An email ticked in: “You have received a reply to your proposal”.
For a new freelancer looking to land his first freelance project, this was AMAZING.
For a new freelancer with limited experience, this was TERRIFYING.
I had sent so many proposals without a response, that there was no way I could ignore this.
I knew I had to get on a call with this stranger. I had no idea what I was doing and I didn’t want to make a fool of myself.
As Skype was ringing I could feel a drop of sweat slowly working its way down my neck.
A second later, an older man picked up. He seemed foreign to computers — phew, I was in luck. It turned out that he was more interested in my story moving across the globe than my qualifications and work credentials.
I didn’t know exactly how to solve his problem but I had a pretty good idea and knew I could do it with research.
I promised myself right then and there that if this call would go smoothly I would spend as many hours as necessary to fix his problem. I just wanted to get off that call without messing anything up.
In the end, the project went well and I earned my first few hundred dollars.
A month before, I had discovered a website about earning money while learning how to code. It was equally exhilarating and terrifying: I couldn’t program for shit and I had no clue what clients expected of freelancers.
I was terrified of getting on a call with a client in case they had a question that I couldn’t answer. So, I priced my service low and worked my ass off giving each client plenty of free hours until I knew they were happy.
At the time I was living abroad while finishing my studies and weren’t ready to move back home.
Earning those first few hundred dollars -even though it wasn’t much- made me realize that it would eventually be possible to move abroad again and live entirely off of freelancing online. It blew my mind.
Many of us are daydreaming about beautiful beaches and a lifestyle full of adventure and freedom.
We realize that our job wasn’t what we expected, our boss isn’t doing things the right way and we want out. We turn to freelancing to get freedom and control. To work on things we enjoy, things that are meaningful.
Many of us discover freelance websites like Upwork only to get stuck sending proposals and never hearing back.
Sometimes we’ll get lucky or a project will fall into our lab through family and friends. It’s nice but not something we can count on.
So, I wanted to figure out what the best approach would be if I were to start freelancing again from scratch.
By comparing two popular approaches: simply emailing businesses and using a freelance platform, you’ll get an idea about what works if you are new to freelancing.
Keep in mind that for the rest of this article, I’ll be using Upwork to represent the online freelance platforms as it is the biggest platform out there at the moment.
I know there are many negative reviews about online freelancing platforms and this is not one of them.
Their platforms’ business purpose is to drive profits — not hold our hands or have our best interests at heart. That is our job.
They do what they think is best for their business and we would probably do the same if we were in their place. Just like they might feel the same if they were in our shoes.
Best in test: Is emailing or using Upwork the best way to earn your first $1,000 freelancing?
I experimented with both for five months each to understand which one is better for you to earn your first thousand dollars with freelance projects.
I spent about 40 hours per week (the equivalent of a typical full-time job) and during this case study, I will be looking at hard data like:
- How many businesses I contacted
- The number of clients landed
- Hourly rate
- Average size per project
- Total earnings
- Total number of hours worked
- Effective hourly rate (after fees and incl. unpaid hours for pitching)
But one thing is the hard data, another is the qualitative experience such as:
- The quality of the clients
- How interesting the projects were
- How my pricing was received
- How long it took to land the projects
- The opportunity of recurring work
I like to think that the qualitative points might be more important because many of us are not only looking for money but especially freedom and control.
I’ve used the same approach to contacting clients across both experiments. By default the process had four steps:
- Send a message to gather interest and share ideas
- On Upwork, they are referred to as a proposal and via emails, it was an introduction email followed by ideas in a second email if they were interested
- Ask the client for a phone call
- Send them a proposal or recap of what we agreed on
- If we were a good fit, the business would hire me for a project
Sometimes, a potential client would want to do it differently like jumping on a call right away, and in those cases, I followed whatever they preferred to make it convenient for them.
My theory was that everyone sends a lot of copy-paste messages, so by reaching out to fewer businesses and go in-depth with each one, I might get an advantage.
That proved to play a key role but more on that later. Let’s begin by looking at the Upwork-experiment.
Case study: five months and $8,988 earned on Upwork
I know it says $10,000 earned but that isn’t entirely accurate as a couple of the projects were after the experiment. Ultimately I earned $8,988 before fees.
That comes out to about $1,800/month during the experiment with an average size of $642 per project and about three projects per month.
The type of projects I worked on were general online marketing tasks like running ads, building sales funnels, and related copywriting.
From research, I knew that many freelancers on Upwork send copy-paste proposals like this one:
Sometimes, they’ll even copy-paste different sections of the project description and send that back to you as a proposal. “It’s a numbers game” as they say.
In order to stand out, I picked fewer projects to apply for and instead wrote in-depth proposals to impress them. On average, I spent an hour on each one.
