Online Careers Anyone Can Test-Drive

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I turned 30 this month.

30 is a psychological turning point for many of us. With a decade of work experience under our belt we’re no longer rosy post-grads. Our career has had enough time to shape our disposition toward life.

Maybe we’re happier. We’re better off than we were.

Maybe we’re feeling helpless. Our career isn’t what we thought. We grabbed onto a safe job at some point. Now we look up and see that safe job has become our career. Like it or not.

No matter how old you are, with age your career options become constricted. Even having a soul-crushing day job can be justified when you consider the paycheck it gives you. It’s easy to dream big when you have nothing to lose, but once you’ve found security it’s better not to rock the boat.

I disagree.

If you’re unhappy with your career, that absolutely needs to be addressed. You aren’t just exchanging your labor and time for that paycheck—you’re paying your life force. Waking up to spend the bulk of your day doing something you hate is a harmful way to spend one day, much less 40-50 years. Fulfillment in your career is absolutely worth fighting for.

But you no longer have to stop your old career before beginning a new one—quitting dramatically on day one, figuring out the next step on day two. By using online resources, you can explore on the side, get an education on the side, and even begin to work on the side.

We live in a time when it’s possible to test drive career changes—everything from learning new skills to getting paid for it—free from significant risk. As your side hustle gets momentum, you can consider taking it full time. No need to let go of one branch of the tree until you’ve got a firm grasp on the next.

In this article, I’ll lay out a few careers you could get into. At any age. From any place. With any prior job experience. Even better, many of these careers can be done entirely online. How does a zero minute commute time sound?

I won’t ask you to shell out for another student loan. The cost of bachelor’s and master’s degrees is a joke that we haven’t learned to laugh at yet.

These careers don’t require you to be a genius. If you can commit to learning a new craft and honing it, you can succeed.

These careers require passion. Work ethic. Creative thinking. In other words, qualities you possess. Come as you are.

Digital Design

Many designers started their career with a bachelor’s degree in design. But does holding that degree mean you're a great designer?

No way.

Companies that hire designers know this. Only hopelessly old-fashioned companies will demand an art degree for a design position (though it might appear on the job posting). What matters is your portfolio. No school or internship holds a monopoly on your ability to contribute to that.

What school and internships will give you is an excuse to work on projects, constructive criticism on your work, and a spoon-fed curriculum of topics to research. Without school, you will need to figure those out yourself.

Study the fundamentals of design. I’ve listed a few good resources below. But also study the world around you.

As you start to become aware of good design, take pictures or screenshots and add them to an inspiration folder. This becomes a great resource when you’re starting a new project. There’s no harm in copying layout, icon, or typographic ideas in your own compositions. You might even remake a great design as an exercise. No problem, so long as you don’t try to pass it off as your own work! In fact, blatant copying is a great way to understand some of the techniques behind your favorite works.

As you’re learning, go ahead and work on projects that you want to work on. But your creativity will be stretched further by following an external prompt or specifications. You can find such design challenges within general design books and courses. But for a more directed source of challenges, try the book Creative Workshop: 80 Challenges to Sharpen Your Design Skills. You can also submit your work to one of’s design challenges.

You don’t need to be a jack-of-all-trades. Logo design, infographics, poster design, document design, website design, motion graphics, branding... all have enough work to sustain a career. There are a lot of designers out there working on drastically different types of work. It’s very hard to get bored.

Once you’re capable of creating work that can satisfy other people’s needs, you’re ready to get paid for it. Get an account on On Upwork, you can find hundreds of postings from companies and individuals who need work done. Pick and choose the jobs you can handle, put in a bid, and start getting paid. As you get jobs under your belt and quality portfolio pieces, you can charge more for your work. Clients may even approach you directly.

Clients are your lifeblood. I’ve been one of these clients before, hiring several designers through Upwork. Two of those designers blew me away with their work so much that they began getting regular commissions.

As a designer, you don’t need to get all your clients through a marketplace like Upwork. Get your name out there with a portfolio website, profile on Behance and Dribbble, and good old fashioned networking.

The ultimate client is a company offering a full-time position. Many love the gig lifestyle, but secure employment is always an option here. This is the moment where you can stop working in the evenings and weekends and start making a day job out of it.

