Freelancing for a Living


When I first started freelancing, I never thought it would yield any decent monetary results. I wanted to make a few extra bucks, sure, but I definitely didn’t think freelancing for a living was a possibility; I was wrong.

A little over a year ago, I was sitting in front of the computer with a broker leg and a desire to make money online. Like most people, I had no particularly valuable skillset.

This sounds harsh, but it’s true. What I mean is, I didn’t know how to write code, I didn’t know the intricacies of graphic design, and I definitely didn’t know the first thing about business consulting, etc. (I still don’t really know how to do any of these things!)

Nevertheless, I managed to make a little over $62,000 in one rolling year working a maximum of 5 hours a day, 3 days a week, mostly in the comfort of my underwear from exotic places around the world.

Freelancer Profile

So how did I do it? This is a quick guide that covers all of the bases on how to freelance for a living. It covers what worked for me, and why I think it worked. And hopefully this will serve to fast-track the early stages of freelancing for anyone that wants to make a living outside of a nine-to-five job.

4 Tips to Get Started

Starting is the hardest part. You’ll have no client reviews, no credibility, and no experience. The good news is, every successful freelancer once started from nothing, too. You’re not alone.

Trust me when I say that if I can make a living freelancing, you can too. Most people get discouraged after they submit a dozen or so proposals for jobs and get denied. Don’t let this be you.

Getting denied sucks, but it’s a part of the freelancing game. Here are four tips to help you start.

  1. Pick a niche that you will enjoy doing for a few hours every week and market yourself as an expert (graphic design, creative writing, language translation, website design..the list goes on)
  2. Do your first job for a great review – don’t focus on the dollar amount
  3. Persist – the reason most freelancers fail is because they quit
  4. Leverage your good review from your first job to land a higher paying job, then rinse, wash and repeat

Pick Your Freelancing Platform and Niche

The two most common freelancing platforms are and

I think both platforms are great, and I actually recommend signing up for both platforms. You might find more jobs available in your niche on one platform vs the other.

After you’ve created a profile and uploaded a clear photo of yourself, it’s time to pick your niche.

I picked writing, specifically financial writing, partially because I was interested in it and partially because it seemed like the only thing I could actually do. While writing and programming seem to have the most job postings, there are tons of other niches out there!

If you aren’t fond of writing or math, check into being a personal assistant or offering consulting services for new cryptocurrency companies.

My advice is to pick a specific niche.

“Writing” by itself it too vague. Niches like financial writing, romance novel writing, or academic essay writing are far easier to brand yourself as an expert in.

It sounds crazy, but because I had an understanding of and interest in economics and markets, I was able to brand myself as an “expert financial writer.” Without question, self-describing as an “expert” helped me land more jobs.

Keep this concept in mind when you pick your niche. Always be confident in the services that you offer or clients will sense the insecurity and hire someone else.

Your First Job

This was my first proposal that I sent to a client. As a new freelancer with no reviews, I knew I stood no chance of landing a job for a high dollar amount like $250. What client would take a risk on a new freelancer for $250? This was my thought process, so I aimed low and secured a job for $5.00. When I made my first $5.00, I was ecstatic. I still remember the specific people who laughed at me for doing a job for $5.00, but I never let it negatively affect me.

This is a screenshot of my actual first proposal as a freelancer that got me hired.

First freelancing cover letter

I stated how I had previous work experience writing articles from universities I attended – this helped my case.

There are three things that made my proposal stand out among the 30 proposals the client received.  

First, if the client read my whole proposal, he would be able to tell that I actually cared enough to read the job description. The bulk of freelancers never read the job description! This is never a good idea. Effortless freelancers merely copy and paste the same proposal for dozens and dozens of jobs. This is so bad! Clients can immediately see past any proposal that sounds like:

Dir Sir/Madam, I am the best fit for this job. Please consider hiring me because I have much experience in this field.

