The 7 Biggest Problems With The Gig Economy

Adam Bergen
May 23, 2019 · 10 min read

You walk into your corporate office job on Monday morning, a cup of strong black coffee firmly squeezed in your hand; the death grip is unmistakeable. You wouldn’t dare let someone take your caffeine from you; you need this sucker to survive. The weekend flew by as usual, and you’re left wondering how you’ve put up with 8 AM conference calls for the last five years straight.

The misery is at an all time high, and you want out of this rat race. Right now, you have about as much energy as a sleepy three-toed sloth. And it never seems to gets better. You fantasize about quitting, down to the unnecessary details of what you’d wear as you walk into your boss’s office to inevitably let them know you’re a replaceable commodity.

The corporate grind is looking miserable, and the gig economy is looking really, really tempting. And while it has its pros like the perceived flexibility and freedom, it’s also a dangerous game to jump into and play.

I’ve been a writer and computer programmer for a number of years. With only the need for a laptop, I’ve entered the freelance game on a few occasions, only to find the same problems occur time and time again. Let me explain.

What Is The Gig Economy?

The gig economy is simple: you get paid by the gig instead of having a job that pays hourly or is salaried. You choose your own hours, time, and desire to find jobs. You go after gigs when you want, or you can sit back and take a little time off. You have the freedom to hustle non-stop, or you have the freedom to sit around sans motivation while watching your bank account wither away like a wilted piece of lettuce.

The choice, ultimately, is yours. There’s a word often associated with the gig economy — freedom. Ah, how enticing. You’re no longer chained down to a corporate job. You’re no longer considered a desk jockey. You no longer have a boss you’re forced to appease. Because really Bill, sometimes I don’t want to show up to work on Monday morning from a hangover… and the fact I want to cry at my desk daily.

Why The Gig Economy Sounds Good on Paper

It sounds deliciously viable for two big reasons:

  1. You have the flexibility to run your own show, and
  2. You have the option to pursue any venture you see worthy of your time.

What more can you ask for, really? A bonus, of course, is you don’t have any crappy corporate environments you’re immersed in. Because wearing business casual and showing up to a world where pastel green is the brightest color you’ll see besides beige gets old when you do it every fucking day.

Freedom and flexibility; completely interchangeable and completely enticing as a reason to enter the gig economy. Everyone fantasizes of “doing their own thing” because it sounds cool. “Yeah, I’m my own boss.” The jealous haters then pop up like whack-a-mole. Doesn’t phase you though, as you wake up to the sunlight gently brushing your face to remind you it’s time to get up, while they’re sitting in traffic Tuesday morning at 7:40 AM with another 35 minutes to go in their commute.

You’re brewing a Nespresso in your cashmere robe, but they’re rushing to their 9 AM daily conference call. You’re left wondering how lucky your inept ass got. You’re pan-searing a home-cooked lunch of cod, spinach, and macaroni, but they’re unpacking their cold bologna sandwich in the break room, rummaging for enough change to complement their meal with some Cheetos from the vending machine. You win.

Your work sandwich doesn’t look like this.

Why cook such an incredible lunch during the day? Because fuck it, why not?

Part of the allure in the gig economy is your ability to pursue whatever project, venture, or job you see worthy of your time. You have to weigh it against your skills, your ability to pay rent, and a few other things, but all things considered, you’re no longer doing the bullshit tasks just so you look busy in your boss’s eyes.

Now, it’s about doing real, tangible, cool things that spark your interest. It’s about doing things you’re good at, and at the same time making some money off of them. Or, it’s about choosing gigs which let you take that vacation whenever you feel like it, for however long you feel like it. You’re no longer forced to compare your time at work with how many vacation days you’re carrying around. Hell, you could even work from the vacation if you wanted. They have a term: they’re called digital nomads.

But as slick and foolproof as this entire operation sounds, it’s a dangerous game for seven distinct reasons. Let’s dive into why.

Problems With The Gig Economy And Why You Should Be Extremely Cautious

Look, I get it. You hate your corporate job and are looking for any reason to get out. From what you gathered, and what your parents don’t understand, the new generations (like Millennials and Generation Z) don’t have to spend 30 years at the same company to make a living. In fact, company loyalty is almost non-existent . You could even argue it’s dead. These days, people hop around when a better opportunity presents itself. For good reason I might add: companies are quick to cut a long-time employee when things get rough.

So with all this hopping, skipping, and jumping around, one theme becomes clear: you’re in better control of your own career destiny than any generation before you. You have the ability, and the means, to pursue jobs which align more with who you are. And the data’s in: Millennials, for instance, are doing just that: they’re pursuing careers and jobs which align with their passions and purpose .

Now imagine this: you have the ability to pursue things that excite you, but you don’t necessarily want to get tied down into a corporate job. You’ve got some pretty original and/or creative skills, so a dilemma now surfaces: what the hell do you do?

Well, you enter the gig economy.

But there’s a slew of problems awaiting your arrival.

1. You have even less freedom

One of the biggest, if not the biggest, appeal of the gig economy is your ability to have the freedom and flexibility to do a lot of things: from the time you spend working, to the projects you take on, to the clients you work with, and more.

But I’d argue you have less freedom than you think, and even less freedom when compared to a corporate job. Because while it’s true you no longer answer to Bill Watkins, Vice President, you’re answering to every client you take on. And guess what? A client likes their work done a certain way, sometimes to the point of being absolutely out of their mind. And guess what? A client won’t pay until you do the work the way they like it, unless you magically convince them they’re being ridiculous. Good luck telling a client in so many words that they’re being ridiculous. It ain’t easy.

