Upwork is a global freelancing platform operating in 180+ nations. The site can be a freelancer's dream, but it can also be their worst nightmare if they NEED to make money quickly. If you don't know how to navigate the platform nuances, you can wind up spending a bunch of money and never making a dime.

For me, getting established on Upwork was incredibly difficult and took several months. There were several times that I contemplated giving up. This article is an attempt to capture what I learned along the way, so you can hopefully achieve success faster. With 5 million clients using the site, there is a lot of potential income to be made!

After you set up an account, the site will offer up onboarding videos that can help you learn how to submit proposals, track your time, and utilize other important features. It's a good idea to watch as many of these videos as you can. Once you start winning gigs, you will need these skills to engage well with clients.

Beyond the site-provided tips, I would advise the following:

1. Build an Easy-to-Skim,
Client-Relevant profile.

Originally, my profile read a lot like my resume and LinkedIn profile. It used sophisticated language and spanned a wide array of keywords and roles. However, the Upwork crowd and search algorithm prefer specificity, personality,... and emojis. (See the emojis I used HERE.)

For example, those who are seeking a "PowerPoint Presentation Specialist" only want to hear about your presentation development skills and not much else. This presented challenges as I wanted to pursue gigs spanning Instructional Design, PowerPoint Design, and Digital Video Production. I wound up figuring out a way to appeal on all of these fronts, however, an easier option would have been to use "Specialized Profiles". Check out this VIDEO about how to use this cool feature. (Hey, LinkedIn, you should take note!)

Another resource I found helpful in this step was this VIDEO by Josh Burns.

2. Differentiate Yourself from other
Freelancers

in your Profile and Portfolio.

When a client reviews proposals, their thought will be along the lines of "who here will be the safest/best option for my project?". They need to understand what YOU bring to the table that other freelancers may not. Your work style, samples, certifications, approach, and professional practices can cultivate confidence in selecting you.

Since I didn't have on-site reviews for prospective clients to refer to, I decided to incorporate a few off-site ones. Upwork provides a feature to help with gathering off-site feedback. If you scroll toward the bottom of your profile, there will be a section between "Work History on Upwork" and "Certifications" where you can request off-site testimonials from past clients. I didn't want to bother my clients who had already provided a testimonial, so I just incorporated these into my profile summary. However you choose to include them, this element will help prospective clients to feel more confident in your stated skills.

Again, if you want to see how I spelled all of this out in my profile, click HERE.

3. Craft an easy-to-adapt Cover Letter template

and tweak it slightly for each gig.

Submitting proposals quickly increases your chances of winning gigs. So, it's best to have a standard cover letter that you can copy and paste when a gig is announced. I wrote one up in Word and stored it in my phone so I could quickly respond to new offerings, even when away from the office.

When a gig came available, I would copy the letter and paste it into Upwork, where I would then tailor it to align with the gig. This minimal tailoring only takes a minute or two. In a pinch, you can just submit the standard letter, but it's best to customize it if you can.

The formula I used to write my cover letter was:

Greeting
Request for consideration - job title included
Why choose me?
What can you expect when working with me?
Call to action (e.g., "let's schedule a time to chat")

4. Sign up for new Job Alerts and respond within 5 minutes

to get a better chance at being viewed.

According to DemandSage, there are about 18 million skilled freelancers on Upwork, from all over the globe. This means you have a LOT of competition!

Your best chance at winning gigs is to submit a proposal within the first 5-10 minutes of posting. Clients often post their job and then hang out on the site for a few minutes to see what comes in. Even though you don't have much experience, they may click on your proposal out of initial curiosity. When they circle back later on, they will likely have 50+ proposals to review and will likely only read those who have proven work history on the site.

Once you have submitted at least one proposal, Upwork offers a "Job Alerts" option where you can receive emails or on-screen notices about new gig postings. This enables you to respond quickly to new postings. Click HERE to learn how to turn these notifications on.

5. Lower your expectations so you can build work history.

Initially, I tried to get my typical off-site hourly rate. No one was interested. They didn't want to risk that amount of money on an unproven freelancer. After hearing Josh's advice to start low and work your way up, I started bidding on the jobs that no one else wanted. Things like "build a 40-slide PowerPoint presentation from scratch with all of the coolest animations and transitions... for $10". Yes, this is a COMPLETELY unrealistic expectation, but some users either don't realize this or intentionally prey off our need to prove ourselves on the platform.

Either way, it is a means to an end... one that you WANT! I only had to do a few low-paying gigs (about 10 hours of work total) before I had enough positive reviews to start intriguing better paying clients.

One important caveat, especially as you are working on these low-paying gigs, is to ALWAYS ensure a 5-star review. Your low-paying clients may make ridiculous requests, but an early scuffle can cost you big time down the line. Eat some crow now so you can dine like a King later! Don't ever quit mid-gig, remain professional even when being asked to jump through hoops, and offer up win-win solutions. After several positive gig experiences, you will earn a "100% Job Success" badge, which will show up on your profile for prospective clients to see.

