Working on a windy day at Playa Colorado in Nicaragua in 2019.

How to Start a Career as a Location Independent Technologist

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Editorial note: I am using a lot of jargon in this—very, very long—post. This is intentional. Some are subtle hints, some will hopefully give an introduction to things you’ll be running across in contemporary IT work. Have fun with it!


When I finally committed to the notion of leading a full-time nomadic lifestyle, I completely underestimated the impact it would have on my social life. I’d been working as a part-time, location-independent consultant for almost two decades. Through a series of very bad decisions on my part in 2018, most of my close friends had distanced themselves or walked away from me altogether. What did I have to lose?

Not much, actually.

But making friends in your forties is challenging. It’s even harder when you’re consistently transient. So I did what anyone else would do—I turned to Facebook.

I stumbled on a handful of groups centered around things like vanlife, camping in your pickup truck, and being a “digital nomad”. It was a relief to find so many kindred folks from all over the world in one place, virtual or not. Not the same as meeting someone in person, but still a great start.

One of the recurring questions in all these groups is, “What type of work do you do?” There’s a lot of overlap, and “digital” type work certainly seems to be a common characteristic. But a lot of people are just figuring out to how get started and are looking for advice.

I offered some work-related advice in one of these groups and there was more of a response than I expected. After just a few seconds of banging out a comment, I realized that the answer wasn’t exactly Facebook comment material.

So, without further ado, here is my wholly incomplete and thoroughly biased guide to Starting a Career as a Location Independent Technologist.

Where Did I Start?

I spent the majority of my working life purposefully building a business that would allow location independence (thank you 4HWW). Back when I got started, full-time remote work wasn’t very common—technology wasn’t quite there and there was just was no good precedent. The assumption was that “working from home” meant that you were fucking off at the beach, usually an apt observation. You had to pay your dues sitting in a cube farm or—if you were really lucky—an actual office. And I did exactly that for a few years before I was able to go completely remote nearly fifteen years ago. The good news it that nowadays, remote workers—and even completely “virtual” companies—are extremely common. You can get started while working remotely if you have a good plan and know where to look.

My start was on the “operations” side—think IT support, maintaining servers, that type of thing—back in the mid 90s. Futurists were proclaiming that “e-commerce” was the next big thing, bravely predicting that one day soon nearly all shopping would be conducted on the Internet. Most people in those days hadn’t used the Internet much, maybe email, but certainly not the World Wide Web. This notion of shopping online was crazy to almost everyone.

But not my boss—I worked for a guy that sold dildos, true story—was all-in. He walked into my office one day and, on the spot, put me in charge of e-commerce. I had no clue what the hell that meant, but it sounded like a promotion and I was getting tired of managing servers and POS systems. I hunkered down and did my part to usher in the era of shameless sex-toy consumption.

The change in job title instantly shifted me from operations to programming, or nowadays, “development”. I had played around with a TRS-80 when I was a kid, but otherwise, I had little relevant experience. I taught myself a now mostly dead web programming language called Cold Fusion (laugh it up, it got the job done), and I was off to the races. I loved every second of it. I had found my professional calling, my craft.

Today I mostly consult on strategy, cloud computing, automation and devops, and software architecture. I still write code, but it’s usually for my own products, some new startup I’m involved with, or just to stay up-to-date.

Where Do You Start?

At the beginning, probably. But it can, at times, be hard to find the beginning in tech (and yes, this really is what things are like).

There’s a tremendous amount of specialization in infotech. Just in software development, you can pick from literally hundreds of niche areas. And even within these there are sub-specialties. For example, in web development you have: full-stack developers, front-end developers, back-end developers, database developers, API developers, language-specific development (do you want to code in C++, Java, C#, JavaScript, Python, Ruby?), framework-specific developers (do you want to specialize in Node, React, Rails, .NET?) to name just a few. The array of options is huge.

