Sole Proprietor, LLC, or S-Corp: How to Set Your Freelance Business Up for Success

Sole Proprietor, LLC, or S-Corp: How to Set Your Freelance Business Up for Success

If you’re a new-ish freelancer without a degree in accounting, trying to decode the legalese online about business entities can feel like translating an ancient manuscript. The acronyms, the liability language, the tax implications… It’s a lot. But there comes a time in every entrepreneur’s journey when they’re faced with the big question: Sole Proprietorship, Single Member LLC, or S-Corp?

We’re here to help you figure out how to structure your business for your greatest ease and benefit. So in this article, we’ll try to lay it all out in human terms, so you get a better sense of what these business entities are and how to decide which one is right for you. (Note: We highly encourage you to talk to a CPA or tax professional about how to structure your business—this is just a starter guide to help you understand each option.)

Sole Proprietorship, Single Member LLC, or S-Corp

Sole Proprietorship

What It Is: A Sole Proprietorship is a one-person business that can use an assumed business name (AKA a “Doing Business As” or “DBA” name) without forming any formal business entity.

The Pros: It’s easy, plain, and simple. You don’t need to register your business with the state or file separate taxes for your business. You just file all of your work income on your personal tax return.

The Cons: You have no protection from legal action, so if someone decides to sue you, they could come after your personal assets and potentially ruin you financially. You also need to provide your personal social security number as your tax ID on documents, so your SSN will get passed around to your clients via paperwork. And, you’ll have to pay the 15.3% FICA tax (AKA “self-employment tax”) on all of your income.

Who It’s Best For: A Sole Proprietorship is good for you if you’re just starting out with a side hustle and you’re not worried about the potential legal ramifications.

Single Member LLC

What It Is: A Single Member LLC is exactly what it sounds like—a limited liability company that is owned and operated by one person. This is by far the most common way to set up a freelance business.

The Pros: There is legal separation between you and your business, so if a client decides to come after you, they can’t touch your personal assets. It’s also relatively inexpensive to set up. Costs vary state to state, but you’re typically looking at $100-$200 to set up an LLC. And when you file your taxes, it’s streamlined—everything is done through your personal tax return, so you don’t have to file a separate return for the business.

The Cons: You will pay the 15.3% self-employment tax in addition to your personal income taxes. A single member LLC is considered a “pass-through,” meaning all profits and losses pass directly from the business to you, the individual owner. So, you may end up paying more in taxes than a corporation would.

Who It’s Best For: A Single Member LLC is good for you if you’re a serious freelancer and you want the protection of legal separation between you and your business—but you don’t want the headache of filing additional IRS paperwork each year (see below).

Single Member LLC Taxed as S Corporation

What It Is: An S Corporation (or “S Corp”) isn’t actually a legal business structure—it’s a tax election that determines how your business is taxed at the federal and state level. So you could register your business as a Single Member LLC but elect to file your taxes as an S Corp (and many entrepreneurs do).

The Pros: With a Single Member LLC electing to file as an S Corp, you get all the benefits of a Single Member LLC, plus a break on taxes. You actually pay yourself a wage as the business owner, so you get to skip that aforementioned 15.3% self-employment tax that comes with the other two options. Instead, you split the 15.3% with your business, paying 7.65% in personal payroll taxes and 7.65% in business payroll taxes (which you can write off as a tax deduction).

The Cons: S Corps require separate filings for the business and for you, which can make tax season a bit more complicated. You’ll also be required to pay payroll taxes on a quarterly basis, so you can’t skip out on filing four times a year, if that’s been a habit. (Hey, it’s not the worst habit to cut.) And although you get a break on the self-employment tax, you do have to pay the FUTA tax (or unemployment tax) now, which is 6.0% of the first $7,000 you paid to each employee (you) in wages throughout the year. And, of course, you’ll still pay personal income taxes on the salary you make, as you would with any designation.

Who It’s Best For: Electing to file as an S Corp is a good move for you if your business is making profits in the six figures and you’re willing to file extra paperwork each year in order to save on taxes.

