The Ultimate Guide to Freelancing

The Ultimate Guide to Freelancing

What is freelancing? Self-Evaluation: Is Freelancing for You? Is freelancing right for you? If so, what work would you do as a freelancer? Why do you want to freelance? After all, as a freelancer, you’re the one deciding what you make and when you make it. You’re not simply an employee of a business; you are the business. You have to organize your own benefits, taxes, and accounting. Freelancers don’t have employers to manage and provide benefits, taxes, and the like. Getting Started as a Freelancer Before you dive into completing jobs and making money, you need to set up your business.

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Freelancing is an attractive way of life. The independence, autonomy, flexibility, and unlimited financial potential are all incredibly inviting, especially for employees who are tired of their mundane work environment. But, there’s still some mystery surrounding the enigmatic career choice.

As a freelancer, how do you make money? Where do you find work or jobs? How do you figure out what to do? What about insurance and benefits?

These questions are what typically stop people from pursuing a full-time freelance career. And these questions are the ones we’ll answer in this guide.

I was a freelancer before joining HubSpot — AKA the best career decision I’ve ever made. Starting my freelance business was a very intentional choice made in the midst of working a very unfavorable job. Freelancing was the most difficult 18 months of my life, but it completely rerouted my profession and led me to where I am today. It was more than worth it to take the leap into the unknown and pave my own career path.

Whether freelancing is your lifelong dream or a means to an end, we’re going to walk through each element of starting your own business, making your own schedule, and managing your own clients. By the end of this guide, you’ll know exactly what’s expected of you as a freelancer.

What is freelancing?

Freelancing is doing contracted work for multiple clients and companies. A freelancer’s field of expertise can range from content creation to app development to tutoring, and he or she could also be referred to as an independent contractor or self-employed worker. Over 57 million Americans freelance, including almost 50% of millennials — more than any other generation. Also, based on economic trends, the majority of the workforce is projected to be freelancing by 2027.

Self-Evaluation: Is Freelancing for You?

Before moving forward, let’s take a breather and do a little self-analysis. Is freelancing right for you? If so, what work would you do as a freelancer? What would your niche be?

Here are a few questions to ask yourself to evaluate whether or not you’re ready for a freelance career.

Why do you want to freelance? Are you looking for a more flexible schedule, or are you merely trying to escape your dreaded commute? Do you want to expand your professional horizon, or are you simply bored at work? You might’ve heard it before, but the grass isn’t always greener on the other side. Pursuing freelancing for the wrong reasons will make it hard to keep going when the going gets tough.

I want to emphasize here that there are no right or wrong answers, simply what’s best for you, your family, and your career goals. To give you some perspective, here are a few answers from fellow freelancers on why they decided to take the leap:

  • “I started off with a few side projects on top of some full-time work, mostly to pay for a couple of pricey holidays! In the end, the side projects grew to a point where I decided to take the leap into full-time freelancing. It was a ‘try it or always wonder’ kind of moment.” — Jade E., Jade Emmons Media, London
  • “After three years of teaching high school and realizing that it just wasn’t going to be for me long-term, I decided to walk away. Prior to teaching, I had a soul-crushing office job, and I promised myself I wouldn’t return to that situation either. I tried my hand at some freelance gigs during my last couple of months teaching and was able to pay my bills. I realized that it was a viable career path, and I had the chops to make it happen full-time.” — Brent B., Brent Writes, Orlando
  • “For us freelancing means freedom. A few years ago, we were at a point where the thought of doing the same thing in the same place for decades of our lives felt stifling. One day, we finally decided to actually do something about it. We researched our options, found work online as freelancers (one of us is an English teacher and the other is a virtual assistant), sold everything we owned, and started our adventure as digital nomads. So far, we’ve been to over 40 cities in 17 countries and can’t wait to see what the future holds.” — Erin B., Eff The Office, Remote

Can you afford to freelance? A freelance career holds the promise of a higher salary and unlimited income potential. After all, as a freelancer, you’re the one deciding what you make and when you make it. But you’ll likely not see that income right away. The first few months (or years) of freelancing typically involves sacrificing income while setting up your business, establishing yourself, and finding clients.

Are you comfortable with being uncomfortable? Freelancing can be majorly uncomfortable. You won’t always know where your next paycheck is coming from, you’ll probably be rejected more times than you can count, and you’ll definitely experience a few days where you think, “Why the heck did I do this? That commute doesn’t sound too bad right about now!” All of these thoughts and feelings are normal; I’ve always referred to them as growing pains. After all, if it’s not challenging you, it’s not changing you.

