Friday, 27 July 2018

The Ultimate Guide to Freelancing

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.

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.

Advantages

  • 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.

Disadvantages

  • 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 phoebephotography.com 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.

“[I chose] Squarespace. It's been so easy to update and customize as my business has changed and grown. I also suggest and use Squarespace for my small business clients when they're looking for a hosting platform.” — Cadence T., By: Cadence, San Francisco

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:

  • Contently — for writers, journalists, and content creators
  • PortfolioBox — for designers, photographers, artists, and more
  • CarbonMade — for illustrators, animators, architects, and more
  • Behance — for graphic designers, illustrators, UI/UX, and more
  • Journo Portfolio — for journalists and writers

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.

“[I registered my business as an LLC] immediately. I wanted to signal that I was serious about it. And it carried a sense of responsibility with ‘being official.’ I also hired an accountant right away. I didn't want to mess anything up.” — Chris C., Real Good Writing, Denver

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).

Setting Up Your Workspace

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.

“For non-chunky tasks (like emails, editing, and outlining), I work from my home office. However, I find the same four walls can get boring, and I get demotivated. That's why I head to my local coffee shop for meaty tasks (like writing).” — Elise D., United Kingdom

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.

Getting Freelance Work

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.

Setting Rates

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 bad when they quote their prices? No, and you shouldn’t either.

“[It’s all about] knowing your worth. It's so hard to see yourself as a commodity, but that's what freelancing is. You're selling your skills as a service. How do you put a price on that? In the beginning, this is truly a hard thing to grasp. But with experience and speaking to peers, you slowly start to figure that out.” — Karine B., The Letter K, Canada

Here are a few popular strategies freelancers use to set their rates. You can also use a combination of the three.

Cost-Plus Pricing

Cost-plus pricing is determining how much it’ll cost you to complete a project and tacking on 10-30% as profit. This pricing model is best for artists and freelancers who use physical material and know the cost of completing a project or service. For writers, designers, and developers, this model might be tough to calculate, unless you’re counting your time as the primary cost.

Market Rate Pricing

Market rate pricing involves taking a look at market averages and deciding your rates based on those around you. To calculate your prices based on market rates, take a look at your industry, location, and competitors with similar experience. (As a novice freelance designer, you can’t quite compare your rates to a designer with 10+ years’ experience, even if they live in the same area.)

Here’s a list of average rates per industry:

Value-Based Pricing

Another pricing approach is to base your rates on what you believe your work is worth. This means that your pricing will differ slightly depending on what client you’re working with and what kind of work you’re creating. For example, creating a commercial for a Fortune 500 company will hold a little more value than that for a local coffee shop, right? Right, so you’d likely charge more for the former. Now, that’s not to say one company has more value than the other; you’re just taking into consideration what they can afford and the overall impact of your project.

  • At what frequency should I charge? Some freelancers charge by the hour, where some charge per project (or per word for writers). This decision should be based on the type of work you’re doing and what you’re most comfortable with. Hourly fees ensure you’re paid for all of your time, where a fixed price guarantees you’ll make a specific amount. Also, being paid by the hour puts emphasis on the value of your time, whereas fixed pricing puts more emphasis on the value you’re delivering your client. If you don’t feel like tracking your hours (since clients will likely want to see a timesheet), you could set a fixed price based on how long you think a project might take you.
  • Should I publish my prices on my website? Again, this comes down to what you’re most comfortable with. Some freelancers opt to publish their prices to create a perception around their overall value. It also helps weed out bad-fit clients who can’t afford your services to begin with. Other freelancers withhold that information in order to get clients on the phone. Keeping your prices private also allows you to change prices when need-be.

“I publish [my rates]. It means that people can get an idea of what I charge before they contact me, which makes everyone a lot more comfortable with the pricing conversation at the end. My rates are based on surveys of my peers and what people at my level of experience charge.” — Angela R., Australia

Finding Jobs & Marketing Your Freelance Business

When you start your freelance career, the majority of your day-to-day will involve looking for jobs and marketing yourself. Until you establish your skills and services and become well-known by clients, you’ll need to put a ton of work into applying to gigs, reaching out to potential clients, and simply getting your name out there.

When seeking freelance work, the first thing you should do is establish profiles on common freelance job sites. Not only does this give you access to open jobs and projects posted by clients, but it also bolsters your name and business name’s SEO by giving you another link to your website.

