Freelance digital marketing: earn your first (or next) $1,000

freelance digital marketing

I sunk into the train chair, finally able to relax.

An email ticked in. “Splendid work, as we old folks say! We’ll see where we can use your skills. They were impressed!” 

I was over the moon. The long hours of freelance digital marketing work had finally paid off.

For someone just a few years into their career, this was terrific news — a stamp of approval from the partners.

For someone with almost no experience giving a professional presentation, it was terrifying.

It was the biggest presentation I had ever given and I was nervous as hell.

After getting up at 4.30 and riding the train for four hours, I had to present for the headquarter, my boss’ boss, and a room full of colleagues I had never met before.

My boss was pleased and I went on a summer holiday, excited about what would surely be a new amazing chapter.

Fast forward two months and I found myself without a job. Something had happened.

I had a few months of savings left and the clock was ticking.


“Damn it”, I thought. “This wasn’t supposed to happen”.

As soon as I got the news, I began looking for freelance work and saw this:

freelance digital marketing job description

I knew that if I worked like crazy, I might be able to impress them and at least get a phone call.

After spending hours researching their business, I realized that I had overlooked their final question “are you based in the US?”

I was based in Asia with an almost 12-hour time difference but it was too late to turn back now.

I tried to convince myself that they might not have worked with a freelancer that far away before.

From my experience in outsourcing, I had helped several clients in the states and I knew it was no problem.

Sure enough, I landed the client and eventually turned it into a $5,000-project. 

freelance digital marketing project review

I was in the clear. For now.

That became the start of an experiment with Upwork that earned me $8,988.


It says $10,000 earned in total but that isn’t entirely accurate because a few of the projects were completed after the experiment. In part one of this guide, we’ll dive deeper into all the juicy details of that experiment.

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PART 1 – What is freelance digital marketing?

Freelance digital marketing is the process of using marketing on digital channels to reach a goal for your future client’s business.

That goal is often to get new customers and the channels might be advertising on Facebook or showing up for the right search in Google.

The whole idea is to understand what a certain group of people want and help them understand how your client’s product can help them.

That means understanding where to reach them, what to tell them about, how to tell them, and a whole lot of other things, in order to persuade them to take an action – usually buying a product.

For many businesses, the goal of marketing campaigns is direct sales while for others it focuses on getting leads to show interest. A separate team is then dedicated to the sales process after someone expresses interest.

To give you an example, someone might not buy an airplane via an advertisement on Facebook but they might enter their phone number and someone from the sales team might meet with them in-person to discuss a deal.

This is the opposite of the classic approach to finding clients offline, say, at a networking event or while playing a sport like badminton as opposed to working out on your own.

How do freelancers do digital marketing?

When digital marketing is done by employees, in-house, they’ll have a set of goals referred to as KPIs (key performance indicators), that dictate the direction and offers a way to measure how things are going.

Because digital marketing is results-oriented, they are often focused on increasing revenue, leads, or decreasing cost.

For freelancers, the process is two-fold because they first have to get clients and then to help them reach their goals.

Being able to show the results of helping other clients is a great way to land new projects, so it can feel difficult for new people to break into freelance digital marketing.

Luckily, there are other approaches you can use that don’t require you to do free work and I’ll dive into those later in this guide.

Common jobs in freelance digital marketing

Because the digital marketing industry has exploded in recent years, many freelance digital marketers chose to specialize in either specific industries (like travel or e-commerce), specific channels (such as marketing on Facebook), or even both.

A few popular options are

  • Digital marketing project manager (someone who works across different channels and might work with specialists on each channel)
  • Content marketer (someone who makes sure articles and other content is awesome for the readers)
  • SEO (search engine optimization) specialist (someone who helps their client show up in Google when you search)
  • Community marketing manager/social media specialist (someone who spreads the word on social media)
  • Email specialist (that guy in your inbox)
  • Advertising specialist (someone who specializes in buying ad space online)
  • Affiliate partner/influencer manager (someone who helps brands partner with your favorite Instagram influencer)

How much does a freelance digital marketer make?

The cool thing about digital marketing is that it is such a new industry, that even though you could get a university degree in the field, you’ll likely learn the same by working on real projects.

The field moves so fast that a lot of the stuff you would learn in school would be too generic or outdated by the time you graduate.

School might be worth it for other reasons but digital marketing is all about experience and you’ll learn that by working in the field.

Based on my experience and this research a reasonable median hourly rate for a digital marketing freelancer is somewhere around $50/h.

That is a broad figure and many freelancers earn both more and less. Let’s look at four examples to see what you could earn with freelance digital marketing using different hourly rates, and having a different number of projects: 

Example 1 – the beginner: $20/h, 15 hours of work weekly

In this example, you might just be starting out with digital marketing and have a couple of clients with a few hours of work per week for each client earning you an extra $1,200 per month.

$20/h, 3 clients, 5h/w each = 15h/week = 60h/month = $1,200 extra/month or $14,000/year.

Example 2 – the intermediate: $35/h, 15 hours of work weekly

In this example, you might have a little more experience but still keeping your freelance gigs as a project on the side.

$35/h, 3 clients, 5h/w each = 15h/week = 60h/month = $2,100 extra/month or $25,200/year

Example 3 – the intermediate: $50/h, 30 hours of work weekly

At this point, things are getting serious and you might have considered that it’s time to quit your job.

$50/h, 3 clients, 10h/w each = 30h/week = 120h/month = $6,000 extra/month or $72,000/year

Example 4 – the expert: $75/h, 30 hours of work weekly

At this stage, you’ll probably be freelancing full time and enjoying the fruits of your hard work.

$75/h, 3 clients, 10h/w each = 30h/week = 120h/month = $9,000 extra/month or $108,000/year

We’ll dive into specific case studies in the next section, so you can see real-world examples. 

Who’s this weirdo?

Call me, yep, you guessed it…. Chris.

This was me quite a few years ago, spending money I had earned freelancing on fried grasshoppers and a pair of epic shorts at a night market.

Many years ago, on a quest to figure out how to turn a potential long-distance relationship into something… less depressing, I discovered that people earn good money freelancing remotely.

Often, we’ll see photos of how people earned $100,000 doing one hour of work with some ‘magic’ system.

I fell for that.

But that’s a story for another day. We live and learn I guess. To be honest with you, there were no shortcuts that worked — it was simply hard work.