Further Resources

Online Courses

Become a Graphic Designer Learning Path on (LinkedIn Learning)

Design a Logo Learning Path on (LinkedIn Learning)

Become a Design Business Owner Learning Path on (LinkedIn Learning)

Graphic Design Learning Path on Pluralsight

Illustrator CC for Creative Professionals Learning Path on Pluralsight

Photoshop for Creative Professionals Learning Path on Pluralsight

InDesign CC for Creative Professionals Learning Path on Pluralsight

Graphic Design Bootcamp on Udemy

Graphic Design Masterclass: Learn Graphic Design in Projects on Udemy

Graphic Design Specialization by CalArts on Coursera


Graphic Design: The New Basics by Ellen Lupton and Jennifer Cole Phillips

Designing with Type by by James Craig and Irene Korol Scala

The Elements of Graphic Design by Alex W. White

Don’t Make Me Think: A Common Sense Approach to Web Usability by Steve Krug

Creative Workshop: 80 Challenges to Sharpen Your Design Skills by David Sherwin

Software & Web Development

Demand is massive, salaries are high, education options are plentiful. There’s never been a better time to learn to code.

If coding sounds arcane and unapproachable to you right now, that’s the exact reason so many are willing to pay for this service. Give yourself a week long crash course and most of that mysticism will fade away as you notice the perfectly logical way in which we give instructions to computers.

Once you learn to code, you’ll notice the huge diversity of jobs. Some developers gravitate towards coding user interfaces. Some towards server-side back end code. Still others specialize in databases including the storing and reporting of large data sets. Data Science is one of the hottest fields in the world right now.

And don’t forget about other platforms. You might choose to specialize in iOS, Android, VR, AR...

The point is that even if the idea of writing code doesn’t initially grab you, there are branches within the tree of specializations that might appeal to you. Not all authors love fiddling around with words, but they love telling stories. Likewise, it’s exciting to use code to bring new things into existence, as part of a team or by yourself.

Online resources abound. I’m going to plug one of my heroes Simon Allardice, whose What is Programming? course on Pluralsight is a thoughtful and gentle introduction to the subject.

For a more interactive experience, I suggest Codecademy, Khan Academy and CodeSchool.

This should give you a taste if coding is for you. If it is, I want to plug a single resource to take you the rest of the way. Udacity is an e-learning website which offers a number of Nanodegrees—miniature specializations that get you working on professional-level projects with a tutor, cohort of classmates, and some of the best lessons I’ve seen.

They do cost money, but we’re talking a few hundred dollars. I’ve participated in two Nanodegrees and can vouch for their value.

I like Udacity for their education resources, but love them for their commitment to getting students a job. Nanodegrees are built around projects as a way to get you pieces for your portfolio. Upon graduation, you can also take advantage of their career team who will help you get an actual job or internship. It’s not a guarantee, but many student success stories attest to the effectiveness of this program.

I need to caution you though. Like a bachelor’s degree, you can drift through a Nanodegree like a disinterested ghost, check off all the boxes, and secure your piece of paper. But that piece of paper doesn’t make you employable.

Nurture a curiosity in what you’re doing. Make side projects when you learn a new skill. Challenge yourself to see an idea through to completion. If you find something you don’t understand, keep digging until you understand it.

I suspect one reason Udacity no longer guarantees employment upon graduation (as they did up to December 2017) is that companies always look for something extra. Passion. Curiosity to make things just for fun. Udacity needs to define a benchmark for what quality of work deserves a degree. But once that benchmark is set, unmotivated students will aim to slink their way over it with the least amount of effort necessary.

Don’t do this. Or at least, don’t do this and expect to get results. The software industry is getting enlightened—they know that you need don’t need a degree to be employable. That’s great news! But the flipside is that a degree is no longer enough. Seek to impress that future employer with every project you do.

Further Resources


Learn to Code Nanodegree on Udacity

Front End Web Developer Nanodegree on Udacity (I completed this one!)

Full Stack Web Developer Nanodegree on Udacity

Become an iOS Developer Nanodegree on Udacity

Become an Android Developer Nanodegree on Udacity

Copywriting and Copy Editing

I group these two very different disciplines together because they both involve the written word.

Copywriting is about composing persuasive articles, emails and sales pitches. Copy editing is the process of revising writing for correctness, readability and accuracy. In my mind they appeal to very different personalities but there’s no reason you couldn’t excel in both.


Your goal as a copywriter is to make your clients money. You achieve that with approachable and hyper-persuasive writing skills.

