How to Build a Successful Freelance Career

A step-by-step guide to earning a living from your writing

Dena@Write-SolutionsJan 17 · 8 min read

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Photo by Mikayla Mallek on Unsplash

I work from home and make a comparable salary to what I would make re-entering my prior career field of being a paralegal. I get asked by aspiring writers all the time about how I got started. There is no magic formula, but I have no issue with sharing what I have learned. I think the field is booming right now, and there is plenty of room for dedicated writers to make a living freelancing.

The new gig economy is here to stay. The gig economy is made up of people working for themselves, freelancing their work, and killing it. It isn’t just writing, either. Engineers, programmers, graphic design artists, and even teachers are finding that there is a market for their skills online. There are some downsides that you need to consider before jumping in, though.

  • No paid benefits. You will have no paid holidays, insurance, or FMLA. I am fortunate to have insurance through my husband’s plan, but the lack of benefits is not something to be taken lightly. If I don’t work, I am not getting paid with no exceptions.
  • Self-employment taxes will take a serious bite out of what you make. Once you get established, you need to raise your rates enough to compensate for the significant portion of your paycheck that will go toward paying taxes.
  • Working from home can be a blessing and a curse. It sounds wonderful for a lot of people, and parts of it are. That said, there can be a downside. I have written in-depth about the pleasures of working from home, such as setting my own schedule, working in yoga pants, and choosing my clients are just a few of the advantages.

The negative aspects of freelance work

Struggling to have others respect the fact that a job working from home is still a job. That means I have deadlines, expectations, and times I can’t be away from my computer. I would not have to explain those things over and over again if I got dressed and went to an office every day.

It can be isolating. Working out in the real world forces us to have social interactions with other human beings. Working from home means less interaction with other people. Even if you are a card-carrying introvert, like me, you will still occasionally miss having coffee with a friend from work or just idle chit chat.

Your job can quickly become overconsuming. With no set hours, you can find yourself putting in long days that do not have equal financial gain.

You have to be a self-starter. If you struggle to keep yourself organized and to move forward on projects without direct accountability, you might struggle in the gig economy.

There is zero job security. No client has to explain why they don’t want to work with you anymore, and even if they do, you have no recourse. You keep your clients happy or your reputation, and your paycheck will suffer.

As a bonus, some clients are impossible to make happy. Regardless of your effort, ability, and work ethic, you will encounter clients who want hundreds of dollars worth of work for next to nothing and will complain even when they get it. Fortunately, these clients are not the norm, and as you gain experience, you are more easily able to spot and avoid them.

Getting started

If you still think this is something that would interest you, I will be happy to share how I got started. I had no contacts to pull from when I decided to make this leap, so I had no choice but to use the platforms. I know plenty of people have negative things to say about platforms like Upwork and Fiverr, but they are where I started.

Take the time to create a killer portfolio. You might want to consider using some of your best Medium articles for your portfolio. Once you have signed up for the platforms, look at the type of writing people are paying for and write a couple of pieces like that for your portfolio. Content is king in the age of the internet, so write a couple of well-edited pieces over anything that showcases your knowledge. Whether it is “How to Write the Perfect Resume,” or “The Role AI Plays in the Legal Field,” you want at least a couple of articles to showcase the type of content writing you can do.


Once you have a portfolio pulled together, decide which platforms you plan to use. I use Upwork and Fiverr. Some of that is a personal preference, but a few of the platforms are overrun with scam artists, and I didn’t want to spend time continually wading through those.

Create your profile, and keep it laser-focused. Remember, this isn’t telling clients how great you are. It is telling clients how you plan to meet their needs. Focus on any specialized skills and experience you have. Look at the profiles of writers who will be your competition. You need to sell yourself, so make sure your profile represents the best about you.

On platforms like Upwork, you will have to bid on jobs. Then clients will pick those they are most interested in and invite you to either do the job or do a sample article for them. Sample articles written for a specific client should always be paid work. You will attach samples to your bid, but if they reach out to request particular work, always make sure you do so under the protection of a contract.