Readers have used the material in this guide to kickstart their own freelance business. One reader said:

a reader in digital marketing freelancing

He went from earning $0 to more than $1,300 a week in about 10 months!

He even learned digital marketing from scratch WHILE learning how to get clients! It’s not something I recommend but it can be done.

His “trick”?

Going above and beyond to help his clients! He shared his story earning $30,000 in his first year freelancing.

Another reader reported earning more money with just a few hours per week outside of her day job.

You can use the strategy in this guide to earn your first $1,000.

Who is this guide for?

This guide is written for you if you are a new freelancer wanting to offer digital marketing services and are working to land clients but never hearing back.

It is also for you if you are an established freelancer offering other services to your clients and wanting to add digital marketing services as an extra service to earn more.

It covers everything you need to know to earn your first $1,000 with freelance digital marketing.

When you have learned the skills of landing and servicing clients it stays with you forever and you can use it, leave it and pick it up again as it fits into your life.

Some people use freelancing as a tool to consistently earn money on the side, some make it their full-time gig and others use it in-between other projects.

Is freelance digital marketing legit? Two real-world experiments earning $18,178

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: 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.


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
  • Fees
  • 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:

  1. Send a message to gather interest and share ideas
    1. 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
  2. Ask the client for a phone call
  3. Send them a proposal or recap of what we agreed on
  4. 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 going 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: $8,988 earned on Upwork

Yeup, my name is Aske but people sometimes call me Chris. Read the story in the email newsletter.

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.


My findings

The approach of writing in-depth proposals to get potential clients’ attention seemed to work well and I landed about 22% 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 (on the other hand, 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 and the quality wasn’t good.

Case study: $9,190 earned by emailing businesses

In this experiment, I used an approach from Ramit Sethi’s Earn1K program that isn’t sold anymore.

Let’s start with a quick recap of the process: the 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”, and 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 found 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 and they had already proven that their business was viable.

So, I ended up going after

  1. Online businesses in the language learning industry with general online marketing and copywriting services
  2. Software businesses in the online marketing industry with blog post writing services
  3. 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 note:

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.


My findings

I contacted 247 businesses and about 24% responded. 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, earning money, and 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 didn’t see any pushback. 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: emails vs. Upwork – which is better 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.

freelance digital marketing earnings case study

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 is 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.

In ten years, will you remember the new computer or iPhone you bought now? We probably won’t.

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 with 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.

Looking back, having to pitch 62 businesses to land a client appears to be the result of a not-so-great industry fit.

I could’ve avoided mentioning it to look better but I wanted to be honest with you because you might discover that it’ll take a few tries to find the best fit for you. This is just a minor speed bump on the road.

My findings

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 are 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:

upwork freelance review example

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.

Final thoughts

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 helped a lot. 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.

Freelance digital marketing: Choose the path to your first $1000

It is now time to set a goal for yourself! You aren’t just freelancing for the fun of it, are you?

Like me, I bet you have something you dream of. Whether that is a new video game console, those shoes that are just a bit too expensive, or perhaps a trip to Japan, now is the time to plan what you want to spend your hard-earned money on.

I recommend starting with something that costs a meaningful amount of money but not so much that you feel like it’s overwhelming. For many of us, that could be $1,000.

The idea is to reward yourself with something cool once you have achieved the first and most difficult part of your new adventure.

When you’ve decided on something to reward yourself with, it is time to pick your freelance idea. Most of you reading this guide will already have an idea. If that’s you, you can skip this chapter…

Find your profitable idea

If you don’t have an idea, start by writing down a list of things you’ve done in the past where you’ve gotten good results or testimonials that you can show.

Pick one of those or ask a few friends what they think you are good at (your mom doesn’t count).

You can also go to Upwork/Fivrr/ and search for projects and check what other freelancers are doing to get ideas.

If you have already had some clients, you know that they will pay for your service. If not, it is key to figure that out. Some businesses will want help solving some problems but don’t want to pay for it.

Or worse.. they can’t.

While there are always exceptions, as a rule of thumb the closer you are to the money (profit) the more you can charge.

For example, you can often charge more for a direct-response sales page than you can for a blog article. And you can probably earn more by building ad funnels that drive sales than manage social media content on a fan page.

Oftentimes, when clients trust you with one part of digital marketing, they will be happy if you can help them with other areas, too.

That will give you the opportunity to earn more while sampling other types of projects and building case studies in related areas that you might want to move into later.

Specializing in a skill, niche or none at all?

I’m sure you’ve heard about niching down your freelance digital marketing services before. Loads of people talk about it, and it usually allows you to command more money for projects while doing less work.

That happens because you can position yourself as a specialist and re-use the same templates, etc. with multiple clients to speed up your workflow.

There is plenty of room for most types of freelancers. Facebook ads specialist in X niche is a popular example. Taking on those types of projects work pretty well if you like to do implementation work. For many of these, it is plug and play- you have a funnel or two that you replicate for most clients.

Others prefer to work on more high-level projects like as an external marketing manager. Here you might be helping with the direction, strategy, and some implementation work. You’ll typically help a certain type of business go from one stage to another.

If you know a bit of email marketing, Facebook ads, content marketing, and the other disciplines, you might want to take on broader digital marketing projects early on to figure out which market fits you the most.

Doing broad digital marketing consulting has given me some of the best clients on Upwork. Clients looking for this type of help typically don’t know too much about digital marketing and want someone who can also help them understand which platforms to use, when and why.

This is an excellent opportunity to provide more value by helping them understand when to use e.g. Google search ads rather than Facebook ads, helping them set it up and manage it over time.

If you’d like to dive deeper into finding your idea, I’ve prepared an in-depth guide here.

Pricing your services for profit

In the beginning, it is all about moving fast and getting projects, so you can learn fast.

The quick solution to pricing is to start somewhere between $15-$50/hour at first, and then adjust it once you have some projects under your belt. The exact number depends on what you are comfortable with.

If you haven’t already, go to Upwork and search for freelancers that are doing something similar to what you are (and has earned money) and start with a rate similar to what they are charging.

That way you know that other freelancers are making similar projects work on those rates.

You simply click the little carrot next to the search bar to switch between freelancers and jobs and start searching.

Below is an example. I could only fit a few freelancers into the screenshot but as you go through the list yourself, you’ll easily be able to get an idea about what to charge as you compare their price with their profile and specialization.

upwork freelancers example

One thing that I like to use for my own research is the green filters button at the top (see below).

