Everything you Ever Wanted to Know About Remote Work, Part 1: The Ultimate Guide to Finding your Remote Dream Job

21 minute read

Photo by Martin Shreder on Unsplash

Recently, a reader wanted to know how to find a job so as to become location-independent.

“I’ve been considering the remote/DN life for a bit now and I have a very basic question I’m looking to get more details on: Where do you find your gigs? Having a FTE position, I always know where my work is coming from. But I’m not sure where to get started with the “gig life”. Any tips?

Great question that I get a lot. In fact, I’d say it’s THE right (and arguably only) question if your goal is to become a digital nomad/remote worker.

On that note: here’s a snarky tweet of mine that hit a raw nerve like a fusion-powered sledgehammer:

Figure this out, and the rest (where to go, how long to stay, where to work, how often to move, how to find coworkers on the road and so on) will be a piece of cake. You definitely won’t need ‘digital nomad courses’ for that.

I’d even say it’s part of the journey, and a source of excitement rather than a challenge (if you think otherwise, you should reconsider becoming a digital nomad in the first place).

But anyway, let’s get down to business!

The 20,000 ft View

Even though I’ve been working remotely since 2008, I still don’t have all the answers when it comes to finding remote jobs (and probably never will). The question might be simple, but the answer is quite nuanced! (not to mention that the landscape is continually shifting: what was true five years ago might not work today, and almost certainly won’t five years from now.)

That said, I will try my best to summarize what I know, and hopefully, we can fill in the gaps together.

Let’s start with an overview - what kind of remote positions are out there? What skills do you need? How hard is to get in? What are the benefits/downsides?

There are near-infinite ways to skin this cat. Here are a few examples:

  • working remotely for an established company
    • negotiating going remote with your current employer
    • applying for a remote-first job
    • remote-first companies: you don’t necessarily need to search for a job opening - the great ones are usually hiring all the time
  • online marketplaces (Low Barrier to Entry - LBTE) Freelancer, UpWork, Fiverr, PeoplePerHour, Guru, Outsourcely
  • online marketplaces (High Barrier to Entry - HBTE) TopTal, X-Team, Codementor, Gun.io, Adevait
  • bespoke solutions - Zerocracy
  • remote consulting
  • independent freelancing
  • selling courses/infoproducts
  • making products (typically, but not exclusively, SaaS)
  • Your very own hand-crafted recipe

Let’s consider these in turn!

Working Remotely for an Established Company - Your Current Employer

You read a few digital nomad articles, are ready to get your feet wet, but still work in an office? You don’t necessarily need to quit right away. Instead, offering your employer to work remotely might be the better choice.

Yay: You know exactly what you are getting into (well, minus the remote part, for now - but that’s something to be excited about, right?!), you know your future colleagues (same as the current ones), the project, the culture - so fewer nasty surprises ahead.

Nay: No huge downsides here, although your boss might not be thrilled that you want to ‘break free,’ so that is something to consider.

Who is it for: Anyone who loves their current project/colleagues but had enough of the 9-5 aspect (long commute, too many distractions, office politics, etc.)

When: You are ready for a change, but not the drastic one quitting and starting a completely new remote job would entail. This is possibly the smoothest transition from 9-5 to remote: a trial period, if you will, that doesn’t involve burning all your bridges.

If you discover it’s not for you, it’s relatively painless to go back to the office (I know, if you are excited to go remote, you might think ’that won’t happen’ - but I’ve met plenty of people who realized that remote work didn’t live up to their Mojito-filled dreams).

Earning Potential: Dependent on your current salary. You probably won’t be able to squeeze out more than you’ve already got, but you shouldn’t be content with less either.

If it becomes apparent during the negotiation that your boss thinks you are worth less as a remote dev, then it might be time to consider one of the other options below.

Check out this fabulous book to up your negotiation game: Never Split the Difference: Negotiating As If Your Life Depended On It

Working Remotely for an Established Company - Remote Job Boards

A whole new world
A new fantastic point of view
No one to tell us no
Or where to go
Or say we’re only dreaming.

- Aladdin

A whole new world, indeed - you have tons of options, even if you’d like to work with a particular stack/technology (and almost unlimited options otherwise). Head over to one of the best remote job boards out there, Remote OK! and choose your tools. Or just browse the jobs in chronological order.

