Mastering Upwork – Top Questions Answered

So it’s finally time – the time everyone warned me about when I started writing coaching and mentoring content. The time to sell an Upwork course……

JK – but in all honesty, is it only me or are more people tired of Facebook Ads course spam?

Learn how to master Upwork
Make money in dollars
Stop being poor
Yaadi yaadi yaada

Thing is, getting started with freelancing isn’t really that complex, it’s hard, but not complex. As lame as it sounds, it all comes down to consistently improving your methodology and doing research.

I can confidently say that a paid course will not guarantee anything for your case. It might help you accelerate your path – but there is still a pretty much a 90% chance you WILL fail on Upwork – at least the first time around.

Table of contents:

Why Paid Courses Don’t Win You Upwork

In recent times, Upwork has officially become a ‘pay to win’ platform. Connects are too expensive, and you as a freelancer in Pakistan/India/Philippines WILL have a harder time affording them compared to your western counterparts. 

Couple that with the fact that most people interested in freelancing generally don’t consider the fact that freelancing IS HARDER than a regular job – you need a lot of soft skills in addition to the skill you are selling to be successful. 

Lastly, as a new account, your first job is easily 50 proposals out for most. At the average rate of 16 connects (yeah that’s what the good jobs cost, ignore the cheaper ones) – you are looking to spend 800 connects just to land your first gig. And if you are wondering, 800 connects are for 120$ or about 33,000 PKR at the current rate.

Silver lining, if there is one, this has actually resulted in a significant reduction in spam applications in my experience. Yes, it is still easier for people with money and connects lying around to beat you. But as a new freelancer, you will generally have less competition on smaller jobs. Which should be the goal to get your foot in the door. More on that later.

Why Listen to me?

As someone, who went from 0 to top rated plus in just 18 months and with only 4 clients (quality matters, don’t be mislead with quantity) – I know a thing or two about succeeding on the platform.

Over the last year I have been actively contributing to https://sadaschool.pk/ discord server as a veteran freelancer. I had the opportunity to cater the most commonly asked questions and clear some doubts. That is what this article is for.

If this does well, I might actually create an end to end Upwork course ‘For Free’ – Upwork is already expensive as it is, you shouldn’t be paying more to learn what’s available already.

That being said, let’s get into it – first I will provide some basic study material for anyone fresh to Upwork – once you’ve been through it, consider the discussions posted on this article for specific queries most freelancers have these days.

P.S This article is from the perspective of a Pakistani Upworker – that is an important distinction to make. Some practices shared here won’t apply to you as someone not living in a low income region. And if you are living in Pakistan, Philippines, India etc – good news! This will perhaps be the only well laid out article you find written for your perspective.

Best Resources to Get Started with Upwork

Below are free resources available for you to get started with Upwork and freelancing in general. No payment or course required. 

Create a bookmark folder, bookmark everything here, visit every day to absorb some.

1 – Upwork Academy

It’s funny how most paid courses are half filled with content from here: https://community.upwork.com/t5/Academy/ct-p/Academy

Yeah, it’s available for free, for anyone. If you are just starting out, I would recommend picking the basics learning path and completing it.

Not only will you learn everything you need to know to get started in a clear manner. It sometimes rewards you with connects as well.

2 – I hate reading, I wanna watch videos

Well you won’t get far then, but here are my 2 top picks:

https://www.youtube.com/c/JoshBurnsTech

And

https://www.youtube.com/c/FreelanceMVP

I would HIGHLY suggest to only watch them once you have landed a gig. They are hyper successful freelancers and are based in the west, some of the things they share WILL NOT apply to you – simple as that. But besides that, their content and general advice is pretty solid. 

But back to what I said above, get comfortable reading and writing if you wanna succeed as a freelancer – that’s like 40% of the job.

3 – SadaSchool Freelancing

https://sadaschool.pk/

Born and bred in Pakistan, this is single handedly one of the best resources available that does a pretty good job of explaining freelancing and roadmaps for beginners.

It’s not an ‘Upwork centric’ resource, but it is still a good one to learn the basics of the skills you need to have as a freelancer.

Go through their masterclass: https://sadaschoolmasterclass.notion.site/Welcome-to-the-Masterclass-238c0e918f38449c90f5d3e0978c58ff

And their roadmaps:

https://sadaschoolmasterclass.notion.site/SadaSchool-Resource-Library-dfb50742bc1d42498704d57b33338f90

They have a discord server as well, which isn’t pretty hype these days. But still feel free to join and ask away your question, people are generally helpful.