It allows us to see how many freelancers are charging each kind of hourly rate and in which categories of work.

upwork search example

There are many ways to play around with this. In this example, you’ll see that most people who have earned $1+ in the sales and marketing category are charging less than $10 (the gray number next to the specific rate is the number of freelancers in that group).

This also shows us that more than 5,000 people have earned money and are now charging $30-$60/hour.

As you are browsing you might feel like you are not as good as some of the freelancers out there when you see their portfolios.

Don’t get demotivated though. While many are legit, great freelancers, it is easy to fake the screenshots or have ad accounts track revenue incorrectly and conveniently not change it.

There will always be some clients that you connect better with based on your personalities. Clients choose their freelancers based on trust. Sometimes case studies help build trust but that is not always the case- and they aren’t always needed.

Generally, I’ve found that the lower your pricing is the more your projects will be focused on execution, and the higher your pricing is the more you focus on strategies and communication in digital marketing.

Generally, it works better to do hourly rates at first because you’ll understand how long it takes to do different projects.

Once you have settled on your goal and a niche or skillset you’d like to work with, it’s time to get clients.

The TINY difference between Upwork and email that changes EVERYTHING

A great benefit of freelance websites is that businesses have taken the first step and told the world that they are looking for help with a project.

Without Upwork, it is a time-consuming task and when we reach out to businesses, many of us are unsure if we’ll be rejected or come across as shitty.

Upwork solves that challenge for us, at least in part. 

The other side of the coin is that we narrow the field of potential clients down significantly. 

If this study is anything to go by, there are freelance projects out there worth more than $700 billion yearly. In comparison, Upwork posts projects worth $1 billion in total per year.

If we can rely on these numbers, does somewhere near $20 million in sales per year (although a part of that might be from freelancer fees).

I couldn’t find any good sources for Fiverr but their revenue appeared to be about $100 million in 2019. There are also smaller freelance sites out there but they won’t change the point, so let’s move forward.

That means that Upwork, Fiverr, and Freelancer’s portion of the entire market is somewhere around 0.16%. Although this not entirely accurate, let’s assume that all the other small sites and job boards particularly made for freelancing come out to about 1% of the freelance market. 

One percent. 

Of course, there are freelance projects we don’t have access to without special connections but it is impossible to find and judge those. 

That means when you commit to using a freelance website like Upwork, you are saying yes to 1% and no to 99% of the freelance projects out there!

The idea itself is good because we don’t want to target every business, we just want a nice slice that is small enough so that we can dominate it and big enough to earn what we dream of.

The challenge is that these freelance websites have a certain stigma and branding to them, so they attract a certain type of client. Maybe that’s your preferred client but if it isn’t, don’t assume that they don’t exist just because you can’t find them there. 

In fact, it seems statistically unlikely that you will find them there!

So where are the rest? 

Some might be using different websites but it is likely that they don’t know who or where to ask for help. 

They might also have been meaning to do something about it but got busy with more urgent things or they might not have realized that they needed help in the first place. 

busy table
You know how things can get busy sometimes

PART 2 – Earn your first $1000 with Upwork

Let’s compare how you can reach businesses on freelance websites like Upwork and via email side by side.

On Upwork we browse projects, find one we like, send a proposal, maybe we’ll even jump on a call with the business and hopefully, they will hire us.

Reaching out with email is a similar process with a few distinct differences:

We first have to decide on which businesses we want to help. We should decide that before going to Upwork as well but there aren’t that many options when you can’t decide which projects are published. 

With email, it is more complex but also allows us more freedom to choose who we’d like to work with.

When we’ve decided exactly who we want to help, we’ll send them a note, introducing ourselves and asking if we can share some ideas with them.

If they are interested, we’ll share ideas with them and recommend a phone call to get a better feeling if we’ll be a good fit. After that, we’ll summarize with a proposal and the client hires us.

In both arenas, we aim to go deeper with fewer potential clients because we know that most other freelancers do the opposite and mass-contact many businesses with generic messages.

With the emails, we have the opportunity to go much deeper with the potential clients because we simply have more options and know more about them.

I made this side-by-side comparison, so you can get an overview:

freelance digital marketing upwork profile example upwork vs email

As you can see, the two processes are similar except at the beginning. Many freelancers use the proposal on Upwork as the actual proposal when in reality it works better to use to share ideas. 

If you have already been doing that, the two funnels are almost the same. 

The difference is that because freelancing is a relationship-based business, it will often be too early to summarize what needs to be done because the client doesn’t trust us yet. By running ideas by them first we get an opportunity to speak more with them and build trust.

Before we get into the secret sauce of how to land clients, let’s look at how you can overcome that weird feeling of contacting someone who hasn’t created a job ad yet.

If you are curious what winning proposals can look like, click here to get 3 real proposals winning projects worth $500, $1,200 and $5,000

Make your Upwork-profile “good enough”

When writing your Upwork profile, I like to look at the market and demand for the skill or niche I’m looking to serve.

Let’s say I want to help small businesses with Facebook ads as an example.

Then I’ll search around for a couple of hours to see if other freelancers are doing something similar. I like to pull up some of their profiles and check if what they earn, and the type projects they work on, are something I’m interested in.

Note of caution: you will find a TON of people that are earning pennies and you might feel like you are about to make a terrible decision.

That is normal. You’ll often see a few profiles here and there doing much better than the rest. These are the ones you’ll want to focus on.

When you find those, analyze their profile text, what they charge, etc. and imitate it. That does NOT mean you should copy it.

I like the strategy of first imitating and then innovating. What that means is you scope their profiles to find the overarching structure and use something similar.

For example, if you notice several profiles talking about how they can increase a client’s revenue or conversions, that angle will probably be a good place to start.

Starting out, I’ve found it to work well to:

  1. Put testimonials at the beginning your profile text
  2. Followed by a few brief examples of things you can help with along with a few sentences describing what each is about (e.g. setting up ads, manage them day-to-day or perhaps build a chatbot)
  3. And at the end, add a few sentences about you as a person, your work ethic/how you work and how it benefits the clients
  4. A CTA (e.g. contact me now)

That is a perfectly good starting point – again, the key here is to move fast and tweak it as you go.

You might not have any testimonials you can add, but don’t get stuck there.