Here are some common job sites on which you can establish a presence and check out some open gigs:

Join some industry or location-specific freelance communities. This will help you create a network of “colleagues” and freelancer friends as well as expose you to open gigs and potential clients. It might seem counterintuitive to make nice with your competition, but it can actually help your business. In fact, three out of my first five jobs were passed on from another freelancer who couldn’t complete them all herself.

“I actually love using Facebook groups like Freelancing Females, The Copywriter Club, and The Denver Boss Babe Collective. Those are groups that get it. They understand freelancing and running your own business and are very collaborative. I also enjoy word of mouth. The best business is a referral, so I let some of that take its course. In six months I've already had three or four referral offers.” — Laura B., Denver

For a bolder, more direct approach, consider reaching out to managers, directors, and editors at the companies you’d want to work with. Simply communicating your availability and sharing your website keeps you top-of-mind when work does arise. Connecting directly also shows clients that you’re proactive and take initiative when needed.

“I often directly pitch clients after an initial introduction has been made through a mutual connection. This helps provide a warm introduction (rather than a cold one) and has proven to be much more effective for landing gigs than applying to jobs/job boards.” — Kaleigh M., Illinois

Lastly, the best way to consistently attract work is to market yourself and your services. Marketing yourself extends beyond applying for specific gigs or reaching out to clients. It’s more so promoting your business as a whole and establishing a presence on social media, publications, search engines, and more. Most of this work happens with little to no pay but more than pays off in the long-run.

Here are some strategies to market yourself and attract more work.

  • Inform your friends, family, and professional network of your freelance business. Even if they don’t need a freelancer, your name might come to mind if they’re asked if they know someone. The more people who know about your business, the more people who can potentially refer you.
  • Stay active on social media. Follow and connect with freelancers, influencers, and potential clients on Twitter and LinkedIn. Engage with their posts by asking questions or sharing content with your network. I personally know of multiple freelancers who landed work by engaging with a certain editor or project manager who simply liked what they had to say on social media.
  • Work for free. If you’re a writer, pitch articles to publications like Entrepreneur, Fast Company, or Inc. to build your portfolio and get bylines. If you’re a designer, offer your work to a non-profit for free to create goodwill and associate your work with a real client.

“I always kept a running list of publications I wanted to write for. Once a publication was on my list, I’d subscribe to their email newsletter, follow them on social, and keep up with their new content. This strategy helped me learn about their audience, which topics they covered, and the tone and style they used. After a week or two, I’d sit down and brainstorm a list of 3-5 pitches. Then I’d send an email to their editor (or fill out their submission form, depending on the publication’s process) introducing myself, citing some relevant pieces I’d published elsewhere, and giving a brief overview of my pitches. The entire email was usually 2 paragraphs. I was pretty successful with this approach — I think I had around a 50% success rate.” — Aja F., HubSpot

  • Establish authority in your niche. Attend industry events (like INBOUND!), teach a local course, or lead a seminar or webinar. One freelancer I know tutors writing students at her local library. Will any of her high-school-aged clients hire her? Probably not, but it still builds awareness of her business while helping others and challenging her to fine-tune her skills.
  • Ask for referrals and testimonials. Reviews don’t have to come from paying clients. Anyone in your personal or professional network you’ve worked with can testify to your skills and work ethic. Consider professors, past employers or colleagues, or mentors. Ask for reviews on LinkedIn and copy them to your website.
  • Say yes! As you establish yourself as a freelancer, keep your mind open to new opportunities. You never know what could lead to a client or job!

“[The best decision I made as a freelancer was when] I went through a period of saying yes to everyone that asked for help. It wasn't until I started to respect my expertise that others seemed to, too (minus the example from above...). It's easy to fall into that trap, but if you don't appreciate your time and talent, neither will anyone else.” — Lauren G., PR and Prose, Amsterdam

Managing Freelance Jobs and Clients

Freelancing means that you’re in charge. You create your schedule, you set your deadlines, and you pick up the slack when things go wrong. The best way to prevent problems (and impress your clients while you’re at it) is to have a solid project management process in place. Not only will this help you approach each project with assurance and organization, but it’ll also communicate professionalism to your clients.