That said, when just starting, you will need to grab some low hanging fruit. Why? Because no matter how much professional experience you have, on the platform, you are new and untested. Bid on some lower-paying, short-term jobs. What you are seeking here is 5-star reviews. These reviews are critical to establishing an excellent reputation.

Never use a form letter as your introduction when you bid on a job.

Read the job description, and take the time to craft a customized letter letting the client know why you are the right choice for the job.

The trick is not to stay here too long. Once you have three or so great reviews, raise your rates and start bidding on the jobs you want. Do not get discouraged. It is not uncommon to bid on 8–10 jobs without hearing anything back. Once you do get an offer, write as your entire reputation depends on it, because it does.

You want to raise your rates early in the game because once you are charging $125 for a 1,200-word article, you do not want to have months of history writing the same types of pieces for $40. Clients will question why you are suddenly worth so much more.

Be prepared to explain that you were new to the platform, and needed to establish the quality of your work. Now, you have quality work and an established reputation and feel confident that you can deliver their money’s worth.

The problems with clients lead me to one of the serious downsides to the platforms. The clients hold all the power in these jobs. They can leave a negative or lukewarm review, no matter how hard you have worked to give them exactly what they requested. If you stay in the game long enough, this will happen to you.

You have almost no recourse, except to continue earning enough great reviews that the negative ones look suspicious. Platforms like Upwork let you review the client as well. The problem is that it is double-blind, so most freelancers leave a decent review for the client, hoping the client will do the same.

Before you bid a job, read the reviews the client has left for other freelancers. Are they mostly positive? If they have hired eight prior freelancers and only left one negative and one mediocre review, and the rest are positive, then the odds are good that they are fair in their expectations.


You may have the advantage of already having a network. I had to start from scratch. Either way, places like LinkedIn are a great way to network off the platforms. It made me uncomfortable to think that my entire career depended on a couple of platforms that could disappear, or block or ban me for any reason. Almost from the beginning, I made it a priority to find some private clients.

I now have four long-term clients that keep me busy enough that I have to turn down all but the most appealing jobs. Two of those clients are on a platform, and two I connected with privately. That feels like a comfortable balance for me. If you are working on the platforms, I highly recommend networking to find clients separate from the platforms.

Set short-term and long-term goals

If you do not have definitive goals, then it can become easy to be distracted and lose sight of what you set out to do in your freelance career. One of my early goals was to have 3–5 long term clients where I did not constantly have to hustle the next gig. Another goal, as stated above, was to connect with clients off the platforms for job stability.

My long-term goals now revolve around better time management. I still struggle with taking on more jobs than I should, leaving me no time to pursue other goals like spending more time writing about things that matter to me. As I type this, I have probably 12–14 hours worth of writing, if all goes well, due by tomorrow afternoon. Hence, I shouldn’t be writing this article but working on my client’s stuff instead. Baby steps, but I will get there eventually.

Do not make excuses

Life does happen, and you will eventually be forced to miss a deadline. However, before that ever happens, you want your clients to be so impressed with your work ethic that they never question your reason for being late. That means you have to treat every client, whether they are paying you $15.00 or $5,000 like they are the most important client you have ever had.

Turn down work that you do not feel equipped to handle. Whether the job is too complex or out of your comfort zone, or you do not have the time, it is better for your reputation to turn down a job than to deliver late or shoddy work.

That, in a nutshell, is what I have done to build my freelance career. I still have important goals that I hope to achieve. I want to work smarter instead of harder now. I am shifting my focus to cultivating great clients and trying to find a balance for doing more of the type of work that matters to me. For instance, I feel passionate about removing the stigma surrounding mental health. I am actively pursuing clients who are working for non-profits or have established voices in the mental health field.

I think the most important lesson I have learned is that you never reach a point where you can say “okay, good enough.” Your career is stagnant the moment you stop moving forward. My last piece of advice is that there are no short-cuts and no way to avoid bumps in the road. I have spent many hours wondering whatever made me think I could do this, but to paraphrase the iconic words of Dory, “just keep writing.

Published by writesolutionsdena

I am a freelance writer specializing in content marketing for law firms and other businesses. I also keep my legal skills fresh by working as an on-demand paralegal in the gig economy.

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