Some clients will look at your profile and some won’t. Generally, you’ll want to spend more time searching for the right jobs and writing good proposals than perfecting your profile text in the beginning.

Below is an example from my own profile.

freelance digital marketing upwork profile example 1
freelance digital marketing upwork profile example 2
freelance digital marketing upwork profile example 3

It could be better but it gets the job done. It clearly displays what I do, and I’ve added social proof through a few features on other websites that are available in my portfolio and by adding real testimonials right at the top.

Then I’ve outlined things that my clients typically want help with, to give people browsing some ideas on how I can help.

Some will be concerned if the text is too long and think people will never read it. I am not. Some potential clients will only read a little bit and if they are not a good fit, they’ll leave.

That is a good thing – I don’t want to attract everyone, just the right clients.

For your profile photo, use a simple photo of your face where you look neutral, smiling and friendly.

Using the Upwork-tests have not made a difference in my experience.

A trick to finding good digital marketing projects

Photo by Warren Wong on Unsplash

When getting freelance projects using Upwork there are two main options:

  1. Invitations to private projects (invite-only)
  2. The general market with projects everyone can apply to

I will not cover invitations in this guide because you are unlikely to get any in the beginning. Instead, let’s talk about the general market with projects everyone can apply to. The process is simple:

Someone posts a job on Upwork and a freelancer (you) send a proposal and get the job. The best process I’ve found for digital marketing projects is:

  1. Search for a project
  2. Send a proposal
  3. Speak with the client on the phone
  4. Start the job
  5. Finish the job and get paid
  6. Repeat

So let’s start from the top: searching for a project.

I find this to be an underutilized skill- often people complain that they can’t find any good jobs on the platform after a while. Usually, they are just searching for the wrong keywords.

Upwork has several filters that can help you a lot in your search. I’ve found that one of the easiest ways to land a client is by focusing on writing proposals that are in-depth and uniquely relevant to the project description. That means if your proposal is copy-paste-able it isn’t specific enough.

Most freelancers write one or two proposals and spam them to every job – that’s why you’ll often see the project descriptions asking you to mention a code word to make sure you’ve read the whole description.

In comparison, more experienced, successful, freelancers will have a number of templates and they reuse parts of each to get a good balance between sending proposals for many projects and make them personalized based on what has worked for them in the past.

This is a good process to adopt as you get more experience but as you are starting out you need to focus on learning what works.

Right now, in digital marketing, there are generally three different types of projects that pop up again and again:

  1. The project with two lines of info
  2. The ad agency
  3. The blog that wants cheap SEO articles

This is a current trend and it will (of course) change over time. Luckily, there are many other projects but since these three categories appear, again and again, we can use them to explain the framework.

Usually, it won’t work to send the same proposal for all three project categories. In the beginning, it’s easier to pick one category and focus on making that work. It’s similar to the approach of niching down your services.

For the sake of the example, let’s say you decide to start by helping agencies with Facebook ads.

As a digital marketer, we want to test different proposals for this type of client.. so we first figure out how to land this client type and then only after succeeding, we will crack how to land other types of clients.

This is a common example of a project description:

freelance digital marketing project description example

As you browsed other freelancers earlier, you probably noticed that most people are highly focused on conversions.

If you want to send a proposal for this project, you’ll want to have something to say about conversions to cover what they will hear from everyone else and then pick a way to take it to the next level or by adding something more depending on what is important to this type of client.

Since we KNOW that other freelancers will most likely be saying the same thing, we can address that in our proposal e.g. by saying:

“[…] while many other freelancers will be focused on showing you screenshots of conversions and how many good campaigns they have launched in the past, I focus on not only that (see attached screenshots) but also A, B, C […]”.

If you know it will happen, address it! The project owner will feel like you can read their mind.

If you don’t know exactly what to do to be different, don’t worry. You’ll become better and better the more you speak with your clients and leads. Getting on the phone with them might feel uncomfortable at first but is a great way to discover those details.

Until you are able to do that, list down a number of things you think they would value in addition to conversions and test each one with a few proposals.

Here are a few examples to get you started:

  1. Friendly and easy to work with
  2. Speaks the same native language and is great at communication
  3. Can help them upsell other services in your skillset e.g. email marketing or search ads

Side-note: You’ll be surprised how many clients value being friendly and easy to work with above being the best at your hard skill as long as you are good at what you do and can get results.

Ten proposals for each angle is a good place to start because roughly half the projects in the digital marketing category never hire anyone.

Pro-tip: Try searching for projects in your native language or with clients from your home country and using that as part of your pitch.

It works even better if you are not from an English speaking country as competition will be less and you generally connect better with those from your own country.

The smaller the country the easier it should be. If you are from a huge country like India you might wanna narrow it down even further!

Personally, I prefer to look through 85% of the best projects in 30 mins and maybe miss a few here and there – instead of looking through 100% of the projects in 2.5 hours just to make sure I didn’t miss a single thing.

Upwork has this brilliant “save search” feature so you can search every day by just the click of a button. After browsing around for a few hours, you’ll like have found some good search filters you can save for later.

upwork search example

I’ve found that the search filters that show good projects, can change frequently because of the keywords clients use. So it is great to do a little research for new search filters on a monthly basis. Otherwise, you might feel that all the good projects are suddenly gone after a while.

As we saw in part one, I’ve found it to work well to consistently apply for 2-3 jobs every single day. There are always new jobs coming and I’ve found that jobs that are more than a few days old or have 20+ proposals tend to be much harder to get.

I also like to look at the number of projects the client has hired for. If it is less than 35%, I’m reluctant to send a proposal because there is a high chance they won’t hire.

bad client example

Of course, you can increase the number of proposals in the beginning if you want to move faster as long as you still spend the same amount of time on each proposal.

Often you’ll see a bunch of projects you are interested in. If you know you’ll only apply to 1-2, you’ll force yourself to pick the ones you think are the best fit which in turn will make the quality of your proposals better.

In this game, consistency is king.

When looking at projects, I always use this quick rule of thumb: does the job description give enough information for me to write a personalized proposal? That’s the one thing you’ll want all project descriptions to have.

This is a great example of a job with no chance to send a personalized proposal for.

bad project description example

If not, then I skip it.

You can often ignore the budget put on the project as most clients simply don’t know what to enter. Because they are afraid of getting scammed, they just put something random like $100.

