How to Use Upwork Like a Pro with Laura Pennington

How to Use Upwork Like a Pro with Laura Pennington

Better Freelancing Episode 031:

How to Use Upwork Like a Pro with Laura Pennington

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Six Figure Writing Secrets
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Episode 031 Takeaways

  1. Clients on Upwork are pre-sold on hiring a freelancer.
  2. Don’t be afraid to decline jobs on Upwork that don’t suit you.
  3. Include fewer, higher quality work samples with your proposals.
  4. Always proofread your pitch thoroughly before hitting send.
  5. Use the “fast, cheap and simple” method to win your first jobs on Upwork.

Episode 031 Quotables

“Whether you’re new or established, [Upwork is] a great place to go to get immediate work.”
— Laura Pennington

“Make sure your work samples are amazing. They need to be the best possible and they need to be easily viewable.”
— Laura Pennington

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Better Freelancing — formerly known as Better Blogging — is the video interview series that explores the best practices of successful freelancers. Catch new episodes bi-weekly, with occasional bonus episodes! Subscribe to my YouTube Channel for updates.

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28 thoughts on “How to Use Upwork Like a Pro with Laura Pennington

  1. Hi Brent,
    Wonderful to see Laura’s Interview on your blog.
    Freelancing is really a great field to start a career. A lot of people are starting freelance writing as their profession.
    In starting people do freelance as their part time options and soon they turn this into full time profession.
    It is important to forecast the challenges that came as you choose this career.
    The major problem is finding the clients that most of the people face.
    Laura has come with great solution for this.
    Thanks for sharing.
    With regards,

    • Hi Saurav,

      Thanks for checking out my interview with Laura.

      Indeed, a lot of people struggle with finding new clients… and unfortunately, many freelancers think they are “above” using platforms like Upwork to source new clients. From my own experience, I can say that Upwork (then Elance) made a huge difference for me in the early days of my freelancing career. (Still helps, actually…)

      We appreciate you taking the time to watch and comment, Saurav.

      Have an awesome week!


      • Hi Brent,

        Thanks for posting this interview. I have a question though: Is Upwork still the same for freelancers as it was in your early days?

        I’m asking this due to the increase in fees by Upwork.

        Let me know what do you think or do you have any insights on the same?

        • Hi Karan,

          Well, it’s tough for me to talk about the “early” days of Upwork since Upwork is a relatively new platform — do you mean the early days of Elance and oDesk?

          If you’re strictly talking about the fee hike, I’d be inclined to agree with Laura. Considering Upwork is an online marketplace of small business owners who are ready and willing to hire freelancers, I think that 20 percent is well justified.

          I mean, the alternative is winning all your own clients… but that also means giving up your time to go proactively seek out, pitch and close them. I’d rather give up 20 percent and skip all those steps.

          But even then — as Laura said — once you gain more experience, you can generally factor Upwork fees into your proposal.

          I hope that answers your question.

          Maybe if we’re lucky, Laura will add her two cents here. 🙂



          • I was just looking forward to compare the pricing of elance and Upwork (20% + processing fee) and the different is somewhere around 15% and that’s something huge… I agree Upwork to be the right platform to start the freelancing career but still for newbies now a days, it would be a tough challenge. Although, some people are now a days actively involved solo ads blasting. What do you think about that? That’s a different question but it just striked my mind.

        • For clients with total projects under $500, you’re paying 20% to Upwork. Once you pass a threshold, though, you go to 10%.

          On Elance, the standard fees for 8.75%. To me, there’s very little difference between 10% and 8.75%, especially since Upwork is essentially delivering these leads directly to you like Elance did. They’re also giving you the escrow or hourly work protection (which is huge, considering how much time a lot of freelancers spend in their early days chasing down money.)

          Now, if you can get the client to work with you on much bigger projects with a total amount billed over $10k, you drop down to 5% fees.

          So, who does this benefit? Big projects and long-term clients. Long-term clients more so. If you can get a recurring gig with a client paying $500/month, you’ll be in the 10% range pretty quickly. If you’re bidding on one-off projects of $250, then you won’t ever hit that threshold, so factor the 20% into your pricing. Either absorb it on your end if you think you can talk this client into more work (thus increasing your per-client take and reducing the fees in the future) or consider it a cost of doing business.

          As I always tell my students, ongoing projects are always your friend, on Upwork or not. The Upwork fee cut just makes the case even stronger.

    • You’ve pointed out a great reason to use Upwork- the clients are presold and it is a great lead source when used properly!

