Have you ever wondered how to transform your under-utilized skills into money-making machines? Or maybe you know about freelancing but not where to start and how to succeed? Well, this post will go through each step in the freelancing process, so you will be able to make thousands of dollars from skills you have gained over the years.

Let’s hop right in.

Quick rundown on what freelancing is

A freelancer is a person who is self-employed and not necessarily committed to a particular employer in the long-term. Most freelancers provide a service for a temporary employer, get paid, then move on to a new job. Although some long-term commitments exist, they are never locked in to a particular employer like normal careers. Freelancing work is often done remotely; for example, I do all of my freelance web development from home for companies located in other states, Europe, and even Asia. You are virtually your own boss and set your own hours. However, this requires a certain degree of self-discipline. We will get into managing all of this soon.

Pictured above, the hardworking freelancer works from a remote location and receives payment from a client that he is not bound to over the long-term.
Image courtesy of Lifehacker Australia

My success story

To hopefully provide some motivation, I will give my own story of freelancing. Everything I’m about to say is completely possible for everyone, although it takes a lot of hard work, dedication, and some lucky breaks. But we all know that luck is just where preparation meets opportunity.

I started my freelancing journey as a high school student. The common belief at the time was that the only way a teenager could make money was by getting an introductory, close-to-minimum-wage job, at a local store or restaurant. I believed this too as I made my way through the first few years of high school. That being said, it wasn’t money that drew me to freelance work, it was curiosity. More specifically, I had a deep curiosity in developing websites, programs, applications, etc. So I started to devour any resource I could find that related to programming.

Before you know it, I was hammering out websites left and right, mostly for personal interests or for school activities. Many of the websites I coded never were published, but it was the learning that mattered. I continued to work at getting better and better when I came across a freelancing website. I discovered, a place where I could get paid for my web development skills.

Over the next months, I spent loads of time sending proposals and beefing up my work portfolio. This period of time was by far the most difficult. In fact, I only made a few hundred bucks over the span of several months. But this wasn’t important, as I was gaining the experience I needed to get more and more jobs. My work started as simple fixes and other small, low-paying jobs, but eventually began to rise into much higher paying jobs that required a wider breadth of skills.

Soon, I was getting offers everyday that I had to decline because I didn’t have the time. People were desperately running to me for help — almost throwing money at me. I even secured a job with a web design and development agency that I still work at today.
Who knew that some wild curiosity could land me high-paying jobs?

The point of this background story was to inform you that anyone, even young kids in high school, can take on freelancing and make a lot of money from it. All you need is natural curiosity in your subject field and the desire to learn and improve every day. It takes a lot of hard work and dedication, especially when you start. But it is most definitely worth the effort.

Pictured above was the first job I ever received on Upwork. Only $5, but the 5 star review was very important in launching my career as a freelancer.

Pictured above was me in my home laboratory around the time I started freelancing in high school. As long as you have the curiosity and dedication to succeed, a person of any age can outperform adults that have college degrees. Don’t let your age discourage you from the field of freelancing. Carry confidence in your ability.

Is my skill right for freelancing?

This is a very important question as you do not want to spend hours grinding away at setting up your freelancing lifestyle only to realize that there is absolutely no market for your skill. Before you hop right in to freelancing, you need to do some research to find if a market even exists for your particular skill.

This is actually surprisingly easy to figure out. Hop on to a freelancing site like or and make a search for your skill. If there are many jobs posted recently with that skill in the keyword, then it is likely a very marketable skill.

Below I am going to list off some of the common jobs on freelancing sites. This list is not all-inclusive.

  • Web development and design
  • Mobile application design and development
  • Graphic design
  • Creative writing
  • Data entry and transcription
  • Video and audio editing
  • Virtual assistants
  • Various programming and scripting tasks
  • Data analysis and data scraping

See anything above that interests you or you have experience with? There are many marketable skills that are not included in the list; use the search method described earlier if you are unsure.