In fact, I’ve found this principle to hold true for many of the features Upwork allows clients to add – another one is when they have to pick if they want a freelancer that is entry-level, intermediate or expert.

It seems kinda random what people put there and often you’ll see those that want an expert but only want to pay $5/hour.

When you’ve created some saved searches that you are happy with, it is time to send proposals.

$1,200 case study: How to write proposals that get responses

Let’s start with another example. Below is a client’s review of a previous project I completed, along with the project description and the specific word-for-word proposal that landed the project.

The client’s review

freelance digital marketing project review example

The project description

freelance digital marketing project description example

The Upwork proposal

freelance digital marketing proposal example 1
freelance digital marketing proposal example 2

So, what is going on here?

Note that I scrolled through his previous reviews to find his first name and added that.

I started out by sharing my experience helping a different business in the same industry to show something he could immediately relate to. along with generalities about similar types of businesses based on my general experience.

Then I shared two other examples from my experience and show why they are relevant (different businesses but targeting the same audience).

If the examples you show are not 100% relevant, it is key that you show the client WHY they are relevant or what part of the projects that made them relevant enough to bring them up in the situation.

Towards the end, I talk a little bit about my interest in language learning since he mentioned that in the project description specifically along with a testimonial from another client and set the CTA as a general question to learn more.

The goal of a proposal is not to get you the job although that would be nice. Rather, it is to get you the phone call. That’s the only thing that matters.

And the first few lines at the top of the proposal has its own unique purpose: to get the potential client to click “read more” and read the rest of the proposal. Each proposal only shows the first few lines in the client’s dashboard (see screenshot below).

upwork freelance digital marketing

Generally, a good starting hook is something personal or unique to the project. This is where your project research comes in.

I like to keep the hook to 2-3 lines and then add 5-10 lines more with further explanation followed by 2-3 lines at the end that tells them about attached screenshots and testimonials.

Particularly the 5-10 lines in the middle can be expanded as I show in the example above.

It really comes down to how much you are able to show that is relevant along with how many questions they have added to the project description.

You don’t have to add the part about testimonials if you are just starting and feel stuck if you don’t have any.

Some people are afraid of giving away too much advice. I am not, I prefer to work with clients who, even if they could figure out how to do it, are too busy and want a premium white-glove service.

I always like to keep the proposal short because I assume that they are busy and have many proposals to go through.

I’d much rather get them on the phone because it allows me to get a feeling for how we communicate together and from that if we’ll be a good fit.

For the last bit of the proposal; I like to add testimonials and the CTA.

Rather than get tempted to send the perfect proposal and fall in love with a certain project, you’ll benefit more from a consistent system.

It will give you a perspective of how different clients are, which in turn will allow you to learn which type you prefer to work with and how to spot them through their project descriptions.

I highly recommend that you track your proposals at least for the first while to see how you perform. You can copy my template sheet here. Just click File > Make a copy.

I’ve seen freelancers feel bad because they felt like they were sending out a ton of proposals and never hearing back.

When you track your proposals you’ll probably feel better noticing the same as I did: that around 50% of the digital marketing projects never got hired for. It sucks but at least it is not our fault since no one got hired.

And of the remaining portion (besides the clients we land), they typically hire a much cheaper freelancer meaning that the client would never be a good fit anyway.

Another benefit of tracking your freelance digital marketing proposals is that you’ll build your intuition about which project descriptions will be a good fit for you, and which types of proposals work.

I like to track the performance in batches of 20 proposals, meaning I’ll run the conversion-numbers after I’ve received an answer for 20 of them (no reply is also an answer).

I usually wait 10-14 days before logging the result of a proposal to give them time to hire – that also allows me to find the person hired via the project description itself and check which pricing they went for.

Dodging scammers with the write-back

The writeback is when a potential client replies to your proposals which allows for the two of you to communicate via the Upwork chat system.

This part is more art than science and depending on the CTA in your proposal you generally have two options:

  1. Schedule a time for a phone call
  2. Ask 1-2 questions to vet them if you are unsure if they will be a good fit

For the first one, you’ll want to assume they are busy, so you’ll benefit from making it as easy as possible for them.

I like to propose two different times (in their timezone) and give them the option to suggest others if none of them work. That’s it.

That could be as simple as “I’d like to learn more about your business. Would you be able to jump on a quick 20 min-call on [DAY] at [TIME] or [DAY] at [TIME]? (in [X] timezone).

For other projects, you might want to know more before deciding whether to go ahead and schedule a phone call or not.

I’ve found that too much messaging back and forth at this stage kills things, so I like to carefully ask 1-2 basic questions to understand if they are in the right niche and will be a good fit.

They should either be related to the call or be something that can show you a red flag, that might make you want to avoid the call (e.g. if they want to start the project three months from now or have unrealistic goals). The goal is to avoid remove any terrible clients (or scammers) before you waste time on a call with them.

Example questions are:

  • What do your products cost? (if they want help with ads, for example, this should give you an idea if it can be done profitably)
  • What is the most important thing for you to accomplish with this project?
  • When are you looking to get started?

When you are ready to jump on the phone with a potential client…

Avoiding crazy clients with a phone call

The phone call isn’t needed for all types of freelance digital marketing projects. I’ve found that for things like content marketing it is less needed compared to ads management.

While you might not need it, I still prefer to do them. It allows me to get a better feel for if the client and I might be a good fit. At the very least, I’ll learn something about what is important to the client that I can then use in my next proposal to another potential client.

I can’t cover every possible phone call situation you might come across, so I’ll cover the most common ones my readers have experienced in the field.

The key is that you both get your questions answered and make sure you are on the same page in terms of the work needed to be done. It’s a red flag if the client is being evasive and doesn’t want to answer your questions. It’s a recipe for disaster down the road.

The call is a powerful way to get them to trust you and most importantly allow you to provide more value and show them how good you are (meaning more dollars to you).

It is much easier to ask questions to learn more about their business, how you can provide value, and to make them feel special rather than guessing these things.

That will usually give you an instant win and clients will like you. It is great because you can later refer back to the things they said when evaluating results and proactive ideas you might have.

I’ve found that most phone calls tend to last around 45-60 minutes which is a good amount of time for the most part.

If someone tries to drag it out (it happens from time to time) to learn from you rather than hire you, you might want to let them you have another meeting about to start and tell them that you’ll follow up with them after.

