How I Went from Having no Jobs to Working Full Time on Upwork.com as a Software Developer

JMath
4 min readSep 3, 2020

Recently, I have found that my success on Upwork.com is a product of strong momentum. Once I had a 100% job satisfaction score and over $3,000 made through several jobs, I have been getting responses to most of my proposals. When I first started out — with roughly the same level of skill — nobody wanted to hire me. Freelancing on Upwork is a momentum game. If you don’t achieve momentum, you are losing to your competition and wasting your time. Here is how you win:

Do the work before you write a proposal.

This may seem like a waste of time. It probably sounds crazy, but hear me out.

Let’s say there is a project that has requirements specific enough that you can get started as soon as you read them. Let’s also say that the project is small enough for you to complete it within a few hours or at least complete a portion of it within a few hours.

An almost guaranteed way of getting the job is to complete the project, then write your proposal stating that you have already taken the liberty of starting or completing the project. If the hiring manager has not already found someone and employed them to do the job, this will most likely win you the job because they will be confident that you will give them what they want.

This won’t always work. Maybe half the time you will be wasting your time, but it helps to build your portfolio and will therefore get you more jobs down the road. Freelancing is competitive. If you don’t have the humility to take a chance and do some work potentially without getting paid then enjoy competing with people who have more Upwork.com experience than you. You will be betting on your luck rather than your skills and work ethic.

Get the paid membership plan.

“Connects” are the tokens that are spent to apply for a job on Upwork. Free tier users get 60 connects per month and unused connects to do not roll over to the following month. If you have enough connects through your free membership to apply for all the jobs that you are interested in, you are not being aggressive enough in your job search. If you get the $15/month paid membership, you can buy more connects for $0.15 each and any unused connects will be rolled over to the following month.

Also, with the paid membership, you can see the low, high, and average bid for each job before proposing. That way, you will know if you are probably wasting your time because of your pricing model. If the average is $15/hour and you are charging $30 and there are 50 people who sent proposals already, you will be less competitive and should perhaps spend your time applying to other jobs.

Bottom line — the paid membership for Upwork allows you to search for jobs more aggressively and is well worth the money spent if you are serious about freelancing.

Watch like a hawk.

Apply very aggressively. Most jobs will come from Europe and the Americas, so it is best to look for jobs during their respective business hours. If you wait until after the job has been posted for six hours, there will likely already be freelancers who have jumped on the opportunity while you were sleeping and are in the interview process before you have even sent your proposal.

No hiring manager wants to wait more than a day to hire someone online when they are sending out a request for proposal to thousands of people — all in different timezones. Figure out which would be the optimal time in the day for you to apply to jobs and spend at least an hour per day applying for jobs until you have gained sufficient momentum. If you are out of jobs to apply for, don’t forget to look again in a few hours or the following day.

Tips for your proposal:

Be personal. Do NOT use templates for your proposals. The hiring manager can always tell. Write a paragraph in your proposal to tell about your experience that may be relevant to the project which you are applying for. If possible, express your eagerness to work for them because you are genuinely interested in the type of work that they are doing. It makes a manager more comfortable to know that you are interested in the work for more reasons than just the money. This way, they will be more confident that you will do better work and be more passionate about achieving success.

Give a reference to your LinkedIn profile at the end of your proposal. Make sure your profile is well built and well connected. This will give you a great deal of credibility and make you stand out as a genuine professional rather than just another random face on the internet looking for fast money. At the very least, it will create more traffic to your LinkedIn profile and help you expand your professional network online.

Don’t keep your clients waiting. Always ensure your clients are satisfied by overdelivering on deadlines and documentation to limit the amount of questions or concerns they might have in the future. Get to work!

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JMath

One part software developer, one part nomad, two parts curiosity.