It’s 2018. Companies have an arsenal of multimedia options at their disposal. But the written word still has the greatest persuasive power for converting browsers to buyers. That fact is reflected in the huge demand for copywriters who are good at their job.

Even if persuasive writing is not your thing, companies seek out dependable writers of all genres. We live in a content-rich world. Generating that content takes time. That’s why an individual who can deliver crisp writing on time and to specification has so much value.

Writers working through Upwork create articles, blogs, technical writings, fiction and persuasive copy. Like designers, writers bid on projects that companies post, deliver the work, and get paid. As you build up your history of successful jobs you’ll be able to bid higher and more selectively.

If you’re not yet confident in your writing skills the best thing you can do is to write as much as you can. Start up a personal blog or write articles on what you’re passionate about. Even long-form posts on Facebook can get you thinking about how to write for an audience.

Copywriting is its own beast. You should understand the basics of marketing, particularly customer psychology. The successful copywriter is not the one who can write the most perfectly, but the one who can grab you from the first sentence and string you along to the end.

Short sentences. Short paragraphs.

Memorable phrases that grab you by the ears and don’t let go.

It’s also valuable to understand the basics of SEO. Great online content is not just engaging, it’s easy to discover. Knowing how to write keyword-rich content will make your clients very happy.

There is a plethora of copywriting resources online. And since they’re generally taught by copywriters, you’ll find their pitches particularly persuasive!

But older content has not lost its potency. We’re talking about the written word and human psychology after all. The nouns and verbs might change, but the underlying soul stays the same. For a great resource, check out The Gary Halbert Letter or the book Ogilvy on Advertising.

Regardless whether you go the copywriting route or for some other type of writing, web presence and networking skills are all-important in securing long-term clients. A personal blog will be a great resource, as will relationships with local businesses and answering CraigsList ads. Get yourself on a freelance writer directory to give yourself the best chance of discovery.

Of course full-time employment is very possible for writers if that’s what you want. Search for Technical Writer, Content Writer, Copywriter or Marketing Writer jobs.



The Gary Halbert Letter

The Kopywriting Kourse by Neville Medhora

Copywriting Master Course - Work From Home 3 Hours A Week! on Udemy

Copywriting: How To Be A Crazy Good Copywriter on Udemy


Ogilvy on Advertising by David Ogilvy

The Copywriter's Handbook: A Step-By-Step Guide To Writing Copy That Sells by Robert Bly

This book will teach you how to write better by Neville Medhora

High Conversion E-Mail Copywriting by Scott Frothingham

The Adweek Copywriting Handbook by Joseph Sugarman

The Ultimate Sales Letter by Dan Kennedy

Copy editing

To be a great copy editor, you don’t have to fly into a rage when someone uses the wrong form of “there”… but it helps.

Copyediting requires a meticulous and encyclopedic command of the English language. Your role is to stand between the writer and the public, checking the text for correctness, accuracy, and readability.

Despite the reputation copy editors get for being comma pushers, there’s actually a high amount of artistry to it. You’re not just a glorified spellchecker. You’re the champion of great writing.

When a piece of writing arrives on your desk you not only look for grammatical violations, you look for the heart of the text and whether each sentence is performing its job. Yes, depending on the job you might be limited to checking for grammar or spelling violations. But in another job you might serve as the gatekeeper to publication, commanding authors to rewrite their work and submit again.

More likely, the expectations laid upon you will fall somewhere in between. And those expectations won’t always be stated outright. It takes intelligence and maturity to understand the power structure at play in each specific job.

Good copy editors know that the English language does not have one set of rules. Instead, they familiarize themselves with a number of style guides—including an organization’s internal style guide if they have one. They know that AP style requires spaces on either side of their em dashes, but Chicago doesn’t. If they don’t, they at least know it’s something to look up. Consistent, intentional usage is key.

You’re more likely to run into issues getting copy editing jobs if you don’t have formal training—an English degree looks attractive to a prospective client. Some companies make you go through an editing test. If you’re going the freelance route, your best assets are satisfied clients. Short-term copy editing jobs can be found on Upwork, CraigsList, and your local community.

If you decide to get formal training, don’t go back to school for a degree. UCSD offers an online certificate course that can be completed in less than a year for $1200. This program will give you expert feedback on your work, access to thoughtful instructors, an awareness of how your role within an organization should affect your work, and a treasure trove of resources that you’ll use on a daily basis.

