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Become a Successful Freelancer

Did you know that 36% of the American workforce is made up of freelancers? Or that freelancers contribute $1.4 trillion to the U.S. economy?

As crazy as these numbers sound, they’re also reassuring—especially if you’ve been dreaming about leaving your day job to become a freelancer and start your own business. In short, the dream is real, and many others have done it before you.

So the good news is that you can start freelancing, like, today. The bad news? Your fears about leaving your day job are very real.

Not only will you be leaving the security of a steady paycheck, but you’ll also be letting go of perks like health insurance (for you and your family, if you have one), paid leave, vacation time, and more. You’ll also be responsible for every single aspect of your business, from marketing and client communications to accounting and admin.

So yeah, scary. Can it be done? Absolutely.

After all, freelancers like Joanna WiebeRyan Robinson, and Melyssa Griffin have all done it—and gone on to build massively successful businesses. But here’s the thing: Leaving your day job to become a freelancer full-time is not easy or fast. And we wouldn’t recommend quitting your day job just yet.

Joanna didn’t leave her job at Intuit without a plan. She knew she was going to start CopyHackers and had laid down the foundation of a launch before she quit.

Ryan kept working his day job until he’d built his content marketing business to six figures!

And as miserable as Melissa was in her teaching job in Japan, she didn’t quit until she was earning enough income as a web designer to know she could make it work.

So as much as you may hate your job or want to jump right into the exciting and exhilarating world of freelancing, there’s a right way to make the switch. So take a deep breath, settle in, take some notes. Or better yet, bookmark this page, because we’re going to walk you through how to become a freelancer online—from transitioning from your day job to freelancing full time.

Ready? Let’s go!

The 3 Things You Need to Do Before You Start Freelancing

Before we get into the nitty-gritty of moving from full-time employee to full-time freelancer, there are three things you need to figure out to make sure freelancing is the right path for you.

1. Lock in Your ‘WHY’

Why do you want to become a freelancer? While there could be many reasons you find freelancing attractive, what’s that one reason that’s compelling you to take the plunge now?

Is it working on projects that excite you so you don’t have to slave away on projects that don’t?

Is it the freedom to set your own hours so you don’t have to miss another recital at your daughter’s school?

Or is it getting away from micromanaging bosses?

Your “why” needs to be your north star. It’s the thing that won’t let you quit when things get tough (and I assure you, they will).

For example, as a freelancer myself, my big “why” is building a life that gives me the freedom to call my own shots, in every aspect of my life.

Every time things get hard or I get a job offer with nice pay and excellent perks, I think of the things I’d be giving up if I took a day job. I think about being unable to take the summer off to travel and spend time with my family. I think about the personal projects I’d no longer have the time for and the big plans I have for my business. Most of all, I think about the freedom I’d be giving up if I accepted a day job.

In my 10 years of freelancing, every time I’ve been tempted to accept a day job, either by a great offer or desperate times, the answer has always come back no.

When you’re struggling to find clients, when a client still hasn’t paid and you have bills to pay, when it feels like everything is falling apart, your “why” will stop you from quitting and going back to your day job. It’ll force you to keep going until things work out.

So lock in your “why” before taking the plunge into becoming a freelancer full time.

2. Give Yourself a Deadline

Like it or not, human beings are natural procrastinators. And as pumped as you feel about freelancing, you aren’t any different.

Right now, you’re reading as much as you can about how to be a freelancer. You’re making notes and figuring things out. But you probably haven’t made any hard decisions yet. Plans only work when you act on them. So give yourself a deadline.

Actually, you need to give yourself a bunch of them. Decide specific timelines for:

Figuring Out Your Niche

What are you good at? What do you do really well in your day job?

If money and responsibility weren’t a consideration, what kind of work would you want to do? Would you write all day long, go on photo walks, or sketch whatever catches your eye?