Avoid asking for a job, you don’t ask for a job from people looking for a job. Logical, right?

4 – It’s me, it was me all along, I also want to help you

I wish I had unlimited time, but it is marching towards our inevitable death (wink wink). When I can though, I really want to put in the effort to share coaching and mentoring content with fellow Pakistanis. If you would like me to answer anything specific feel free to email at hello@thewanderingpro.com or reach out to me at: https://sknexuspk.bio.link/

Currently, I try my best to share any knowledge I have via blogs at https://thewanderingpro.com/

And then also creating helpful resources for professionals, freelancers, and small businesses over at https://www.buymeacoffee.com/sknexuspk/extras – everything ‘for now’ is FREE. 

With that taken care of, let’s get into the top discussion areas for Upwork freelancers.

Learn how to Search for Jobs on Upwork

Your connects are valuable and you must learn how to optimize your job hunt. Almost never apply to jobs that show up on the feed, the system almost seems to be designed to waste your connects and jobs that don’t matter mostly.

Learn to customize your search for your gig, see image below on what that looks like:

Upwork job search filters

Here is what I want you to do to begin with:

1 – Search for the basic keyword for your gig, let’s say you do copywriting, we will use that.

https://www.upwork.com/nx/search/jobs/?q=copywriter

Without any filters you will be looking at around 5k+ jobs. Can’t pick between 2 Netflix shows, let alone 5,000 jobs to apply.

2 – Now you will need to do this from the filters sidebar:

– Select a category if it is well defined in Upwork, otherwise skip it.
– Pick Intermediate and Expert (Entry Level ONLY if you have 0 real world work experience)

– If you’re new check all the fixed pricing boxes from 100 to 1K, if you’re note new, pick to max, uncheck the ‘Less Than 100$’ box

– Do the same thing with your min and max hourly rate, I recommend a minimum of 10 USD/hr (more on that later) and a maximum of 50 USD/hr (coz this Pakistan, not US, remember that)

– For the number of proposals, pick all the options except 15 to 50.

– Payment MUST be verified for the hiring party, check the box.

– Keep the no hires unchecked and the remaining checked in Client History.

The rest of the filters don’t matter much in my experience.

Once done you should have something like:

Upwork sidebar of filters

We went from 5,000 Jobs to 250 jobs – much more manageable.

But wait, this isn’t over yet.

From here on out is where your actual research starts, you need to apply only to jobs that meet the following criteria:

Client criteria to look for on Upwork

– The client has good reviews
– The client’s past hourly rate average matches your demands
– The client has successfully completed contracts in the past
– The job has a well laid out job description
– The client has good hiring ratio – if someone has 500 jobs open and only 5% hire rate, don’t waste your time
– The client has decent spending history
– Don’t waste effort on a job that asks too many questions, usually not worth the time
– Lastly, don’t fall for scam posts – Yes, they happen, keep an eye out for something too good to be true.

If you open any job you will see most of this here:

Upwork client reviews

And with that, now you know everything about searching for jobs at a beginner level. There are some advanced intuitions you will build over time, but for now, this should be more than enough.

Understand Your Upwork Proposals

So you learned how to search for jobs, time to apply to some. Now I will spare the cover letter templates and the formula for writing the best proposal – because that you will have to learn over time. And you will learn, there is no one right formula – hence templates are pretty pointless since understanding the job post matters more.

However, you can refer to the resources shared above for a basic idea on how to compose a cover letter though. One tip I can give you is to first learn to write lengthy, then worry about filtering and cutting down things. Don’t stop at writing 150 word cover letters.

What I will share here are some crucial details you need to understand when applying to jobs.

The detail being this:

Job Screening Image

The screening section of the employer/client.

I have highlighted some key things you as a freelancer need to understand in the attached image, let’s dive in em:

Location, Hourly rate, Earnings, JSS Score, and Badges:

These 5 things will have the highest impact on your proposal’s strength, especially when applying to people who understand Upwork and have hired a lot on Upwork. They can instantly gauge a candidate’s ability just by viewing these numbers and associating them with their skill level.

Things for you to keep in mind for Upwork job applications

– Always maintain a 90+% JSS, anything below basically means you are no longer viable to scale on the platform as a freelancer, You can learn more about what affects your JSS here: https://support.upwork.com/hc/en-us/articles/211068358-Job-Success-Score

– Badges do matter, especially once you get Top Rated, you will see that your view rate has increased from when you didn’t have one. On average to get Top Rated, you need to be working for around a year, 4-5 jobs, around 2-5k USD earning depending on industry and kind of work.