Yay: Instead of going with a well-defined option (i.e. your current job), you’ll browse offers and pick ones that best suit your needs, skill set, and goals from a huge (and ever growing) pool of options. This is a great way to balance the possibly too well defined, single option and the too nerve-racking option (freelancing, bootstrapping) where you constantly have to scramble to put together the puzzle pieces.

Nay : It’s a more time-consuming option than the previous alternative, which will potentially (and very probably) consume a lot of time in order for you to find the best match.

To some extent, you are buying a cat-in-a-bag here (more so than going remote for your current employer, or taking a shot at a remote-first company with a well-defined culture and documented history like Buffer, Automattic, or Hotjar).

Some of these jobs are still tied to a continent (like North America) or time zone .

Who is it for: Typically more experienced developers (although companies hiring remote juniors do exist, but they’re relatively rare). This is still among the safer bets (compared to, e.g., independent freelancing or creating your own products), so it is one of the compelling options if you’re just getting started with remote work.

When: Virtually anytime - whether you are getting started, have been working in a 9-5 for decades, or anything in-between.

Earning Potential: Highly variable, depending on the company/position. Generally, though, you can expect a decent offer.

Remote-First Companies

Here’s a great list: Top Remote Companies

Yay: This is very similar to the previous option, except these companies have better-than-average remote cultures, well-fleshed-out processes (which are usually well documented - for example, Buffer is famous for being very transparent about their salaries, operations, leadership and pretty much everything else).

The ones I know about organize yearly off-site team building sessions (everyone travels to the same location to meet in person, have fun, etc.) and provide other, remote-specific perks.

Nay: The transparency and success of these companies also mean that an incredible amount of people know about them and want to get jobs there. Thus, of all the possibilities listed, you can expect the toughest competition here.

On the other hand, unlike in the previous point, you don’t need to spend large swathes of time searching for the right company, since that is given. At the same time, you should expect to spend more time on the preparation.

That said, this isn’t really ‘lost time ’ because even if you don’t get hired, you’ll still be able to use the preparation you’ve put in on the next application.

Who is it for: More experienced developers, or candidates possessing unique skills (remember, you have to stand out in a HUGE crowd).

When: any time, but you need every edge you can get over the competition - therefore, ideally you should already have at least some remote work experience, or be a more senior, well-rounded developer.

Due to the sheer number of applications these guys get, you’ll need a good grasp of the application process, hand-crafting your CV and cover letter.


Because these companies filter out candidates aggressively (I heard this from a HotJar VP during a coffee). If you are a beginner, you will end up in the ‘nay’ pile for reasons you can’t even start to guess.

You also need to tailor your application, your narrative, and your communication to the specific hiring process this company has.

Earning Potential: High! Even in the rare case that the salary is not going to be that great, they are going to offset it with hard-to-resist perks.

Online Marketplaces - LBTE

Yay: Practically no entry barrier (just create an account, set up your profile, and you are ready to start applying!)

Nay: No entry barrier for you means no entry barrier for anybody. Captain Obvious also does birthday parties!

But what does this mean?

Well, you’ll be compete with a humongous pool of developers globally, with many offering their services for rock-bottom prices (think $3-$5 per hour).

If an excellent (or well, any) new offer appears, (not just) these guys are going to be all over it like flies on shit.

Most of these recruiters are clueless, so they’ll look at prices first and think ‘gee, I hit the jackpot - I can hire this guy from (insert a poor country here) for $3 per hour, that means he can deliver 500 hours of work for a laughable $1,500. Let’s hire him.’

The fact that he’ll most likely get what he’s paid for doesn’t make selling your $20+ services any easier, even though you might well provide the quality of work he needs.

Long story short: crazy competition, clueless clients, race-to-the-bottom wages, lots of yak shaving (time spent on everything but coding), a constant source of frustration and more. Generally, most of the horror stories you read are born here.

Who is it for: Beginners/juniors. I would argue that even for them it is going to be the most useful to only get their feet wet, learn how to communication with prospective clients get a feel for the work, and get out while the getting is good.

That said, I know a few guys who make decent money on Upwork - but it’s usually happening after a long history of working together, or if you spent a lot of time on the system and managed to figure it out.