Curious? Dip into the world of serious copy editing with a few of the books listed below. Or check out the English Language & Usage Stack Exchange and Editors’ Association of Earth Facebook group to find a community of passionate people discussing the finer points of English.



The Copyeditor's Handbook by Amy Einsohn

The Subversive Copy Editor by Carol Fisher Saller

The Chicago Manual of Style, 17th Edition

Associated Press Stylebook 2017

MLA Handbook, 8th Edition

FranklinCovey Style Guide: For Business and Technical Communication

Microsoft Manual of Style

More careers

When brainstorming careers for this article, I quickly realized that this could become a novel if I wasn’t careful. So allow me to list a few more careers that fit into this mold.

Computer Hardware, Networking, The Cloud

I had a class in high school called A+ Certification, which is essentially learning how to fix computer problems. At the time, the idea of making a career out of fixing computer problems didn’t seem very exciting to me—I spent a year and a half working for our school district’s tech department and installed Windows XP about a half a million times.

But A+ Certification is just one step on a long pathway that takes you into more and more advanced certifications. Start with A+, move onto Network+, soon you’re learning advanced topics in cybersecurity or infrastructure. Then you can get into the vendor-specific certifications: Cisco, Microsoft Azure, AWS. These are high-paying jobs. Folks with AWS certifications pull down an average of $119,000 salaries.

So if you’ve considered the technical support route but were scared off by the prospect of fixing people’s email all day, consider the 3-5 year range. If you have a natural inclination towards computers anyway, you could do a lot worse.

Translation and Interpretation

Know a foreign language? Monetize that!

Translation work can be found all over the internet. Upwork is one example. One Hour Translation is another. There’s also Gengo, Lingosaur, Unbabel, Freelancer… You can do this work from home.

Of course translation can be a full-time job of its own. But many people like the flexibility of accepting work when they’re ready to work. Look out for translation agencies in the native country of your second language. I got involved with a media translation agency in Japan which can connect me with video subtitling jobs.

Interpretation is another way to monetize your language ability. It’s much too intense for me, personally, and it’s more likely to require you to move around from place to place for the jobs, but it’s a great and profitable option for those who can handle it.

Photography and Videography

I know about ten people from high school and college who have gone on to make a freelance photography or videography career for themselves. Some do it on the side, some do it as part of a larger service offering.

You will probably need to invest in some quality equipment before getting started, particularly for video, but with enough clients this career can pay off. Wedding photography and videography is particularly lucrative (we happily paid high prices for our wedding photographer—it’s not something you want to mess up!)

Since you will need to be geographically close to your subjects (telephoto lenses only zoom so far), you’ll need to seek out clients by advertising locally. A few of my photographer friends pay for their own travel to neighboring states coupled with an impressive web presence in order to find clients. Social media presence is a must! If you’re a photographer, learn to use Instagram. A great IG game can spin your previous jobs into powerful advertisements for new clients.

Virtual Assistants

Virtual Assistants are flexible, organized individuals who save their clients’ time.

It goes like this: a professional figures out (perhaps after reading The 4-Hour Work Week) that not all of the tasks they do in the day require their expertise. They then decide to delegate the more repetitive, time-consuming tasks to somebody else.

So they find a virtual assistant and train them on whatever it is they don’t want to spend time on. It might be managing their email, researching topics, managing their social media, scheduling, even writing letters and thank you cards. Really, anything that frees up the client’s time could be in the job description.

For this reason, good virtual assistants have excellent organization and communication abilities. They don’t need a lot of hand-holding and can figure out how to streamline repetitive tasks.

Many people look overseas for their virtual assistants, but there is plenty of demand for domestic virtual assistants. Particularly if they are depended upon to write or proofread English on behalf of the client, or if the time zone overlap is critical.

To get an idea of the life of a virtual assistant and some of the jobs they do, check out the Administrative Support section of Upwork.


I hope you takeaway from this article a sense of how many options there are. Did you see any that you could do? Obviously there will be some skill gaps, but likewise there are plenty of educational resources to help you span those gaps.

My challenge for you is to humor me. If you feel any dissatisfaction with your career, look into some of the options I listed above. Read some of the resources, try your hand at some of the work.

I think you might be surprised.

Not by the ease of the learning resources. Not by the amount of demand there is for these jobs online.

But by how much of your own potential you have yet to unlock.