Whether you’re just starting out as a new freelancer or you’re finally taking steps to legitimize your freelance business, we applaud you. This stuff ain’t easy or simple, but it’s well worth it to learn the lingo and make the right choices based on your situation. The more comfortable you get with the legal side of your business, the more confident you’ll feel when tax season rolls around—and really throughout the whole year.

Why We’re Building Harlow Using Freelancers

Why We’re Building Harlow Using Freelancers

Growing a business in 2022 looks a whole lot different than it did just a few years ago . After two years of a global pandemic, the remote work landscape has transformed. Businesses big and small are adjusting their staffing models to accommodate the new normal. And simultaneously, more and more workers are leaving their jobs to pursue a freelance lifestyle, with 28% of Americans now freelancing full-time—an increase of 17% from 2014.

28% of Americans are now freelancing full-time.

COVID was, unquestionably, a huge catalyst for this shift. Nothing says Quit! quite like cabin fever and existential dread. And in 2021, we experienced a “Great Resignation,” with record-high numbers of Americans leaving their jobs. But lockdown is not the only reason our freelance numbers are rising in the U.S. If anything, mass burnout just accelerated a trend that was developing long before COVID came to town.

The gig economy has been growing for years, and it’s thanks in part to the rise in remote work. As technology has evolved to better support distributed workforces, more companies have gone remote, with employees scattering the country and even the globe. And as companies have adapted, workers have gotten a taste of the freedom and flexibility that a remote lifestyle offers. (Spoiler: It’s great.)

Today, over half of non-freelancers are considering freelance work in the future. For workers, the growth in remote work raises big questions: Who do you want to work for—a company or yourself? Does the independence of freelancing outweigh the stability and benefits of a full-time job? And how much would your quality of life improve if you were to set off on your own and work on your terms?

All of these trends were taken into account when we started to ideate and build Harlow – a tool specifically designed for freelancers to manage their business.

While we know eventually Harlow will grow through a mixture of full-time employees and freelancers, we decided early on that we would lean on freelancers to grow and build our business as much as we possibly can (especially in the beginning.)

Here’s why.

Here's why we're building Harlow using freelancers.

#1: Freelancers know freelancing.

Our product is built for freelancers. Hiring them just made sense. We’re passionate about staying close to our customers, and having knowledgeable freelancers on our team helps us tune into the challenges our target customers are facing, so we can better solve their problems. You can trust you’re on the right track when the people building your software, writing your copy, and designing your website are the same people you’re marketing to.

#2: Freelancers help us stay competitive.

They work with other businesses that are innovating and growing in their respective industries. They’re exposed to a myriad of problems and solutions each day, which gives them a wide perspective of what works and what doesn’t. This gives us a major competitive advantage. We know that the folks helping us grow are continually growing themselves.

#3: Freelancers help us move quickly.

We’re typically working with experts in their fields. They’re ready to rock sooner than an in-house hire would be, which means we can build and innovate more quickly.

As two former freelancers turned co-founders, Samantha and I are big fans by default, so it’s extremely gratifying for us to work with other freelancers who we can learn from each day. We built Harlow because we deeply believe that the future of work can and should be freer. We left our full-time jobs years ago seeking more balance, stimulation, and autonomy, and today we’re building a business from the ground up with those values front and center.

We’ve learned that you can prioritize your well-being while also creating a thriving business. Professional success doesn’t have to come at the expense of your mental health or your family.

It’s our vision to help other freelancers claim the lives they want by building businesses that sustain them and fulfill them, rather than depleting them.

When and How to Raise Your Freelance Rates

When and How to Raise Your Freelance Rates

Any seasoned freelancer will tell you to raise your rates regularly. As your expertise grows and your offerings evolve, so should your rate. But when do you do it? And how? Below, we’ll walk through the major moments when you should raise your freelance rates, then share some pro tips on how to do it confidently.

When to Raise Your Rates

#1: When You Add New Skills or Offerings (time to repackage!)