  2. Hey Brent, So glad to see this post on Upwork.

    I am huge fan of Upwork. Wonderful guidelines for newbie to be a perfect freelancer. It was interesting moment for me, watching the guidelines of using Upwork by Laura. Complete information on Upwork. She explained very well and I have learned many things from watching video. I must say that it is posted to fulfill my knowledge to be a perfect freelancer.

    Best and informative things in this video. It is difficult to get a client on Upwork. Glad to know about Elance too.
    I sincerely appreciate you for sharing such useful post on the using Upwork.

    – Ravi.

    • Hi Ravi,

      Well, Elance and oDesk no longer exist — they were both replaced by Upwork. And it can certainly be challenging to win your first couple clients on Upwork, but it does get easier from there. If you need further assistance, I recommend you check out some of the freebies Laura gives away on her websites.

      Thanks for watching and commenting!

      Good luck,


  3. Hey Laura,

    Thank you so much for your UpWork wisdom. 😃

    I have an account but never had success with clients that want to pay decent rates. The amount of jobs is perfect, it’s just picking the right ones I have trouble with.

    Like you guys mentioned, eating the UpWork cost is not a big deal, but getting paid $0.02 a word is not worth it. I get approached for jobs like these quite often and I always wonder how people ever make that work. It seems like a crappy way to make a living.

    I will dust off my shoulders and get back on the UpWork horse. I know it IS possible to find good clients. Any particular criteria you tend to look for?

    Thank you both for the great interview, Brent and Laura.

    Have a fabulous week.

    – Jasper

    • In the early days of freelancing, Jasper, I used to take those really low-paying jobs some of the time. I don’t think I ever went as low as $0.02 / word, but certainly $0.04 to $0.05 / word. But to go that low, I would ask the prospective client for one of two things:

      a) Give me a byline and credit for writing the article, or
      b) Allow me to use it as a sample in my portfolio.

      In so doing, I started to build “evidence” (as I call it) of my talent.

      If the prospective client refused both of those points, I wouldn’t necessarily decline the job. I would stop to consider how quickly I could do it… could it be a “fast, cheap and simple” job as Laura talked about? Could this job be done quickly and allow me to apply to better jobs in the future? Building up my reputation on Upwork (then Elance) often got me noticed by better clients.

      And lastly, if all else failed, I looked at it this way… did I have the time to do the job? Even if the pay sucked, $45 was better than $0. I often underscore this point. No, $40 or $50 for a 1,000-word article isn’t glamorous… but if I have nothing else going on for the day, and I can spare an hour or two to knock it out…? Sure. Back then, when I first started, every little bit helped.

      Those are my thoughts, anyway.

      Laura is the real Upwork pro, so I’ll let her give you a better answer.

      Thanks for watching and commenting!



    • Thanks for your patience with my reply! I am on a three week vacation in the UK but wanted to give you some insight! Definitely look for someone who is easy to work with. If the person wants to make you answer thirty questions before even hiring you, while this might turn out to be a good client, that happens perhaps ten percent of the time. It’s like fishing-throw that one back. Clients with good work history comments from other freelancers are always a plus too since that means they treated someone else well and paid that person on time.

      My favorite clients are also those who know what they want. A vague job description is not necessarily a bad thing but it can lead to more work on your end if they have no idea what they want. Clarity and positive comments from others are very valuable!

      • I want to thank both of you for your helpful comments.

        I totally agree with you, Brent. Sometimes it’s worth it to write at $0.04 if you are building a reputation at the same time. I actually gave them a very reasonable offer back at $20 for 400 words, but they insisted on their $0.02 rate and would promise me a lot of work if it all went well. But at that rate, I would have to write faster than I think. In cases like these, I’d rather write a free guest post on a reputable site.

        Laura, your tips are very valuable and I’m sure these will also be helpful in looking for clients on the new nDash network that just opened it’s beta doors. Can’t thank you enough. Enjoy the rest of your vacation. 🙂

        Have a great week, both of you!

        – Jasper

    • Hi Robin,

      You know, it’s funny you should say that… because I definitely found it easier to win good clients on Elance versus Upwork.

      But Laura did provide some great tips here. I’m going to use her “fast, cheap and simple” method to boost my Job Success Score a little bit, and complete a few more tests as well. (I completed about a dozen on Elance, but only one so far on Upwork)

      Thanks for commenting, Robin.


    • Don’t give up! Persistence is key on Upwork. Find a strategy that works for you and keep refining it!

  4. Hi Brent, Hi Laura,

    I am SOOO going to grab your report, Laura.
    I loved Elance. Never had any issues with them. I was saddened when the migration took place because I’ve experienced some difficulties with Upwork and wasn’t thrilled with some of their policies. But, no place is perfect. My profile has reviews and a history and I’m hesitant to give that up.