When it comes to making this decision, it usually comes down to three things:

  • What are you good at? Think skills: multi-tasking, organizing, writing, drawing, etc.
  • Will someone pay you for it? If there are already successful freelancers in this niche, then you have your answer. If not, this is where market research comes in handy.
  • What do you enjoy doing? It could be a hobby or work-related. Something that you will happily do all day long.

The answer usually lies in the middle of these three questions. If you need more help deciding what services you should sell, we have more information in this guide.

For Cherry Thomas, it was photography.

Even though Cherry went to school to learn photography, she ended up getting a job in a financial firm where her career flourished.

But even though her career was going great, she knew photography was still her one true calling. So, while she handled a multibillion-dollar portfolio during the day, she launched By Cherry Photography and freelanced on weekends, vacations, and whenever she could take time off.

In a nutshell, I took the unsexy route: I kept my day job until I knew I could make the side hustle work. Also, it was important because the day job paid for my side hustle. Photography equipment is not cheap!

If you still need ideas, think about what help your friends and family come to you for. Do they ask for your help on budgeting, proofreading their documents, or dealing with tough situations?

And if you don’t enjoy doing any of the things people come to you for help with, find the answer to this seemingly simple question: What do you love helping people with?

When Lynne Somerman decided to go freelance, she thought about what she loved and who she loved helping the most. The answer came almost instantly to her because she realized she was already doing it.

I started largely because I love doing what I do (financial coaching) and it started because friends and friends of friends asked me for help when they heard I’d managed to make some big changes in my own life. I realized that I could potentially make a business out of it, especially if I helped business owners understand their finances, so I added bookkeeping to my coaching as well and started marketing.

I was also in a job that I knew wasn’t a great fit for me but wasn’t so poor a fit that I’d leave unless I found something that was a great fit. So, I decided to start my financial coaching business, The Wiser Miser, while I worked full time. Took me 18 months to build my business enough to quit my day job.

Finding Your First Client

Are you really a freelancer until you work with clients? It’s easy to get lost in the research, planning, and setting-up phase of your freelance business. If you’re not careful, another year will have passed and you’ll still be without a single client.

Giving yourself a deadline to land a client makes it real. It will push you to go out there and market yourself. We’ll discuss getting your first client a little later in this article.

Quitting Your Day Job

Quitting your day job is not an easy thing to pull the trigger on. You’ll be throwing away your security blanket, and that is a scary thing to do.

But the ultimate goal of starting a freelance business on the side is to quit your day job and start freelancing full time. If you aren’t deliberate with your planning and timeline, you’ll never be ready to quit your day job.

And no, we don’t suggest you quit your day job and then start freelancing. Seriously, don’t do that. While it’s true that many freelancers started after they were laid off, every single one of them would have preferred not to face that situation.

While there’s no specific timeline to quitting your day job, some freelancers have transitioned in as few as three months. For others, it takes a year. It all depends on how well you plan the transition. We will discuss this transition in more detail from here on, which will give you a better idea of how to set this deadline.

But no matter what happens, don’t quit your job until you…

3. Do the Math

While you don’t have to wait until your freelancing income matches (or surpasses) your day job income, you do need to figure out some money-related stuff.

Things like:

How much money do you need to survive/live comfortably/thrive?

Those are three different states of freelancing, so you should come up with three sets of numbers.

1. To survive: The amount you need to survive includes money for rent, food, health insurance, utility bills, school, and installments of any debt/loans that you may have to pay. Basically, all the necessities of your life. This is the amount that you absolutely must make before leaving your day job.

2. To live comfortably: This includes everything you need to survive, plus things like entertainment, a car, food other than Ramen noodles, etc.

3. To thrive: What does the top of your game look like? When you think of a lavish lifestyle, how do you envision yourself living? Is it having enough money to take a vacation and travel? To send your kids to summer camp? To buy/renovate a house?

List your expenses for each set of numbers. Not only will doing so tell you how much you need to make, it will also make it immediately clear to you when you’ve moved from surviving as a freelancer to living comfortably, and finally, to thriving.

