admit it takes balls (excuse my non lady-like manors) and a lot of work, and honestly, that’s why it’s not cut out for everyone.

Unfortunately, you can’t just wake up one day and decide to start a blog and “become a travel blogger” that makes a living overnight. Those people that are actually earning an income while travel blogging I always thought were the absolute rare extreme (I still do). Not to mention they work hard day in and day out to create a blog and content for people to read. You can’t exactly just work at your regular job and call yourself a travel blogger because well, you have to be constantly traveling getting that content.

 I always knew I wanted to travel the world, and to be honest, when I would dream of traveling the world, having a job wasn’t in the cards. I just wanted to explore – and that’s exactly what I did with my first year of traveling. I traveled like a true backpacker with a budget for cheap hostels, beer and a train ticket to the beach. No souvenirs. No shopping. No fancy tours. I was living the dream until I ran my savings down to $2000 to get my life back together once I got back to California. It’s scary watching your life savings dwindle away but was it worth it? Hell Yes.  This trip was now 10 years ago (holy crap why didn’t I start this sooner?!) and it completely changed my view on what was important to me in life.

My goal when I got back from that trip was to never get another accounting job so I didn’t get stuck. I never wanted to work in finance again. The hard part about being an accountant is everyone needs one. So, eventually, I took the easy route to save money for my next adventure and I got a job in an accounting department. Three years later, I was still working in finance, still saving for my next adventure, still waiting for my right opportunity. Stuck.

I did though, start one of those travel blogs. It was more about the crazy stories I got myself into while traveling as a single female, mainly because plenty of stuff kept happening that even I couldn’t believe. I also wanted to share the adventures and inspire others to get out there and explore too. I was giving myself a goal to have it running within 18 months and when I had enough traffic that I would take it out into the world and use it as a tool to make a living while traveling. Except, I’m no technology smarty, so I ran into all kinds of issues and then I would get bored and discouraged and forget about it. I would get motivated again and write blogs but not even my friends wanted to follow along with me(rude;). I had about 20 followers and they were probably random bots from online or random men that had nothing to do with traveling. I couldn’t get the right audience’s attention if I threw a rock in their face and said Hey Look At This – You Will Like It. I was a nobody and it stopped me from trying several times. It was hard, intimidating and scary to continue to try.

What I am trying to say is, if you aren’t super techy and you think you have no hope of being a digital nomad because you can’t start a savvy looking blog, think again. There are jobs out there that actually allow you to work remotely and live the dream that you want to live – and I am going to tell you how to find one and potentially make your way from an in-house position to a remote one like I recently have done.  

1. Save As Much Money As You Can

Just in case the plan doesn’t go according to how you want it to. While I was working my butt off I was also side hustling making money and putting it in the bank in case my boss said no when I finally popped the question. My main side hustle was Airbnb. I rented out my apartment for $140 per night and I had money depositing into my account ten times a month instead of two from my regular job. It was the only way I was able to save about $7,000 in less than a year. I would highly recommend hosting on Airbnb to anyone who is trying to save some money. Click here to sign up to be a host.

If you want to read more about how I gained financial freedom by using Airbnb, I have a whole series of posts that teach you exactly why you want to do it, how to do it and where to go while you’re renting your place.

2. Find The Right Job – and Boss – This Is The Key Ingredient For Success

I’ve worked in a few different industries and it seems these days everything is online on a cloud or the computer you are given is a straight up laptop. Tech and Marketing industries are good ones to be in to be able to potentially work remotely. I technically don’t work in either, I’m an accountant and like I said everyone luckily needs one. I’ve worked for both industries and each time I was either working on a cloud – that could be logged into from any computer; or the computer I was given was an actual laptop.

I even applied for remote jobs only at one point. I used a website that was strictly used for that – finding jobs for you that allow you to work remote. Yes, it does exist! It’s called Flexjobs and they will help you if you don’t think you are fit to work in the marketing or tech industry. You pay a small fee per month or per year to get access to this awesome website that will give you the freedom you are looking for. A very well spent investment if you ask me. Sign up with my link here for a 30% discount on that already small fee and help yourself start your dream life.

However, if you see the potential in your in-house job to work remotely like I saw, I am going to show you how to potentially turn your in-house job into a remote one. It all starts with picking a job that has remote potential. As I worked from the cloud or a laptop, I always saw the potential. It does not have to be in your job description just yet. Maybe you already have a job like this, and maybe you need to go out to search for one. Either way, having the right job as a starting base is key here.

3. Work Your Ass Off

Once you land that job, do not slack. This is the “hard” part because you are about to put in a crap ton of work for a potential lay off or disappointment when you ask to be remote in about a year – yes, it takes time, like anything else good in your life does. Don’t expect to get this job and within three months be working remote. You need to build up the trust with your team, management and boss before they would even consider allowing you to be remote.