Proposals like this aren’t personalized. They suck! It’s a great way to waste a bunch of your time and not get any jobs. Spend the time and do it right, and you will be rewarded.

Second, I stated that I would revise the writing assignment until the client was 100% satisfied with it. What client wouldn’t want to hire a freelancer that offered that?

And third, I took the time to write a brief sample of what I thought the client was looking for, and I included it in my proposal.

I was hired thirty minutes after submitting this exact prompt. Now, I don’t recommend copying my proposal word-for-word, but this method works for your first job as a freelancer.

Completing Your First Job

Getting hired for your first job as a freelancer is only half the battle. You MUST do a good job and impress the client in some way – seriously.

The easiest way I have found to impress clients is by finishing the assignment early. They love this.  

Even if the client gives you two days to finish the project, try your best to finish it in a day, but don’t indicate that you rushed the project or didn’t spend a lot of time working on it.

After you’ve completed the assignment, message the client and say something like this, “Hey there, So I have been working nonstop on this and I’m really happy with how it turned out. Let me know if you would like any changes. Thanks.”

That’s all you have to say. Keep it simple.

More likely than not, the client will be highly impressed with your quick turnaround time and won’t want you to make any changes. Sometimes, they ask for the changes.

This is okay. It’s always wiser to make the changes and have a 100% satisfied client, than to have an unsatisfied client that indicates their lack of satisfaction in the freelancer feedback.

Here’s a screenshot of the feedback my first job “Legal Writing”:

Even though the client for the “Legal Writing” job said, “on time delivery,” I was early. Regardless, it impressed him enough to mention it in my feedback. He was happy with my results.

With this review, any future client that may look to hire my services will see that I have a proven history of getting projects done on-time and to the liking of clients. This is precisely what I wanted to achieve; it was a pivotal building block.

Your Second Job

Again, I aimed low, dollar wise, for my second job because I knew I likely couldn’t sell myself to write and article for $250, even though I had a good review from a $5 job. This will not be the case for everyone. If you have previous history as a writer, graphic designer, coder, or whatever, then by all means try to land a high-paying job for your first/second gig. It’s tough in the freelancing world, however, because even if you were a reporter for the New York Times, your freelancing profile still won’t show feedback and stars – and this is where I’ve found clients mainly focus.

For my second job, I applied for a $25 essay task, which I knew I could complete in about two hours.

For your second job proposal, leverage your 5-star feedback from your first job.  

Say something like this in your second job proposal:

“Not only am I well-versed in the field of copywriting, but I also received perfect 5-star feedback from my previous client.”

Replace “copywriting” with whatever the required skillset is for given job.

Again, this might seem like common sense, but you would be shocked how many freelancers never mention their glowing feedback. As a freelancer, it’s one of the biggest assets you have! I know this is true, because when I switched to the client side and hired freelancers to work on projects for me, 90% of them never mentioned their feedback or actually read the details of my job posting.

Here’s an example of a proposal I submitted talking about my feedback from previous clients.

In some proposals, I’d say things like, “feel free to check out my profile and see the perfect reviews I have.” And in other proposals, I’d say something along the lines of, “in addition to my experience in this field, I also have perfect 5-star feedback from every client I have ever worked with.”

Let me tell you something… this approach works.

Clients like to know that they are hiring a freelancer that other clients like.

Either approach is fine, really. Just make sure to mention that you have great feedback from clients, and that you have a proven track record of surpassing expectations.

Interaction with Clients During Interviews

After getting a few jobs under your belt, you’ll want to make sure you are communicating as effectively and efficiently as possible with every prospective client.

I always try to keep interactions with clients succinct.

Remember to respond quickly and answer their questions fully. Imagine a client has to choose between two freelancers:

  1. A freelancer who is answering all of their questions quickly, with perfect grammar/spelling, but only has a few 5-star reviews
  2. A freelancer who has many 5-star reviews and lots of earnings but is slow to respond or doesn’t answer all of their questions during an interview

I can guarantee you the client will most likely select the freelancer who is attentive, despite the quantity of quality reviews. As long as you have a few 5-star reviews, it’s enough to get your foot in the door.

