The Accidental Freelancer – My First $5 K on Upwork (During The Pandemic)

I didn’t intend to become an Upwork Freelancer. While we covered Upwork when we launched the site earlier this year, I was far more interested in drop servicing, particularly with local businesses. The industry seemed ripe for improvement and there’s just so much more flexibility when you can meet clients face-to-face. Especially if you’re pitching prospects outside of software and digital marketing.

And then Covid-19 hit, sending everyone to their basement. As my own job prospects got murky, I started to take a much closer look at Upwork with new respect. Once you pushed past the hordes of low paying jobs, there were some good things here. Able to find potential clients without leaving your basement? Check. A reliable way to ensure you get paid? Done. So the real question is: could I get someone to pay me what I think I’m worth in my day job?

In the interests of truth and justice, I decided to run an experiment. In the past 90 days, I applied to over 150 gigs on Upwork offering rates which are generally competitive with my regular job. As a result of this, I accepted offers for five projects which generated over $5,000 in billable income.

The other cool thing about how Upwork operates? In most cases, I can see who actually won the gig, how much they bid, and how much work they did.

Here’s what I learned along the way.

Rule 1 – Don’t Compete With Idiots

You may have heard that Upwork freelance marketplace is a great place to find freelance writer gigs. This is indeed true. However, this has attracted a ton of entry level writers onto the platform. Most of whom have a the same generic profile, with a few idealistic or upbeat sayings that are the freelancing hipster version of being basic. You literally all look alike.

But it’s all good. Post a generic content writer assignment and you’ll get 20 to 50 applicants. Most of whom are identical. For the statistically inclined, they have a 2% change of being hired.

Actually, it’s probably much worse than that. With that volume of candidates, most hiring managers will rank on either rate (lowest first) or experience (highest billings). And yeah, pitching does matter, so the veterans have an edge there too. In short, the odds of getting hired for generalist gigs really, really sucks.

I won’t dwell on the fact that the clients for these gigs basically have you at their mercy. Expect to get hit with revisions, adjustments, and other low level extortion as the price of a good review.

The usual advice for new freelancers? Cut your rates for the first few clients and “polish your profile”. Hopefully you won’t be exploited too badly… and run out of energy before your earnings and ratings build to the point where you can attract better paying clients.

Most guru’s will tell you to invest in their magical job proposal template. You know, the one they use to land six figure clients left and right, while driving their Lambo down the street in the opposite lane. Doesn’t matter. You’re still engaging in price competition.

There’s a better way. It’s time to become that special snowflake you dreamed about.

Rule 2 – Find Your People

Believe it or not, I got my first writing gig on Upwork by quoting at double the client’s budget and at least 4 X more than other writers. Since then, I’ve converted her into a steady monthly customer and won offers from other clients in doing business in the same industry. At higher rates.

My secret weapon? Over a decade of experience working in my client’s target industry. While it’s hardly unique experience, I’m the only writer who made that connection. My competitors are basically irrelevant: I’m the only visible expert applying for the gig.

That means I get more interviews, close more deals, and have more leverage to set rates.

Actually, I’ll take this even further. Don’t waste time applying to any gig where you don’t have unique expertise to bring to the table. With a special emphasis on the word “unique”. Here’s why…

My job proposal success rates, by project type and relative fit.

  • Digital Marketing – ZERO win rate
  • Content Writing – 3% win rate
  • Industry Expert Content – 11% win rate (and 80% of billings)
  • Gigs in Target Industry – 33% win rate

With 150 data points, the market has spoken. I’m now an industry expert who does content writing.

By the way, this is the exact opposite of what I would have expected from a traditional employer. My digital marketing and analytics resume is impressive. My credentials as a journalist are borderline non-existent. I would be laughed out of any newsroom in the city. To my knowledge, there is no actual job called “industry expert”. And yet… it works. Relative advantage is more important than absolute expertise; don’t ask your self what you do best, ask what you do better than everyone else on the platform…

While I still need to level up as an industry expert content writer, at least I’m not fighting legions of people willing to work for peanuts. So niche down. You’ll have far more luck hunting gigs in a small pond where you’re the big fish than competing in an open casting call with 50 peers. Find your people and focus on them.

Rule 3 – Lead With Unique Value

Ah, the Upwork Profile. The most over-analyzed piece of the freelancer marketing equation. Often the subject of bloviating self-adoration and utterly meaningless platitudes. Let me simplify what to put on a freelancer profile.

The bare minimum.

Seriously. The same goes for any job proposal as well. There are handful of things that you want to say to a prospective client that will get you hired. The key points of difference that signal to a new client that you’re the answer to their problem.