It’s your decision as to how much you want to earn before you transition over. We recommend covering your basic needs first and also having some money in savings.

How many months of savings should you have before you go full-time freelance?

Once you have crunched the numbers for the first question, it’s time to decide how many months of savings you want before you quit. Ideally, it should be three to six months. This will give you the buffer you need to make decisions that pay off for your freelance business in the long run, without having to scramble for short-term gains. You also won’t have to worry about finding clients or matching your full-time income right from the first month.

How will you replace your full-time benefits like health insurance?

Before you quit, explore your insurance options. One of the biggest benefits of a day job is having health insurance for yourself and your family. Unfortunately for freelancers, the individual costs go up and there aren’t many options to choose from.

In the U.S., depending on the state you live in, there are multiple coverage options under the Affordable Care Act insurance exchanges. Also, there are sites like Freelancers Union that make things easier by handpicking health insurance plans for freelancers. Not sure what kind of insurance you need? They also have a handy quiz to find the benefits and insurance plans you need.

What will your business expenses be?

Every business has some expenses—even those run on nothing but a laptop. Once you start freelancing, your internet connection, laptop, smartphone, and any business services and apps you pay for are counted as your expenses. If you work from a dedicated home office, you can also count a portion of your housing and utilities costs as business expenses.

Pull up a list of expenses you already have and see which ones are necessary for any freelancing you do. They’re now your business expenses and will continue to be after you leave your day job.

As your business grows, you’ll likely start investing in more software and services. You’ll find a lot more info on business tools and services that your freelance business might need later in this guide. For now, while you are transitioning and still at your day job, keep it lean, and keep a running tab of any purchases you make or expenses you incur for your freelance business.

Knowing how much you need to make, save, and invest is crucial to starting your freelance business. If you don’t have the answers to the above questions, you could end up making costly miscalculations and missteps.

Doing the math allowed Ryan Robinson to become a freelancer and hit the six-figure mark in just a year, working with clients like LinkedIn, Zendesk, Intuit Quickbooks, and more.

It took me almost a year to get to the six-figure mark with my freelance side business, and it wasn’t ever easy. I remember charging $250 for my first paid blog post with a client and doing the math—it looked like I’d never get to the point where I could freelance full time for myself.

So I took the fact that my freelance work was a side project as a luxury that gave me the room to experiment… I didn’t NEED the income from my freelance clients to survive, so I began doubling my prices per article, working on my selling skills and seeing how I could tweak my offering to offer more value that’d be of interest to my dream clients.

Your 3-Step Guide to Becoming a Freelancer While Working a Day Job

Once you’ve locked in your “why,” given yourself deadlines, and done the math, it’s time to finally dive deep into the nitty-gritty of starting a freelance business while working a day job.

Just a word of caution before we start…

Don’t try to do everything at the same time or you’ll end up overwhelming yourself. So many freelancing dreams die because aspiring freelancers make the mistake of taking on too much.

In the beginning, it’ll be slow going. Keep reminding yourself that you have limited time to work on your business while you still have your job. So instead of doing a whole bunch of things at the same time and getting overwhelmed and exhausted, follow the plan below and take it step by step.

Step 1: Research

If there’s one thing we emphasize at Foundr, it’s the importance of research. Imagine freelancing with a day job—sacrificing family time, working nights and weekends, and investing money in your new business—only to find out a few months later that your idea isn’t profitable.

We get it. Research isn’t sexy. You want to start working on your freelance business right now!

But if you don’t do the research first, you won’t be able to make the right decisions.

When it comes to research, freelancers often make the mistake of focusing too much on figuring out whether freelancing is a good option in the first place. At this stage, you’ve already decided that it is. What you need to find out now is whether your specific freelance business idea is profitable or not.

Justin Blackman realized the importance of research the first time he tried – and failed – to freelance full time.