Grabbing the quality jobs is more about ‘hacking the system’ with fantastic copywriting, knowing how and where to find great clients (and how to spot, reject, and fire bad ones), tweaking your profile to perfection and so on (observant readers might have noticed that ‘hacking the system’ doesn’t contain coding!)

While this skill set is precious for any developer, if you’d instead prefer concentrating on coding at this point in your career, you’ll want to spend that time elsewhere (you know, sharpening your code-fu, for example).

When: If you are just starting out.

Earning Potential: Low. It’s possible to crank it up to a decent level (there are plenty of devs making $50/hour or more on Upwork), but you’ll probably find it easier doing that elsewhere.

Online Marketplaces - HBTE

I once tried getting into TopTal just for fun. Well, it was not fun (unless shitting bricks under time pressure is your idea of ‘fun’). I got through the first round (said to be the most difficult) on my initial attempt, only to crash and burn in round 2 (you have 15 minutes to solve a problem fully, while a recruiter looks on over your shoulder. Also, the solution has to work correctly considering edge cases. I went off-track on a stupid edge case and ran out of time.)

Yay: Unlike LBTE marketplaces, you can make a decent buck here, the competition is way lower (since the barrier to entry is so high - Toptal, for example, claims that they employ the top 3% of developers. I hear others are even more strict). Once you’re in, you can expect a steady stream of work with good to great clients, for reasonable money (depending on your negotiation skills - I mentioned ‘Never Split the Difference’ above - it’s worth mentioning again!)

Nay: You have to be well-prepared (and prepare some more for the specific company of your choice), and it’s going to be a time consuming, arduous process. There are multiple rounds: HR call, automated, timed coding interview (Codility, HackerRank etc.), live interview (anything goes) and finally a take-home assignment which will usually take weeks to complete (they don’t expect you to reimplement Facebook, but still, the app has to be polished, tested, contain some show-off codes/features, etc).

The assignment is then reviewed again during a live session, and it’s not unheard of to fail this round, so it won’t be a walk in the park (i.e. rather than just commenting ‘cool app, bro!’ they are going to grill you properly, getting into the nitty-gritty details and throwing you various curve balls).

Who is it for: Experienced/senior devs only. You can apply regardless of your skill level (if for nothing else, to see how it works), but it’s a challenging set of hurdles you have to jump over to succeed.

When: Anytime, as long as you are an experienced developer.

Earning Potential: High - my sample size is not representative by any means, but the few devs I spoke to were charging between $50-$100 per hour.

Remote Consulting

Since there are various (sometimes conflicting) definitions of software consulting out there, let’s use this one - Software Consulting:

What is Software Consulting? The providing of expert knowledge in the software space to a third party for a fee. Software consulting is most often used when a company needs an outside, expert opinion regarding a business decision.

In other words, rather than writing code, you are telling your clients why and how they should write code (notice that according to this definition, you are not supposed to write any code yourself, but rather dispense your hard-earned knowledge in exchange for cold, hard cash)

Yay: Choose your clients, change projects often (this might be cited as a negative thing as well - your mileage might vary), work on well-defined tasks, dictate high prices, ‘hire’ (and fire) your clients, a high level of flexibility

Nay: Nowhere near the stability of a ‘proper’ remote job (on the flip side, nowhere near the restrictions of a proper remote job either). The volatility (changing clients/projects often, working for a different amount of time on each) might be off-putting to some.

Who is it for: Developers with specific expertise in a narrow topic or tool. You really have to be the belle of the ball to take a shot at true consulting.

When: Whenever, as long as you have that specific skill that makes you a true expert and possess unique knowledge. The idea is that it’s easier/cheaper for the client to hire you than to figure it out themselves.

Earning Potential: Very high

Bespoke Solutions

It’s difficult to list these precisely because they are unique and special (so you’ll have to shake and kick the Google tree harder than usual), but I’d like to mention one that stood out: Zerocracy. Zerocracy is a one-of-its-kind company/way of banging out projects.

Yay: There are very few things I can wholeheartedly say this about nowadays, but: Zerocracy is zero-bullshit certified. It can’t get any more transparent than this. Puzzle Driven Development (PDD) is a fascinating new way of managing tasks in a project, it can’t be compared to any other methodology I worked with so far (SCRUM, agile (whatever that means), RUP etc., have nothing on PDD).

The processes are so clearly defined, so intuitive and simple to follow that when I first came across this, I was thinking ‘why the hell isn’t everyone doing project management like this?!’