In the meantime, until you’re paid or you can convince them to do it your way, you’re stuck answering to them. At a corporate job, when you leave work…it means you can basically put it aside until the next day. But Bill doesn’t care what time you clock out; he wants his stuff done yesterday.

What about that freedom again?

2. You’re up against people who undervalue themselves

One of the shittiest parts about getting a gig is the bidding process. Typically, you’ll use a platform like Upwork or Fiverr (which I’ll discuss later) to find clients and bid on the jobs they post.

Suddenly, you aren’t a hot commodity anymore; your ability to craft slick-looking websites or whip out sharp copywriting is nothing special when you’re bidding on a project against 30 other freelancers. And here’s the worst part: 28 of them undervalue themselves and their work, and in a desperate attempt to get some work, underbid you.

The client, who has no idea just how time-consuming their project takes and the ideal skill level required, is elated to have someone bid pennies on the dollar. They think they won the lottery and got a deal of a lifetime. Your reasonable bid, which is still below what you’d prefer, gets trashed immediately. See ya, sucker.

You stood no fucking chance there, cowboy. Sad face.

3. You’re up against people who provide shitty work

As much as the problem above can be a real buzzkill, there’s one even worse: the plethora of low-grade, shitty freelancers who bid low because, well, their work is worth that.

And yet again, Client Clueless, Inc. gets excited because they see a cheap bid and it only means one thing: they save money on their project. Reasonable bids come in but they’re triple or quadruple the lower bids. They get trashed.

The bidding process as a freelancer.

So there goes the client choosing the cheap bid. The work comes in, and it’s awful. So awful, in fact, that it doesn’t take a genius to label it as practically a con. The client gets mad. They want to hire someone who can actually do a good job and are now willing to pay fair price after realizing they fucked up. Unfortunately, your offer has long been trashed and you’ll never know they need a redo because you’ve moved on.

4. You’re up against clients who have no idea just how much services can cost

If you find yourself in the creative fields, this one burns. It feels like half your time spent with a client is making them understand why you’re charging X instead of 50 to 75% of X. No, 1,000 words of copy isn’t worth $20. It’s not even worth $50, let alone a $100 if you’re decent. No, I can’t build you an entire website for $300. Somehow, this is what clients expect.

Do you blame them though? See issues #2 and #3 above. When that’s all a client sees in the bidding process, it’s all a client knows. Couple it with their desire to save money and you’re walking on a tight rope.

5. You’re up against sites like Upwork or Fiverr that take a hefty cut and attract trash

See, sites like Upwork know they’re providing you with the potential to land jobs in the gig economy, and they make you pay dearly for it. In fact, Upwork takes a 20% cut for the first $500 you make with a client, and another 10% for anything below $10,000. That means you’re literally paying them $20 of every $100 you make, only because they brokered the deal. So if a project is $500, you only make $400. And because most projects are one-off and usually below $500, they figure it’s the biggest chance to get their piece of the pie.

Here’s the worst part: your bid has to be the price before Upwork takes their cut. In other words, you have to bid $500 knowing you’ll get paid $400 at the end of it. So you have to factor in a little cushion on the bid price, which drives up your overall bid. And as seen in problem #4 above, it doesn’t help you.

It doesn’t help you at all.

6. You’re constantly trying to find new clients or projects

Unless you drive for Uber or Lyft, you’re going to be spending a lot of time chasing clients down. Even on apps like Upwork and Fiverr, you’ll constantly have to get new projects or clients because most jobs aren’t recurring. They’re one-time.

The best gigs are the recurring ones with a long-term contract in place (i.e. retainers). But let’s be honest: those are much more difficult to find. And so half your time will be spent on working, the other half on trying to outbid some fucker way out on the other side of the world, or some schmucks who completely undervalue themselves because rent is due and they’re desperate.

Sounds miserable. That’s because it is.

7. You’re constantly creating

Unless you’re building a business to scale, you’ll be spending time creating at any job you take.

That means each client you work with will require original, new, and fresh work. Rarely anything can be used from client to client. With only 24 hours in a day, you have a limit to what you can produce. If you’re so busy you find yourself not having time to service all clients, you could argue this is a good thing. I’d agree; it’s a good sign when you’re that busy.

But when you reach a point where you can’t handle it all yourself, you only have two choices: either drop clients or hire someone else to help you. The idea isn’t to get so much work you’re putting in 14 hour days. In either situation, you’re losing money.

On the other hand, if you were trying to build something to scale, you could just kick your feet back (to a degree) since everyone uses the same product or service.

See, The Gig Economy Isn’t All Unicorns And Rainbows

It’s a tough crack to make it out there as a freelancer. Competition at anything in life is at an all-time high. People value themselves differently. Clients think they can get a DaVinci masterpiece for the price your eight year-old cousin would charge. It’s just the reality of the industry.

But with all this said, some people still pursue it, because they can. And mainly, they hate corporate desk jockeying. I don’t blame you if that’s you: it can suck your soul right out of your body.

But if you’re looking to quit the corporate grind and strike out on your own, it’s important to get into it with the right mindset. The mindset that all those sexy things you heard about being your own boss isn’t all it’s cracked up to be.

If you’ve got the mental stamina and drive though, it can be one of the most rewarding decisions you’ll ever make.

Thanks for reading! Originally published at

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Adam Bergen

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Chasing the Friday feeling on Mondays | Helping others focus on what’s important |

The Startup

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