Pictured below is the screen after searching for “web development.” It is clear that this field is very active on this freelancing site becuase of the abundance of jobs posted in the last 20 minutes of searching.

Where to find jobs?

Finding jobs is undoubtedly the most important part of freelancing, and most certainly the most difficult when first starting out. There are two common outlets of freelancing jobs: jobs from online freelancing sites and freelancing for local businesses outside of a freelancing site.

Getting jobs outside of a freelancing marketplace carries several challenges and advantages. The primary challenge of freelancing outside of an online marketplace is the difficulty of obtaining jobs. You will have to be or become an active part of the community and build many connections that will gain you jobs. This is easier for some people than others. You may even have to blindly approach tens of hundreds businesses asking if they need your services — the overwhelming amount of rejections can get to some people. However, working outside of an online marketplace allows you to directly help your own community, and there are no percent-based fees on your wages that all freelancing sites take (they have to make money too).

Freelancing marketplaces have made the task of attaining jobs much more accessible. In fact, one of the most difficult parts of online freelancing is choosing what website you would like to use. A simple Google search of “freelancing website” returns an overwhelming number of freelancing marketplace websites. I recommend researching into each website and finding the advantages and disadvantages of each.

An optimal freelancing website would have the following features:

  • Large, active community of employers — this means more jobs to choose from
  • Low limit on monthly job applications — most sites give you a set amount of job proposals before you have to upgrade to a paid plan
  • Low service fee — virtually all freelancing sites have a percentage fee on your earnings
  • Good support system — this is a no-brainer for most online systems
  • Easy payment system
  • Built-in hour tracking system — this is essential for hourly tasks to ensure that you get paid for the hours you work
  • Additional features such as a ‘Top Rated System’ that helps out top freelancers

I ended up choosing Upwork to freelance on; however, do your own research and find the one that works best for you. Most importantly, once you start on a freelancing site, don’t hop around to others, trying to get jobs from all of them. Focus all of your efforts on one site to build a solid reputation to get more jobs. This brings us to our next section, ways of building a good freelancing reputation.

Here is an infographic of some of the most popular online freelancing marketplaces. Look into each of them and see which one works best for you. Then stick to it and start building your reputation.
Image courtesy of

Building reputation to get more jobs

Not only will a high reputation get you more jobs, it will get you higher-paying and more interesting jobs. Building reputation is a process and will require time, patience, and hard work. The freelancing world is savage and extremely competitive; developing a good reputation is the only ticket to success.

First and foremost, any freelancer needs a portfolio site to highlight their work. You will link this on your freelancing profile and use it as an extension to your profile. Most freelancing profile pages do not offer the customizability you need, so an external portfolio is perfect for this. You will look more professional than other freelancers, landing you more jobs than your competitors. You can learn more about how to create a portfolio site at my blog post on the advantages of a portfolio site and how to create one.

Luckily, building a solid reputation doesn’t require a sophisticated game plan. All it takes is a portfolio full of past jobs. That’s correct, you just have to do your job, do your job a lot, then document these jobs in a portfolio. Easy.

But here’s where the confusion comes in. “But Tom! If getting jobs requires lots of past finished jobs, then how do you get the initial jobs, in the first place? It doesn’t make sense!” Here’s the answer: do it for free. That’s right, do the initial jobs for free or for very little cost in comparison to your competition. Build up your portfolio by doing free (or very cheap) jobs or by completing your own personal projects that you can highlight on your portfolio. Once you get a good set of jobs on your portfolio, jobs will come flying at you.

Start grinding away at jobs, and you will see a marked improvement in jobs and wages over time. My first job I ever completed on Upwork landed me a whopping $5, we all start at the bottom.

Pictured above is what happens when you build a strong reputation on a freelancing site. That graphic is essentially what freelancing is all about; high rated freelancers have an enormous advantage over lower-rated freelancers that do not have a good reputation.

Writing good proposals

A freelancer’s success is only as good as its job proposals. Proposals are written applications to a job in an effort to secure the job. It is the first thing a client will see when you reach out to them, so it is obviously very important. We will go through the basics of developing a solid proposal, and then I will provide an example of a proposal that actually won me a job out of 50+ applicants.