    I agree with what you said regarding newcomers. It helps to have some work and reviews under your belt. It builds momentum and confidence. Once you’re established, though, it’s important to respect your time, effort and talent – and those fees sure do add up.

    As usual, Brent, awesome interview. Great to meet you, Laura.

    • Hi Dana! Thanks for your kind words.

      It seems that the rating systems are a bit different between Elance and Upwork. I never received anything less than a perfect 5-star review from clients on Elance. Yet when my profile carried over from Elance to Upwork, my Job Success Score was only 84 percent. I think this was largely due to clients who I repeatedly did jobs for that stopped giving me feedback on each one.

      As a result, I have significantly more jobs in my history without a rating than with.

      So, I too am in that boat where I need to do more of the “fast, cheap and simple” jobs on Upwork to build my ratings back up. Frankly, I’ve sort of neglected Upwork thus far in 2016. I need to change that!

      I’m sure you’ll find a ton of value in Laura’s content, Dana. Have an awesome week!


    • I’m so happy to hear you got something valuable out of this! Yes make that Elance history work for you! Refer to it when you bid with new prospective clients!

  5. Hey Brent and Laura,

    While I was pleased to hear about your success on Upwork, I’m going to have to reserve judgment for the time being. To date, I’ve found it to be a time-waster. However, I’ll check out Laura’s guide and see if I can make better use of the platform. Especially with regards to searching for better quality work.
    Right now I think the Upwork fees are too high, and the clients are just looking for cheap labor, and those two don’t make for a healthy bank balance:-) So let’s see if I can get better results and then report a positive back here!

    – David

    • Hi David,

      I’d love to see you report back here after checking more of Laura’s content.

      As far as Upwork being a time-waster, perhaps Laura can reply to you and go into a bit of detail about some of her wins with the platform?

      At the time we recorded this interview, she had just won a client on Upwork for $7,000 / month ongoing. I think there’s a lot of potential with Upwork, but it takes grinding out some of the “fast, cheap and simple” jobs in the early days to build up your reputation and get the ball rolling.

      The fees don’t bother me. I mean, even at 20 percent… it saved me hours of prospecting for new clients and pitching on my own. So I’ll happily give Upwork 10-20 percent or whatever they want. Generally, I just factor those fees into my pitch. My service at $299 / month becomes $373.75 / month. All good.

      For that matter, I’ll often apply to jobs with a very low budget. Doesn’t mean I change my prices. My rate to do the job as outlined might be, let’s say — $800 — but the client entered a budget of $150. I’ll send a proposal anyway. And funny enough, oftentimes the client will tell me they had no idea what to enter for a budget. They really weren’t sure what their job was worth. But they’ll gladly have me do it for what I’m asking since I’m the strongest candidate who applied.

      Same goes for hourly jobs. I used to avoid those because I didn’t want to work for an hourly rate. What I discovered was that I could enter any hourly rate I chose, but put right in my proposal that I would prefer to bill on a monthly basis. Clients are often happier with this arrangement if they can pay a fixed rather versus hourly.

      Your comment reminds me a lot of my last expert roundup post. Because every freelancer has his or her own preferred method for winning new clients. And there’s nothing wrong with that.

      Thanks for watching our interview and commenting, David!


    • David I will share that when I started on elance it took me a few weeks to get my first job and then I found a system that worked. Until that point I thought it was a time waster too. I have gone back twice since the merge to Upwork and used my strategy to land more than $30k in work for 2016. I usually stop when I’m nearing the overbooked point and then reappear a few months later when I need leads. There are awesome clients there, but they are not easy to spot. It’s hard to sift through all the people wanting to pay $5 for 500 words but there are decent clients. Did you know that you can also use the thumbs down feature to show you’re not interested when you read a bad job post? That way it gets minimized to the header only and you can scan more quickly when you’re doing a job search. Also always use the search tool I.e “white paper” “SEO blog” etc. it will get overwhelming if you just look at all the writing jobs. Speeding up your process will make it less like a time waster. I apologize for any typos here – on my iPhone during a three week jaunt abroad!

  6. Great tips. I have always been a great fan of upwork. Very practical advice for the beginners as well as established freelancers. Thanks Brent for sharing. Thanks Laura for helpful tips.

    • Hi Sunil,

      Yes, Laura provided some great tips here.

      Much like you, I have always been a fan of Upwork — and Elance, before it became Upwork. But even with a couple years of experience on the platform, Laura reminded me of a few things I hadn’t thought of recently, such as how to factor fees into my proposal price.

      Thanks for commenting!

      Chat soon,


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