I didn’t learn much in high school. But one of my gym teachers told me something that stuck: The easiest way to get across a minefield safely is to walk in someone else’s footsteps.
Looking back, I haven’t always heeded his advice. There were more than a few Upwork lessons I had to learn 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 realize I was even stuck in them at all. 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 went to the store by herself and picked out an outfit for him. Then she brought it home and said, “Can you try this on?”
In other words she made it easy for Noah to say Yes.
There’s a huge Upwork lesson in that story.
When you’re writing a proposal, it’s much easier to get a client to say Yes to a Skype call than to hire you.
So now I end most of my proposals by asking clients for a quick Skype call, which works wonders. (Thank you, NK.)
2. Not understanding what clients really mean when 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 in the job description because it’s customary to include it.
You see something similar happening in some of the job 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 have a good attitude”
- “I’m terrified of hiring the wrong 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 teach the right person”
- “I don’t know how to write an effective 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 hire 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 tired of skipping over jobs that looked good so I decided to try something different.
I went ahead and applied to a copywriting job that said “must have branding experience” — even though I had none — just to see 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 job, I also learned a new skill that made me more valuable.
In that case “must have branding experience” really meant “must be willing to learn.” But you never know if you don’t try.
3. Thinking that making clients happy has 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 was getting paid to do the work, it all needed to be hard.
If you think about it though, that doesn’t make sense. 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 realized you can gain a lot more if you don’t feel the need to always feel pain.
Your clients will gain more too because you won’t be so busy reinventing the wheel and you can get a lot more done for them in the same amount of time.
4. Listening to experts
In my first year on Upwork I spent a lot of time hanging out in online forums, trying to learn how to be successful.
Mostly what I learned was a painful lesson.
Just because someone’s written 7,632 messages in a forum doesn’t mean they know how to succeed. And it sure as hell doesn’t mean they’re interested in helping you succeed.
Actually the people who spend the most time “helping” others in online forums are usually the least successful. (Why do you think they have time to sit there and post messages all day?)
And a lot of them try to steer you in the wrong direction by actively discouraging you or deliberately giving you bad advice.
Here are two examples. Keep in mind both of the messages below were in response to someone who specifically wanted help succeeding on Upwork:
Do you think either of these messages is designed to help you? Or to discourage/sabotage you?
(Hint: I’ve talked with thousands of successful Upwork freelancers, and not one of them has told me the key to their success was taking junior college classes. What the hell is junior college, anyway?)
5. Not understanding how clients think about money
Upwork clients have a certain way of thinking about money that isn’t obvious to most people.
The first time I got paid $50/hr on Upwork, I thought, this must be some kind of fluke. Why would anyone pay me this much to write some simple emails and blog posts for them?
Well there are a ton of good reasons clients are happy to pay that much. But I couldn’t see them because I was projecting my own money issues onto clients, instead of seeing it from their perspective.
Here’s a story to show you what I mean.
Last week my wife and I went to Lowe’s and bought 2 chairs for $200. Before we paid, I asked the salesman if the store could assemble the chairs and deliver them to our house.
He scrunched his nose and started to shake his head like he was going to say no, but then he surprised me by saying, “Well, we could…but it’d be an additional $75.” I could see from his body language that he couldn’t imagine anyone paying the $75 just to save an hour or two.
Did you spot his mistake? He was doing the calculation from his perspective, not mine.
For me, 2 hours of my time is worth more than $75. I would have easily paid double that.
In almost every situation I can think of, clients can (and will) pay more than you probably think. The trick is to set your price from their perspective, not yours.
Now you tell me
I’d love to hear about your experience on Upwork. Have you made any mistakes you’ve learned from?
Please share it in the comments so we can all learn from each other.
If you’re brand new and don’t have any experience yet, let me know which of the mistakes in this post surprised you the most. By talking about it you’ll be 10x more likely to avoid it.