"I'm a huge fan of over-organization so I use tools to get myself organized and get stuff done so I can get paid faster. I use Notion to organize everything from to-dos to the actual writing product in one place, so my clients get a workspace they can refer back to with all of our assets. Spending a couple of hours on this stuff each week really makes me much more relaxed and eases the freelance anxiety when I don't have any work coming in. Using [tools] also gives clients a great impression that you've got it together and takes the pain out of choosing to work with you!" — Owen W., Amsterdam

The first step to managing your projects with ease is establishing a place to record deadlines, meetings, events, and important dates. This could be on your Google Calendar, iCal, or even a paper planner. There’s no right or wrong answer here — you should choose what works best for you.

"The key to successfully managing a project is organization (and remembering the things that everyone else forgets). Since I don't have the best short-term memory, my project management tools are critical. Trust me, to-do lists are not enough. I prefer Trello and Asana, but there are some other great resources out there. The more involved a project, the more likely the tiny details are to slip through the cracks. Project management tools keep everything in one place, and make it easy to delegate tasks, keep track of deadlines, and move tasks through the pipeline." — Christina P., HubSpot

Beyond your calendar, it helps to use a project management or to-do list tool (or a combination of some) to help you stay on track and hit deadlines. From a HubSpot poll of over 80 freelancers, here’s a list of the top five platforms they use to manage their freelance work:

Lastly, figure out how you’d like to communicate project information and updates to your clients. (As for how often you’ll communicate with them, that’s also up to you and will likely take some time and practice to figure out.) Remember, as a freelancer you not only need to create amazing work but also please your clients, as clients lead to referrals … which lead to more work! I’ve compiled a list of tips for working with clients below.

  • Set expectations early. From the moment you begin working with a new client, ensure no question goes unanswered. Be proactive in setting expectations for projects, your personal availability, deadlines, and payment. If you feel like you’re providing too much information, you’re likely providing just enough.
  • Put it on paper. Whether you’re connecting with clients over email, phone, or Slack, ensure all decisions and expectations are reflected in official documents. This includes proposals, contracts, and invoices. Doing so creates legitimacy for your freelance business and creates official documentation if things go awry.
  • Watch out for client “red flags.” If a client starts asking questions about availability and payment that make you uncomfortable, listen to your instincts and consider whether or not you want to work with them. It’s OK to say no. Questions like “Will you be available any time I call?” or “If I don’t like it, do I still have to pay?” are examples of red flags and might mean that client isn’t a good fit for your business.

“I'm surprised by how consistent it is for bad clients to show the same red flags as one another during the early stages of working or talking with them. Clients that will be outright disrespectful, ghost us mid-project, or be slow to pay tend to have a few things in common that can be noticed right away: They balk at our rates or try to negotiate down the price without adjusting the scope or value of the project. These clients also tend to require everything immediately but take weeks or months to pay for the work after completion. I'm glad my business has matured enough that I can avoid these clients when they approach me now, but it was much more challenging in the beginning stages.” — Alexander L., Lewis Commercial Writing, Fort Worth

Getting Paid for Freelance Work

Money, money, money. We all need it, but not everyone has to manage it as meticulously as freelancers do. When you run your own business, you must have a hand in everything, from how you invoice to what tools are managing your money.

And when it comes to money, setting your rates is merely half the battle. The other half involves billing, getting paid, and managing your freelancing financials.

The process of billing and receiving money can be uncomfortable, but getting paid is quite literally what keeps your business alive and allows you to maintain your freelance lifestyle. Thankfully, technology has made it easier than ever for today’s independent workers to manage their financials within a single platform.

Here’s a list of the top five financial management tools per recommendations from over 80 freelancers:

These tools can help you upgrade from the old school word-processor-plus-spreadsheet system and build gorgeous invoices, process payment in multiple ways (by bank card, direct deposit, etc.), include any necessary taxes and fees, and even handle reminders for clients who are delayed in payment.

Let’s take a moment and dive into invoicing and billing. One important thing to acknowledge about freelancing is that sometimes clients don’t want to pay (or they don’t pay at all). There are some measures that can help if this happens, but there are also some invoicing best practices that you can follow to minimize this risk overall.

