Takeaways for Every Upwork Copywriter

  • A lot of great clients are on Upwork
  • You can get great repeat business
  • Upwork’s top clients often reach out privately

Author’s note: I originally wrote this post about Elance, which has since rebranded to Upwork. While the strategies laid out here remain as effective as ever, we’ve made some minor cosmetic updates to reflect the change. Enjoy.


Last year, I caught a lucky break.

One of my most trusted mentors advised me that, if I wanted to make real money and have an enjoyable freelancing career, I shouldn’t waste my time on Upwork (formerly Elance).

But the lucky part wasn’t the warning. It was the fact that it came too late. I’d already been “Upworking” for the past 24 months, and had just closed a six-figure year.

I was featured in Business Insider for earning six-figures on Elance (now Upwork)If I’d gotten his tip a couple of years earlier, I probably would have listened. And it would have cost me a major matzoball o’ cash.

Note that the mentor in question does not have some weird criteria for evaluating time-wasting activity. Even as I and many others ride Upwork with our arms stretched out, screaming “King of the world!” like Jack from Titanic, most pros still see the platform as something closer to the ship’s boiler room, a fiery pit where soulless freelancers mindlessly churn out drivel in exchange for tarnished pennies. Copywriting legend Bob Bly once went so far as to call Elance “the cesspool of freelance writing.” (I still can’t figure out where that is in relation to the boiler room, but either way, it’s pretty dang low.)

These people — including, strangely, many avid Upworkers themselves — believe that the site is nothing but a sucker bet. The gutshot straight draw of freelancing.

Popular arguments go like this…

The averages argument: The average Upwork freelancer brings home dog crap. If you check out the earnings on the site and divide it by the total number of freelancers, you’ll get an amount tinier than the universe immediately following the big bang.

The supply and demand argument: Upwork is a stone cold buyer’s market. With scads of freelancers bidding on jobs, rates (and freelancer morale) tend to quickly disintegrate.

The starving writer argument: Most of the jobs posted on Upwork pay well, IF your idea of a nice life is sleeping in your car and calling ketchup packets “meals.”

Now. I have just three things to say about these bold claims.

1) They are all true.

2) They will never change.

3) Not a one of them has got diddly shit to do with how I and many others have made money on Elance and Upwork.

Put another way, all of the anti-Upwork arguments are about what most freelancers and gurus observe when they look at the platform.

Unfortunately for them, there is plenty more they can’t see. And it’s precisely in this unseen area that the real money is being made on Upwork, right under most people’s noses.

Welcome to Upwork’s Invisible Game

Entrepreneur Brandon Gadoci says: “In life, there are two games that are always being played. One you can see, and one you can’t.”

Upwork is no exception to this rule, and I’ve been using the term Hidden Upwork Economy to describe Upwork’s invisible game for over three years.

Of course, most freelancers have no idea the Hidden Upwork Economy exists. And the ones who do aren’t likely to talk about it for fear of giving away a key trade secret. Of all the Upwork advice that’s been published (most of it junk), I’ve never once seen this idea so much as hinted at.

So, freelancers tend to land on Upwork without any kind of plan. Then they quickly get discouraged when they see all the low paying jobs — and the morass of competitors they believe they have to beat for the privilege of actually winning one.

At this point many roll into the fetal position and give up for good. Others make the more unfortunate decision to linger on. They try to make the most of Upwork’s harsh waters by working their asses off, capitulating on prices, and telling themselves that, hey, things could be worse.

But this pseudo-strategy never works.

The moment you try to win on Upwork by doing what seems natural, you’ve already lost. It’s like trying to beat poker pros by just playing good cards, attempting to outwit a car dealer by haggling harder, or making a mad dash to escape the friend zone by simply being a nicer guy. Or, to put it into Erlich Bachman terms, trying to beat Upwork without understanding the dynamics of the Hidden Upwork Economy is like bringing piss to a shit fight.

Now I’m sure you’re probably wondering just what the Hidden Upwork Economy actually looks like. Good question, especially given its invisibleness and all.

As I see it, the Hidden Upwork Economy consists of 3 key parts that fly totally under most people’s radar — a sort of perfect storm for Upwork badassery. (A word of caution: leave any ingredient out, and your Upwork-based freelancing business is likely to collapse like an ill prepared angel food cake.)

Let’s discuss.