The first time I tried, I failed hard. I only made $600 over three months, because offers were a mess, my goals were unclear, and I didn’t know how to acquire customers. I didn’t understand what it meant to run a business.

It wasn’t long before Justin went back to working 9-to-5. But he still thought about becoming a freelancer and was determined to try again. He researched, planned, and gradually built his copywriting business, Pretty Fly Copy, before he handed in his resignation.

Build that knowledge first. Join groups. Get training. Know what licenses, software, and level of income you need to make it work—and be specific with your business. It’s a lot easier to succeed when you have a plan.

The research phase is the hypothetical phase. This is where you dream big and research the heck out of every aspect of your freelance business.

Here’s a list of questions you need to research to figure out whether your business idea is any good.

Is there a market?

If you can’t find clients, your freelance business will never succeed. It’s why becoming a freelancer while you’re working a day job is so ideal. There’s minimal risk and you don’t have to worry about paying the bills while you feel out your target market.

One of the easiest ways to conduct market research is by talking to the people and businesses in your target market.

When contacting businesses you’d like to work with, ask them if they work with freelancers or whether they outsource your services to freelancers. Why or why not? To stand out, ask them about their problems and frustrations in the past when working with freelancers, or dealing with the type of work that you do.

Here is a great resource for figuring out if there is a market for your services.

Who are the notable freelancers in your field?

This one’s easy. It’s time to stalk the competition.

Look up freelancers who are already working in your niche. Research them and their businesses. How did they get started? What advantages did they have? What kinds of clients are they working with? Find out as much about their businesses as you can.

You don’t have to be adversarial with your competitors. The freelancing community is extremely supportive. Take the time to build relationships with your peers and reach out to ask for advice or help. If you’re in the same city, offer to take them out to lunch or coffee.

When I first started out as a freelance writer in 2009, my go-to resource for advice was a blog called Men with Pens. The copywriter behind the blog, James Chartrand, seemed genuine and approachable. So when I needed freelancing advice, I reached out to her via email. Not only did she respond every time, but her advice also got me results.

Back in the day, Men with Pens was the copywriting business I wanted my own to grow up to be like. Over the years, I continued to learn from her and when she launched her copywriting course Damn Fine Words, I was one of the first to sign up.

Important: Don’t get discouraged by another freelancer’s success. Remember, you’re just starting out, and they’ve probably been at it for years. Even seemingly overnight successes have years of hard work behind them. Chances are, they had someone help them out once, and will be more than happy to pay it forward.

But here’s the thing: Talking to prospective clients and other freelancers is just one way to conduct market research. You can also use tools like Google Keywords and Google Trends. Read more here on how to use these tools to validate your freelance business idea.

Step 2: Planning Your Freelance Business

Now that you’ve validated your idea, it’s time to take all of that research and turn it into your business plan. And while you can go crazy making all kinds of elaborate plans, I recommend focusing on these five things.

Pick a Specialty

At this point, you’ve probably developed a pretty good idea of what you want to do. Writer, photographer, designer, financial coach—the possibilities are endless, and depend entirely on the market, plus your skills and interests.

Now all you need to do is pick a specialty, either by type of service or by industry. This is not as hard as you might think, but it’s something a lot of freelancers overlook or avoid.

This is important, because choosing a speciality helps you stand out. Let’s say a client is looking for a nutritionist for their 12-year-old. They run a search, ask for a few recommendations, and narrow it down to four nutritionists that look promising. But they still only need to pick one.

Who do you think they’ll choose? A nutritionist who works with anyone or one who specializes in working with pre-teens? As a parent, the client would want someone who understands what their child needs, knows how to deal with children, and has experience helping other children of the same age.

Generalist freelancers are a dime a dozen, and will always have a harder time getting work. As a freelancer with a speciality, you might not be the right freelancer for 99% of the potential clients out there, but that 1% that you’re a perfect fit for will make 100% of your clientele. When they need to hire someone with your speciality, they’ll hire you because you’re exactly who they need. They’ll pay premium rates and trust your expertise.