When invoicing…

  • Bill at least half up front. It’s not uncommon to ask for at least 50% down before starting work. This is a show of good faith from your client and also provides some funding up front so you can get to work.
  • Be crystal clear on your invoice. Spell out all your pricing, due dates, and payment terms on your invoice. Leave nothing to chance. You never know when a client will try to wiggle out of what they owe you.
  • Bill promptly, based on your terms. If you say you’re going to bill weekly, bill weekly. If you say you’re going to bill five days post-project, then do so. Be true to your word. It shows professionalism and trustworthiness, and it keeps your clients from silently backing out of what they owe.
  • Offer multiple payment options. The tools mentioned above can process multiple forms of digital payment, but it’s also good practice to offer to accept payment the old school way, too. Be sure your business address or P.O. Box is reflected on your invoice so that clients can send you a check if need be. Accepting all forms of payment leaves no room for your client to say, “Sorry, I just can’t pay.”

The Not-So-Fun Freelance Stuff

As attractive and enticing as the freelance lifestyle seems, it can be equally as complicated. Working for an employer might mean long, boring hours and commutes, but they also take care of a lot of stuff behind the scenes — including taxes, benefits, and retirement funds. And these are things you cannot take for granted.

Thankfully, freelancers can set up and manage their own benefits and taxes, but it does take a little extra research and work. We’ve spelled out the need-to-know details below.

Paying Taxes

Everyone loves tax season, right? Well, if you’ve been used to a big return each April, it’s time you change your expectations of tax season. Since freelancers don’t pay taxes with each invoice or paycheck, they’re expected to pay in full each tax season. This can mean thousands and thousands out-of-pocket, which can really mess up your cash flow if you’re not careful.

PRO TIP: “Simply, keep regular accurate records. I previously used a spreadsheet for my accounts that required everything to be manually input but calculated outgoings, income, and tax. Every time I input a new project I got a new bottom line. Tedious but essential. I started using Quickbooks last year which generates a similar outcome with each invoice. Plus, I know this might sound a bit patronising, but don't spend the money calculated for tax. It's easy to see the number in the bank account, but always know what is tax — the taxman cometh and he does not suffer fools, gladly or otherwise.” — Christopher S., Lestaret, United Kingdom

This is one of the necessary evils of the freelance lifestyle. Thankfully, there are a few steps you can take throughout the year to lessen the impact of tax season on your freelance business.

  • Stash away 30% of each paycheck. Whether you set up a business savings account or literally withdraw cash, it’s good practice to “pretend” like taxes are being removed from each invoice you receive, similar to how an employer would do so. 30% might seem steep, but it’ll help you be prepared for taxes and have some extra savings for large business expenses.
  • Pay quarterly taxes. Instead of paying one large sum each April, pay an estimated tax amount each quarter. This relieves your bank account of a massive withdrawal and helps you avoid any late fees or potential interest payments.
  • Save every receipt and research applicable expenses. Expenses can quite literally save you at tax time. Self-employed folks can write off anything and everything to do with your business, like Wi-Fi, rent for the square footage of your home office, mileage to client meetings, and 50% of business-related meals. Be sure to save all records of expenses in case you get audited.
  • Hire an accountant. Freelancing is an incredibly independent undertaking, but you don’t have to do everything alone. If you’re not a tax expert (which most of us aren’t), don’t be afraid to hire a tax accountant to help you better understand your responsibilities. There are plenty of accountants that specialize in self-employed taxes, and these folks can help you find new expense opportunities, manage your funds, and prepare for any audits.

Setting Up Insurance

Another sacrifice of freelancing is forgoing company-sponsored benefits. And let me be the first to say that those are super important, especially for folks with families and chronic health issues. If benefits and insurance pose a major question of whether the freelance lifestyle is right for you, you’re not alone.

If you have a spouse or domestic partner, take a look at their insurance options. This is the most ideal avenue as company-sponsored benefits are usually less expensive than direct options through insurance providers. Even if your partner has to pay a little more to upgrade to an employee plus partner or employee plus family plan, it’s worth it.

If you don’t have a partner or he or she doesn’t have the option to include you in their benefits package, don’t fret. There are some insurance plans and providers that cater to freelancers and self-employed people, such as the Affordable Care Act’s SHOP coverage. Organizations like Freelancers’ Union also organize health insurance resources to make any research and decisions less intimidating.

If you’re leaving a full-time job, you might be able to tap into the Consolidated Omnibus Budget Reconciliation Act (COBRA), which allows you to keep your health insurance for up to 18 months after employment ends. You’d have to pay 100% of the premiums (including your former employer’s share), but this option might buy you some time until you make a permanent decision regarding benefits.

