Jaylon Ramsay
Mar 10 · 13 min read

If freelancers could invent our own clichés, one might be:

No two jobs are the same.

Each gig we take on brings with it new personalities, new challenges and new rewards. Despite these differences, most any freelancing gig will fit into one of these twenty types.

Where does the job you’re (supposed to be) working on now fit in?

Have you done each of these kinds of jobs before?

My guess is that most experienced freelancers will have encountered quite a few!

Image found: blog.siasat.pk

1. The magnum opus

The job you’ve always wanted, the job you’ll tell your grandkids about. You get asked to write a book, land design work for a super-company like Coca Cola or get an article published in Forbes.

The money doesn’t really matter — though it’s probably pretty good! Because this kind of opportunity doesn’t come along every day, you make this job personal, you obsess over it and make sure every single detail has been polished to a brilliant shine.


These kinds of jobs can feel more like play than work. They’re hard to forget for all the right reasons, and can take your credibility and perceived value as a freelancer to the next level.


Magnum opus jobs can be time vacuums. Being paid $X, 000 for a project doesn’t work out too much if you spend a hundreds of hours polishing up the bells and whistles.

2. The English Patient

Widely regarded as a good movie, I’m talking more about the reaction Elaine (the Seinfeld character) had when forced to see the film — which she hated — for the third time:

The English Patient job instills the same feeling of never-ending pain and boredom. It just won’t end.

When you think it’s finished, you discover that something isn’t working. When you close the door on it, the client asks you to revise this element, and tweak that paragraph.

It’s the job you quoted at twenty hours that ends up taking a hundred and twenty. It just… won’t… end.


If you’re getting paid by the hour, the money might help soothe the pain.


If you were paid in advance based on a quote, you’ll be cursing like a flea-bitten trooper while you wonder how this happened again.

3. The “everything that could go wrong, did go wrong” gig

This project gives you nightmares. You perfected your design, only to find it looked like a Picasso painting in Internet Explorer.

Your draft article got lost when your computer water-cooling system sprang a leak and started a small electrical fire.

You spilled ink on your painstakingly-crafted poster concept. You deleted the wrong file, and the application broke.

The frustration and disappointment makes you wish you hadn’t accepted the job in the first place. Your only goal is to get the thing over and done with.


You learn from your mistakes.


Sanity -2.

4. The favor for a friend

Your best friend just happens to be launching a blog. You offer to design it for them, happy to work for a client you can trust, and you also offer them a rate that’s well below your usual.

This sounds like a great idea, until you discover that working for rock-bottom rates isn’t fun once the glow of appreciation and excitement has worn off. As a result, you start prioritizing the job last in order to do the work that really pays your bills.

As the project stretches longer, you ultimately know that your friend isn’t going to start making angry phone calls in the same way a client might. Unless, of course, it gets too out of hand…


You give your friend access to a service they might otherwise not have been able to afford. You also get to work for a client you know and trust and care about.


When things go wrong, they also get tricky. It’s impossible not to take a terse business email personally if the author is a close friend. If you let them down, or if they let you down, your friendship might suffer, either through broaching the issue directly, or slowly cultivating silent resentment.

5. The Ramen Noodle fund raiser

You know you’re worth more than $10 an hour. You nod your head when other freelancers talk about the importance of charging what you’re worth.

But when faced with an empty pantry or a stack of increasingly urgent-looking bills, most of us will put comfort before honor.


If the only work you can get is low-paid, it’s probably still better than no work. What would you be doing instead? Some would argue you should spend the time looking for high-quality work. Other freelancers would argue this task is a little tricky when you can barely afford the internet required to market yourself.


Too much of this kind of work can negatively influence the way you perceive the value of your own services. Being confident about asking for $50 an hour when you’ve been working for $10 is a tough leap, and some freelancers find it difficult to get their mojo back.

6. The pot of gold

You’re not quite sure how you landed it. If all your jobs were paid like this one, you’d be stinking rich.

You’re doing easy work for $50, $75, maybe $100 an hour.

You tell your friends about it and smile when you earn in 90 minutes what you usually make in a day.

You make sure to tell the client that you’re available for any other work they need you to do. Anything at all. Really — anything.


Making good money feels great and boosts your confidence about the kind of rates you can achieve.


Your bread and butter jobs might seem lackluster in comparison. It’s important to remember that these pot of gold jobs won’t be the core of your income. Appreciate them, but acknowledge that you should not always expect money to be this easy.