Next, let’s talk about what kind of work you’d do as a freelancer. This step is another common roadblock for folks who want to freelance … they’re simply not sure what to do. The answer is simple, though. It might just take a couple questions to draw it out.

What are you good at? This five-word question can determine a lot for you. What are you skilled at? What do others ask you to do for them? Notice that I didn’t ask, “What are you an expert at?” Experts are few and far between — all you need to decide right now is at what you’re willing to become an expert.

What brings you joy? This question isn’t always applicable. There will be days and times that you simply don’t want to work or might be sick of your chosen field. That’s life. But, above all, there’s usually one skill set or profession that brings you joy. What makes you feel good to accomplish? What are you proud to share with friends and family? This is probably what you’ll excel at as a freelancer.

The Pros and Cons of Freelancing

Now, let’s pull the spotlight back and look at freelancing as a whole. Regardless of fit or type of work, there are definite benefits and drawbacks to a career as a freelancer. Let’s look at a few.


  • You’re the boss. You choose your schedule, rates, and which clients or jobs you want to take. If you feel like working in your pajamas, you can. If you want to take a three-week vacation, you can — it’s completely up to you.
  • You could pay less in taxes. Freelancers can take advantage of more tax deductions on meals, travel, and more. Federal and state taxes aren’t withheld from each paycheck. Freelancers pay the IRS directly, instead.
  • You (can) make more money. Freelancing is high risk, high reward. Your salary is whatever you want it to be. It all comes down to how much you charge and how often you want to work.
  • You have a better work-life balance. Instead of commuting every day, you can simply stroll to your neighborhood coffee shop. Instead of rushing to the gym over your lunch break, you can take an hour to workout whenever you want. When freelancing, you can work whenever you want and live wherever you want … it doesn’t have to resemble a typical 9-to-5.


  • You’re the boss. You have to make all the decisions and do all the work, from bookkeeping to managing cash flow to selling your services. You’re not simply an employee of a business; you are the business.
  • You have to organize your own benefits, taxes, and accounting. Freelancers don’t have employers to manage and provide benefits, taxes, and the like. They have to do it themselves with the help of tools or guides, like this one. Also, purchasing your own insurance is typically more expensive than through a traditional employer.
  • If you don’t work, you don’t make money. Sure, you can take a three-week vacation, but you won’t make any money while you’re gone. As a freelancer, your time is quite literally money. Spend it un-wisely, and you could be giving up valuable income.
  • Instability can interrupt your work-life balance. There are a lot of unknowns with freelancing, the biggest being where your next paycheck might come from. This instability can cancel out any work-life balance achieved through freelancing. For some, having stability and predictability in your career is worth a long commute or unfavorable schedule.

According to an UpWork study, the biggest drivers to freelance are flexibility, freedom, and earning potential, and the biggest barriers are income predictability, finding work, and benefits. If these things are motivating or demotivating you, you’re not alone.

Everything You Need to Know About Freelancing

In the following sections, we’ll touch on everything you need to know to start a freelance career, from branding to clients to making and managing your money. We want to minimize the unknowns and equip you with plenty of knowledge as you pursue freelancing.

The information and recommendations in this article were collected from real freelancers across the world (including some from HubSpot employees who previously freelanced). I’ve also included real anecdotes and examples that will shed some light on what it’s actually like to be self-employed.

Any pressing questions you might have about becoming a freelancer? Consider them answered.

Getting Started as a Freelancer

Before you dive into completing jobs and making money, you need to set up your business. You need to know exactly what you’re doing and how you’re branding yourself. This will not only attract clients, but it’ll also provide direction when you feel stumped or at a loss for why you’re freelancing. Here are a few things you should know to make sure your freelance business survives in the long-run.

Building a Brand

A personal brand is valuable when establishing authority as a freelancer and creating a long-lasting impression with clients. Whether you use a design tool like Canva or outsource your branding to an agency, personal branding should be one of the first things on your to-do list.

Along with a memorable logo, your personal brand should also include a business name. You can brand your business after your own name or a third-party name.

“I chose a business name for a few reasons: 1) It’s easier to brand. Business Casual Copywriting could be easily turned into its own aesthetic, with its own voice and tone, and its own identity. My own name would’ve left me with less leverage. 2) The company can grow bigger than just me. If my business name was just ‘Joel Klettke Copywriting’ — well, I’m the be-all-end-all of that business. With a moniker like Business Casual Copywriting, I can bring on subcontractors and turn the company into something larger if I decide to. 3) It’s easier to remember. Nobody can spell ‘Klettke’ correctly on their first time or pronounce it confidently without help. Business Casual is a more memorable name that rolls off the tongue.” — Joel K., Business Casual Copywriting, Alberta

Another element of your personal brand is your online identity. This typically includes a dedicated website and social media accounts where you can display your logo and business name, portfolio, testimonials, and services. Nowadays, every freelancer should have a website, especially if they work with clients remotely.