As I got better at recognizing good projects, I discovered that there often weren’t that many good projects available at once. The best approach seemed to be sending a few proposals every single day. It came out to 2.7 proposals per day on average (incl. weekends).
Upwork offers us a limited number of proposals we can send per month, so it was important to make the proposals count. We are able to buy extra “credit” but only a limited number.
Before we go through the data from the experiment I should share a couple of notes:
Sometimes I felt pressured to give a refund to avoid anything less than a five-star review thinking that it would hurt my future chances of landing work.
These refunded projects are excluded from the data. It was only a couple of projects but they were all small (a few hundred dollars or less), so I doubt they would have any significant impact except emotionally.
It’s also important to mention the Upwork fees since they can be confusing.
At the moment, Upwork takes:
- 20% of the first $500 per client
- 10% of the remaining project fee up to $10,000
- And 5% of the rest
During the experiment, my average Upwork fee came out to about $114 per project.
I wanted to make this as easy as possible to follow, so I’ve included the bank transfer fees within the Upwork fees in the data you’ll see in a second. On the smaller projects the fees were far less than the average, so including the bank fees in that section will give you an accurate overview without complicating things.
And finally, the effective hourly rate you see at the bottom is for the total number of hours worked incl. Fees and the unpaid hours of pitching clients.
The approach of writing in-depth proposals to get potential clients’ attention seemed to work well and I landed about 25% of all the projects I applied for.
The biggest time-waster was that about half of all the jobs I applied for never hired anyone (or they secretly hired someone off of Upwork).
In the projects where they hired someone else, usually that person offered a much lower rate either hourly or project-based.
About two-thirds of the clients I met during the experience appeared to be stressed out but I did meet a few great entrepreneurs that I still keep in touch with. Most of the businesses were new businesses with little traction or none at all, and some were hobby projects.
Almost all of the projects were one-off projects that took about a week to land and a couple of weeks to complete. The average project earned me $642 before fees.
With the clients where I landed recurring work, I earned a few hundred dollars extra for each project.
Early on, I managed to expand one project from $500 to $5,000 which was a great win. I worked hard to find similar clients during the rest of the experiment but I didn’t get any, and it turned out to be a rare case.
Generally, my pricing was received without push back. Although it sometimes felt like it might have been too expensive for the clients.
Some of them liked my work and asked if we could continue with a lower hourly rate because the businesses were small (it could be because they didn’t see the value. I often ask for feedback and it didn’t come up, although it is possible that some have been too polite to say it).
Overall I found that the biggest challenge was not landing projects but rather getting profitable, bigger, projects that would offer me more money and stability.
I got stuck in the cycle of constantly pitching new projects to keep earning something and because I spent most of my time doing that, I couldn’t break through the barrier and earn more.
In fact, out of the total about 800 hours, I spent during the project, 179 hours were on billable work. That is about 22% and the remaining 78% was spent pitching.
My guesstimate is that I spent about 50-75 hours in total offering free extras to go above and beyond with the clients that had already hired me. I consider that pitching because the purpose was to get more work from the same clients.
I received some job invites here and there but rarely anything specifically for me. Almost every time, it felt like a generic message sent to many other freelancers as well.
Case study: five months and $9,190 earned by emailing businesses
In this experiment, I used the approach from Ramit Sethi’s Earn1K program that isn’t sold anymore.
Let’s start with a quick recap of the process: his approach is almost the same as what I did on Upwork by going deeper with fewer businesses rather than mass-contacting hundreds or even thousands of businesses with a generic message.
Most email-approaches feel “spammy”, so because that is a big turn off for many I wanted to point out that this approach is different. Standard mass-emails usually look something like this:
In contrast, I spent about an hour on average to send a personal message to each business. I learned that the key is to understand the type of customers you want to help before reaching out, so you can talk about their exact challenges.
The first step was sending them an in-depth personal comment and asking if I could share some ideas. That way I could qualify which ones were interested and thus which ones it would make sense for me to spend the most time with.
If they were interested, I would send my ideas and ask for a phone call to talk further followed by a proposal.
I grouped the businesses into “buckets” of about 50 in each. Sometimes I would try a new combination of industry and the service I was offering for each bucket I contacted.
Unlike on Upwork, I could target any business I wanted as long as I could find some insights about them that I could use to get to know them better.
I took the liberty of going after established businesses because I figured that
- They are more likely to be able to pay
- They had already proven that their business was viable
So, I ended up going after
- Online businesses in the language learning industry with general online marketing and copywriting services
- Software businesses in the online marketing industry with blog post writing services
- 6-7-figure online course creators/coaches in the online business and marketing industry with blog writing services
The reason you are only seeing three types of businesses is that I went after online businesses in the language learning industry with different services: copywriting and a few variations of general online marketing services.