7. The “it will look good in your portfolio” job

You’re opposed to the idea of spec work. You think it’s a bad thing for freelancing, and you’ve denounced it on blogs and in forums.

But one particular opportunity comes up that you can’t help but accept:

A competition you’d do anything to win, or the chance to work for the client you’ve always dreamed of.

You give in, but you feel guilty about it.


Spec work shows itself when you get nothing in return. From the perspective of those who get the jobs, or those who win the competition, it probably seems very much worth it.


Most people don’t get the jobs, or win the competitions.

8. The “fake it ’til you make it job”

You knew you were unqualified and not quite what the client was looking for, but you submitted your proposal on a lark. To your surprise, you got the job.

The money is good, but you’re faced with a challenge:

How can you fake it ’till you make it?

Creativity is key here, and you’ll usually find clever ways to cover yourself.

Unusually, formal language in your emails won’t go astray either — after all, you’re one of those ‘experts’, right? It’s all about appearing confident while you shake in your boots beneath the desk.


Most of these jobs are complex, challenging and will look good in your portfolio.


Future clients may expect the kind of work you ‘faked’ to be your standard offering. The more time you spend faking it, the more likely you are to be caught out: for example, when a client asks for Lightbox and you open the blinds in your meeting room.

9. The chore

There’s play, then there’s work, then there’s chores.

Chores sit at the bottom rung as the work we’re obligated to do, but would love to forget about. The ‘chore’ stage usually only manifests itself after you’ve started a project.

If you’d known the job would be this boring and unrewarding, you wouldn’t have accepted it. Jobs usually become chores when they involve unforeseen repetitive tasks:

When that online store is 70% finished and you discover that you have to manually enter details for each of five-hundred stock keeping units because you didn’t read the brief properly.


Like cleaning the house or doing the washing, chores feel good when you finally get them done.


Boring and unimportant.

10. The balloon gig

“We need you design a website.”

When the site is 30% completed: “We’re really pleased with how this is going. Could you redesign all our brand imagery to suit the site?”

When the site is 50% completed: “Could you possibly create the copy for our About and FAQ pages? Our copywriter is on holidays and we need someone we can trust.”

When the site is 70% completed: “I’ve discussed this with our marketing department and they’ve said they need the website to be fully optimized for search engines.”

When the site is 90% completed: “As a finishing touch, could you create a simple Flash game to determine whether a visitor is allowed to enter the site or not?”

When the site is finally done: “Great work, we’re really happy with it. In fact, we want to expand into the online auction sphere. How hard would it be to create an add-on section for the site, kind of like eBay, but targeted at the Web 2.0 crowd?”


If you’re hungry for work and don’t mind being a jack of all trades, you might love this kind of gig.


If you’re not a copywriter, an SEO strategist, a Flash designer or willing to design an eBay-style auction website as an afterthought, balloon gigs can mess up your schedule and keep you away from what you really want to do.

11. The burnt toast gig

Toast smells great until it burns. This is the kind of work you do for the client who eventually reveals themselves to be…

  • strangely paranoid
  • unwilling to pay you
  • unusually eager to send a barrage of panicked emails when you don’t respond to a question within four hours — even if it’s the middle of the night where you are.

It’s the job that starts off great and takes a slow or sudden turn for the worst.


At least it started off great. After all, some jobs start on a low note and stay there.


The smell of burnt toast tends to linger long after the toast itself is gone.

12. The ‘Lost in Translation’ gig

Either your client actually does speak another language to you, or they might as well do so.

They say one thing, you act on it, then you find out they meant something completely different.

You explain something, they confirm they understand, only to send panicky emails asking why you’ve done such and such thing.

You and the client, despite your best efforts, just don’t ‘get’ each other.


A reasonable client will accept some of the blame for communication errors and give you a longer leash to compensate.


When the client believes they’ve been clear as crystal and that you’re the one who can’t follow simple instructions.

13. The passive-aggressive project

The work is good, the job is interesting, but you’d sooner go to lunch with Bill O’Reilly than your client.

For whatever reason, you don’t like them, but that dislike must always hide behind a veneer of politeness and professionalism — making it all the more frustrating.

The best you can do is resort to small acts of resistance, like not saying ‘Have a nice day’ at the end of your emails.