Let’s give you another simple checklist of what you need in a proposal:

  • Completely unique — employers can tell if you use the same template you use for every other proposal. Use words that are specific to the job you are applying for. This is very important.
  • List of your skills and how they apply to the project
  • Link to a portfolio site (see my blog post on portfolio websites)
  • List of projects that you have completed that are similar to the project
  • Your proficiency in English
  • If you live in a close time zone, include this
  • Emphasize that you are available for communication at all times
  • An outline of how you plan to tackle the project
  • Any other pertinent details that you can think of

Here’s an example of a basic proposal that won me a website redesign job:

Hello Ian!

I would love to help rebuild your website from the ground up. After looking at the current website, I have some great ideas to completely restructure the rather unappealing website into a clean and professional page.

I have years of experience programming in HTML, CSS, JavaScript, Twitter Bootstrap, PHP and MySQL. I also have experience on the design side including logo and web design in Photoshop and graphic design using Illustrator. This experience allows me to build nearly any website possible in a fast and efficient manner.

Some of my past work includes: (actual website names omitted for privacy reasons)

I will work until the job is complete to your fullest satisfaction. I am also a native English speaker, so communication would not be an issue.

Within a couple days, I could have this website complete and ready to convert visitors into clients.

I have a precise plan for quick and proper development of the new website:

1. Redesign the site: Make a quick mockup in photoshop for the new design and get your approval before coding.

2. First Version: Code the first version of the site and receive feedback from you.

3. Revisions: Repeat step 2 until the website is 100% to your satisfactions.

4. Implementation: Work with the client to properly send the website live and manage it.

In these 4 steps, we will be well on our way to completely overhauling your website into something beautiful.

I look forward to working with you,
Tom Overman

Your proposal should not be a carbon-copy of the proposal above; add your own flair into it. Make it unique. My example is just there to give you a feel for what works for me.

If you are working independent of a freelancing website, then this process is very different. If you are not using a freelancing website to get jobs, then you will not have the ability to send a bunch of proposals to various jobs. You will have to market yourself to local, potential clients in other ways, but once you have a potential client locked down, you will have to create a proposal that highlights the purpose, process, milestones, payments for the project. Proposals should end with a signature. This covers all bases because you do not have a freelancing website that guarantees your pay. There are many online proposal tools, a good one that I have used for both freelancing and within the company I work at is proposify. Proposify makes creating and storing template proposals a breeze. Give it a shot, it will make your life a lot easier.

Avoiding scams and closing contracts

Many freelancers will make the vital mistake of not securing a sound payment system, leaving them hopelessly scammed by a client that steals hundreds of hours of free work. There are several ways to combat this issue. After describing how to avoid scams, we will dive into closing contracts.

The single best way to avoid scams and ensure proper payments is developing some sort of milestone system. A milestone system splits a project up into steps that are clearly defined as to avoid confusion. Upon completion of each milestone step, you get paid for your work. Simply set up the steps and the amount to be paid after each step; if the client does not pay after the first milestone step, then you saved hours and hours of work that would be unpaid. Most online freelancing sites have a milestone system built in for fixed-price contracts.

Another method is the hourly contract system. You simply track your hours on some type of tracking system, then report the work after each week and receive your payment. Most freelancing sites, including Upwork, have a tracking system built in that will automatically bill your client each week based on the hours you worked.

NEVER work on a fixed-price contract that does not have a system setup for payments after segments of work — you will likely get scammed. The only exception to this would be on fixed-price contracts that are short and not worth a lot of money; something like a $40 bug fix would be useless to split into milestones. However, a $600 website build contract needs a milestone system.

If you are not using a freelancing website, then set up the milestone system on your proposal that was discussed earlier. Because it is a contract that the client signed, they are legally obligated to pay after completion of the milestones. Cover all of your bases; clients can be sneaky.

