So you want to work remotely...

A few weeks ago, I met a fantastic guy who is contemplating next steps for work. He is great at what he does, and is thinking about what direction to go in his life. He's young, and thought working remotely sounded pretty cool. I agreed, and then spent the next week or two thinking about what's required to work remotely. 

Here's the email I sent trying to explain all of this.


Hi {redacted},
Prepare yourself for a long email. I’ve had a lot of thoughts rolling around my head related to this, and you’re getting them all. I’m going to work on cleaning this up and maybe sticking it online as a blog post for later. I’ve talked with many people about working remotely, so… here are some thoughts:
Glad you got the bug for remote working!
There’s lots of good things that come with working remotely, but there are lots of real and perceived barriers.
So, let me offer some more encouragement and advice. 
First, there’s the matter of framing how you go about working remotely. Obviously you want to work remotely, but put yourself in the shoes of a prospective employer. They don’t care if you work remotely or not - they want you to do great work for them and make them an effective, profitable organization. 
So, if I can make up the imaginary “Josh’s Rules of Getting a Remote Job”, this is what they’d be:
Rule 1: Getting a remote job is exactly the same as getting a regular job, but a little harder
Companies that hire remotely tend to be younger, agile-er, and smaller. So every employee matters. Making a bad hire can be catastrophic in terms of money and opportunity cost. Your job is to make it very, very obvious that hiring YOU is a great decision. In fact, you want to be so good at what you do that passing up on you is a terrible decision. 
This right here is the difference in mental approaches from an “average” job hunter and a high-performing job hunter. 
The average person talks about all the reasons that they’re qualified to do the work, how quick they are to learn, how happy they are for the opportunity, etc. None of this puts a CEO/hiring manager/team lead at ease. Of course this person wants to work at my company. I have a kick-ass, quickly growing company and pay my employees well. I need more than a willing person.
Rule 2: A top-performing employee approaches a job opportunity the same way a consultant approaches a possible gig.
First, qualify the opportunity. Is this something that you could do well?
Next, assuming it’s a job they could do well, get into “proposal” stage. “If I were hired to do this job, these are the things that I would do, these are the projects I would work on, and here’s the impact it would have on the company’s bottom line.”
^When you can walk someone down the path from “Hire me” to “I’ll help you make $$$/year more than you would otherwise”, if $$$ is 5x your annual salary, you’re in a pretty good place. All of a sudden, rather than the risk being “hire this guy and it might not work out” it becomes “If I don’t hire this guy, I might miss this opportunity”.
AND! By framing the conversation like this, you’re showing that you are aware of their needs as a business, and that you’ll hit the ground running. You don’t need your hand held, you’re able to execute ideas as appropriate. 
By the way - none of this is making up BS. There's tons of ways you can make contributions to a company and help them retain users, get new users, save money, earn more money, grow accounts, bring in new business, hire better people, keep existing employees longer, etc. This is another topic for another time, though. Just know that you need to focus on the value you provide to a company. 
Rule 3: A top-performing employee has concrete numbers and stories showing their skill. 
You’ll be asked about your prior experience at your current job. Don’t just say “I did {job} at {company}”. That’s boring. That makes you a risky hire. 
You’ll say something like “When I was a {position} at {company}, I was tasked with {responsibility}. Not only did I do that task well, but I took on a few side projects to increase the effectiveness of the team, and decrease the friction of some processes. For example… {story showing how you made improvements that impacted the business, with figures to back it up}."
Rule 4: Your online persona is the primary thing that will get you hired. Craft a good one. 
When you see a job opportunity go by, you don’t just submit a resume and let it go. You find the person in charge of hiring, or someone on the team, or the company CEO, and you send them a short email. In that email, you make it easy for them to discover how competent and skilled you are. 
That could be as simple as a link to your personal website in your signature. A personal website is extremely useful for showing a lot of things at once:
1. Tech savvy (it is simultaneously extremely complicated and unbelievably easy to set up a personal website. With a little googling, you can do it. This is good. Try to get If not, look for,,,, etc. Look around. Find people that have strong personal brands, see what their URL is, and try to get that. 
2. Room to show that you can communicate effectively. Remote companies live and die on the written word. Can you communicate something interesting via text? What do you write about? It doesn’t matter, as long as you might be helping someone. Before you publish anything, answer this question: “Does what I’m about to publish have the potential to help someone?”
If the answer is yes, publish.
3. Showcase your non-writing skills. Do you put cool stuff on Instagram and Twitter? Well, put those on your personal website. Do you read a lot? Make book recommendations and include a reason or two for why someone should read the book. Are you athletic? There’s ways to show that too. 
4. The skills required to work remotely tend to overlap heavily with the skills required to create a website. Software is eating the world, so get conversant in the technology.
5. You don’t have to go full web-developer to put a website online, just as you don’t need to be a software engineer to work at a software company. But know the tools available to you that allow you to be effective at technical tasks. The idea behind using Squarespace  or Wordpress to publish a website is the same as using KissMetrics or FullStory to gather customer data.
Phew. That’s it for now.
PS All of this is general advice. You’ll need to become a specialist. That’s hard work. Holy crap, it’s hard. That is a whole other topic. But this is maybe a helpful starting point.
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Read what they think about things, and you’ll be wiser for it. :)