Everything outside of that is irrelevant.

Your typical client reviews dozens of applications. Get to the point. Stand out. Don’t try to sell every aspect of your services in the job proposal or on your profile. All you want to do is trigger an invite.

The one exception to this I’d recommend is using the job history descriptions to stuff some relevant keywords into your profile. Mention the skills that you want to be found for several times. All of that text is buried at the bottom of the page, so most clients won’t actually read it.

The top of the freelance profile page needs to be focused and hard hitting. The same for the first several lines of your job proposal. Unload 3 key points which set you apart from everyone else and are directly relevant to the assignment. Ask for a meeting. Done.

Rule 4 – Don’t Be Afraid to Bid Over Budget

One nice benefit of freelancer plus is it lets you take a peek at the distribution of rates for the Upwork job that you’re bidding on. Keep notes.

Along the same lines, it is worth investing the time to check up on past proposals, to see who won and at what price. Again, I recommend keeping notes about what price the gig settled at and how much work was ultimately done on the project.

Tracking job application results like this will start to give you a feel for where the market really is. This should guide how you bid on job opportunities going forward. That’s one of the strengths of working on a freelancing platform such as Upwork, since you get a lot more data that you would from a typical freelance client.

Rule 5 – Screen Clients Aggressively

The wealth of data about clients is by far the best benefit of the Upwork freelancing platform. Unlike an offline freelance client, you can see their hiring history, buying patterns, and job feedback. This is immensely helpful in optimizing your time.

Let’s start with the job posting. Is it well written, clear, and generally sane? You may have a keeper. Does it display any signs of delusions of grandeur, excessive client ego, or an abusive attitude towards freelancers? Just hit next. That rarely improves once you’ve got a contract and they can decide if you get a good review.

Now, look at their hiring history, specifically the comments section. Do they treat their typical freelancer with respect? Do they sound fairly reasonable in disputes? They could be a keeper. Do they lose their cool and start screaming names? They may not be a good fit.

You also need to look at the client’s average hire rate across the history of the account. One thing I noticed: a large fraction of the job postings appear to expire without actually ending in a hire. This was substantially worse for clients who didn’t have a history of hiring on Upwork. From what I could gather, it looks like 40% of the gigs posted by experienced clients ended without a hire. This jumped to 65% if the client posted the profile was new to Upwork.

Lesson: be cautious about over-investing in a client who is new to Upwork. It seems like you may need to make a “double-sale”, first selling them on the idea of hiring you and then getting them comfortable with the Upwork Platform. A repeat user is more to the point – they know the drill. Then again, if you like the job post, apply. Several of my favorite gigs were sketchy clients.

One more item you can judge from looking at a client’s profile: what are the odds of getting hired for additional work? The value of this will vary by job type: the finance and strategy work I’ve done is mostly one time projects, whereas a freelance writer can often solicit additional articles. This can substantially increase the value of a client.

Rule 6 – Understand Hourly Projects vs. Fixed Price

There are two schools of thought in terms of how to bid a freelance project.

If you quote an hourly rate, you’re relatively safe from client changes. On the other hand, the client may ask to monitor your work, which is an intrusive annoyance in my book. That being said, you’re still basically an employee in many ways.

Fixed price contracts, while reviled for being used for low paying jobs, place full control over the production process in the hands of a freelancer. Any delays are your issue (as are changes) along with any revisions or rework. On the positive side, any productivity savings are yours to keep. This also lays the groundwork to learn how to outsource work for non-Upwork clients (note: respect the Upwork TOS – only do this for non-Upwork clients.).

Don’t be afraid to bid either project type – or bid gigs one way and set up the contract another. Fixed price gigs get less scary after you learn how to estimate your time for a gig properly. This is particularly true for things like writing – you eventually figure out how fast you write per hour for certain types of work. You’ll also speed up with experience: my largest writing client used to take two hours per article, which I’ve managed to accelerate by about 40%.

Freelance writing is primarily a fixed price business, by the way. Rates are quoted per thousand words written, usually by content type. This is similar to what you may see on another freelance website.

One other advantage of bidding fixed price vs. hourly projects: it allows you to obscure your true hours worked, in the event you want to over-deliver for strategic reasons. For example, I’l typically bid a new client assessment as a fixed price project equal to a few hours of work. That being said, I may invest two or three times that amount if I see potential future business, using the project like a paid sales call. Along the same lines, if I’m taking a project in an area where I’m trying to learn a new skill, this lets me avoid discounting my time as a training rate.