The point here is that, when getting started, you don’t know what you don’t know. You may think that you want to be a mobile developer (that express gravy train has left the station, by the way), but through the course of learning Objective-C or Swift or Java or React, you may discover that what you’re really interested in is API development (an application programming interface, a mechanism frequently used alongside mobile apps). You double-down on building RESTful JSON web APIs, and then, blammo, in ten years they become obsolete. And you move on to the next thing.

It’s all a big experiment, and it’s all very dynamic. That’s the game. If you commit to this path—and you will have to if you really want it to be fruitful, this is not a get-rich-quick endeavor—you will be in a state of constant change and lifelong learning. Malcom Gladwell’s contention of expertise falls apart here. You will never truly become an expert in this stuff as a whole, it just changes way too fast. And this is why you absolutely must specialize.

In my opinion—and I already warned you I’m biased—programming is probably the best place to start. It’s free to learn online and in high-demand. You might not make a career out of it development specifically, but if you stay in IT you’re almost guaranteed to need some level of programming experience. For example, network administrators frequently code bash or Powershell scripts to automate complex or recurring tasks, and tons of other commercial businesses systems are customized by writing code. Even other careers, like marketing and biology, are beginning to require some level of programming skill. This is a trend that will only expand.

Master the Basics

Let’s go ahead and address the elephant in the room.

Do you need a college degree in Computer Science or Information Technology to get started? Well, that depends.

If you have aspirations to go into management—and if your goal is to be location independent, this is a terrible idea—then yes, you’ll probably need a four year degree. Outside of that and certain highly competitive positions, shops tend to lean more towards actual experience and ability than credentials. More than anything, they want to see passion and ability. If you’re planning to work as a contractor, then you get to set the rules, but you’ll still have to demonstrate this. How you brand and market yourself is the key differentiator here.

I have some bad news for you recent college graduates: four years of school is not actual experience. Most colleges don’t even scratch the surface of what you’ll actually be doing. Instead, they give you an education on the fundamental concepts of engineering and mathematics, and they teach you how to learn. And it’s this knowledge—not the degree itself—that can make a huge difference in your career. If you want to reach the upper echelons of your craft you absolutely must understand the science involved.

I also have some bad news for those of you jumping in without a degree: absent of any real on-the-job experience, a degree is one of the only indicators that you might actually know what the hell you’re doing. And, for the most part, you don’t. It’s a conundrum that you’ll have to hack your way through. But if you’re persistent and creative, you can pull it off.

For now, do the extra work to understand the basics and what’s happening under the proverbial hood, even when it seems unnecessary. Don’t rest easy with “just make it wok”. When the next new hot language or technology arrives, your command of the underlying mechanics is what will put you ahead of the curve. Investing time in this now will pay massive dividends for you on down the road, I guarantee it.

Hacking Experience

So, if you need experience to get a job and a job to get experience, how do you ever actually break in? Get creative.

Fake It Until You Make It

I accidentally underbid the first consulting project I sold by about $100,000. I knew I was way off on my pricing as soon as the client saw the quote. They accepted it almost immediately with no negotiation. Oops.

I still saw this as a win though. I’d learned enough about the technology involved to author a detailed proposal outlining how we would build this new system, but I had no clue how to actually do it.

In hindsight, I realize that the tech stakeholders on the project knew what I was up to. They were getting a deal that would look great to their bosses, but they knew they were going to have their hands full with a rookie. And they were right. I floundered like a cat in a dryer.

Fortunately, they were kind enough to guide me through the process and ignore some pretty embarrassing missteps. I don’t know if they felt sorry for me or just wanted to get it over with, but they taught me things that would shape the course of my career. In any case, I spent the next three months sitting a tiny table in Starbucks twelve hours a day, seven days a week with a pile of tech books and my laptop. And it’s one of my fondest work memories.

I’m not suggesting that you outright lie—you will get called out—but you’re going to have to come with some level of confidence to get your foot in the door. Most experienced people in this business have been there and they’ll probably give you a chance. Just don’t let that confidence drift into arrogance, a great way to be immediately shut down. And this world is smaller that you might think.