So now that we got that out of the way, let’s get into closing the contract. The goal here is to make the client happy so that you get continued work from the client. Long-term clients are the most cost-efficient because you do not have to put in time and resources to find new clients.

Upon completion of the project you are looking for two things in addition to the final payment: a good rating/testimonial and additional work from the same employer in the future.

First, make sure that the client is absolutely satisfied with the work. You may even want to suggest an improvement that they didn’t think of — this shows initiative and creativity. At the end of completion, give the client a rundown of how you completed the project and any pertinent information. For example, if I created a WordPress website, I would give the client the login credentials to the admin portion of the website and a quick rundown of how they could make changes to the website. Be as respectful and helpful as possible — remember, you are trying to build long-term business relationships.

After the client is satisfied with your work, politely mention that you are available for future work and would love to continue work for them. Then leave them a solid client review and gently ask for a good review if they were satisfied with your work. Mention that a solid review helps enormously and only takes a couple minutes.

And that’s about it. You may continue work for that client or never hear from them again; that is the life of a freelancer.

Pictured below is the time tracking system created by Upwork. This system logs your hours and adds them to your total weekly hours that the client then must review and pay, weekly. This system prevents scams pretty well.

Common mistakes to avoid

I’ve been doing this for a while now, so I have encountered many mistakes that are completely avoidable. Here’s a list of common mistakes to avoid that will save you a lot of grief (I will add more to this list as I think of them):

  • Do not become discouraged and quit after you are denied from the first 20+ jobs you apply to. Becoming a successful freelancer takes time.
  • Do not use a proposal template. Clients will notice how bland it is. Make unique and detail-filled proposals; most of your competition will use templates and lose the job to you.
  • Once you build a reputation, do not undercut your prices. You would be surprised how much more clients will pay for an experienced freelancer.
  • Do not just apply to a few jobs when you are a beginner, thinking that you will have too many jobs to handle. Chances are you will get very little of these jobs. Apply relentlessly to many jobs until you finally get the first bite.
  • Do not run the clock on hourly jobs for a bit more pay. Clients are not mindless; in fact, many of them are very experienced in the field you are working. If you finish a job quickly and efficiently, you will very likely get future work that will make you a lot more than the idiotic clock-running that many freelancers commit.
  • Do not promise things you are unable to complete, it will haunt you in the end.
  • Do not hop around to a lot of different freelancing sites. Stick to one after you review your options.
  • Always set up a milestone or hourly-pay system. See earlier section on this for more information.

A quick word to fresh beginners

So, you’ve decided to hop into the world of freelancing. I remember when I first started. I was a high school student with some mediocre web development skills. If you take on freelancing with a burning passion, then you will grow, you will get better, and you will undoubtedly make good money. The problem is the “passion” part; you really have to care a lot about what you do and be extremely dedicated to make it in the freelancing world. It is probably the most competitive field you can get into.

Keep looking ahead at all times. Just because it isn’t working your way at first doesn’t mean you should give up. Every freelancer goes through the lag phase when first starting.

One of the most important things you can do is consult with established freelancers. Ask them how they started, how they established a reputation, etc. Comment below or even privately contact me, and I can help you. Asking for advice is important in any field, but even more important in a field as competitive as freelancing.

Lastly, the longer you wait to get started, the further behind you will be. Start now. Start the grind. Cherish the grind.

Final conclusions

So now you know how to get into freelancing, you understand the challenges you will face, and you know how to avoid some common mistakes. This just serves as a quick introduction to freelancing — you will learn a remarkable amount as you embark on your freelancing journey. I wish you the best as you start freelancing, and if you have any questions, don’t hesitate to ask me.

Tom Overman

Tom Overman

Tom is a web designer and developer at Octane Web Design. He also works with the SEO team very frequently. In addition to his work at Octane, Tom works on a variety of technical projects as a freelancer.

Years of work in the web industry have shown him how to hustle for jobs and freelance with a laser focus. He constantly works to improve his web design and online marketing skills. Tom currently attends the University of Texas at Arlington and majors in Biomedical engineering.