This approach gave me more freedom but that also made the project more complex because I didn’t know if I was doing it correctly. By trying a few combinations I figured I would be able to compare them if I didn’t hear back from anyone.
In two combinations, I tried offering blog post writing services to software businesses in the online marketing and business industry, and for 6-7-figure online coaches. In total, I contacted a hundred businesses and only landed one client.
I used to help similar clients with blog posts in the past but the market has changed. It can work but it didn’t pay off that well for me compared to the other options I tried.
Let’s run through the data but first a couple of notes:
With this approach, there are no real fees except for transferring the money, so I used Paypal’s fees as an anchor. There are also cheaper options like bank wires or by using Transferwise.
After landing one of the clients, I realized that a fellow freelancer would be a better fit for that project, so I connected the client with him in exchange for a referral fee. Since I spent time landing the client and earning a fee from the project, I have included that in the data as a referral fee rather than a client landed.
I contacted 247 businesses and about 24% replied back. From there, the number of potential clients that were interested naturally became fewer and fewer for each step we went deeper:
- 59 businesses replied to my first email (24%)
- 47 of those wanted ideas (about 80%)
- 21 of those wanted a call (about 45%)
- 17 of those wanted a proposal (about 81%)
- And 4 of them became clients incl. The referral (about 25%)
I spent about 167 hours on billable work out of the total 800 hours during the period. That comes out to about 21%. The remaining 79% was spent pitching potential clients.
My guesstimate is that I spent about 100-150 hours going above and beyond with free work for the clients that had already hired me. I categorized it as pitching time.
I figured my time would be better spent there since reaching out to businesses with the first email took the most time. So, if I could spend say half that time on landing projects from existing clients instead, it would be well spent.
During the experiment, I declined some smaller projects, referred some to other freelancers, and recommended other solutions depending on what would be best for each business.
I probably could have earned more by taking those projects and you might decide to do that, if you re-do this experiment. I was betting that by not accepting them, I would have more free time to land fewer, larger, projects.
One of my biggest concerns with this approach was coming across as spammy, so I wanted to show you that was not the case.
I only got one negative reply, which is unavoidable but among 247 businesses, that is less than 1%. I also got amazing responses like:
Three out of four clients offered me recurring work. That means I didn’t have to spend as many hours pitching new businesses but instead I could spend more time
- Billing clients and earning money
- Impressing the existing clients, so they would hopefully offer me more work
As I’m writing this, I’m at the final stage of closing more projects from the same clients and if they come through, the earnings I can report will be more but they won’t be earned during the five months period, so they don’t count.
The quality of clients felt good as the business owners were established and appeared to feel calm and not frazzled if something wasn’t going their way. My sample size was low, so it could be due to other things, though.
The average size per project has been $2,780 per client, so far. I offered a smaller “starter” project at around $1,000 and then moved on to more projects as the clients felt the value for money with my services was great.
There is a saying that good clients pay more AND are easier to work with and I found that to be true in this case.
I went above and beyond to impress them and they were easy to work with: no unpaid “extra” projects (unless I offered them), slow payments, or bad behavior but that doesn’t mean that it couldn’t happen in the future.
My pricing was well received. I charged $50/h and I haven’t seen any pushback yet. Although some of the projects were paid by the project rather than an hourly rate.
On average it took me about 3-4 weeks to land the first project for each client and a month or two to complete.
The verdict: Is emailing or using Upwork the best way to earn your first $1,000 freelancing?
Now for the fun part: let’s first compare the two experiments and see which one was the winner in terms of hard numbers:
As we can see, the numbers that matter like the total earnings and effective hourly rate (the hourly rate after fees and including unpaid hours) are similar.
The main difference is the total earnings after fees: reaching out with emails generated an extra $1,342.
In this case, the biggest difference between the two are the fees with $1,139 more on Upwork. While it is a nice chunk of money I don’t consider it a life-changing amount in the grand scheme of things.
Two extra projects on Upwork would have mostly covered that considering the average size of a project on Upwork was $528 after fees.
I was surprised to see that the overall numbers were that similar, even though I had to pitch much less on Upwork to land a client compared to via emails. One client per every four I pitched compared to email where I had to contact almost 62 businesses on average to land a client.
That makes sense because the clients create the job ad on Upwork, so we know that they are probably serious about hiring even though half of all the ones I pitched didn’t hire anyone.
On the other hand, it felt easier to work with the clients outside of Upwork because there were fewer of them.
That meant that I could go deeper with each one and better understand their business instead of having to learn about a new one for every proposal. That also made it easier to balance everything throughout.
