Are You Determined to Be a Freelancer? Start Today.

There are so many articles about how to become a freelancer or how to start. It’s crazy. We read stories from people like Ryan Robinson who kept his day job until his freelancing earned six figures. SIX. FIGURES. Swoon. I’m not even close to six figures.

“I grew my freelance business to over six figures in revenue on the side before quitting my day job in 2016.” Ryan Robinson 

So that goal may be daunting. For me, I didn’t have a choice. I had to start freelancing. I also didn’t have a partner. I started freelancing full-time when I lost my dream job — as a widow.

I have mentored so many people in my 34+ years of working. I wish I had the courage to listen to myself as a thirty-something instead of doing it at 43 years old. With that said, you will be fulfilling every role of a business when you freelance.

The buck stops with you. Always. There is no one to dump on. You can only blame yourself. Barry from Sales doesn’t exist anymore. YOU are Barry from Sales. And you’re Karen from Client Services too.”

Warren Laine-Naida

Stop procrastinating by taking a dozen courses and buying every book there is. You don’t need it to start. The way you start is to start. 

I mean, you may need to educate yourself on marketing, best practices in business, hire an accountant, and all of that. If you do all that first, you’re never going to get going. You have to start.

How Do You Just Start?

The key to just starting is believing that you have marketable skills. What does this mean? It means you have a professional service that people will give you money for. I know what you’re thinking, “Wait, how do they give you money?” We will get to that. There are so many ways to collect money. Don’t worry about all of those details yet. Find the need. Fill it.

I’ll tell you how. Do you really want to know? It’s not glamorous. Here is the noholdsbarred, no-bullshit way I started freelancing. You ready?

How Did I Start Freelancing?

I started freelancing in the early 2000’s because I had some dental work (surprise to those who know me) and needed extra cash. 

Someone needed a website. Great. I built it. After two of those, I quit. Who wants to argue about orange when that’s the hex code they gave me? Whoosh. 

Someone needed me to tutor their kid in algebra. Great. How does $20/hour sound? Perfect, I’ll be there. Does Tuesday work? Bring cash. Drop off your kid. Done. I did that for ten years.

Someone needed help with their social media. Great. I’ll set it up and teach you how to do it. Three years later, I was still managing their accounts for free. Oh sorry, one person gave me a gift card to a restaurant. Lesson learned.

Those weren’t all ideal situations. But, they gave me experience and taught me lessons. When I started charging for social media (I needed more dental work), I charged $250 a month. I later figured out that was way too low. No worries. Adjust. Change. 

Why Continue Freelancing?

Usually, the reason to have a side hustle is financial need. Freelancing is a great way to make up those literal deficits. That’s reality. It’s not always a sexy story of an epiphany you have while picnicking on a hill overlooking the ocean with the love of your life. 

I had a full-time job as the Office Manager for a general contractor. Why freelance? Well, there are a couple of reasons. First, I needed money for (wait for it) dental work. Secondly, I realized (read: finally believed my peers) that I am intuitively good at marketing and should try to get a job in that field.

Great. I worked 16 hours a day — for six months — until I got hired full-time for a dream job at an advertising agency. Working those hours did not give me work-life balance. (Which is a privilege, by the way). It was hard. It weighed on my marriage. It kept me distant from friends. I was exhausted. But I knew my husband was getting older and I needed to work from home. Getting that job gave me time to be at home for the last six months of his life. That’s reality. Not sexy.

A little more than two years later, I began freelancing again? Why? That’s too long and sordid to detail. (I know I said there were no-holds-barred. But yeah. I got fired.) The point is that I found myself in a place where I a) needed to make money; b) wanted to control my destiny; c) continue being a remote worker.

Freelancing isn’t all about sitting on the beach and working for four hours a week. It’s as serious as you want to take it.

Okay. So, we covered, “just start.” Let’s go deeper.

Freelancer Step One — What’s Your Service?

Take out a pen and paper and write down services that you are good at. Freelancers are typically service providers. This can be anything from cleaning houses to dog walking, to building websites, to bookkeeping. 

What are your marketable skills? Write them down. No, seriously. Write them down.

Freelancer Step Two — What Service Do People Want?

Okay. This may require a bit of a think. Almost a come to Jesus kind of think. Maybe you need to do this with a best friend. What are your marketable skills right now? Who do you know — right now — that would hire you for one of those services? Reach out to them saying, “I was thinking of offering this service. What do you think? Would you pay $1,500 for a website?” Get their opinions. Write down what they say. 

I’m a big believer in taking notes in notebooks. Your brain works differently when you write notes than when you type. And for the love of God, don’t send the GenPop a Google Form. That looks like work to them. They won’t fill it out and if they do, they’ll be annoyed. You don’t want to annoy your potential customer base.

Freelancer Step Three — What Will People Pay? What Should I Charge as a Freelancer?