Investing in Retirement

Retirement planning isn’t reserved for the “officially” employed, and you definitely don’t need an employer to set up a 401(k) or IRA. Freelancers and self-employed folks have many of the same options as those who work for a company, such as the Roth IRA, SEP IRA, or self-employed 401(k). This article by Fidelity breaks down which account might be best for you and how to get started.

As a freelancer, I started a Roth IRA and set up direct deposits into the account. I did this directly through my personal wealth manager, but there are plenty of tools and platforms that can help you.

Regardless of how you plan to invest in retirement, always start as early as possible and stay consistent with your deposits. Your future self will thank you.

Staying Connected as a Freelancer

Freelancing is a lonely career choice. In fact, when I talked in-depth with over 20 freelancers, most of them said the most difficult part of being a freelancer is how lonely and isolating it can be. But this shouldn’t stop you from pursuing a freelance career — it should simply prepare you to put in a little more work socially.

As a freelancer, since you’re not going into an office anymore, you’ll likely find yourself spending more and more time alone. You might also find that you talk to yourself more often … or that may just be me. Regardless, freelancing requires stepping outside your comfort zone and working hard to build relationships and joining communities — just like you’d do at work.

Meeting others can help you not only stay connected and up-to-date on new jobs and freelancing trends but also refine your skills and learn new ones. Here are a few ways you can stay connected and keep learning as a freelancer.

Take an Online Course

Taking an online course is a fantastic way to inexpensively master a new skill while being exposed to a new network of people. Better yet, some courses are free, and some allow you to become certified so you can increase your credibility. Online courses are a great asset to a budding freelance business and are much, much more manageable than going back to college.

Here’s a list of courses recommended by the 80+ real freelancers I surveyed and spoke with:

Along with these courses, you can also check out dedicated course websites. Platforms like Udemy, Lynda.com, and Treehouse provide hundreds of free and paid courses that cover a multitude of topics and specialties.

PRO TIP: “[The best decision I ever made was] joining the first iteration of The Copywriter Mastermind. It leveled up my business in so many ways. We're still together as a group today, and our Slack is my #1 go-to for business advice, client management, and copy review.” — Lianna P., Punchline Conversion Copy, New Orleans

Hire a Mentor

When I started freelancing in October of 2016, hiring a mentor was the very best thing I did for my business. I didn’t need help writing — I needed help figuring out how to write for other people … and make money doing it.

My mentor showed me exactly how to be a freelancer, including how to find business, pitch myself, set my rates, and more. Without her, I wouldn’t have started out so strongly with my freelance business. Not only did she equip me with all the tools and confidence I needed to dive in, but she also passed along a few jobs that she couldn’t take herself.

The process of hiring a mentor, coach, or consultant isn’t the same for everyone. Depending on your budget, industry, expertise, and location, you might fare better with a coaching course or a local consultant. Some of the above-mentioned courses teach how to freelance, too.

Join a Freelance Community

Whether you’re working from the heart of New York City or middle-of-nowhere New Mexico, today’s technology makes it incredibly easy to stay connected to other freelancers. From social media to dedicated forums, there are plenty of ways to join communities, build a network, and make friends.

Sites like Freelancers Union and American Writers and Artists Inc. offer memberships that provide resources and access to elite communities of freelancers and creatives around the world. As for social media, there are plenty of freelancer Facebook groups you can join and engage with. Some groups provide work, while others simply provide a place to chat and ask questions. If you’re on Slack, you can also hop into a Freelancer slack community, such as Digital Freelancer.

Lastly, don’t shy away from your local freelance network. Nothing quite beats a face-to-face meeting or conversation over a cup of coffee. Organizations like Creative Mornings or local co-working spaces put on networking events and get-togethers that allow you to meet other freelancers in your area. These opportunities provide human interaction in an otherwise majorly digital lifestyle.

Over To You

This ultimate guide to freelancing is long for a reason — there’s a lot that goes into this massive career move. But that’s not to say you shouldn’t or can’t do it.

In fact, freelancing is a pretty straightforward process. After addressing any questions and concerns regarding how to establish your personal brand, where to work, where to find jobs, and how to stay connected, the only unknown that remains should be: Are you willing to take the leap?



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