There are also several key milestones on the platform:

$100+ total earnings
$1K+ total earnings
$10k+ total earnings

Prospective clients can limit your ability to submit proposals based on these levels and often search with these levels considered. The highest paying gigs tend to limit responses to those who have made $10k+.

The Advanced Preferences section of the client view in Upwork shows where selections can be made for Success Scores and Amounts Earned.

6. Low-hanging fruit should be picked carefully.

While you are bidding on these low-paying gigs, be cautious of those who have not completed the "Payment Verification" step. They could be unscrupulous individuals who are trying to get your work efforts for free.

I don't mean that you should never submit for a gig that doesn't have Payment Verification, though. You just need to ensure the client has completed this step BEFORE you begin work for them. Other freelancers may steer clear, which could provide you with an opportunity to win the gig. Sometimes, payment verification hasn't happened because the client is new to the site and missed the step. Other times, the funds may not be there at all. Just be cautious here.

7. Ensure project milestones are funded

before you start work on them.

To protect yourself, it's a good idea to set milestones for fixed price gigs. If you don't, you could do all of the project work and not be able to collect payment. Milestones can be a bit tricky to time at first. Originally, I thought the milestones should be things like "present mockups". The problem with using the end of the milestone as the name is that the client may resist funding the milestone before they receive the mockups. You want them to fund the milestone BEFORE you do the work on the mockups.

I found it was better to label milestones with the start of the step, for example "begin work on mockups". This helped clients to feel better about funding them. The funds aren't released until they approve fund release, so the client is still protected too. When presenting the mockups, I would then ask for them to approve the release of funds. So the order would look like:

Have the Client Fund the Milestone > Do the Work > Submit the Work > Have the Client Release Payment

8. Use your Early Earnings to purchase more Connects,

so you can continue bidding on gigs.

I've typically purchased 100 Connects at a time at a price of $15.00. Most gigs will require 10-20 Connects to submit a Proposal, and you will have the option to "boost" your proposal toward the top of the list. I've found it's far more effective (and frugal) to submit right away, rather than worry about boosting proposals.

You will likely find that you burn through Connects quickly in the beginning. It's helpful to reinvest your earnings in Connects until you start making a decent rate. This can save you extra steps (withdrawals and payments).

Upwork truly takes an investment of time (about 3 months) and money (about $200-$500) to get traction going.

9. Invite off-site Clients onto the site

to help establish your work history.

If you still aren't winning bids, you may need to get more creative. One approach I used was to invite some of my off-line clients to run our work through Upwork. They need to be aware that Upwork is going to charge them a 5-10% fee on the total project cost (or hourly rate). You also need to be aware that you will lose 5-10% of your pay to Upwork fees. As long as you figure these fees into your pricing, you can use the work to establish yourself on the platform.

One thing to be aware of, however, is that Upwork expects you to keep all client engagements online, even with those you bring to the site. If you violate this policy, your account can be suspended and you can no longer use the platform.

10. Slowly Raise your Rate over time

and move onto higher paying opportunities.

As you achieve earnings milestones and demonstrate your capabilities to deliver successfully on projects, you should begin to raise your rate. You can gauge the appropriate increase by the rate you are able to attain on gigs. For example, if you are winning gigs at $25/hour, you should raise your rate to $25/hour. If you are winning gigs at $75/hour, you should raise your rate to $75/hour.

You can also consider a rate increase when you start getting invitations to submit and/or direct inquiries. I started to get invitations to submit proposals at about the $1k earnings mark. I haven't yet achieved the level of having new clients hire me directly on the site (although my previous clients have messaged me directly to begin new projects). It is my understanding that by the $10k mark, this should be regularly happening and you likely won't have to submit proposals anymore.

One of the benefits of the platform is that neither freelancers nor clients have to make much of a commitment. This model draws a certain type of crowd. Some take this lack of commitment too far.

Unfortunately, I had to learn this lesson the hard way. I had a client make me an offer for a gig that was going to fill my available hours for several months. I started turning away other opportunities (from returning clients and offline clients) in order to make space in my schedule for this long-term project. The week before the project was supposed to start the client let me know that they weren't going to need me as much as they originally thought. I was left scrambling to fill my hours.

I've also heard of instances where clients have made promises in messages but never initiated the contract, leaving freelancers without work unexpectedly.

Clients also may not take the time to leave a review after the gig is over. Or, they may have had unrealistic expectations, which is frustrating when you are trying to build your presence (and giving 110%).

My advice (to maintain your peace of mind) is to never count on work until you have a contract in place (and even then, be aware that it can fall through at any time). Additionally, never count on a positive review until you actually receive it.

Originally posted by:

Angela Watts 🔹 M.Ed., SHRM-CP, CCTC

Psychology Informed Learning Experience Designer (LXD) │ Award Winning Writer │ WSJ & Forbes-Featured Careers Expert | Multi-certified HR Pro | Part-time Freelancer (PowerPoint Pitch Decks & Instructional Design)

March 27, 2025