Subsidize With Your Friends and Family

Doing business with friends and family can be dangerous, but it’s an option. Have an uncle with small business that needs a website or help with his network? Offer to do the work for free or at a greatly reduced price. This gives you an opportunity to learn, hopefully with less pressure, and maybe a little money to boot.

A word of caution here: be absolutely clear that whatever pricing you offer is considerably below market value and that this is helping you launch your new career. Here’s why:

First, there are going to be problems. Software bugs, network downtime, blatant fuck ups. And you’re probably not going to know how to manage these situations smoothly. The last thing you want to do is disrupt your sister’s business continuity or get fired by your parents. Set very real expectations and put them in writing. Sounds cold, but this is of particular important with family and friends.

Second, if this is the first time your mark has been involved in this type of project, you could be setting a dangerous precedent. Their perception of pricing, value, and effort will all be radically skewed, and this can make it nearly impossible for them to hire competent people on down the road. And then they’ll come back to you for more discount work. This ultimately commoditizes your skills if you take the work, and if you turn it down because you have better options you risk straining the relationship.

Contribute to Open Source

There is an entire ecosystem of software out there called “open-source”. This is software who’s source code is publicly accessible. It’s typically free (as in beer) if terms of a license agreement are met. And if you go into programming—particularly web or mobile development—you will be using tons of it.

Most open source software is built by teams of volunteers. They range from experienced professionals working full-time corporate or consulting jobs, to students, to people just getting started, to hobbyists. They all have one thing in common—passion. And it’s a great place for you to get real experience working with a real remote team, potentially on a high-profile project.

Once you feel like your skills are ready, seek an open-source project that you find interesting and ask to become a contributor. Not only will you get to put your skills to the test, you’ll also get to see some really well written code, some really poorly written code, and you’ll have people reviewing your work and giving you feedback. Be honest about your experience and realistic about what you take on. Github is the epicenter of OSS.

There’s a potential short-circuit career path here: if you get on an OSS team that’s lead by people working on paid projects (most of them) and you’ve proven yourself, they are your way in. Work your ass off, get to know the project leaders, ask questions, and they’ll probably be willing to give you a chance when you’re ready for a job.

Take Some Continuing Education Classes

Most colleges have a continuing education department and most of these offer some type of programming, network engineering, or database management classes. They’re usually pretty affordable (look at smaller community colleges) and, like open source, are usually led by people working in industry.

This is a great way to learn and it’s a great place to ask questions and get real, hands-on help. I had a student when I was teaching in Atlanta that would bring his personal projects in and we’d review his code after class. The guy was fascinating and I learned at least as much more from him as he did from me.

And just like in the open-source world, if the instructor is gainfully employed elsewhere (most of them) and you impress them, they’ll be able to introduce you to local recruiters, hiring managers, other developers, and maybe even pass your resume around. Build a relationship first then ask for help.

Network

This, more than anything, will have an impact on your ability to be successful long-term. Knowing people who can mentor you, provide feedback, open doors, make introductions, or give referrals is a constant in all business. Networking in knowledge work, especially if you’re a freelancer, is really just an exercise in sales. You’re selling your own winning personality and your ability to help someone make more money. Might not be the woman you’re talking to, but I bet she knows someone.

Go to Meetups, trade meetings, presentations, whatever you can find wherever you are. Walk up and introduce yourself to people, awkward at first but you’ll adjust (remember that confidence thing?). Exchange business cards. Tell your story—people chained to a desk love our kind of story—and then turn that into how it benefits them. Ask for advice, offer to help. Take notes, follow-up. Learn how to use a CRM.

All-In or Side Hustle?

Assuming you’re not currently a full time student, you have two basic options for getting started…

First, keep working your “day job” and learn programming in your spare time. There are plenty of places to do this online for free. Ditto for many capable development tools—look for open-source tools like Atom or free or “community editon” packages like XCode, Visual Studio, or IntelliJ.