Whichever freelancing platform you choose, I highly recommend downloading the respective mobile application so you can keep conversations going when you’re away from your computer. Upwork’s mobile app is great for this.

A lot of clients want to have a quick phone call, often via Skype, before starting the job. Don’t be afraid to do this. Some of the best paying jobs I landed were because of Skype calls that went well.

The Evolution of Your Career as a Freelancer

Eventually, when you complete enough jobs and receive stellar client feedback, clients will begin to discover your profile and invite you to their jobs. This means you will no longer have to go through the process of applying to each job and writing detailed, individual cover letters. This is great news, but it doesn’t come easy. You have to WORK to get to this level.

Overtime, you will notice that clients invite you to bigger and better jobs. And you will also notice that when you apply to higher fixed-price or hourly jobs, you’re more likely to be hired.   

Freelancer earnings go up overtime

Look at how my earnings progressed over the months. Remember, my first job was for $5.00. The job I did in Jun 2017 was for $650!

Without a doubt, the feedback from former clients is your biggest asset as a freelancer.

This is some of the feedback I received from a high-paying client:

Freelancer Reviews

Once a prospective client sees this review and sees how satisfied a former client was, for nearly $9,000, there is no way they’re thinking they will be left unsatisfied if they hire me. This is what you want.

I often thought of freelancing as a video game. It’s always difficult to start out at prestige level one, but after playing for a little while, you slowly start advancing to the higher levels. As you progress, more upgrades, modifications, perks, etc become available to you, and these help fuel your success to higher levels.

Essentially, glowing reviews with high-dollar transactions allow you to rapidly grow as a freelancer. They’re tools. It’s like a job resume on steroids, because none of it is self-described. As a freelancer, all of your reviews are written by actual people who you worked for! Imagine having that on a resume…

Top Three Takeaways for Freelancers

Before you decide to make a dollar freelancing, consider taking these three rules into account. I would have loved to get this advice when I started.

My overall process was a long and arduous one full of trial and error (this article is the abridged version). I spent a considerable amount of time figuring out what worked, what didn’t, and then concentrating all my effort and resources on the things that worked. Here’s the meat and potatoes:

#1 Set your Rate High from the Begining

This seems counterintuitive. Who in their right mind would want to hire someone with a high hourly rate and little to no experience?

Well, it’s basic psychology, folks. We have all heard the phrases like, “people want what they can’t have,” and the concept of setting a high hourly rate is somewhat similar. Let me explain.

Simply put, clients are more likely to assume that a freelancer with a high hourly rate will do a better job than a freelancer with a low hourly rate, like $10 an hour.  

The simple fact of the matter is, a low wage like $10 an hour is associated with a minimum wage job in America. Whether the client knows it or not, seeing a freelancer application for $10 an hour is less impressive than seeing a freelancer application for $55 an hour – period.

Clients have a tendency to believe a freelancer with an hourly rate of $55 MUST be more experienced than a freelancer with an hourly rate of $5, even if that’s not actually the case.

Look at this correspondence I had with a client recently. I wasn’t taking it too seriously, because I didn’t need the job, but it is highly interesting nonetheless. Note how I employed all of the aforementioned tactics

I kept the messages succinct and replied VERY quick.   

In retrospect, I might have played a little too hard to get, but look at the response!

You’re in demand and you deserve it. This is impressive.   

When you act like you know what you’re doing, people believe you.

By setting my rate high, I gave the impression that my time is valuable, that whatever work I would produce would be amazing, that I deserve a high rate, and that I am in demand – all very desirable things.