One thing not to do: start working without a contract or specific milestones (for fixed price). Without that, you’ve got no protection from an unscrupulous client. You can let the client float some work once they’re established, but never start a fixed price project without an activated milestone. This protects you from flaky clients; with an active milestone, you can submit your work for payment. If the client doesn’t reply within two weeks, you get paid by default. Not exactly how I want to collect the money, but it beats having a client ghost you without payment.

Don’t neglect the long game here. The future success of your freelance business will be dictated by the quality of your client relationships, the portfolio of skill sets you can deliver, and the efficiency with which you can deliver them.

Rule 7 – Analyze Win/Loss and Cut Quickly

I highly recommend you periodically review your bidding history to look for trends. This will tell you which slices of the market are giving you an audience and, more importantly, where the final hourly rate and project sizes are settling.

If you’re like me and pursue multiple areas, you will eventually wake up and realize all or part of a specific market is below where you want to be. I dearly love working on SEO projects – but not at $30 per hour. My competitors can have that business, with my most sincere compliments!

Along the same lines, don’t be afraid to dig into your data to mix and match your customers into new market segments. My current “preferred potential clients” are spread across three Upwork service categories, united by similar needs. You can set up custom keyword searches on your home page to alert you when potential clients post a job.

Rule 8 – Over Deliver on Your First Project For a Client

All other things being equal, it pays to go the extra mile on your first project. There’s always the opportunity to get a good review, which helps your job success score.

More importantly, there’s a lot of repeat business on this freelance platform! The average project that I bid on generated at least $780 for the winner, based on checking profile statistics. Higher value skill groups generated more than that, between $1000 and $2000 in total billings. Incidentally, getting repeat clients gives your job success score a boost. So more money AND better reputation for future clients.

Every freelance writing client I’ve worked with has repeat orders in their history. Finance and strategy work is proving less predictable, although I’ve had several clients tell me they want to do more projects in the future. Either way, the easiest way to grow your billings is to turn one time buyers into repeat customers.

Rule 9 – Don’t be Cheap. Burn Connects.

I’m not trying to be an Upwork fanboy here. But seriously, do the math.

Connects cost $.15 each. My typical bid uses 4 connects. The average proposal within my target market scores a deal 10% of the time. Doing a lot of math, that means I’m acquiring clients for $6.

The typical client I’m chasing drops $780, per my analysis above. My personal per-client average is already north of $1000, with plenty of additional work supposedly coming.

$6 per client is a gift from the freelancing gods.

Heck, even my broader group of content gigs with a 3% close rate is a fair deal at those numbers. I’m spending $18 to bag a customer in that world.

So target good clients, keep your rates at the right level – and don’t be afraid to burn some connects along the way. It’s a smart move.

Rule 10 – Cultivate Multiple Sources of Work

It’s risky to depend on a single freelancing site or job board as the basis of your freelance career. You need to find ways to diversify your income to turn this into a true freelance business. Think about where Upwork should fit within a larger portfolio of freelance job prospects.

One option is to join a second freelancing site. I’ve got mixed opinions about this strategy. While this will diversify your risk of issues with your Upwork account, it doesn’t address the ebb and flow of a freelance marketplace. We saw a slowdown in the pandemic and rates dropping in many skill areas. Plus you need to level up on that freelancing site, which is a substantial investment of time.

Another option is cultivating local clients. This is the time honored path, especially for gregarious types who don’t mind a lunch or two…. While this may be slow during the pandemic, it’s a good long term plan – and you can use Upwork to outsource projects in the event you land too much business.

The other option is backstop Upwork by working on your own projects on the site. This is my own strategy for my freelance business. We operate several websites, which require content and SEO. When someone else is willing to pay me a higher amount, I’ll go do freelancing. If not, I can put the time into my own projects. We have a pretty good idea of what the future earnings per article will look like, which helps me set a target hourly rate (or fixed price equivalent). We just do basic publishing – I’ve seen many thought leaders move into creating their own courses or webinars.

In any event, always be working towards having a solid Plan B.

Summary: How to Get Started on Upwork

My best advice is to keep it simple. Start by looking for your people, scanning jobs for the strongest fit with your experience and lobbing some bids in to test the waters. Ask questions. Watch to see what people respond to. Go from there.

Don’t cut your rates. To be frank, I don’t think it really does that much to help your pitch and it sets a low starting point for future negotiations. Focus on the value you bring to a project and don’t be afraid to walk away from clients who won’t respect that.

I get more from a well thought out pitch than any of the holy grail profile features or “portfolio of samples” that many Upwork guru’s keep pitching. Focus on the client. Focus on their needs. Excel.

A simple formula and it works very well.

Go for it.

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