Maybe you took a few development classes and you can now not only design beautiful websites, but you can also build them. Or maybe you’ve added content strategy services to your offerings, in addition to writing monthly blog posts for your clients. Whenever you uplevel your current skill set or add new offerings to your business model, it’s time to upsell your current clients and raise your rates for new clients.

This is also the perfect time to repackage your services. Whenever you repackage your services into new offerings, you should consider adjusting your pricing model too. One of the main goals of repackaging your services is to be able to add and sell additional value. Maybe that means up-leveling from hourly rates to project-based, or charging partial payment up-front. The key is to lean into the value of the new package.

#2: When Your Life Gets More Expensive

If you’ve kept your rates unchanged for years but your cost of living has increased, it’s time to raise your rates accordingly. Inflation is a totally valid reason to charge more. Just this past year alone, the inflation rate shot up to 7%, the highest it’s risen in a year since 1982. That adds up for businesses and individuals. As you pay more to live, you should earn more too.

#3: When You Gain More Experience

It may seem obvious, but many freelancers don’t consider the basic passage of time as reason enough to raise their rates. But the longer you work, the more experience you gain. It’s a no-brainer that your rates should increase gradually along with your tenure. One of the most effective ways to raise your rates is to schedule it at regular intervals—and then stick to that schedule. You can let your clients know in advance that you raise your rates every year or so, and write it into your contract so they agree to it up-front.

#4: When You Don’t Get Pushback from Clients

If no one ever questions your rates, it’s too low. I know this one is a little controversial, but remember, companies are saving a ton of money by using a freelancer—they don’t have the overhead of computers, healthcare, taxes, etc. So if all of your new clients blindly accept your rates, you might be undercharging based on the market and the value you provide. Genuinely consider this the next time you’re drafting a proposal or planning for an increase. A little pushback is actually a good sign that you’re charging (closer to) what you deserve.

How to Raise Your Freelance Rates

Many freelancers waffle on raising their rates out of fear of losing their clients or turning away good opportunities. But a little preparation goes a long way. Here are three simple tips for raising your rates without a hitch.

#1: Communicate it to your clients clearly.

Spell out the reasons why your rate is increasing in a way that emphasizes the value you provide to your clients. This is the moment to plug your services, your growing experience, and your relationship with the client. If you need some inspiration, freelance writer Kaitlyn Arford created some amazing email templates for negotiating higher rates. Choose the one that makes sense for your situation and modify it accordingly.

#2: Give your clients plenty of notice.

You’re more likely to get a positive reply from your clients if you let them know that your rates will be increasing well in advance. Two months heads’ up is ideal. This gives them time to rethink their budget if needed and make any necessary changes in order to accommodate.

#3: Add rate increases to your contracts.

For future clients, consider baking a regular rate increase into your contract. You can effectively bypass any client conflict this way, because your clients agree to it upfront. Just be sure to name the intervals your rate will increase at (i.e. quarterly, bi-yearly, annually, etc.) and the amount your rates will increase by (i.e. percentage or flat rate).

Go get paid more, confidently.

As former freelancers ourselves, we know the anxiety of a rate increase all too well. But it’s like a rite of passage for entrepreneurship. It can take time and practice to get comfortable asking for more. So make a practice of it. Keep your email templates on hand. Create reminders for yourself. Pretend you’re paying someone else. Do whatever you need to do to stick to it. We believe in you.

Video: 4 Tips for New Freelancers

Video: 4 Tips for New Freelancers

Making the leap from a full-time job to freelancing can be intimidating. Marketing yourself?! Naming your rate?! It sounds like a LOT when you’re leaving the security of a full-time job. But if you’re passionate about working for yourself, I’m here to tell you: It’s very doable. And it’s absolutely worth the effort.

Planning ahead and putting some careful thought into your offerings, your lifestyle, and your needs can make a world of difference, setting you up for success from the start. Here are four tips to consider as you begin your freelance journey.



Hi! This is Andrea from Harlow and today I want to talk about my four tips if you’re just getting started freelancing.