Of course, for some tasks, low rates are perfectly acceptable. But it’s very difficult to make a living with a low rate as a freelancer, because you inevitably will not be working 40 hours a week. You might only work 10 hours a week at $100/hr for one client for a period of two months. Often times, a 40 hour freelancer workweek is simply too much to manage when you have multiple clients.

The only exception to this is if you happen to land a gig from one client that’s full-time, where x amount of hours per week are guaranteed. Many developers I know have setups like this, but it’s not so common for writers and other creative freelancers.

#2 Be Okay with the Bulk of Your Earnings Coming from a Few Clients

Freelancer Earnings by clients

In my case, the majority of my yearly earnings came from just three clients.

I don’t think this will be the case for all freelancers, but it’s likely to be similar. Many clients need multiple tasks and some clients only need one task. However, it is also possible that this client pattern is a direct product of my own freelancing strategy.

Sure I would do jobs for a few hundred dollars here and there, but I always loved either applying or getting invited to a job that mentioned the words “long-term relationship.” The key is landing jobs that will offer consistent work, even if it’s only for a period of two months. Completing a bunch of one-off jobs is very time consuming and underscores the notion that a 40 hour freelancing work week with different clients is overwhelming.

Some of my highest paying gigs were only for a few months at a time, but my output was at max capacity… writing two or three articles a day. These are the golden nugget jobs… the jobs that pay the big bucks. From the beginning, clients are usually very clear whether a job is likely to be long-term or not.

#3 Check the Client History Before you Apply for or Accept a Job

I can’t stress this rule enough.

Under no circumstances should you accept a job offer from a client who has a history of poor feedback. Freelancers can leave feedback after a job is completed, and if you see lots of similar negative feedback, run away.

You do not want a negative review on your profile. Some clients are very demanding and will leave a negative review regardless of how well of a job you do. Although you might be able to remove it by contacting customer service, it will significantly lower your chances of securing futures jobs.

Of course, some freelancers may have had bad experiences with a client, so you can’t trust every review of a client. However, if you see a lot of similarities, describing how the client is too demanding, or the client disappeared for weeks on end, be extra cautious.

Moreover, check the client spend history. If they have been a client for three years and have only spent $45, chances are they will never be a long-term high-paying client and may not even higher a freelancer for the listed budget. Deceptive clients might lure you in with a high listed budget, and then try to get you to do the job for $5. This isn’t always the case, but it’s something to be mindful of.

Fixed-Price vs Hourly

As a freelancer, you’ll have to choose between doing fixed-price jobs or hourly jobs. I really had no preference. Fixed-price jobs tend to be more one-off type of jobs, and hourly jobs tend to be more long-term, but it’s not always the case.

I noticed early on that having a high hourly rate gave me more negotiating power with clients offering fixed-price jobs.

If a client wants to pay $100 for you to write a 700 word article, and you want to charge a fixed-price of $250, your hourly rate needs to justify it.

If your hourly rate is $30, that doesn’t make any sense, unless it’s going to take you 8+ hours to write a 700 word article, which it probably won’t. This is another reason why you should set your hourly rate high from the get-to. Eventhough you may not land any hourly jobs, it may actually make you more money by getting larger fixed-price jobs.

Final Thoughts

To recap, pick a specific niche, be confident in your niche, do a measly job for a positive review, leverage your positive review to land larger jobs, set a high hourly rate, and respond to clients quickly. This is the formula, folks.

Freelancing has changed my life. It’s given me the freedom to go anywhere and do anything I want, within reason.

amazing breakfast Kevin Ott enjoying wine in France

After I had some success freelancing and felt financially comfortable, I went mobile. I freelanced from France, Italy, Prague, Indonesia, Panama, Nicaragua, and countless other countries.

Fun in the snow

The way I see it, the employment landscape of the 21st century is rapidly changing. Now more than ever, it’s possible to make a living online. Freelancing for a living is a reality, not just a dream. I genuinely hope this article can serve as both inspiration and guidance on how to beat the system *somewhat* and earn a living beyond the traditional bounds of society.

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