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The Complete Guide To Getting Your First Remote Job


In 2015 I was offered a remote contract from a guy I’d met in an airport bar. No joke. If my best friend wasn’t sitting beside me during that layover, I’m 100% convinced that everyone would think this was completely made up. 

I’d finally earned enough accrued vacation to take time off and was headed to Mexico. He’d overheard me talking about a SEO portfolio site that I’d recently made, and that I was going to start looking for new side projects. After a quick conversation and a week to think things over at the beach, I flew home and took the offer (gulp)

It was really scary to leave an established company, but I’m happy I did. The past three years working on distributed teams and as a freelancer have been some of the most rewarding years of my career. Working remotely has helped me grow personally and professionally in ways I never could at an office, and I’m grateful for everything I’ve learned and everyone who has helped me along the way. I hope sharing a few tips I’ve picked up will help you on your journey to starting a new chapter in your life. A chapter that involves you sipping coconuts on the beach.

(I think we all know I’m not actually typing anything in this photo)

1) Make it real by making an action plan. Start by taking baby steps.

“A goal without a plan is just a wish”

This quote is the frame of mind that helps maintain focus and stay the course when applying for remote roles. When you first sit down to frame out what you’re looking for, it’s important to set clear goals and make solid plan. Write everything out and give yourself deadlines. Once you do start working remotely you’ll be expected to perform your role independently. Start now.

Here’s a quick list of things you should include in your plan of action:

  • Why you’re looking for your next role – Make sure you take time to think about why you’re ready for something new and why this is what you’ve set your sights on. Understanding your motivation is key.
  • What you bring to the table – List out your skills and experience. Clean up your CV, Linkedin, and other networking sites. Have a clear understanding of the value you will bring to your next role.
  • Who you know – Chances are you know more people than you realize. Cast a few lines to people in your circles and see what happens. You’d be surprised.

There are an infinite number of remote opportunities and they’re all a little different. For example, some companies may require you to be in specific timezone or country. Not everyone allows for globetrotting. Take note of the job ads that will work for the lifestyle you’re trying to attain.

If your goal is to just drink mai tais on the beach, then a remote job might not actually be what you’re looking for. Just sayin’.

(Above is not a future picture of your office.)

2) Choose a skill that most businesses need.

Before you start sending out hundreds of resumes, you should already know which field you want to work in and have a clear idea of your skill level in that area. It goes without saying, but it’s a waste of everyone’s time (including yours) if you start applying for roles that you’re not qualified for. If you’re just starting out, apply for entry level roles.

Build a specific skill set that will help you market yourself. For example, if you want to find a role in digital marketing, pick a stream to focus on (ie. SEO, Copywriting, Paid Ads, SEM, etc.). Get really good at one thing that you can build upon.

If you don’t know what skill to pick, we recommend these skills because they’re needed by almost every business:

  • Customer Service
  • Digital Marketing
  • Programming
  • DevOps
  • Project Management
  • Copywriting
  • Design

3) Freelance gigs are your gateway to a full-time remote job.

When I originally gave notice at my former tech company to work remotely, I thought of freelance work as both intimidating and overwhelming. Billing, negotiating, and all that other stuff was something I didn’t have to deal with before. I liked it that way.

What I later realized was that freelance opportunities will give you a taste of what remote work looks like for you. It will keep your skills sharp and push you to network. When you do find your dream job, this experience will be mega points for you in an interview. Use that.

Skills you gain (and can later reference) from freelance work include:

  • Time management
  • Tactics you used to stay focused
  • How you tackled working independently
  • Communication strategies you used to push the needle forward
  • Why you liked working remotely (hint: it’s about more than the pajamas)
  • Sincere feedback on why you didn’t like working remotely – you’ll get flagged if you dodge this one

It’s a big risk for a company to offer a full time remote role to someone who’s never done it before. With freelance experience under your belt, this will be a non issue.

4) There’s no point in applying without a portfolio.

We’ve covered this in detail so we’ll just drop a quick quote below and move on. 

 (this is the portfolio that helped me land my first remote job)

FromThe Complete Guide to Building an Online Portfolio

If you’re serious about stepping away from a traditional office role and becoming a full time remote worker, there’s a few areas where you’ll likely have to step up your game. Remote work is not reserved for mysterious entrepreneurs in the know, it’s for those who are willing to showcase what they bring to the table. Successful remote workers all have one thing in common: initiative

5) Don’t waste your time with general job boards.

You can’t just stare longingly at a coconut and hope for the best. Well, I mean you can try…

(this coconut will not help you find a remote job) 

When you start looking for your first remote job you have to know where to look. Obviously, good places to start are with job boards that cater to remote work opportunities.

Start building an idea of what your ideal remote job will look like and pair that with your research about the companies you’re studying. This will help you build a clearer path for what you’re looking for. Make a vision.

6) Apply to jobs right when they’re posted. It’s a minor adjustment that makes a huge difference.

It will take time to find the right opportunity. Focus on results.

There’s a lot of data that indicates that timing will impact your job hunt, and this stands true for people specifically looking for remote opportunities. I don’t subscribe to the idea that the day of the week or particular hour you submit an application carries a lot of weight in your results. However, it’s easy to get caught up in the glamour of a job ad without noticing that the author has been inactive for a month or two. The age the of the job ad will be a leading indicator in the response rate you receive. 

Things move quickly. You should too.

Putting it All Together  

When you put it all together, you should have a clear vision of what you offer and where you’re trying to go. Here’s a quick checklist of what we covered:

  1. Make it real by making an Action Plan. Start taking baby steps.
  2. Choose A Skill That Most Businesses Need.
  3. Freelance gigs are your gateway to a full-time remote job.
  4. There’s no point in applying without a portfolio.
  5. Don’t waste your time with general job boards.
  6. Apply to jobs right when they’re posted. It’s a minor adjustment that makes a huge difference. 

There are a lot of remote work opportunities out there and finding something that fits your passion is possible. The reality is, when it comes to finding your first remote job a lot of standard advice applies. In fact, in a lot of ways it’s just like any other job search, but with a few key differences. This guide was designed to help you better understand what those differences are so you can ditch the cubicle and start enjoying the freedom of remote work. 

Over the course of the past three years I’ve been put to the test and thrown into the realm of remote work full throttle—the ups, the downs, the contracts, and the job hunts. If you have any questions about how you can make remote work a reality for you, feel free to drop them in the comments below. 👇

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