What should you charge as a freelancer? The answer is more than you think. When you first start, you’ll have to throw out pricing and see what sticks. Then you can go back and do some job costing and figure out how much you should charge. This includes covering your own sick days, vacation, and retirement. If you want the freedom of freelancing, then you have to be responsible like a business owner. Get out of the employee mindset.

Each customer will teach you something about yourself, your services, and how you want to do business. This is the process. You can’t really skip it too much.

Create a pricing sheet, even if it’s just a Google Sheet. A landing page on your website is better. Don’t worry about getting the price just right. It’s okay to change your prices. This is the beauty of a web page versus print. Print is forever. Websites are not.

Freelancer Step Four — How Will You Get Paid?

This one is easy nowadays. Freelancers can get paid with Zelle, PayPal, Venmo, checks, and yes, paper money still works. 

You can create an invoice in Google Docs with a template, keep your records in a Google Sheet, and boom. You’re in business with no money down. 

When you’re ready, Freshbooks is a great option since they price by the number of clients you have. I started with Google Sheets and have used Freshbooks since October of 2017. Since I started my LLC this year, I will be transitioning to Xero which, ironically, will cost me less. But hey. This is how you learn.

Freelancer Step Five — Market Your Freelancing Services

This could mean direct calls or texts telling your friends you now offer dog walking on the side. It also means creating a website, Twitter, and other social accounts, and then using them. You have to tell people you’re taking clients and keep telling them

If you already have a website, set up a landing page for your services and fees. Be upfront. This establishes boundaries with clients. Don’t worry about making mistakes. The more mistakes you make, the better you write your estimates. In construction, we write “good for 30 days” on our estimates for a reason. I adopted that quickly when I began freelancing.

Freelancer Step Six — Start a Budget

Why is starting a freelancing budget step six? Because you won’t know all of the SaaS tools you’ll use to market your writing, web development, or marketing skills. You may even be using these tools for marketing your dog walking, house cleaning, or lawn care. It costs money to be in business for yourself; even for a freelancer. 

Freelancer Step Seven — Block Your Time

This is especially important if you have a full-time job. You will need to figure out times when you will work. This is best done with time blocking. If you have a partner, you’ll need to have that conversation with them, too. Set boundaries early. Your freelancing time will come out of your leisure time and maybe even family time — at first — until you can make freelancing your full-time job.

Freelancer Step Eight — Tax Paperwork

For a while, my “freelancing” was a “hobby” according to my tax accountant. You’ll have to chat with yours. If you’re not a corporation or LLC, you may need to have a W-9 ready to give to clients. The IRS has the W-9 form online. Easy peasy. Save it as a pdf in a place you can have on-hand for when you’re asked to send it.

As of the time of this post, any company that pays you over $600 in a year is required to send you a 1099. Those are due to you by January 31 each year. Some will be late. It happens. You’ll need these for tax prep. Again, it’s important to chat with your tax accountant. And don’t opt-out of the self-employment tax; you need it for Social Security and Medicare.

I use H&R Block Small Business Tax Filing which starts at $85. A professional tax preparer reviews my forms before they’re sent to federal and state. I’m fine with that. You can always hire a CPA or do it yourself. It’s up to you.

I’m a huge believer in outsourcing. The things that distract you from your billable time are things that should be hired out. Yes, I can do my own taxes. I did before. This is worth spending money on. 

Freelancer Step Nine — Evaluate Your Client Work Each Quarter

It’s good to look back and reflect on the last three months. What worked? What didn’t work? This is when I realized I way under-charged for my social media services. I’m not going to lie; the first year was hard. I don’t write blog posts every year like some companies do, because nobody really cares and they’re super braggadocious like Christmas letters from people whose families are perfect. However, I did write about the first year. It will be hard. Very hard. If that intimidates you, you’re not ready to be a freelancer.

Freelancer Step Ten — Are YOU Really Ready To Be a Freelancer?

I mean it. Are you ready? Can you take the criticism? It will come. Can you step into the spotlight? Can you be yelled at by people for no legitimate reason? When you freelance you are the boss. And, more importantly, can you commit to doing the work on time every time. It’s not a job where no one cares if you miss deadlines. There is no probation. If your work is late or sloppy you will lose clients and — even worse — brand legitimacy.

“When it comes down to it, you have to believe in yourself, believe in your business, understand it might not pan out, and know you’re willing to stay the course to successfully start a freelance business.”


You have to want to be in business for yourself more than you want money. It will be a sacrifice. Your spouse will call it a “hobby.” Your friends will be mad that you don’t want to go out to the bars every night. 

Being a freelancer is ultimately about being who you are — who you really are — and who you want to become.

If you can endure those very real obstacles, you can start being a freelancer today. Well, maybe tomorrow because, honestly, this article is super long and now your kid is asking you for help on their school project. Okay. Tomorrow then. Start tomorrow.