Hidden Upwork Economy Component #1:
Sleeper Hit Clients

A Sleeper Hit Client is someone who — despite a nondramatic Upwork debut — turns out to be a rockstar client who pays well, makes a good working partner, and is likely to keep hiring you in the future. Naturally, this type of client needs to be at the centerpiece of the Hidden Upwork Economy. Otherwise, I’d be describing a Tootsie Roll Pop with no Tootsie Roll in the middle. And who wants that?

Most freelancers think there aren’t enough clients like this on Upwork to support a six-figure income, but remember, you need to go beyond the obvious.

For starters, most Upworkers would do better to reframe the question of “How can I make a full time living when there are so few high paying clients?” to “How many premium clients do I actually need to find on Upwork in order to make six figures?”

Personally, I was able to break the 100k barrier in 2014 while working with just 27 clients. And four of those were repeat clients from the previous year, meaning I only had to find two clients per month to make these numbers work.

It ain’t easy, but it is doable.

Especially once you realize that there are far more great clients on Upwork than you think. Hell, there are probably more than even I think. As I’ll explain soon, most of them are buried deep within the weeds of the Hidden Upwork Economy, but many Sleeper Hit Clients are “hiding” right in plain sight.

See the thing is, very few clients jump on Upwork and hire premium freelancers right off the bat. Most need to get their feet wet first. Yet sadly, the conventional wisdom is to instantly profile clients as “shrimp” if they haven’t spent a ton of money yet, or even if they’re (gasp!) unsure of what their budget should be. Can you see the fatal flaw in this approach, or do you need Julia Roberts to go all Pretty Woman on your ass for good measure?

Look at the screenshot below. 4 out of 5 of the clients represented there are bona fide Sleeper Hit Clients. Three of them had no payment history at all — something which most “experts” consider a “red flag.”

Examples of great freelance clients you can find on UpworkThese are by no means isolated occurrences. Forget about what clients spent yesterday, and start asking yourself how much they might be willing to invest in high quality work today.

Hidden Upwork Economy Component #2:
Repeat Business

Maybe you glanced at Upwork’s job marketplace this morning and saw only a bunch of low paying gigs.

But what you didn’t see were all the well-paying projects won by freelancers without the client even creating a post. These jobs were casually awarded after a message from client to freelancer that sounded a lot like this:

One of my Upwork clients asks me to do thousands of dollars of new workI’ve received offers like this every single week for years. Yet, again, it’s totally invisible to anyone watching from the outside.

You’ll see a similar pattern of high repeat biz from all of Upwork’s top performers. It’s a huge part of why Upwork can appear to be a dystopia to anyone following the game, while being pure cornucopia to freelancers playing the invisible game.

A very encouraging implication here is that the most talented Upwork freelancers are more likely to collect a modest amount of clients than constantly fight you for a bazillion new ones. Personally, I decline dozens of high quality job invites each month, and I know many other successful Upworkers who do the same.

So if you’re someone who knows your shit (or you’re willing to learn it), there’s as much showroom space for you to shine on Upwork as there is anywhere else. Probably more when you consider that most serious freelancers still steer clear of the joint. (Be sure to send them a thank-you note after you come in and clean up, will you?)

Hidden Upwork Economy Component #3:
Invite-Only Jobs

Invite-only jobs represent the very essence of the Hidden Upwork Economy.

While one of the biggest complaints about Upwork is the flash mob of low bidders who descend on jobs like wedding crashers, invite-only postings are a far more exclusive party.

As it turns out, Upwork’s top clients don’t necessarily put up public jobs and wait to see who applies. Instead, many silently shop around for a freelancer who fits the bill they’re looking for, and then reach out to that person privately, by inviting them — and often only them — to discuss their job.

Yes, you heard me right: you can easily be the only VIP on the guest list (see screenshot below).

One of the many Invite-Only job invitations I've received from clients on UpworkFor added encouragement, check out the opening words of the client’s message to me. If you’re used to writing proposals for public jobs, you’ll immediately notice how the roles are somewhat reversed; clients posting private jobs are usually already sold on working with you.

Over 90% of the clients I’ve picked up in the past couple of years have come from people directly seeking me out in this way, making Upwork — or, more exactly, the Hidden Upwork Economy — the most powerful lead generation tool I’ve used to date.

Next Stop: Hidden Upwork Economy, or…Bermuda Triangle?

In spite of everything I’ve just shown you, some people still insist that Upwork isn’t a beatable game. That I’m an outlier. That the relatively small number of Upwork freelancers who are kicking ass are just a blip on an otherwise empty radar.

Y’all are a pretty cerebral crew; what say you?

Hit me with your thoughts, opinions and questions in the comments below.


PS: When you’re done commenting, grab my top 5 Upwork hacks for free here.