Nay: There are no real downsides here, but the MC running this fabulous show, Yegor Bugayenko (@yegor256, Yegor’s Blog) has some strongly held opinions and an exotic work style. However, there is definitely a (well-defined) method to his madness.

I agree with him on most things, but you might not, so be sure to check out his blog, youtube videos (YegorTube) to make sure you also agree, and you’re OK working under these circumstances.

Who is it for: Everyone who can adapt to the very atypical work environment (for example - no Slack, or any other form of communication among people on the same project. Talk about fully remote!)

You are assigned a mentor from the get-go, so unless you are a total beginner, and you are a fast learner, you could give it a shot - but see the next point.

When: I would not start here if it were my first remote job. Unless you are truly senior and have ample experience with various methodologies, consider leveling up elsewhere first.

Earning Potential Dependent on your experience - potentially very high. Even if you don’t start with a very high hourly rate, your prospects of moving up the ladder are probably the best of all the methods discussed so far.

Independent Freelancing

We’re moving from ‘packaged solutions’ (where most things are more or less well defined up front) to the realm of ‘roll your own.’

Independent freelancing means that you define some services you’ll offer, prepare a portfolio, set your prices and go client hunting.

Yay: Freedom! Like, real, almost-no-strings-attached freedom. If you have enough money, you can take off as many time as you want between projects (cash in the bank is the only limit - three-month trekking in Patagonia? Go for it. Mount Everest base camp - be my guest!)

If you are doing great work (word-of-mouth is still a powerful driving force), you should be able to make more money than with the other methods we’ve checked out so far.

Nay: As always, freedom comes at the cost of stability. It also means a lot more work (see next point), potentially feast and famine cycles, managing things you never thought a software engineer should manage, less coding than in a typical job, and more stress.

Who is it for: Seasoned developers who are OK putting in more work than the ‘traditional’ workplaces require.

‘More work’ doesn’t necessarily mean coding, but things like: finding clients, chasing payments, maintaining an online presence, communicating way more than you ever thought possible, extra paperwork and more.

Risk-averse people should think this through thoroughly, OR have a sizeable financial cushion to weather the dry spells.

When: Once you learned the ropes elsewhere and feel confident about your skills as well as the lifestyle. I would not recommend this to remote beginners or junior devs.

Earning Potential Unlimited!

Well, it’s limited by the billable hours you put in. Ideally it should be eight hours per day at the very maximum, preferably less (seeing as you’ll also have to do non-billable things).

Your hourly rate is going to have certain limits as well (if that’s not the case, you would be probably chilling on your yacht near your private island instead of reading this article).

If you multiply two limited numbers, the result will have an upper limit as well. However, this upper limit is going to be typically way higher than what we’ve discussed so far. Given the volatility and amount of risk involved, this is only fair!

Creating Courses/Infoproducts

Do you have experience with a topic that others would like to learn, and you have a knack for presenting your ideas in an easy-to-understand way? Creating courses might be your thing.

If you think this option is for experts only, you are wrong! Check the ‘Who is it for’ section to see why.

Yay: Along with the next point (making products), this option gives you the ultimate, no-strings-attached freedom: there are no meetings, set times, deadlines, time zone or geographical restrictions. No bosses nagging you, colleagues interrupting you, meetings distracting you.

It’s just you and the course you are creating. So Zen!

Nay: While ‘ultimate freedom’ might sound great, you can’t have your cake and eat it too!

For starters, you will need exceptional discipline - lack of meetings, check-ins, planning from your manager (and accountability to ensure you are sticking to the plan), milestones, deadlines etc. are non-existent by default.

While this might sound awesome at first, you will soon realize that without putting a system in place, you won’t get very far. Once the honeymoon phase fueled by the initial burst of motivation will be over, procrastination, second-guessing yourself, loss of focus etc. kick in.

Loneliness is another factor - unless you are creating the course together with someone else (not a very typical scenario), you will feel alone and isolated at least some of the time.

Last but not least: it will take a relatively long time to see the fruits of your labor.

Of course, there are solutions to all these problems (topic for another blog entry - tl;dr: create your own systems and stick to them, join accountability sites like wip.chat, work from coworking spaces to fight loneliness). My point is that you have to make a reality check and know what you are signing up for - great freedom comes with great responsibility.

