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Remote Work and Travel

Top 4 Ways to Get a Remote Job

Greg Caplan, Founder and CEO of Remote Year, shares his tips for how to get a remote job. Tip #1: Tap into your network.

Let me start off by saying that there’s no one right way to jump into remote work. The important thing is taking the leap.

In my experience, both in my personal life and through witnessing thousands of lives that have  changed as a result of Remote Year, it’s obvious that remote work has the power to significantly improve the way we live. It allows us to take back control over the hours in our day, using them to not only create work that is meaningful, but to live a lifestyle that is inspiring to others. When we have the flexibility to work outside of the conventional office environment, we open our eyes to new perspectives, discover new and innovative ways to solve old problems, and connect with people who we would not have met were it not for the moment that we decided to burst out of our comfort zones.

It all sounds too good to be true, but I promise that it isn’t. As a professional who is searching for more from their life, can you transition into a flexible working style? Yes. Let me share an example with you - the story behind how I made the move to remote work.

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How I Set Myself Up for Remote Work

Before I started Remote Year, I was working a 9-5 job at Groupon. I felt stuck and decided to start trying to figure out how to travel while working remotely.

The first step that I took to make that dream a reality was reaching out to my network. I started to talk to the people who I had worked closely with, people that I had really strong relationships with. I asked them if they needed help with pieces of their business related to marketing as that was my background.

I talked to a couple folks and, when I found one friend whose company could use some help with marketing that I could provide through independent consulting, we agreed on the terms and what that help would look like. I knew I could successfully pitch a remote work agreement to other companies once I had built up my confidence with that first client.

Top 4 Ways to Get a Remote Job | Remote Year

The most important thing that made my remote work journey successful: I started with my network. The number one tip I would give to people who are interested in transitioning to a more flexible position: start with your network.

There are plenty of remote job boards out there, but the best way to find a job in any situation is to start with your connections. Remote job boards are great for fully-distributed companies because there are a lot of people applying to the jobs that are listed as candidates are becoming more and more interested in positions that offer flexibility in location. On the flip side, the not-so-great thing about remote job boards is that there is a lot of competition for those jobs. If you can’t work remotely in your current position, start with your network.

After years of helping others find their path toward a life of freedom and purpose, I’ve been able to narrow down the top 4 ways that you can find yourself a remote job. Here’s where you should start:

Top 4 Ways to Get a Remote Job

Ask your current employer

The first route  you should take if you want to pursue remote work is to figure out whether you could do so with your current employer. Though asking your boss if it would be possible to start working remotely can be a bit intimidating, it will also save you the effort of having to find a new source of income or a new job.

Think you can’t work remotely because of the industry that you’re in? Think again. Technology has evolved over the last decade to make it simpler for people in almost any profession to work remotely. I like to think about it this way: if you could do 80% or more of your daily tasks solely from a phone or computer, you could work remotely. If your current 

role isn’t so technologically dependent, it may be possible to transition into a different role within your company in order to work remotely. The only thing that’s stopping you is you.

Want to take your current role remote? We can help.

Tap into your network

If it’s not possible for you to work remotely for your current employer, start to search for opportunities within your professional network. When I say “network”, I’m not talking about the people you’ve connected with on LinkedIn but barely know. I’m talking about the real, authentic connections that you’ve made with people over the course of your professional lifespan. Ask for connections through your connections. You need to tap into your relationships with the people that truly understand your skillset and could help point you in the right direction toward your next big career move.

Top 4 Ways to Get a Remote Job | Remote Year

Start a cold job search

If you’ve tried the two ideas above and they haven’t panned out, it’s time to start a job search. I never recommend this route right out of the gate because I believe that your network will always be able to provide you with opportunities that a cold job search will never show you. Your connections have other connections that might just have an “in” at a company where they could use an extra hand on a project, but they never put up a job listing for it. You never know what you could be missing if you don’t reach out to your network first.

If you’re going to search for a remote job, here’s how to do it right:

  • Start following companies that are fully-distributed and keep track of the jobs that they list. Reach out to their hiring manager to see if they could use any help in the areas that you’re well-suited for, or set up an informational interview to get your foot in the door. Another pro tip: free work will get you noticed. If you have feedback for their website or see a problem that you know you could solve, share it with them. It will show that you’re paying attention and that you care about the success of their company.
  • Look for jobs that aren’t necessarily listed as “remote”, but have responsibilities that could easily be done outside of the office. When you get to the negotiating table, you can mention location flexibility as one of your requirements for accepting the job and make your case at that point in the process.
  • Don’t mass-apply for any remote job that you can find. You should still have a passion for the work that you’re doing! Find a position that sticks out to you as an incredible opportunity and make your interest known to that company’s hiring manager.

Utilize project-based services

Finally, if you just want to dip your toe in the water of remote work, you can check out services like Fiverr, Upwork and Catalant for one-off projects that can help you make some cash on the side of your full-time gig. These tasks can help support you as you search for a remote job, or as you’re building up a larger remote clientele.

Best Jobs to Work Remotely

Depending on your skillset and desired line of work, remote jobs are either easy or difficult to come by. Those who thrive in a tech-based environment shouldn't have any trouble finding remote work, while those who are in the medical field may have to search a bit harder. Either way, the location independent career space is growing. Here are a few lists that we've compiled to help you get started in your remote job search.

Everyone’s transition into remote work is different and unique. Though I recommend speaking with your employer first about how you could turn your role remote, or reaching out to your network to see if they know of any remote work opportunities, it’s important to find your own path toward remote work. It may not be a simple, straightforward, bump-free road, but the reward of having the freedom to live your life in the way that you want to live it is worth it.

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