This is a mix of science and art, and the only way to get good is by practicing. It is normal to get nervous before the phone calls – many people don’t like talking with strangers on the phone.

It has worked well for some readers to reframe this to be a casual coffee meeting (which it is), similarly to if you are meeting with a friend of a friend about a potential job or to learn about a new sport.

I overcame it myself by setting a goal of having the first 10 phone calls within the first month. That helped a lot.

How to talk about your experience (even if you feel like you don’t have any)

marketing meeting example
Photo by Dane Deaner on Unsplash

As you get more experienced, you’ll know where to direct the conversation, so for now, I’ll help you get started and you’ll want to tweak it to your own style as you go as we all have different personalities.

I like to lead the conversation by preparing some questions and focus on getting the client to talk 80%-90% of the time.

I do that by using follow up questions when they have told me something and sprinkle my related experience or knowledge in as I see fit. That way it doesn’t feel like it’s an interrogation.

Generally, you are looking for ideas where you can give the client a quick win and a way to turn that into a bigger win down the road.

If you want to do things like manage ads for clients, they will often ask for proof of your previous work e.g. screenshots of an ad account that shows performance.

I have rarely seen that happen outside freelance websites. You are much less likely to be asked about your past performance, if you focus your proposal on showing expertise and giving specific recommendations to the project – they will usually be so blown away because no one else bothers to do it.

If they are specifically asking for it in the project description, you should prepare it in advance or avoid that project altogether.

If it does come up during the call and if you don’t have some case study to throw at them, you are probably best off talking about what you’ve done at your current or previous jobs.

Below are some sample questions to give inspiration for your calls. You’ll want to tailor these to your specific service or niche as you move forward.

Example questions

1) Who are your best customers?

2) What is your business goal?

(besides ‘sales’, force them to be SPECIFIC. If they don’t know or don’t know how to calculate e.g. conversion rate, that is another added value you can give them either right on the call or afterward in an email.)

3) What have you tried before? What worked and what didn’t?

4) Do you have a timeline in mind?

(What kind of budget are you looking to spend on the project? – some people don’t want to share this as they are afraid of being overcharged, so you’ve got to feel out the situation.)

5) When are you looking to get started?

(If the answer is more than 10-14 days in the future, I like to tell them that they can get back to me when they are ready – unless they want to pay me to do some preliminary work. Often something happens during the time period and the project never gets started or is delayed. Write them off as a “no” unless they are paying you already.)

6) Have you worked with any freelance digital marketer before?

(If yes, you’ll want to ask about their experience and what could have made it (even) better. It will help you understand exactly what that person did wrong and you can avoid making the same mistake.)

Should you offer a discount?

freelance digital marketing - discount
Photo by Rajiv Perera on Unsplash

Often they will want to confirm the price. With freelance digital marketing, it is a bad sign if they focus on the price upfront instead of learning about how you can help them solve their challenges.

The best way is usually to talk about value first and pricing last, so I like to divert it as much as possible but if they keep asking you should tell them.

Starting with an hourly rate helps you avoid getting into a project where you later kick yourself because you realize it requires more hours than you expected – or even worse they try to add more to the scope of work.

If that happens when you are on hourly rates, you’ll just open up the Upwork tracking software and bill them more hours! Win-win.

Personally, I almost never change my pricing – it has to be an amazing project before I’ll even consider it. And I never (ever) do it during a call with the client just like that. You’ll want to strategically use it – not on a whim.

Alternatively, you can tell them that you are happy to send a proposal with a different price for a different scope of work and that you can send them one after the call.

That gives you some time to think about it without committing to something you haven’t thought through right there on the phone.

Seal the deal (and avoid this common mistake)

You’ll be talking about when a good starting date is. Normally, 2-3 days in advance is good.

Starting earlier might make you come across as needy, and starting later than a couple of days from now might make the client interested in choosing someone else — you have to be the judge in each situation. This also gives you some time to get access to whatever accounts or information you need on their side.

I like to close the conversation talking about the next steps.

Something along the lines of “All you have to do is click ‘hire’ on my Upwork proposal to get started. And I’ll send you a summary of our talk within the next 2 hours along with the next steps for us to move forward” (be specific and stick to it!).

If you’ve had a good conversation you’ll want to keep the momentum going and have them hire you right then and there before they get busy with other things.

I usually mention two hours because it gives them enough time to hire me and if they haven’t yet, I write that in the email.

I once had an awesome call with a lead from Upwork and even though I followed the things outlined above (and he agreed), he never clicked the hire button – even after I followed up with him several times. In fact, I never heard from him again.

My point here is that you should never assume anything unless they’ve technically hired you on Upwork – if they ask you to do anything before, tell them “sure, I’ll take care of that as soon as you have clicked ‘hire’”.

If they try to push the project off of Upwork don’t play along. Tell them you’d like to focus on the project and this makes it easy for you to do.

I strongly recommend that you don’t take projects off of Upwork. Besides it being bad taste (Upwork got you the lead), you have so many things to learn that you don’t need any headaches around getting paid on top of that.

Upwork doesn’t take care of it 100% but pretty much, which is as good as it gets. I’ve never had any problems with payments from clients on the platform.

The reality is that there is a reasonably good chance some of the clients will try to scam you if you work with them off of the platform.

Upwork is great at offering security to both you and your client, so focus on learning the whole process.

PART 3 – Earn your first $1,000 via emails

How to get over the weirdness of contacting someone who didn’t post a job

Here’s an example of an email I sent to a business that I had never spoken with before and landed a job earning me $1,068 for an article. 

freelance digital marketing payment example

Unlike most emails we see out there, it wasn’t salesy or spammy. This is the exact email I sent to get in touch with the business owner at first:

cold email freelance pitch example

As you can see, this approach is different from the typical spam emails we normally get. I spent time making it personal and I wrote it specifically for him. 

Look at this post I found on Reddit. So many people hate sending emails to businesses they don’t know.

reddit hate freelance cold emailing
Image cred

So, why are some people OK emailing strangers while others are not? Why do we think that businesses hate hearing from us? Is it because we have only experienced spam emails like this one? 

example of email spam

Or is it because we are afraid of being rejected?

The point is that emailing businesses you haven’t spoken to before doesn’t have to be icky. You can create a great experience for everyone while earning good money. It’s not about us taking something and the receiver giving it to us. It has to be a win-win.

The reality is that it is all about mindset. I’ll show you three techniques you can use to get comfortable reaching out to businesses and offer your freelance services.