Making the leap from a full-time job to freelancing can be intimidating. I’ve done this four times in my career I know all the unwanted feelings that can pop up. Am I going to be good enough? Will I be able to pay my bills? Can I find clients? Freelancing is definitely hard & it’s not for everybody but if you’re passionate about getting started freelancing I’m here to tell you it’s very doable.

My first tip for you as you’re just getting started is to define your offering and find your niche. I know a lot of freelancers don’t like this advice but I will say it has served me very well in my career and I highly recommend going through this exercise. Really think about the services that you offer and what makes them unique and your offering special and what differentiates you.

Early on you might actually want to take a bunch of different types of projects to figure out what it is that you’re good at and what it is that you actually like doing but it’s really hard to be everything to everybody so getting a little bit more specific about your offering will help you find the right projects. For example, rather than going out and saying, “I’m a content writer & I’ll write any type of content for you.” Maybe you say, “I am a content writer who specializes in long-form content with a heavy research component.” That specificity is going to actually help you find those projects that are a better fit.

And as you’re thinking about niching down it doesn’t necessarily have to be a functional niche either. For example, I’m a demand gen marketer and so I don’t actually need to specify that I’m only going to focus in SEO or SEM, in fact quite the opposite. My business partner and I stayed generalists & we offered a variety of demand gen services but our niche was early-stage technology companies that were just bringing on their first head of marketing and they were looking for help for three to six months. Shorter project-based work was a great niche for us and it really helped us to find that ideal client.

That brings me to my next point which is to find your people. So, I don’t mean just your target audience here but also your community which I have found has been really really important. Freelancing can be lonely and it can be really isolating and it’s important to have people around you that you can ask for advice and help when you need it but also people around to help you celebrate your wins. There are really robust freelance communities on twitter, facebook and reddit and I highly recommend engaging there and just starting to build that community of people you can learn from.

I also want to say that other freelancers are not your competition! I highly recommend you embrace the freelance community and really look at other freelancers as a source of help & information but also potential referrals. You know, these other freelancers deeply understand what it is that you do and there are a lot of them that have prospective contacts and clients reaching out to them and they might not have the capacity so that can be a great source of business for you. I would say if you’re ever in the position where you can’t take on clients it’s always a good move to try and refer out other freelancers that maybe could use the work as well.

My third tip is to figure out your pricing. This one is really hard and obviously, we don’t have all the time in the world here to dive into all of the nuances about this. Your pricing is going to change over time, as it should, but if you’re just getting started I recommend starting by doing some research. Figure out what is average in your industry based on your skillset and your level. Next, I would sit down and do some math – first of all, what is the target income that you need to meet in order to sustain your lifestyle? Realistically how many days of the year are you going to be able to work? And don’t forget holidays don’t forget vacations and don’t forget sick days. Even though you’re a freelancer you’re still gonna be sick, unfortunately. Don’t forget your kids’ spring break- things like that.

Be really be realistic about how many days of the year you’re actually going to be able to work and then think about how many hours of the day are actually billable. It is not possible for me personally to build eight hours a day. That is just way too much. Don’t forget you also have other aspects of your business that aren’t billable – invoicing your clients, putting together a statement of work, trying to market yourself, all of that. So again, be really realistic about how many hours the day you can actually spend on client work and then that will help you back into what an hourly rate needs to be.

Now, this isn’t to say that that has to be your hourly rate or that you should charge hourly but it gives you a baseline so then you can start to package your services and make sure that you’re hitting your minimum income threshold. I will say, as you’re thinking about your pricing whether it’s hourly, retainer-based or project-based don’t forget that it should also reflect everything that you bring to the table. So it’s not just the hours in the day it’s all of the years of experience that you have and your unique perspective – all of that stuff. Be sure to charge for that.

If you’re still unsure of what your rate should be there’s an awesome tool out there called it’s backed by actual humans you input your information give them a couple of days and they’ll come back with what a reasonable rate actually would be for your skillset.