I happened to find a job where I was given a laptop to work from. They even expected me to take it home at night to work from home after hours (ahem, remotely). I was told working remotely full time wasn’t an option but I never let that stop me from living my dream over and over in my head. I had no idea how I was going to pull it off but I knew, that I was either going to work with this job remotely, or I was going to quit again and start over abroad – I didn’t care if I was a barista or a tour guide or working on a farm I was going to get there. And that’s the determination you need to make it happen. I never forced it, I let it casually take its course until I found the right opportunity to ask my boss if I could work remotely. If you are one of the hardest workers at your job, there’s no way they will want to lose you, even if you have to check-in from 10,000 miles away.

4. After 5-6-7 Months Of Solid Hard Work That Shows, Take Vacation Time

 In the tech industry, they are usually younger startups that I’ve worked for in the past and they always had this “unlimited vacation time” policy. I think they think that people won’t actually take any time off because of it and I think a lot of people do not take advantage of it out of fear or out of thinking they won’t be able to catch up with their work when they get back.

Don’t be afraid. This is your time to shine. Take a Friday off, and 3 weeks later take a Friday and a Monday off, and the week after take another Friday off. Ask for it all at once, don’t just ask every week for another day off. Have plans already set for those days so that they sort of have to say yes. It can be scary asking for all this time off but you need to do it and never get behind on your work.

It’s hard to enjoy the balance of both your vacation and the “time off” but this time is for you to show your boss you can get your work done while you are “on vacation.” Even if you are just working from home those days. (Plus, it’s a good time to see if you are a self-motivated worker also – as I said, this isn’t for everyone). Work on a Sunday. Work on the plane. Work in the airport. Pull over in your car and get a request sent. You get it. And if you don’t yet, you will when you start to fall behind because you will if you don’t put in the effort – and it will show.

5. Then Take A Long Vacation

I asked to take four weeks to go to the Canary Islands, after flawlessly getting my work done after taking Friday after Friday/Monday off for about 2 months with a few full weeks in between. I knew this was my ultimate test to my boss to show him that, yeah, I’m in Spain having sangria and tapas at night, but his job was my number one priority. I knew that my work was so well done that they couldn’t afford to lose me. And I did that by working my ass off. For once I knew I was a valuable employee. I had never worked so hard at any job in the past before. I cared about the company and I cared about what I wanted my future life to be like with that company. 

6. Pop The Question

Shortly after you come back from that vacation, ask to work remotely full time. Don’t let too much time pass, maybe two months max. After you show your boss you aren’t really needed around the office, and that you still do the same exact capacity of work or more… if you’re smart you’d do more. Once you earn that respect from your boss, you can then have the conversation of – “I love my job. I love working here and for you. But I also want to live my dream life and travel remotely which I’ve seen a small piece of these last few months and I know if allowed to do so, I would continue to work my hardest or harder”.

My boss tried to put a cap on my remote time, “be back in two weeks” “be back in one month”, but I knew I wanted the freedom to go as long as I wanted to. So I grew the balls again and I said that I didn’t want to come back in a certain amount of time – The reason to travel and work remote was not only to explore and experience new things it was to live in cheaper places and be able to actually save money – I was living in Santa Barbara and I wanted to move to Bali. I said if you really want me here in the office, you can pay for my flights home, and that’s when he understood it. I also mentioned I could travel with or without a job ie. I don’t need you but you kind of need me…my balls were huge at this point. I knew going in there I really had nothing to lose. Because I didn’t. I had saved up enough money, I was either going to travel the world with my dream job or I was going to travel the world, and get a different job.

This worked with my boss, he gets it. He’s young. He wanted to do it himself before he started a family and felt “stuck” himself. This might not work with a dinosaur boss, one that follows all the rules and one that has never left the country and it probably won’t work with a super corporate job either. My boss is a bit of a badass – I really respect him and how he got to where he is. We have a mutual respect – and that’s also what helped my case. We got along well and he respected my hard work and in the end, he wanted to help me live my dream. I think he feels good about knowing my dream came true, really, all because of him. (I’m not crying, you’re crying!) 

Today I am living in Bali, living off one paycheck and being able to save the other watching my bank account grow. I work seven days a week most weeks; the dedication for your job must always come first. But let’s get this straight – I don’t work all day(well sometimes I do but not all days and I’m totally okay with when I have to work a little more). And if it happens to be a weekend and I don’t want to work, I don’t have to. It’s not expected, but I do it to show that I am hugely dedicated to my job. I don’t slack. I don’t get drunk at night so that I can’t work, I don’t get drunk and work allowing for more mistakes. I live a healthy and balanced lifestyle that was once just a dream of mine. And while I’m here, I’m working on that travel blog. I still haven’t gotten far with it, but I know that good things take time, and I’m willing to put in the time and effort to see if I can actually make a dollar from a blog post. Because if having to explore the food, culture, beaches, and things to do and then write about them for other people to also be able to enjoy isn’t the best job in the world, then you go ahead and tell me what is.

I hope sharing these few but simple tips of how I became to work remote may help you to “manipulate” your job to be able to work outside the office too.

Remember, you are in control.  Your life is what you are making of it. There’s nothing to be afraid of and I’m here to motivate you and push you to do what you really want to do. You can always go back to your boring ol’ mundane life – trust me, it’ll be there waiting for you – but don’t. Don’t look back.  Your life will absolutely change for the better and you’ll thank yourself later.

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