Freelancing 101: A Starter’s Guide to Self-Employment

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A pro-freelancer breaks down what it means to be a freelancer in today’s modern world

The term “freelance” dates back to the early 1800s when mercenaries were referred to as “free lances” and fought for whoever paid them the most money. While much evolved today, the term freelance still refers to the act of being a free agent of sorts. Most commonly, it refers to a way of working that allows individuals to offer their skills and services on a per-project basis instead of being beholden to a single employer or company.

Freelancing refers to the practice of working as an independent agent on a per-project or contract basis for various clients, without being tied to a single employer. Freelancers are their own bosses.

What is a freelancer? Understanding freelance

Unlike traditional salaried workers, freelancers are entrepreneurs and small business owners. They don’t have “employers”, they have “clients”. They usually work on a per-project or per-contract, as-needed basis and they don’t earn a set salary. This type of arrangement is also commonly known as “gig work”. Popular freelance fields include graphic design, web design, writing, virtual assistance and development. But gig work can also include things like babysitting, housekeeping or even tutoring. Whatever the case may be, freelancers are professionals who set their own hours and rates and work how and where they so desire.

For instance, when I became a full-time freelancer and was no longer beholden to a specific location (or the morning commute) I relocated to my dream city and was able to double my income. I sleep in most mornings and enjoy the ability to be picky about the kind of work I take on.

But with great flexibility comes great responsibility. Freelancers play multiple roles in their own company. They are in charge of securing their clients and projects. They are also in charge of handling their administrative tasks like invoicing and taxes.

Skills Required for a Freelance Career

To paraphrase Liam Neeson, freelancing requires a special set of skills – beyond the basic skillsets required to perform work in your chosen industry. Those skills include time management, self-discipline, communication, financial management and sales.

Time Management

Freelancers need to hone their time management skills to meet deadlines while juggling multiple projects. Freelancers bear the sole responsibility of delivering work within agreed-upon timelines while juggling multiple clients. This means setting daily goals, prioritizing tasks and keeping themselves on track. Effectively being able to estimate the amount of time a project requires before taking it on is crucial. Freelancers also usually need a way to track their time when working on hourly projects. Oftentimes, freelancers utilize project management software to help them keep everything straight. You can read about the specific software and tools I utilize in my freelance business here.


Professional freelancers know that effective communication and cultivating professional relationships are at the heart of a successful business. They need to be clear and concise with their clients, have a clear understanding of project requirements, provide updates and easily address concerns should they arise. Freelancers must also be able to effectively articulate ideas and listen to client feedback. Finally, freelancers should master the art of standing their ground when clients try to negotiate prices. While some believe things like rates and fees are up for debate, I’ve always treated my freelancing career as any other business and instead chose to stand my ground. A patient doesn’t negotiate prices with their doctor. No one negotiates the price of an entree at the neighborhood steakhouse. If you’re a professional in your field, you need to act like it.

The “free” in “freelancer” refers to FREEDOM, not FREE WORK. Professional freelancers should always be fairly compensated for their work.

– Morgan Overholt

Financial Management

Financial management is usually considered one of the most difficult aspects when it comes to self-employment. Freelancers inherently have irregular income streams – especially when they are first getting started. And so, to survive, freelancers must master the art of budgeting and saving for times when work is more sparse or when they need to take planned time off. Freelancers are also in charge of managing their invoices and keeping track of payments. Some do this by hand but I prefer to use software to manage mine. They also need to manage their expenses, bookkeeping, accounting and taxes. Or, at the very least, do as I do and hire a firm to handle some of those aspects for them.

Sales & Marketing

Finally, freelancers should master the art of sales, networking and marketing. Knowing how and when to close a deal with a prospective client is key. There are a variety of resources and books available on the topic. I suggest studying up. Being a good salesperson is the single most underrated soft skill for a budding entrepreneur.

The Pros of Freelancing

There are a lot of perks to freelance. Several key benefits make the freelance career path an attractive alternative to the “9-5” for many individuals. Some of these upsides include flexibility, earning potential, and control over your own life.

Flexibility Over Your Work Schedule

One of the most appealing advantages of freelancing is the ability to when and where you want. Unlike traditional employment where a fixed “9-5” schedule is the norm, freelancers can tailor their work to accommodate their personal preferences. They can work whenever they want, anywhere they want. Whether you’re a night owl, an early riser or just someone who prefers to take long breaks in the middle of the day, the prospect of being able to work on your own time is alluring. Many even report feeling increased productivity, greater job satisfaction and an overall sense of well-being and fulfillment when no longer being beholden to someone else’s clock.