– The earned amount shows your seniority on the platform. A big number means either you have worked for very long on Upwork, or you have done really high value work – or a combination of both.

– If you are associated with an Agency, YOU WILL show up as an association, be mindful of that when applying to jobs that say no to agencies, don’t waste your connects.

– Lastly, the most painful one for us, location and hourly rate – you WILL be judged on your rate and your location, that’s just the game – no way around it. People are looking to hire freelancers primarily to save costs, BUT at the same time they want quality work also. For newbies in most fields I recommend aiming a 10-15/20 p.h rate – going for 30+ once you are top rated at least. 

Again this is an average across fields, to learn more about your skillset’s going rate, just google the role + Upwork and you will land on a page like this: study this page, https://www.upwork.com/hire/front-end-developers/pk/ and get inspiration.

Lastly, as a new freelancer, you might not have the credentials above, so for you folks, this is the most important detail:

As you can see – the first 2 lines are what is first and foremost apparent to the employer – make good use of it, attach a video or use hooks to get the person to click on your proposal. Don’t waste paragraphs saying hi and hello, get to the point – state the problem and the solution leading to learn more about why you should get hired.

Hourly VS Fixed Contracts on Upwork

First of all, I would urge everyone to watch this full session on pricing models:

Generally speaking, I am biased towards fixed contracts. They are riskier as more of your payments are tied up in milestones, they also are slower to pay out some times since you have to remind the client to process them. And they are harder to land as well on platforms like Upwork.

BUT

They ensure higher quality of work and less burn out for you as a freelancer. And that is no small benefit.

Going with an hourly rate

See the thing is, on Upwork when you land an hourly contract, you get labeled as that rate. Let’s say you are a new freelancer who charged 5 USD/hr a gig, goodluck, now forever your average will be hit by that number making it almost impossible to drastically grow out of it.

This issue in particular is more of a problem for us in low income regions where the ‘I will do it for cheap’ mentality runs rampant and causes hundreds to burn out and quit freelancing.

So my advice is, if you are doing hourly billing, stick to a minimum of 10 USD/hr, because growing from that to the average of 20 USD/hr (low income area average rate) is much easier than from 5 or 3.

For Pakistani freelancers the upper limit I have found after studying a 1000+ profiles is around 35 USD/hour on average. You can do the same by hunting through all the available profiles in talent search.

Going with fixed price contracts

Hey Saqib, I totally understand your point on counting hours and getting burnt out, what do I do as a new freelancer to get fixed price contracts then?

To new freelancers what I recommend is get your foot in the door.

Do a small engagement first with a client, for a fixed price. Clearly lay out what the deliverables will be of the engagement and that you will consider further working after it is over and reviews are completed.

Also be transparent that you will do the said engagement at a lower price because you want to get traction on Upwork and want to show the quality of work you can put in as a new freelancer.

And there you go, you get your foot in the door and then it all depends on your skills from there onwards. If you did your homework, applied to verified clients with a good history, chances are if you do good work for them, you can negotiate a much better plan.

All this said though, there are some roles that are stigmatized by hourly rate, such as dev work. Clients will usually not agree to fixed pricing on such roles. In that case, go with the hourly, but as mentioned earlier, stick to a base minimum of 10 USD/hr – anything below that is digging your eventual grave.

Lastly, I recently did a piece on the limits of Upwork, you can read that here: https://thewanderingpro.com/top-earning-on-upwork/

Optimizing Your Upwork Profile

Unlike on platforms like Fiverr (more on that later) – your profile does not matter that much on Upwork. Profile views rarely translate to hires as a new freelancer so you shouldn’t really worry too much about it.

That been said though, if you have free time, I highly recommend working on the following items whenever possible:

1 – Having the necessary profiles – Build Specialized Profiles!

On Upwork you have a ‘general profile’ being your default when you sign up your account, BUT you can set up two additional profiles.

I highly suggest making use of this feature to cover more ground with keywords and your offering.

DO NOT copy and paste the same description on all three, cater to different audiences or different content depending on what you want to achieve.

You can do it in 2 ways,

Either – add variations of what you offer as a profiles, for example

– Copywriting can be your main profile
– Article writing can be your secondary
– SEO content writing can be your tertiary

Or you can have different verticals of work you can provide as your profile, for example

– Web development using WordPress, Webflow, Shopify
– App development, using React, Swift, Kotlin
– UX design using, Figma, Adobe XD etc

Article on how to setup profiles: https://support.upwork.com/hc/en-us/articles/115013750068-Create-a-Specialized-Profile

2 – Working on ready to use blocks for cover letter

I NEVER recommend having a template for your hook, introduction, and tailored content in your proposals specific to the job post.

