In my previous post, I went over lessons and observations I had learned on Upwork as both a freelancer and a client. Since then I’ve continued to use Upwork regularly and learn more from both perspectives.

Some of the lessons in this list are directly applicable to your work as a freelancer. Others may help to explain client behavior, which can seem inexplicable if you have only experienced Upwork from the freelancer side of the interactions.

Everyone who makes a job post is prompted to select the desired skill level of the potential freelancers. There is just a choice of three buttons at Entry, Intermediate, and Expert levels that you click. No other choices the client makes in setting up the job post influences this setting.

Because of this, there is often not a strong correlation between the job that’s posted and the skill level that is being asked for. I’ve seen posts with long, complicated descriptions of what is wanted being listed as entry level. I’ve also seen “expert” jobs, where the client is supposedly willing to pay higher rates, listed for $5.

This does give some useful insight into how realistic your potential client’s mindset might be. But there’s something else that I think is valuable to know as a freelancer. I used to think that if a client set a job to “expert” but I didn’t consider myself an expert in that field, it would automatically be a waste to apply, because my first impression is disregarding the client’s wishes. As a result, there were plenty of jobs that I thought I could do, but simply because of that setting, I did not bid on them.

Later, while reviewing freelancer proposals from the client dashboard, I realized something: I couldn’t find anything to indicate whether the freelancers were entry, intermediate, or expert level. Perhaps it’s there somewhere, but it’s certainly not obvious. From just looking at the proposals I have no idea what their levels are.

Takeaway: If you’re trying to get hired, I would recommend you propose for any job that interests you, regardless of the skill-level rating.

I posted a job for someone to create a YouTube thumbnail image. I had 17 proposals in less than 12 hours.

• 1 respondent definitely read my posting.
• 3 probably read it, but didn’t say anything to make me feel sure of it.
• 7 were vague or written by AI.
• 5 sent form letters.
• 1 person only submitted a few words.

My advice is to always include something in your proposal that makes it totally clear that you read the client’s job post. This aspect doesn’t have to go on and be long and complicated, as long as it gets the point across.

For this to have any effect, though, it has to sound human. Otherwise it blends into the background as just another AI application that repeats back what it has read in a predictable way. If you’re going to use AI, for it to give you any benefit, you’ll want to edit it to sound human.

Takeaway: Make sure your proposal definitively proves you have read and understood the client’s job post.

As a freelancer, it can be discouraging to see that “20-50” others have already submitted proposals for a job. I find it helpful to remember that most clients aren’t posting jobs because they want to, but because they need some task done right now. The process of reading proposals and hiring a worker can be somewhat unpleasant from the client’s perspective. In other words, you’re sending your proposal to someone who wants to hire someone and get this thing over with.

Takeaway: Don’t let “20-50” other proposals stop you from applying.

You aren’t competing with everyone else who applies. In my thumbnail example earlier, I had 17 proposals, but at least half of them weren’t worth considering. I’ve found this is the case for many jobs I post. The people who send cogent proposals and acceptable samples are the only ones who might possibly be hired, and this is a relatively small fraction of the total proposal number.

Takeaway: Bad proposals inflate the appearance of competition, but you aren’t competing against them.

The first two points I have listed lead into the third, which is that your potential client can only choose from what’s available, not from what is perfect. It is very possible that, although you feel you don’t have a lot of experience for a particular task, you’re the best of what’s there. If the client is faced with the binary choice of hiring you or starting the search over again, it can be easier to just hire you.

Takeaway: Whatever your real or imagined shortcomings, you might still be the best option for the client at that moment, and so get hired.

When you’re being paid hourly, if something comes up with the client and you need to do more work, it isn’t such a big deal. It might even be welcome. After all, you’re being paid for your extra time.

But when it’s a flat-rate job, any unexpected task cuts into the finite amount of money given to you for the original work, lowering your dollar-per-hour ratio.

Here’s a real-life example. I had been hired to do a flat-rate job for a modest amount of money. The job description listed two tasks that both involve writing, but are definitely separate skill sets. Because the rate for the job wasn’t that big, I figured it only applied to the first task. The second one would surely come with a second payment, and had only been mentioned to show the overall scope of the project.

That was my logic. The client thought differently. I ended up doing both tasks for the original payment.

I could have saved myself a surprise by asking at the start: “Just to confirm, for this project you want A, B, and C done, correct?”

If I learned there was also X and Y to do, I could have either taken the job knowing exactly what it would be, or negotiated a higher fee, or not taken the project.

There can be a tendency to jump on jobs without questioning them too much, out of worry it will drive the client away, but you’ll save yourself surprises later on by confirming exactly what is wanted at the beginning.

Takeaway: Confirming all tasks and expectations at the start of a flat-rate job prevents misunderstandings that could obligate you to extra work later.

In my earlier Upwork post, I talked about situations where it is wise to turn down work. To summarize, they were:

• Very low pay without any ancillary benefits (like learning a new skill, doing something you find interesting, getting your first client).
• You have zero interest in the work.
• You’re reasonably certain you won’t be able to complete the work effectively.

As a freelancer, it can feel like you’re being a bad worker if you turn down a task. This can create an incentive to agree to as much as possible, even if it’s outside your skillset or what you were originally hired to do.

However, from the client’s standpoint, it usually isn’t a big deal if someone turns down work. You move on and hire somebody else. It’s much better to know up front that the freelancer can’t do the work than to start the job and find out the hard way.