We don’t have to be salesy or spammy

We’ve all seen spam emails like these:

freelance spam example

And through our jobs, most of us have gotten unsolicited emails like this one, too: 

freelance spammy examples

Getting one of those feels like someone saying “hi stranger, I don’t care about you but here’s why you need to care about me”. 

Most of us don’t want to come across that way and would never dream of acting like that face to face with someone. In fact, many people sending them out probably don’t even realize how it sounds or they might feel pressured to send them.

I’ve found that we often dislike those emails because they are not relevant to us. If you get an email about your dream shoes being on sale, wouldn’t you at least look at it?

Just because many other marketers act spammy doesn’t mean you have to do the same. This is your freelance business and you can choose the approach you prefer.

Some freelancers prefer to send out generic emails because they don’t worry if other people think they are spammy, while others prefer to build deeper connections with the businesses they are reaching out to.

The business might already be looking for someone like you

The reality is that some businesses are already looking for someone like you to help but haven’t found a good fit yet. Or they might be too busy and don’t know where to look.

After completing the project in the example above, the client asked for my help with an entirely different project because he didn’t have time to do it.

Of course, not everyone is looking for help and in some cases, it just isn’t a good fit. When that happens, most people will tell you politely or not reply at all – it’s rare that they’ll send a negative email.

People want to hear from you

I’m sure you’ve had situations where someone asked for your advice. Whether it was your grandparents asking how to turn on the computer or your friends asking for a restaurant recommendation. When they ask, you’ll help them right?

The difference with cold emails is that many business owners want to ask for help but don’t know who to turn to. If you knew that they were looking for help with something you are good at, would you offer to help?

I bet that many of us would — that’s what happens when a company puts out a new job ad and we apply for it!

So why is that the only time we do it? My guess is that we don’t want to come across as annoying because we hate when people are annoying to us. We might also not want to be rejected and feel stupid.

It’s funny how differently we as a society have decided to talk to each other via email. We are much nicer to each other in person.

Can you imagine meeting a stranger in person and talking to him like a spam email? 

“Hey there, I work for New Corp. and we would like to call you to tell you about our services. What is your phone number? And could you give us the CEO’s email address? We can install a new system in one hour and do anything you want!”

If you’ve ever been to a networking event, you’ve probably experienced people machine-gunning their business cards at you and trying to sell you right there on the spot.

Luckily, most people are not like that. If people reject a warm, thoughtful, message from you, it’s on them. Not you.

Avoid the trap of tools

People tend to recommend us to get a website, be on Twitter, Facebook, etc. Because “it can’t hurt”. But when we only have limited energy it CAN hurt!

When we do a lot of things, it’s easy to get distracted and confused about what will move the needle and earn us more money.

So before we move forward, I wanted to point out that to land clients via email you don’t need anything but an email and a way to get paid. 

It doesn’t even have to be a professional email address. A Gmail will do.

The only other thing you need is a way to get paid like a bank account or a Paypal account. That’s it!

The secret sauce: read the mind of your future clients

I once had a job as a phone salesman and I had to call random lists of businesses every day. Most of them were irrelevant, so there was a lot of time wasted.

To avoid that, we freelancers benefit from qualifying our leads first. 

Often, businesses will post the number of customers on their website. If we can find that, we can usually also find the pricing on their website and if we multiply the number of customers with the average product price, we’ll get an idea about their revenue.

It won’t be an accurate representation of their business but it’ll give you a ballpark idea to go by. The key here is not a particular size but rather to weed out the worst leads: those that are clearly too small to pay for our services.

Because we’ll go in-depth with our targets, it saves us time to research them upfront so we can avoid those that can’t afford us anyway. 

Quick and dirty client research that works

Understanding your customers deeply allows you to earn more than your competitors.

It gives you enough ammunition to approach them in a personal way that will make them feel like you really understand them and their challenges.

Everyone is busy with solutions left, right, and center but the pros know that understanding your customers is at least as important. 

Even if I stood on top of a mountain and spoke to a group of hungry freelancers, less than 1% would do this one thing. So, don’t feel like it might be too late — this is deep human connection and it will never be outdated. 

The simplest way to go about it is to speak with people that are similar to your dream client. You could for example connect with them on LinkedIn and ask them questions such as if they have hired a (your service) freelancer before and what their goals and challenges are.

Email script (don’t copy-paste it. Tailor it and make it your own):

“Hi X,

I’m X and I do Y for a living. I don’t have anything to sell but I’m researching businesses like yours and I’d love the opportunity to ask you a couple of quick questions.

I imagine you are busy, so it doesn’t have to take more than 10 mins and I can work around your schedule.

If this is OK for you, I promise to be respectful of your time. Would it be OK if I send you a few different times that might work for a call?



When you have done that a few times you’ll start to notice a pattern in their responses. The deeper you dig with them, the better results you’ll get when you work to land similar businesses as clients. I like to speak with five to ten businesses and the more the better.

Often, they will first tell you politically correct things, such as that they want more sales. 

If you dig deeper, you could learn that a startup founder might feel pressured by the investors and the board of directors to grow the company, and you might spot an opening where you can help. 

Finding potential clients without being salesy

Now that we know they can likely pay for our services and we understand their challenges, it’s time to qualify those that are interested instead of spending a ton of time on ideas for businesses that aren’t interested. 

We’ll do that by qualifying them via email. I’ve had good results using Ramit Sethi’s script:


[Introduction] I read your article about X and noticed that you’ve recently started using videos on your website.

I’ve been doing video editing for three years and I’d like to offer to help you edit your videos and get them optimized for the web.

That would make them look more professional and load faster, which is important for your readers. And you’d free up time that you could use to create new content.

We can discuss the details, of course, but first I wanted to see if this is something you might be interested in.

If so, would it be okay if I sent you a few ideas on how to help?



The purpose of the introduction is to show the person that we took the time to get to know them and that we are not like everyone else out there.

You’ll read about many people out there suggesting that you use a similar script or approach. The difference is that most people are too vague with the introduction in the first line.

They might write something along the lines of “I like your blog articles, really great stuff”. That is too generic.

Don’t copy-paste this script exactly but rather tailor it to sound like you. As a rule of thumb, if you can copy-paste the introduction, it isn’t personal enough.

In a world where everyone will try to spend as little time as possible, we can make our future clients feel special by showing we took the time to get to know them – they will recognize the effort.