As long as they pay you on time and are clear about what they want from you, what does it matter? Even self-employed people have to learn to get along with people they wouldn’t normally choose to associate with.


As much as we like autonomy, we have to communicate with our clients. Keeping the disdain out of your emails and conversations can require more effort than the work you’re being paid for.

14. The top-secret gig

Almost every freelancer has done a job like this:

The client is usually a web entrepreneur who believes their mysterious ‘start-up’ is going to be bigger than Gmail, Mint, YouTube, eBay and Grand Theft Auto IV combined.

Here’s the problem:

They can’t do everything themselves, yet anyone they work with is a potential ‘million dollar idea stealer’.

As a result, you’ll be questioned, psychologically profiled, faxed non-disclosure forms, given vague descriptions and briefs, and usually forced to refer to the project by its special code-name ‘Talon X’ or, in the company of others, ‘Delta Sky’.


Any client who thinks your work is going to help make them rich is almost always willing to pay any rate you like. They’re impatient to start making money, and thus rarely care to shop around. You can usually charge whatever you want without causing the client to blink.


It’s really hard to do creative work when you don’t know what it is exactly you’re helping to create.

15. The ‘feet of the master’ job

The surreal has happened and you’re working for an idol. You’re blogging for Darren Rowse, designing for your modern-day Andy Warhol, illustrating a book for your favorite author or coding your favorite sports-star’s personal blog.

These jobs are both rare and something every freelancer should try and experience. This is the stuff you remember for a long time.


You get to work for, maybe even collaborate with, someone who has been important to you.


They might make better idols than they do clients!

16. The charity job

You’re working for $12 an hour and proud of it.

Why? Because your work is helping good people, or good causes, and you feel good, too.

Seriously, I give you a toast to that!


You feel good about it, you get karma points.


Big not-for-profits or charity initiatives generally invest a large proportion of donations or funds back into growing their reach. It’s not always justifiable that this doesn’t extend to paying freelancers a healthy rate.

17. The outsourced gig

You don’t remember much about this one, mainly because the market research was done by Abhijeet in India, the copywriting was done by Mia in Canada, and the logo was created by a design firm in the UK.

You added your own touch, of course, but it was a collaborative effort.

Stripped of all romance, you paid other freelancers less per hour than you made from their work, and took most of the credit to boot.


You’re practicing the same strategies used by small and large businesses everywhere to earn a profit and free up time you can use to pursue other work.


Managing employees can be a job in and of itself. It’s important not to fall into the trap of spending more time managing your outsourcing than it would have taken to simply do the work yourself!

18. The job you won’t talk about

The money was good, but the client, or what you were helping to create, was a little shady. In some cases, a lot shady. Whether it was spammy, scammy, seedy or sleazy, you finished the job, took your payment and very deliberately left it out of your portfolio. In fact, let us never speak of it again.


You got paid. Sometimes you have no choice but to accept whatever comes your way, even if it’s not the proudest work you’ve ever done.


If you know what you’re doing is not a positive thing, or that your creative work will be used to dubious ends, you’ll feel a little less proud about what you do. You can’t really quantify that loss.

19. The job you didn’t know existed

You still can’t believe that somebody out there wants to pay you $45 an hour to write about competitive pinball, or to illustrate a comic book designed to teach 3–5 year olds the ins and outs of income tax, or to photograph cracked and dry heels for use in a direct marketing campaign for a new kind of heel balm.

In other words, it’s the work you never imagined doing when you envisioned your freelancing career.

That doesn’t mean it’s bad — it could be great — but it’s always very weird, and you generally don’t share the specifics with others (lest your mother declare that you’re “taking photos of feet” for a job at the next family dinner.)


Highly specialized and obscure work can be among the best-paid. Plus, it’s unlikely to feel like you’ve done the same job ten times before.


Weird work often comes with weird clients.

20. The reason you’re a freelancer

Photo found at yourstory.com

If this list seems to emphasize the negative, that’s only because it’s easier for this comedically limited author to make that stuff (kinda) funny.

Hopefully, most jobs you do are like this one:

They make you glad you decided to become a freelancer.

You might not be making $50 or $150 an hour, and your client might be a little late to pay sometimes, but ultimately, you’re in control of your work and your business.

Your career is guided by choice rather than a sense of repetition and inevitability.

If this kind of job is your bread and butter, you’re doing something right!

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +432,678 people.

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Jaylon Ramsay

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