Takeaway: Turning down work when it’s outside your skill set or interests is better for both you and the client, who can then find the right freelancer for the job.

Replying to messages in a timely manner is good. Replying to them immediately can make communication more difficult for the client. If you see an indication that the client is actively typing, don’t send a message.

There have been some instances when I hired someone and needed to send that person a fairly lengthy list of instructions in the chat. Because of the way I was adding attachments and collecting my thoughts, it made sense to send the long message in several pieces, taking ten or fifteen minutes to write all the segments.

If the freelancer answered too quickly, before I had time to finish the sequence, this could derail the chat. Because of this I now usually write everything out in a separate document and send it at once.

The freelancer could save me some trouble, and let me follow my natural inclination for how to write messages, simply by waiting a few minutes and responding only after I was clearly finished with the entire message. I doubt I’m the only client out there who thinks like this.

If you’re trying to be an optimized freelancer and not potentially annoy your client, give messages a few minutes of waiting time when it seems there may be more on the way.

Key Takeaway: Waiting a few minutes before replying to messages can help clients complete their thoughts and avoid disrupting the flow of communication.

It can be frustrating, from the client’s perspective, to have to chase down status updates and prompt the worker to respond. It’s much more convenient to be told that you should be hearing something back in three days, or a week, or whatever. This way you know not to ask for an update unless it has been longer than that time.

I think one reason people hesitate to give time estimates is out of concern that they’ll look bad if they take longer. But there’s no reason to give yourself a super short deadline in your estimate. All you need to do is tell the client something, even if it’s a range and not a specific time.

For longer projects, where there will be no visible progress to the client until you deliver the finished product, it’s helpful to write periodic check-ins without being asked.

Most people don’t like doing extra work, feeling uncertain, or needing to roust a response. By sending updates generously you make things easier on the client.

Takeaway: Provide regular updates proactively to keep clients informed and reduce their need to ask for progress reports, making the process smoother for both parties.

If you’re using Upwork chat, and something happens to your account or the other person’s account, it can be quite difficult to reconnect. This happened to me once, where a sub-account of mine was mistakenly erased by a client, and I permanently lost all chat content for every message sent through that account.

There were a lot of names in the chat by that point, which I didn’t remember exactly, so I couldn’t directly message them to reestablish the chats. From their perspective, I just disappeared one day.

It’s a good idea to get a second method of reaching anyone you do work with on a regular basis. Asking to communicate outside of Upwork before a contract is started is against their Terms of Service, but getting a secondary way to communicate later is good business.

Takeaway: Establish a secondary communication method with regular clients, such as email or phone, to avoid losing contact if account or platform issues happen.

Although the freelancer and client have the opportunity to rate each other, the relative importance of feedback is much higher for the freelancer. This is because, especially when starting out, you need good feedback to grow your profile and help get hired, and you are in competition with many other people.

The client, on the other hand, mainly just needs to offer money to attract a lot of workers. Only if the client’s feedback rating is severely negative is this likely to start driving people away.

Key Takeaway: For freelancers, positive feedback is crucial for building a profile and securing jobs, whereas clients primarily rely on their budget to attract workers.

Leaving feedback for you is work for the client. Some people will forget about it, or not want to make the effort. People who are upset or really happy are more likely to leave feedback on their own.

Directly asking for feedback after a job ends is likely to get you more of it than if you do nothing. But it’s important to keep a couple of things in mind.

To leave feedback, you’re forcing the client to terminate the contract, and therefore have to pay a contract initiation fee to hire you again. You’re asking for that person to do more work and potentially pay more money without a clear benefit in return (because your potential feedback on the client’s profile just doesn’t matter as much).

It’s the style of some people, perhaps many people, to avoid confrontation. When such people are upset or dissatisfied, they’ll just go away. It’s possible that–whether this is a fair assessment of your work or not–some clients have had a bad experience with you. They choose the most passive option to handle it, which is to leave no feedback. It’s important to keep in mind that they may be unhappy without directly saying something to you, or without the job being obviously fraught with issues. Some people are just not direct about these sorts of things.

If you come at them asking for feedback, you’re potentially prompting them to vent the frustrations that would otherwise have remained unspoken.

Upwork has the “private feedback” section, so it’s possible that someone will leave you a 5-star review publicly, while writing to Upwork a 4,000-word essay about what a pain it was to work with you. Actively prompting feedback carries some degree of risk.

Takeaway: Actively seeking feedback can increase your ratings but carries the risk of prompting hidden frustrations from dissatisfied clients to be expressed.

There’s one situation where I would advise actively seeking feedback. If you have worked with a client for tens or hundreds of hours, and your contract ends under positive circumstances, it’s worth asking for feedback. The chance of being surprised by that point is quite low, as you know the client, and it can look odd on your profile to have a long project listed without feedback given for it.

Takeaway: Actively seek feedback from long-term clients when the contract ends positively. The risk of negative surprises is low and it enhances your profile.

It’s fine to have a general message at the end of a project that you’d be happy to work with a client again. I advise against popping up in the chat after some time has passed to say you can do more work. This is because, realistically, if your client needed more work from you, you’d hear about it. The chances are relatively small of you missing out on a great job because the client really needed you but totally forgot about you. It’s much more likely the client either doesn’t need you then or doesn’t want to work with you again.

Takeaway: End projects with a general offer for future work, but avoid reaching out later to solicit more tasks, as clients will contact you if they need your services again.