Increased Earning Potential

Another notable advantage is the potential for increased earnings when compared to traditional employment. With the freedom to set their own rates, freelancers have the unique opportunity to control their income and even give themselves raises. They can also work as little, or as much as they want. For example, I was personally able to double my take-home pay after just a few months of going full-time freelance. Earning opportunities for the self-employed are endless.

Control Over Your Life

Finally, we have the greatest benefit: control over your own life. For years I was beholden to a single employer. A single entity had complete control over my entire paycheck, my time, and in turn, my well-being. Freelancing certainly isn’t without risks. However, I know one thing for sure – I have a greater interest in my success than anyone else ever will. I no longer have to worry about being furloughed, fired or passed up for another promotion. My success now depends on the effort I put into the business and nothing more.

I have a greater interest in my success than anyone else ever will.

– Morgan Overholt

The Cons of Freelancing

While there’s plenty of upside to the world of freelance, it’s not without its own unique set of challenges. Common challenges include inconsistent income, and dealing with difficult clients. Below I will address how to make the most of those difficult situations.

Inconsistent Revenue & Expenses

One of the primary concerns for new freelancers is the fluctuating nature of their income and associated costs of doing business. Unlike traditional employment where paychecks arrive with predictable amounts at regular intervals, freelancers often experience irregular cash flow, making financial planning more challenging. But pro freelancers can overcome these challenges by ensuring they have an emergency fund tucked away, budgeting for slower times including planned time off or sick leave and diversifying their income streams. There’s also the matter of managing several business expenses, like health insurance, contractors and even internet access. Again, this is simply a matter of budgeting. But do remember, all business-related expenses are tax deductible, which softens the blow.

Bad Clients

Finally, we have perhaps the most hated aspect of freelance – dealing with the occasional annoying client. I find that the best way to deal with bad clients is to learn how to spot the red flags and avoid them altogether. Even still, every so often, I find myself in a less-than-ideal situation with an unhappy client that ultimately leads to either a strain on my mental health, financial health or both. These things are largely unavoidable and even the most successful businesses have to deal with the occasional bad egg. Whenever possible, you should try to remedy the situation. But for those situations that have become untenable, make sure every contract includes a clear termination clause that allows you and the client to go your separate ways. I promise that bad clients become a rarer phenomenon with time as you get better at spotting a bad situation before it starts.

How to Get Started

For those interested in starting a career in freelance I suggest the follow the steps outlined below. For additional advice and information on freelance including specific strategies I used to find clients and send job proposals, and personalized courses, be sure to check out my Freelance Guides and Resources page for related content. Details on the below steps can be found in my How To Start Freelancing guide.

  1. Choosing a niche or industry based on your skill sets
  2. Creating a portfolio of work (like a website, or LinkedIn)
  3. Creating a profile on Upwork, Fiverr and
  4. Reaching out to your personal network
  5. Implementing a process (or tools) for project management
  6. Implementing a process (or tools) for invoicing and payments

Frequently Asked Questions

How does freelancing work?

Freelancers work independently on a project-by-project basis for clients or companies. Freelancers have the freedom to choose the projects they want to work on and the clients they want to work with. They also set their own rates and are responsible for general daily administrative duties like invoicing, paying taxes, managing customer lists and more.

What types of jobs can freelancers do?

Freelancers can do a wide range of jobs, depending on their skills and expertise. Popular freelance jobs include writing, graphic design, web development, social media management, and virtual assistance, just to name a few.

Which platforms are best for finding freelance work?

At the time of this writing, the big three freelance platforms are Upwork, Freelancer, and Fiverr. Each of these platforms allows freelancers to create a profile, showcase their skills, and bid on projects that match their expertise. While I’ve personally found the most success on Upwork, no single platform is better than the others. I always suggest trying them all when you’re just getting started.

What are the benefits of freelancing?

There are loads of benefits to freelancing. Like the ability to decide the kind of clients you want to work with, the ability to set your own hours and the ability to set your rates. Freelancing allowed me to ditch the morning commute, move to my dream city and sleep in most days – all while earning more than double what I used to at my last salaried job.

How can someone get started as a freelancer?

To get started as a freelancer, I recommend identifying your best skills and areas of expertise and choosing a niche where those skills can be put to use. You’ll also want to build a portfolio – or many – and create a profile on multiple freelance platforms. I also suggest reaching out to your personal and professional network and letting people know you’re available for freelance work. Be persistent in your efforts to find work.

Are freelancers typically compensated for their work?

Yes. The “free” in “freelancer” refers to FREEDOM, not FREE WORK. Professional freelancers should always be fairly compensated for their work.

Are you a freelancer or small business owner? Connect with me on social using the links below.

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Morgan Overholt

Morgan has almost 20 years of professional experience in graphic design and a bachelor’s degree in Computer Science. Her successful freelance business has been featured in articles that have appeared on, Refinery29 and Business Insider Prime.

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