But oftentimes, overtime, you will notice that a lot of job posts ask for similar details, like project history, or what tools you use, or any work history.

So an effective way to work on these is to have blocks ready to integrate into your tailored proposals as you are applying to jobs. Create a living doc and have ready to use blocks where needed as needed, some examples below:

What is in my Toolkit Block

Project Management Tools – Jira, Monday, Confluence, Basecamp 2/3, ClickUp, & Trello
Content Marketing and Strategy
SEO & Keyword Research (Search Console & Google Analytics)
Computer Repairs (Apple Certified Macintosh Technician)
Stocking, Pricing & Finances (FileMaker Pro)
Import & Export documentation (PK Specific)
Business Documentation (MS Office and Google Workspace)
Business Development (Corporate Tenders, Sales Prospecting, & Billing)
No-Code Web Dev & Content Management (WordPress & Wix)
CRM (Zendesk, Zoho, & SalesForce)
Corporate Communication (Slack, Gmail, & Zoom)
Live Streaming (OBS & Streamlabs)
Design (Animoto & Canva)
UI/UX (Miro & Figma)
Web Hosting Management (GoDaddy, BlueHost, & Hover)

Achievements Block

Lastly, some numbers to remember my by:

Revamped the lead-to-launch process for 2 Development Agencies, resulting in a 30% increase in revenue.
Implemented a new quote estimation tool that reduced sales lag by 20% and improved lead conversion by 35%.
Streamlined the Help Centre to reduce the load on support calls and tickets by 30%.
Developed and implemented a marketing strategy that led to a 50% increase in organic leads.
Ensured 90%+ satisfaction among enterprise clients.
Consistently generated over $100K in revenue per quarter through upselling additional projects to existing clients.
Introduced a robust reporting mechanism that helped the company expand it’s organizational structure by 50%.
Improved the onboarding process to ensure rapid team growth and increased retention rate by 10% during probation periods.
Reduced ticket resolution time by 30% by automating manual processes on the IT help desk.
Boosted the company’s local presence by earning over 300 5-star reviews on Google Maps/My Business in 2 years.
Cut IT inventory costs by 20% by forecasting customer demand based on market trends and new product launches.

Client Reviews Block

Words to remember me by:

Custom Web Development Agency – 5 Star Review

I run a Web Design and Development Agency based out of the US. Saqib was crucial in helping my Agency grow and scale. We did over $300K in sales in 2022 and Saqib was a big part of it. He was a versatile team member who made significant contributions in being the product manager/strategist for enterprise clients, and helped build out repeatable and scalable processes at the same time…….

Matrix Marketing Dev Enterprise – 5 Star Review

Every winning team has a “Most Valuable Player”, and Saqib is that MVP. Leaving a job in his hand is to forget worrying about its success – you will have the certainty that Saqib will do his best to deliver the best results. The problem and the solution are always viewed from a 360 degree perspective by him. His conviction will always be able to take you to the next level!

Mobile App Development Enterprise – 5 Star Review

Saqib is a very unique mix of talent and expertise. As a Business Owner I need people who can adapt to any task at hand – his versatile experience as a Product Manager sets him apart.

Projects Work History Block

Here is a summary of projects I have worked on that I will be more than happy to discuss in detail over a call.

Project: Custom CRM with EMR functionality
Key Integrations/Tech: Django/Next.JS, GCP, SalesForce, Pathify, Jotform, HIPAA Compliance

Project: Healthcare Service Platform
Key Integrations/Tech: Custom WordPress implementation, Dedicated Healthcare/Community/Admin panels, Complex Gravity Form integration

Project: Parcel Delivery Platform
Key Integrations/Tech: Custom Quote Calculation based on Geofenced data, Supported multiple delivery types (A to B, Wait and Drop, Multipoint Dropoffs) Mapbox API Integration, Gravity Form integration for quotations, Stripe auto invoicing integration

Project: Talent Show Platform
Key Integrations/Tech: Custom Angular-based WebApp, Multi account setup for families of exhibitors, Show series setup for hosts, Intricate point system and payout calculation, Live attendance management

Project: Itinerary Marketplace
Key Integrations/Tech: Custom React-based WebApp, Strapi open source backend integration for CMS, marketplace setup for buyers/sellers/admin, filtering and categorization algorithms