So my last tip for you is to put it in writing. No matter what, make sure you have a contract in place. It can be so tempting when you land the first client – say it’s your friend or maybe it’s even your old employer – to just go ahead and do the work and get the money in your bank account. Do not do that. Make sure you have a contract in place. Anyone that’s been freelancing for a while will definitely tell you a story of getting burned by not having the right contract or contract terms in place.

You can find contracts online and I highly recommend consulting a lawyer if that’s available to you. Your contract should include the scope of work and what the exact deliverables are to ensure that you’re going to get paid and then what your payment terms are. With payment terms, indicate whether you’re going to be paid upfront for the work or perhaps you’re going to invoice afterward and the terms are maybe net 15 net 30. Also, be sure to include any clause if there is a penalty for not paying on time and I highly recommend including a termination clause as well so that if needed you can get out of this contract or your customer can get out. But again, I highly recommend that you make sure that you’ve got a contract in place.

So those are my four tips for you:

1. Define your offering find your niche
2. Find your people
3. Figure out your pricing
4. Do not forget that contract

Key Elements of a Great Freelancer Contract

Key Elements of a Great Freelancer Contract

You’ve landed a client! Please take a beat to celebrate your radness before reading on. Ready? Cool. Once festivities are complete, it’s time to talk about contracts: what they are, what they include, and how to create them. Below, we’ll answer all your essential questions about freelance contracts, so you can get to work ASAP.

It’s time to talk about contracts

What is a contract?

First, let’s clarify something: Contracts and proposals are not the same thing. Although they’re often used interchangeably, these two documents serve very different purposes. A freelance proposal acts as an extension of your pitch. It summarizes your action plan and outlines your pricing structure. It’s the step you take before sending over an official contract, and it gives potential clients the opportunity to ask questions and make changes.

A freelance contract is a legally binding agreement required to kick off a business relationship with a client. It will generally reiterate the statement of work included in the proposal, and include all the additional fine print that ensures you get paid. Contracts protect you from liability too, including terms and agreements around payment, confidentiality, intellectual property, and so on. It’s crucial because it removes ambiguity and prevents misunderstandings. Plus, it protects you in the event something bad happens.

Some freelancers do choose to combine their contracts and proposals, so if that works for you, go for it. We prefer to keep them separate, because sending the proposal first encourages a pause—you and your client can consider the scope of work and nail down the plan before proceeding to all the fine print. Plus, combining them can be a bit overwhelming.

Creating a Good Freelancer Contract

The number one rule of thumb: Be as specific as possible. Contracts are designed to protect you, but if you omit important details, they aren’t enforceable. So be thoughtful about the clauses and conditions you state. Once it’s signed by both parties and work commences, you’re on the hook for whatever you’ve promised in writing.

Here are the key elements of a good freelance contract:

  • Name the parties.
  • Include your scope of work (which is usually in the proposal).
  • Include price, payment terms, and penalties for late payment.
  • Name deadlines, especially if payment is tied to product milestones (e.g. “25% on December 10 after the first wireframe is delivered; 25% on January 5 when the landing page is live”).
  • Define copyright ownership: Who owns the IP?
  • Include a termination clause for both you and the client, stating how many days notice is required in order to end the contract.
    Include an indemnity clause.
  • Require a signature by both parties.

Your freelance contract won’t cover everything, so your client may ask you to sign a non-disclosure agreement (NDA), a non-compete, or a data protection agreement (DPA) as well. What you sign is always up to you. Just be sure to communicate clearly about what the expectations are. And read the fine print before signing! Unlike every other online contract we mindlessly agree to—you didn’t read your cell phone company’s contract either, did you?—this one is super important, and has very real legal implications. So pop on your reading glasses and get to it.

Have additional questions about how to create a freelance contract? Not sure where to start? It never hurts to contact a lawyer. We’re huge fans of Brittany Ratelle. A talented lawyer for creatives, Brittany can help get your business legally legit without all the confusion and painstaking Googling. Give her a shout if you’re in need of support.

If you’re a Harlow user, you can also use our contract template to make sure you’re covering your bases. You can sign up to use the product here.