The next sections in the script describe who we are and how it is relevant to them. Remember, no one cares about us but we know they care about themselves, so let’s focus on that to get their attention.

At the end, we gauge their interest by asking if we can send them ideas. If we don’t hear back after e.g. two follow-ups, it is probably not the right timing for them.

Impress the clients that are serious with your ideas

When someone is interested in hearing more, research their business well and impress them by going in-depth with your ideas. 

This is where it pays off to be a freelancer that can help with execution rather than a consultant that only offers advice. You can spill as much knowledge as you want with two benefits:

  1. You can show that you are an expert on the subject
  2. You can impress them by giving free advice others would charge for

You’ll want to focus on their core business problems and how your ideas help with that. In some cases, you might even offer a free sample or mock-up. 

If you are a designer, you could send them a mock-up. 

If you are a writer, you could send them some relevant keywords you could write about that might help them get traffic from Google.

If you are a marketer, you could also send them some keywords for either Google, Youtube, or the app stores (if they have a mobile app).

If you are a developer you could send them ideas for how they could make their website load faster.

The goal is not for the client to hire you right when they see the ideas – they just have to be interested enough to want to speak with you on the phone.

Using a phone call to find the gold

Your social skills will make the biggest impact during the call because freelancing is a relationship-based business. The purpose is for us to understand the client’s needs and get them to trust that we can help them do a good job on their project. 

I like to aim for speaking 10-20% of the time and have the client speak about their business for the rest of the time.

It is common to feel nervous about the phone call. It might help you to think of it simply as a coffee meeting on the phone. You don’t have to sell them on anything if you think it isn’t the right fit for them. 

This is about exploring if it might be a good fit and learn what kind of challenges they have.

The better you understand them, the easier you can bridge your services to their business, and the more profitable projects you’ll land.

It can be done via email but speaking with them almost always gets you better insights and you can feel out if they might be the type of client you want to avoid. 

It is always a great idea to prepare for what the client might ask you. Usually, they will want to have:

  • A deeper look at the ideas you sent them
  • Your background and relevant experience
  • Your fees, timeline and next steps

You’ll also want to prepare some questions to better understand their business such as:

  • Who are your best customers?
  • To get customers, what have you tried? And how did it go?
  • What is your business goal this year?
  • If we work together, what would that look like on a daily basis? 
  • Have you worked with any freelancers before? How did it go?
  • What are your biggest sticking points/bottlenecks right now? How have you been dealing with them? 
  • How much time do we have to get this done? 

Win the deal with a proposal

If you agreed to move forward on the call, it’s time to put together a proposal. 

It could be as simple as a recap of the ideas you agreed upon on the phone call along with price, timeline, and how frequently you’ll update the client on the progress.

Below is an example of a fairly long proposal with four projects and you could make it shorter, especially if you talked about fewer projects.

freelance digital marketing proposal

The text is copied for convenience if you are on mobile (some details are replaced with ‘X’ for privacy):

“Oh, this is great! It looks like optimizing them could be an easy traffic win for us! Thanks for sharing, X. I didn’t include anything SEO-related in the proposal below because I figured it would be too many things at once considering the points we have already talked about but I’m happy to help with that, of course.

You mentioned that your goal is to get more customers to go from learning X and extend the X to 2 months.

The projects we spoke about (X) will impact driving new customers more than improving the retention.

You did mention the focus on driving a larger pool of customers, so I think I’ve found a pretty good approach for us to start out with:

I figure that there must be a particular reason as to why customers X. It is probably hidden either in the data or in the head of the customers. So, it might take some digging before we can decide the best solution to solve it.

I’m cautious to go open-ended into a project like that because it is so easy for it to become a time-waster with no real result for us. I could drive that project with the lowest priority while focusing on the other projects first as tasks like scheduling 1-on-1 interviews with customers can take a bit of time (I like to knock this out in a few days but it is just not always possible because the customers aren’t available).

Of the other projects, all other things being equal, X will be the quickest to get us results. I can start by getting them up and running first and then move on to focusing on improving the performance X and the collaborations with X.

For X, as I understand, it is mostly a project for developers since it seems to require that we call Apple/Google’s App Store API as they run with specific X internationally. Is there anything, in particular, you had in mind? (We can easily run tests with ads internationally if needed)

You mentioned that we might not be ready to move forward on some projects because of X, so I envision the next 2 months could look like this:

Keep in mind that I don’t know exactly how much past data, etc. we have available so I’ve given a range below. In my experience, planning the projects out first makes it much easier to execute and will ultimately save you time and money when I execute as it helps us know that we are working on the big wins rather than something with little impact.

Month 1 (Feb/Mar)

  • Test X in-depth to understand if it is a viable channel for us at scale (e.g. with X for 30 days)
    • Investment: X
  • Marketing X
    • Investment: X
  • X  collaborations performed the best in the past 
    • Investment: X
  • X: via data and customer interviews, figure out why many customers drop off X and prepare an action plan with solutions for how to double it
    • Investment: X

Month 2 (Apr) – it is tricky to be highly specific here because it depends on the outcome of the first projects. I’ll need to potentially create a new proposal for you based on the outcomes and what you prefer to move forward with.

  • Continue the X test until the four weeks are completed
  • Marketing in X: Execute on the big wins based on the plan
  • X: Execute on the big wins based on the plan
  • X: Execute on the big wins based on the plan 

Pricing: X

Depending on what you prefer, I can, for example, have a weekly update in your inbox when you wake up every Friday morning (and we can tweak the communication style as we go to whatever you prefer).

What do you think?



  • When you learn this approach to landing freelance clients, it offers you more freedom than freelance platforms ever could but can take longer to get started
  • Understanding customers well is the most important part because you’ll know how to help them and that is what they’ll pay for. Not whether you reach out via Upwork, email or something else


  1. Chris, thank you for such a detailed article 🙂
    I loved your point about starting the project in 2-3 days and not immediately, and how that helps keep a healthy power dynamic and establish boundaries with clients. That point is something you rarely see mentioned, but is very important!
    In my experience, if you show from the very start that you are not available as soon as the client wants you – that will make the client respect you more, and schedule calls and request with you instead of expecting you to be always ready to satisfy his demands 🙂

    • Chris

      Couldn’t agree more, Vlas 🙂 I’m glad the guide helped.

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