Who is it for: For entrepreneurs who are good at explaining complex things in an easy to comprehend fashion, have strong writing or presentation skills.

You don’t need to be an expert to start here. There are (at least) two ways to succeed:

  1. Be an expert
  2. Be a curious novice - embrace the notion of the ‘relative expert’: you don’t need to be an expert on a global scale, it’s enough if you know more than your prospective students.

The curious novice can do something that the expert can’t: documenting the journey of discovery. The expert, on the other hand, has the ‘curse of knowledge’: (s)he doesn’t know what (s)he doesn’t know.

Read more here: How To Make Money With An Awesome Online Course: The Complete Guide

When: Anytime you feel like you gained enough non-trivial information or a comprehensive, broad overview of a topic and you are ready to put in the work to turn it into an infoproduct

Earning Potential: Unlimited, recurring, create-once-and-profit, sweet dollar rain. 7-figure courses are not uncommon at all.

Making Products (Bootstrapping, SaaS)

If you are even considering this option:

  1. stop reading
  2. visit makebook.io
  3. buy the book
  4. thank me (and more importantly, @levelsio) later

We have arrived at the last point - creating your own products. It’s not coincidental that I left this option for the end: this is easily the most mind-bogglingly complex (but also potentially the most ming-bogglingly rewarding) option of all. Also the riskiest, if you are not a bootstrapping expert.

Most of the options presented previously (remote job board, freelancing etc.) mean that you are building with a themed LEGO box that comes with a precise set of blocks and instructions (you know what you are creating in advance).

This option, however, doesn’t only mean you got a huge set of LEGOs and you can build whatever you want - it also means creating the blocks themselves first.

Does this sound intimidating? Exhilarating? Scary? Stimulating?

You need to make sure which of the above - this option needs extreme dedication, discipline and quite a bit of time to get anywhere.

Yay: See the ‘Yay’ section of the previous point (creating courses) - the positives here are virtually identical (total freedom).

There are some additional positive points here: creating a product is a more social activity than course creation. You can discuss, code together, ask for advice more naturally than in the case of infoproduct making, which is a more individualistic way of working.

Nay: See the ‘Nay’ section of the previous point (creating courses) - the negatives here are virtually identical.

I would add that the risk of going astray is much higher, though. Most product creators fail even before they get started, by building something that no one needs. While the same might happen with a course, it’s much easier to ask ‘Hey, do you need a Ruby on Rails course on Test Driven Development? ’ than ‘Hey, I’m building Frobtastic.com which is a (lengthy explanation that only makes sense to you, the creator), do you need it?’

The bootstrapper’s journey is way more complicated - you often won’t even know the starting point, you won’t have an idea where’s X that marks the spot, and you won’t have a map to get there either. At least with course creation these things are relatively clear.

Who is it for: This is the purest form of entrepreneurship of all the options listed here. The word ‘entrepreneur’ literally means ‘risk bearer’ - that should give you an idea of the undertaking.

That said, it’s very possible to play it safe and bootstrap products on the side. It’s not like you have to go all in or go home. It will take longer, sure, but in this case, you CAN have your cake and eat it too: make a steady income from other types of work while building your stuff on the side.

Once you start making enough money from your new venture, you can choose to leave your previous job.

Phil Knight was just another boring full-time accountant. He started selling athletic shoes on the side. After five years he decided it’s time to quit and focus on his company.

You might have heard of it: it’s called Nike.

When: Pretty much anytime if you are feeling adventurous!

Earning Potential Unlimited. ’nuff said.

Your Very Own Hand-crafted Recipe

This is kind of a filler point, so I’ll keep it short - the above ideas are just that: ideas. It’s a list of the most typical ways of working remotely I know of, but it is by no means exhaustive.

You can mix and match to create all kinds of weird cocktails (for example at the time of writing, I hold a full time remote job, a part time team lead/consulting job, and bootstrapping various things on the side).


Experiment with new things. Discard what doesn’t work for you (even if others claim that’s the best way to make money). Listen, but don’t follow anyone’s advice blindly - make your own kind of music!

Please comment below if you have further questions!

Also, subscribe to the newsletter to receive updates - I’m already working on part deux: “Everything you Ever Wanted to Know About Remote Work, Part II: Hacking the Job Interview by never Taking One”.

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