The type of projects I worked on was similar in both experiments, but the underlying quality of the clients felt higher outside with emails. That might simply be the difference between going after new and established businesses, and it is probably because I had the ability to go after the type of client I wanted.
It appears to be a trade-off between bigger projects that take longer to land and complete compared to quicker projects with a smaller size on Upwork. The average project size after fees were $528 on Upwork and $2,641 with emails.
I also tried going after established businesses on Upwork but as a freelancer, we don’t control how much information we get for each project, so that was difficult.
The lack of client and project transparency seems to be Upwork’s weakness and the strength of sending emails. Being able to control who we reach out to and ultimately work with, is a huge factor in getting the freedom we crave.
Upwork felt stressful because there were so many external factors to consider: Making sure the client leaves a five-star review and that I kept a good “Job Success Score” (a metric to judge freelancers by on Upwork) felt like it was the end-all-be-all of landing future projects because I could freely compare my profile to competing freelancers.
Sometimes, it led to irrational decisions like giving refunds to avoid a potentially bad review. It almost felt like being held hostage because the clients often would get busy and you’d have to continue to ask them to leave a review.
Upwork describes it this way “A high JSS [Job Success] score can help freelancers to stand out in the Upwork marketplace.” To me, that is another way of saying that if you don’t have it, you might be left behind.
And not only that, sometimes everything would be perfect from the client’s side until you discover that they left a review that wasn’t perfect.
Here’s an example a reader sent me:
That is not Upwork’s fault but rather short-sighted clients and because we are the owners of our freelance business, we have to go where we are treated best.
Upwork isn’t all bad though. I felt more comfortable receiving my money through Upwork compared to via standard invoicing because it is an automated process to withdraw the money from the client’s account weekly or is put into escrow at the beginning of the project.
However, it takes about three to four weeks from earning the money to being able to transfer them from Upwork to your own bank account.
I spent about 22% of my time on billable hours on Upwork compared to about 21% with the emails.
Either way, the goal for most of us is to eventually shift that to spending 20% on landing new clients and 80% billable hours.
With that in mind, the email-approach seems to be the clear winner in terms of both money, freedom, and control because I didn’t have to do much pitching to get new projects.
Reflection and critique
I ran the first experiment a few years ago, before accepting a full-time job while the second part of the experiment was done about two years later.
That means that the market and my skills have changed over time (as we saw with the blog writing services I tried).
While I didn’t take any freelance work during the period in between, my skills, emotionally, socially, and especially my mindset has improved. That made me feel less worried about contacting potential clients and being rejected or simply just making mistakes.
I was also able to use the experience I got through Upwork in the second experiment with the emails.
Along with that, my savings account is in slightly better shape during the second part of the experiment and that offered me more stability.
That’s the way of life and the only way I can think of doing it more accurately would be to do both at the same time.
In my experience, we get the best results by focusing on one thing at a time and if you are a new freelancer, I don’t recommend trying both at the same time either.
Since most of us are unlikely to get rich off of freelancing, it serves us the best to take control of our lives and break free from the 9-5 rat-race.
It is an excellent way to get started earning money online and be able to quit your job but in the long-term, freelancing is simply another type of job.
I’ve found it to be a safer job because, with multiple clients, it doesn’t make that big of a difference if one leaves. For example, if you have four clients of the same size, each one is worth 25% of your income.
So, if you lose one, you still keep 75% of your income until you find another client while at a typical job you’ll lose 100% of your income.
It is also a great approach to discover autonomy and get the confidence that you can actually do this — it isn’t just reserved for random strangers on the internet.
It seems like if you can become OK with the fear of potentially being rejected, you can unlock the freedom and control you are dreaming of in your life.
Some of the key things I learned during the project:
- It feels like Upwork is trying to turn relationship-based work into transactional work
- The channel seems only to matter as much as it allows us to target the right businesses for us. Who we chose to help matters much more than the channel we use to get clients.
- For the clients I spoke with, showing a friendly, organized, and ambitious attitude seemed to make a big difference. Coming across as an A player right from the beginning appeared to matter. I’m guessing it is because many clients are used to flaky and unreliable freelancers.
- Going after established businesses made my life so much easier
- I felt that I had more control over my business by learning how to reach out to any business at any given time and being able to help them solve their challenges in exchange for money compared to relying on the right businesses coming to a freelance platform.
- It appears as if you can become OK with the fear of potentially being rejected, you can unlock the freedom and control you are dreaming of in your life.
If you are struggling to land freelance clients, grab 3 freelance proposals that won a $500, $1,200, and $5,000-project.
If you are looking for an idea to earn money freelancing, get these 10 real-life ideas to get you started.