Picking a specialty is a two-step process.

Step 1: Choose the kind of work you want to do as a freelancer.

You’re probably seeing a theme here. Because you’re crafting your very own, one-person business, you’ve got to let your preferences shape your decisions, at least to some extent. After all, you’re the one who has to do the work!

When I first started out as a freelance writer, I took on any and all work that came my way. Product descriptions, website copy, bios, social media posts, about pages, articles…

But I disliked writing almost all of them. It wasn’t until I focused on the kind of writing I enjoyed that the answer came to me. I loved blogging. I was happiest working with clients who needed regular blog posts and even writing them for my own blog.

So I became a freelance blogger.

Think about the different types of specialities that fall under the general blanket of your chosen niche, and move on to the next step. Note that you may need to take on a few jobs in a few disciplines first to find out what you like best. So don’t freak out if you don’t have this nailed down from the very start, or if you decide to change it at some point.

Step 2: Decide the kind of clients you want to work with.

Think about the kind of businesses you want to work with. Is there a specific industry you know a lot about?

Maybe there’s a certain type of entrepreneur that you work well with (startup founders, online business owners, female entrepreneurs). Or maybe you’re partial to a specific industry (health, financial, ecommerce, B2B).

If you aren’t sure, make a list of the ones you find interesting and go from there.

The good news is, your choice isn’t set in stone. If you choose one type of clients and realize they aren’t your ideal, you can always pick another. That’s the beauty of running your freelance business. You have the freedom, not just to make your own decisions, but also to change your mind.

But do you really need to pick a specialty?

In my experience, it’s the way to go.

Generalists have a harder time growing their businesses, even though most of them will argue that there’s more work this way. There will be a broader audience, but the clients who want generalist writers are also more interested in cheaper services. Specialists earn more money and attract higher-quality clients.

For the longest time I was just a freelance blogger. The only criteria I had for clients was that they paid. I always had plenty of work so I never gave specializing much thought. But then I hit a wall where I couldn’t get more than $350 for a 1200-word post.

It wasn’t until I met Josh Garofalo of Sway Copy that a light turned on for me. Josh is a SaaS copywriter whose clients include HubSpot, AWeber, Snappa, and InsightSquared, to name a few.

My origin story is different than that of most freelancers. I’ve never struggled—no slow times, no low-paying work for abusive clients, no hours wasted creating content no one cares about, no slimy cold emails—none of this.


Because I chose a niche that I had experience, education, contacts, and an interest in. From day one, I positioned myself as a SaaS copywriter and consultant. While most freelancers drown in a sea of sameness trying to be all things to all clients, I look like the perfect choice for less than 1% of businesses.

The result?

I replaced my full-time income within a few months of launching my site. My ideal client seeks me out and jumps at the opportunity to pay a premium to work with me. They know they’re getting someone who understands their product, market, and customer better than any generalist freelancer ever will. They know I’ve helped dozens of companies like theirs get more leads and sales.

This is why I always tell struggling freelancers to choose and own a niche. It makes every bit of this business so much easier.

Of all the freelancers I’ve talked to over the years, Josh is one of the very few who planned his transition from day job to freelance down to the last detail, and his success proves that being deliberate and following a plan works.

Create Your Core Offering

Since you’re still working a day job, starting a full-service freelance business may not be feasible. Instead, create one core offering and package it into a replicable product.

Your core offering is what you’ll be most known for. It’s your most prominent service that you’ll go on to build your business around.

Having a core offering makes it easier to create off-the-shelf packages of your services. For example, if your specialty as a freelance writer is blogging, then you can create blogging packages that your clients can buy. Doing so will save you time and get money in your hands faster. You won’t have to email back and forth, ironing out the details, and clients will know exactly how much the work costs and be able to buy it instantly.


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