It’s good practice to match your website domain and social media handles to the name of your business. For example, if you were a freelance photographer, and your business was named Phoebe Photography, your website could be and social media handles could be @phoebephotography. Congruity makes it easier for potential clients to search and find you online.

As for a website, platforms like Squarespace, WordPress, and Wix make it easier than ever to create and design a professional-looking site. These platforms also offer templates that you can use to display your work, like writing or design samples. If you opt out of a dedicated portfolio site (which we’ll discuss below), these themes make it easy to integrate your sampled works into your website.

Your social media accounts should also reflect your personal branding. Every platform has its own benefits and purpose, so don’t fret that you’ll need to be active on all of them. Twitter is good for sharing your portfolio and connecting with peers and potential clients. LinkedIn is great for publishing a live resume and making valuable professional connections. Facebook is handy for joining groups of like-minded people, and Instagram is valuable for publishing pieces of your portfolio — if you dabble in visual work, like photography or design.

There are other places that should reflect your personal brand, too. If you do local work or attend network events, business cards are a great tool to carry with you. Sites like Vistaprint or Moo help you easily create gorgeous print material. Your brand should also be on your proposals, invoices, contracts, and any other materials that go to clients.

Why is personal branding so important? A clean, consistent brand communicates authority and professionalism to anyone looking at your business and will help you establish yourself as a trustworthy freelancer.

Creating a Portfolio

Whether you’re a freelance writer, designer, or web developer, a portfolio of your work speaks volumes to potential clients. Strong copy and testimonials can help sell your services, but portfolios feature your work in action, helping your clients envision your skills working for them. Portfolios also save you precious time by weeding out bad-fit clients before they book an initial call.

Should you include all your work in your portfolio? No. The work in your portfolio should be your very best and show diversity in your skills and clientele.

Common ways of showcasing your portfolio are Dropbox, Google Drive, or links on your website. Here are some third-party portfolio sites you can also leverage to feature your work:

  • PortfolioBox — for designers, photographers, artists, and more
  • CarbonMade — for illustrators, animators, architects, and more

Establishing Your Freelance Business

So, you’ve got a brand and a book of work to show potential clients. What else do you need to legitimize your business? Keep reading to learn more about establishing your business and setting yourself up for success.

Registering Your Business

Freelancers have some flexibility around the legal and financial structure of their business. Some freelancers remain sole proprietors and opt to receive 1099s and work from a personal bank account. Others register their business as an LLC to open a bank account and further protect their assets.

The decision is completely up to you. The only difference is that registering your business will likely cost you a fee. This article by UpWork dives into the specifics of how and why to register your freelance business as a Limited Liability Company (LLC).

You’re set up online, now where are you going to set up to work? Your physical workspace can massively impact your productivity, focus, and motivation, so you should keep this top-of-mind when considering your jump to freelancing.

Many freelancers choose to work out of their homes, whether for convenience, cost, or to be closer to family. A home office is ideal for work-life balance, but the dinner table, bed, and couch are also options. This article from Contently dives into how to create a home office that works.

If it’s not realistic for you to work at home, don’t fret. Today’s working environments are fortunately much more conducive to remote and freelance workers. Between coworking spaces, coffee shops, and public libraries, freelancers of all kinds can find makeshift workplaces outside the house, even if just for the day.

If you’re interested in co-working space, WeWork is a very popular choice for remote workers and freelance workers alike. Many cities have local co-working spaces that allow you to leverage shared desks, studios, and kitchens as well as network with other creatives and potential clients. If you don’t have the budget for co-working space, Google your nearest coffee shop, cafe, or university library. Whatever space you choose, ensure it’s free of distractions and provides favorable work conditions.

You’ve established the foundation of your business in the form of a website, portfolio, and workspace. Now this section will equip you to build the bones of your business — setting rates and getting work. This is perhaps the most important section in this guide and will provide insight into ensuring you become a successful and impactful freelancer in your chosen field.

The process of setting rates and determining fees is perhaps the hardest part of freelancing. Not only can it be awkward to talk about money, but setting rates for your services is essentially putting a dollar sign on your forehead. What are you worth? What if your clients don’t agree?

Setting and negotiating rates can feel very personal, but the key to discussing money comfortably is to take feelings and opinions out of it. Instead, use an economic approach to determine your rates, similar to how a business owner might price their products. Do you think they feel…