Pick a general purpose language to start. Python is a a good choice because it can be used for a variety of purposes, it’s interpreted so getting set up is a bit easier, and it has the same properties as many high-level object oriented (OO) languages. JavaScript is another good place to start, as this is the hot trend at the moment (2019). Frameworks like V8 and Node.js have taken JavaScript far beyond the web browser. ES6 (the JavaScript “standard”) is a major step in the OO direction for the language, further signaling its continued evolution.

Don’t get too caught up in this. There are literally hundreds of programming language choices. Start with what feels the most “learnable” to you and go from there. You’ll pick up other languages over time and as you narrow in on your interests.

Your second option is to get a job that will start exposing you to these things, and that will provide some on-the-job training. Entry-level tech support, QA testing, and technical writing are good places to get your foot in the door. You’ll still be spending your free time learning, but you’ll also be building valuable industry experience and interacting with more experienced people and getting paid for it.

Finding Work

Outside of pestering open-source project owners, begging your teachers, or bugging the shit out of your family, where are the best places to find remote tech work?

Reach Out Directly

Start with companies that are experienced with hiring remote workers. Digital (advertising) agencies, software companies, and small startups are going to be your best bets. They’ll be more amenable to a full- or part-time remote arrangement, because they’re already doing it.

This doesn’t mean that you should completely discount big companies. Even some big companies allow this. I have a good friend that is a technical project manager for one of the world’s largest companies, and he in his wife travel the US full-time in an Airsteam.

Third Party Recruiters

You might also consider using third-party recruiters when you first get started. There are advantages and disadvantages to this, not the least of which is that they’re going to take a cut of your wage. But a good recruiter will have close relationships with hiring managers for thousands of positions. In the States, some recruiters will want you to work on a W2 (full time contractor) status which means you’ll get some benefits but can then also be required to work on-site.

You probably want 1099 (freelancer) or “corp-to-corp” (a business entity, e.g. an LLC) status, but you might not be able to demand this when you first start out. It gives you the most geographic flexibility and legal protection, but it can also make things more difficult for the recruiter. Note that either of these also makes you are a business owner. You’ll have to deal with bookkeeping, extra taxes, insurance, buying equipment and software licenses, and all kinds of other stuff. It’s not for everyone, so understand what you’re getting yourself in to.

If you decide to use a recruiter, do your research and use someone reputable—there are many sharks in that ocean. Ask folks in you network for referrals and ask the recruiter lots of questions. You’ll learn who to stay away from very quickly.

Never, ever work without a contract, read it in its entirety, and seek legal help if you don’t understand anything in it.

Gig Marketplaces

There are also gig marketplaces like Upwork, Fiverr, et al. These can get you some experience, but because they are global this can sometimes commoditize the work—a “race to the bottom” as some would say.

Socio-economic debate aside, these sites are full of customers with unrealistic budgets and limited knowledge of what they’re asking for. Because of this, they can be be difficult to deal with and the risk of a project going sideways is substantially higher. Still, this can be a good way to subsidize your experience, and there are some very good projects to be found, just proceed carefully. Again, reach out to your network for advice on where to go for the type of work you’ve chosen.

How Much Can I Actually Make?

In the US, as a contractor with a couple years of solid experience under your belt (and depending on your chosen direction and location), you can expect to make $25-$50 USD per hour. Potentially more if you’re a real rockstar or are dealing with clients in a location with a high cost-of-living. Full-time work will usually will pay less on an hourly basis, but will also provide benefits, which can usually be factored in at about 30%.

As you gain experience, you can begin to push your rates or salary expectations up, you can experience with other strategies like value-based pricing, block pricing, or fixed fees. You can build your own products and generate passive income. You can use your new skills to get rich, change the world, help others, the sky really is the limit.

Whichever direction you decide to go, I wish you all the best. This is a craft that has given me a great deal of personal and professional satisfaction, has allowed me to learn about all kinds of different things and meet people from all over the world, and has been pretty good to me financially.

Let me know how it goes.

Good luck!

See y’all on the trails!
-klc


All poor career choices.

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