I made these expensive mistakes on Upwork. You don’t have to.

Looking back, I haven’t always heeded his advice. There were quite a couple of Upwork lessons I had to find out the hard way.

But at least I can share them with you now so you can avoid them.

What’s really interesting about these particular traps is that it took me months (or in some cases longer) to understand I used to be even stuck in them in the least. It’s a little like sleeping — you only find out you were doing it once you wake up.

Here’s what I wish I’d watched out for.

1. Not making it easy for clients to respond to my proposals

I once sent out 30 Upwork proposals in a week and didn’t get a single response.

Then I read a story about how Noah Kagan’s girlfriend got him to wear new clothes.

The problem wasn’t that that he didn’t like new clothes. It was that he (like most guys) hated shopping for them.

So his girlfriend did something brilliant.

She visited the shop by herself and picked out an outfit for him. Then she brought it home and said, “Can you are trying this on?”

In other words, she made it easy for Noah to mention Yes.

There’s a huge Upwork lesson in that story.

When you’re writing a proposal, it’s much easier to urge a client to mention Yes to a Skype call than to rent you.

So now I end most of my proposals by asking clients for a fast Skype call, which works wonders. (Thank you, NK.)

2. Not understanding what clients really mean once they say “must have experience”

Before trying Upwork I spent months looking for a traditional job.

But I thought I couldn’t apply to 97% of the jobs I saw because they said “must have a bachelor’s degree” — and I didn’t have one.

Then my wife (who is 10 years younger and 10x smarter than me) told me a secret.

Most of the hiring managers don’t really care if you have a college degree. They just put that within the description because it’s customary to incorporate it.

You see something similar happening in a number of the work posts on Upwork.

When a client posts a job and says “must have previous experience,” that can mean a lot of things.

Here are some possibilities:

  • “I’d consider someone without experience if they need an honest attitude”
  • “I’m scared of hiring the incorrect person and having to redo all their work myself”
  • “I’m tired of having to sift through bad proposals so I want to weed out anyone who isn’t serious”
  • “I’d prefer someone with experience but I’m willing to show the proper person”
  • “I don’t skill to write down an efficient job post”
  • “I’m new to this and want to appear like I know what I’m doing”
  • “I don’t want to hire someone who needs hand-holding”
  • “You can convince me to rent you by showing me one example of your work”
  • When I first started on Upwork, I didn’t realize this “secret language” existed. I took everything literally.

But then I got uninterested in skipping over jobs that looked good so I made a decision to undertake something different.

I went ahead and applied to a copywriting job that said “must-have branding experience” — albeit I had none — just to ascertain what would happen. I thought, what do I have to lose?

In my proposal, I said something that made the client laugh. She ended up hiring me and teaching me everything I needed to know to do the job.

So not only did I win the work, but I also learned a replacement skill that made me more valuable.

In that case “must-have branding experience” really meant “must be willing to find out .” But you never know if you don’t try.

3. Thinking that creating clients happy has got to be hard

Hard work can be a very good thing. But working extra hard for no reason is stupid.

It’s like running until you pass out. It does more harm than good.

The problem is I had a subconscious belief that because I used to be getting paid to try to do the work, it all needed to be hard.

If you think that about it though, that doesn’t add up. Every job has things that are hard, and things that shouldn’t be so hard.

Even surgeons have easy parts to their job, like scrubbing their hands and putting on masks.

But for some reason, I felt guilty if I charged a client $50 for an hour of work and didn’t spend every minute doing the hardest work I could imagine.

So without even realizing it, I made things harder than they needed to be.

For example, I once wrote a series of marketing emails for a client, all intended to sell the same product. In the first email, I’d written a list of bullet points outlining the features and benefits of the product.

The client loved the bullet points.

But instead of copy and pasting them every time we needed to list out the product’s features, I did something crazy: I rewrote the entire list of bullet points a different way each time.


It really makes no sense.

The client liked the bullet points I had. And they were good.

Reusing them would have been smart.

But my subconscious mind told me, “No pain, no gain.”

Once I smartened up I noticed you’ll gain tons more if you don’t feel the necessity to always feel pain.

Your clients will gain more too because you won’t be so busy reinventing the wheel and you’ll get tons more finished them within the same amount of your time.

4. Taking note of experts

In my first year on Upwork, I spent tons of your time hanging calls at online forums, trying to find out the way to achieve success.

Mostly what I learned was a painful lesson.

Just because someone’s written 7,632 messages during a forum doesn’t mean the skills to succeed. And it sure as hell doesn’t mean they’re curious about helping you succeed.

Actually the people that spend the foremost time “helping” others in online forums are usually the smallest amount successful. (Why does one think they need time to take a seat there and post messages all day?)

And tons of them attempt to steer you within the wrong direction by actively discouraging you or deliberately supplying you with bad advice.

Here are two examples. confine mind both of the messages below were in response to someone who specifically wanted help succeeding on Upwork:

bad upwork advice Dear Old Pros: Freelancing degrees do not exist Terrible Upwork advice With friends like this, who needs enemies?

Do you think either of those messages is meant to assist you? Or to discourage/sabotage you?

(Hint: I’ve talked with thousands of successful Upwork freelancers, and not one among them has told me the key to their success was taking college classes. What the hell is college, anyway?)

5. Not understanding how clients believe money

Upwork clients have a particular way of brooding about money that isn’t obvious to most of the people.

The first time I got paid $50/hr on Upwork, I thought, this must be some quite fluke. Why would anyone pay me this much to write down some simple emails and blog posts for them?

Well, there are plenty of excellent reasons clients are happy to pay that much. But I couldn’t see them because I used to be projecting my very own money issues onto clients, rather than seeing it from their perspective.

Here’s a story to point out you what I mean.

Last week my wife and that I visited Lowe’s and purchased 2 chairs for $200. Before we paid, I asked the salesperson if the shop could assemble the chairs and deliver them to our house.

He scrunched his nose and began to shake his head like he was getting to say no, on the other hand, he surprised me by saying, “Well, we could…but it’d be a further $75.” I could see from his visual communication that he couldn’t imagine anyone paying the $75 just to save lots of an hour or two.

Did you notice his mistake? He was doing the calculation from his perspective, not mine.

For me, 2 hours of my time is worth quite $75. I might have easily paid double that.

In almost every situation I can consider, clients can (and will) pay quite you almost certainly think. The trick is to line your price from their perspective, not yours.

Now you tell me

I’d like to hear about your experience on Upwork. have you ever made any mistakes you’ve learned from?

Please share it within the comments so we will all learn from one another.

If you’re fresh and don’t have any experience yet, let me know which of the mistakes during this post surprised you the foremost. By talking about it you’ll be 10x more likely to avoid it.

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