Project: eCommerce App
Key Integrations/Tech: Native iOS App, Native Android App, Store Management Platform, Split and Multi Payment Options

Project: QSR Front End Revamp Project
Key Integrations/Tech: OLO Online Ordering System, Punchh Reward Points System, WPEngine, AWS, Azure, React

Project: QSR Mobile App
Key Integrations/Tech: Revel POS System, iOS Native App, Android Native App, WorldPay Payments

Project: Food Delivery Aggregator Platform
Key Integrations/Tech: Native iOS App, Native Android App, React Native Restaurant App, Custom Rewards and Loyalty Program, e-Currency Implementation, Marketplace Payment Setup

Project: HIPAA Compliant Telehealth Certification Service
Key Integrations/Tech: HIPAA Telehealth Function, Payments Marketplace, Encrypted Data Sharing, Scheduling Tool, Pre and Post Payments

3 – Recording videos, day in, day out

A picture is worth a thousand words but a video tells the whole story. The best way to show off your confidence and communication skills is via videos. 

In your free time, record them. Just record anything. If you struggle with communication I would highly suggest to look into: https://www.youtube.com/@askvinh

Have a video intro on your Upwork profile, and for the jobs you REALLY want, have a structure ready to create one fast.

Typically speaking, you should open up 3-5 reference items on screen share, and record a video explaining them in context of the job post ending with a CTA (call to action).

4 – Working on your portfolio items

Upwork has a really nice system to show off portfolio items. But the NUMBER ONE mistake most freelancers make is that they just slap on some image and call it a day – DO NOT DO THAT.

People can google images if they wanted to, explain your process, and dive deep into the work that went behind your work. I recently did a piece on this over at: https://thewanderingpro.com/how-to-create-better-portfolio-website-with-a-case-study/

5 – Keep working on writing better hooks and CTAs

Hooks and CTAs are key to winning proposals.

The hook gets clients into your proposal, and the CTA leaves them acting on your request.

Learn to write better hooks and CTAs tailored to the job post. Have at least 10-20 hooks and CTAs ready to go at all times when applying for jobs.

Some reading material:

https://www.upwork.com/resources/call-to-action-examples

https://freelancewritershub.com/writing-prompts-for-crafting-compelling-hooks/

Fiverr Vs Upwork – What is Better?

Lastly, we get to the most asked question, is Fiverr better or Upwork. 

Simple answer is, they are different.

But mostly speaking Upwork is better.

The numbers don’t lie, one is clearly doing more and bigger than the other.

But that doesn’t mean you can’t succeed on either.

Here is what YOU NEED to know and what to ignore.

Type of work on Upwork Vs Fiverr

Fiverr is primarily a gig focused platform – gig meaning something that can be offered as a product or a package.

Upwork on the other hand is primarily a job listing style platform – meaning that jobs are posted and are open to applications of relevant applicants.

Method of getting work on Upwork Vs Fiverr

On Fiverr, your profile and optimization is the bread and better. People get hired because their profile shows up when they search for a query. Your profile needs to be optimized to get the best results.

On Upwork, you are applying to jobs, as a new freelancer – your application matters the most, nothing else. Also you are paying with connects for each job application – it is not a free for all.

Earning Potential on Upwork Vs Fiverr

Go look at 1,000 profiles on both platforms and you will quickly find that the ceiling of earning ‘in low income regions’ is higher on Upwork UNLESS you figure out a way to delegate your work on Fiverr.

See, Fiverr is more of a factory mentality, you package a good service, and you aim for the highest quantity of it possible to be sold.

Whereas on Upwork, although you can apply the same mentality to agencies, for solo freelancers, there are much more opportunities to make a higher earning due to the fact your engagements are usually longer and not gig based.

So this really depends on WHAT YOU DO – at the end of the day if your offering is something that can be packaged and delivered effectively, go with Fiverr. And if your offering is a bit more nuanced and has potential for higher value redemption, go with Upwork.

To start out with though, pick and stick to one as double dipping seldom succeeds.

And there you have it, a deep dive into the most important aspects of Upwork beyond the basics. If you enjoyed this, kindly do share with others in need as a lot of work and preparation went into this piece.

To end it off, feel free to ask anything by emailing at hello@thewanderingpro.com or reach out to me at: https://sknexuspk.bio.link/

And if you do decide to support the cause, you may visit https://www.buymeacoffee.com/sknexuspk