7 Things I Learned in My First Year of Freelancing

One year ago I left the comforts of full-time employment for the freedom (good) and unpredictability (bad) of freelancing. It’s been an interesting journey. Inevitably, there were a couple of setbacks and disappointments, but overall it’s been exciting, challenging, and rewarding. I’ve been lucky (knock on wood) to have consistent work and have had opportunities to partner with clients who are smart, fun, confident, and trusting.

I learned some valuable lessons in my first year as a freelancer. And in the past couple of months I’ve been approached by peers in the industry who are looking to take that scary first step into the freelancing world. It’s flattering to be asked for advice, and I don’t consider myself an expert by any means. But I found myself consistently sharing a handful of things that have helped me succeed (survive may be a better word) during my first year and made my life a little easier.

1. Set up a website.

This is the most important thing you need to do if you’re going into freelancing. It’s not optional. I don’t know that I’ve met a single client (or prospective client) that would consider working with a freelance writer (or content strategist or designer or videographer or UX designer or social media strategist or anything else) who doesn’t have a website. You need to show that you can do and have done what you say you can. There was a time when people brought portfolios to interviews. But we live in a web world, and we’re talking about web projects, so all your work should be on the web.

I’ve heard 2 different excuses from people who want to get into freelancing but don’t yet have websites — time and experience.

The keys to success in this field are drive and professionalism. The simple truth is that if you can’t make time to setup a website, you’re not ready to move into freelancing. The tools available (SquarespaceWordPressWeebly) make the process easier and more affordable than ever. The barriers to entry have been eliminated. And you need to view yourself as a business. You wouldn’t expect a restaurant or a salon or an advertising agency to open without a website and be successful. Why is your business any different?

I’ve also met with some younger folks who want to be freelancers, and I’ve heard several times that they don’t have websites because they don’t have enough work to showcase. You still need a website to demonstrate that you’re serious. Put whatever you have on the site (your first blogging assignment, work you did in college, anything) to show that you understand the field. Then expand as you go. This might require some spec work. When I was getting started, I helped entrepreneurial friends for free, or at a steep discount, to gain more experience and build out my portfolio in a range of industries.

You might also need to work for an organization before you’re ready to freelance. I had 8 years of experience as a professional writer and content strategist for a number of different companies before I started freelancing. I was paying my dues and learning the trade. Those years were crucial to my development and have helped me succeed now that I’m on my own.

2. Hit your deadlines. Follow through on your promises.

This might seem like a no brainer, but I’m amazed by how many freelancers I’ve come across that don’t do these 2 very simple, basic things. I’m also amazed by how grateful clients are when you do hit your deadlines and follow through on your promises, probably because they’ve been burned in the past.

When you sign on for a project, you’re agreeing to deliver a defined thing by a defined date. That’s your promise. But it’s about more than contracts and deliverables and payment. It’s about reputation. And when you’re freelancing, your reputation is everything.

Most of my work has come through word of mouth, or because clients want to continue working with me, or people who used to work for a client and have moved to new opportunities want to continue working with me. There are any number of reasons why that might be the case. But I think it’s because, first and foremost, I deliver what I say I’m going to deliver, when I say I’m going to deliver it.

Don’t underestimate the importance of hitting your deadlines. Of course, situations come up where a deadline needs to be moved. A few words on that.

If it’s in your control, never ask for an extension. Get it done. If this means working through the night or over a weekend, so be it. You’ll learn from the experience and plan better on the next project.

If it’s out of your control (maybe other parts of the project are behind schedule), communicate early and often. Know the reasons you’re asking for an extension, address potential challenges as soon as you see them, and never blame the client (even if it’s their fault).

3. Be an expert in something. Know about many things. Don’t try to know everything.

From what I’ve seen, it’s expected that people working in this industry will be familiar with many different areas of the web. The lines between job descriptions are becoming increasingly blurred. So it’s becoming more and more important for freelancers to be familiar with, and have at least a basic understanding of, a wide range of topics.

For people working in web content, in addition to being a strong writer, you need to know about SEO (keywords/phrases, titles, metadescriptions), content strategy (content auditing, message mapping, user personas, governance and sustainability, editorial calendars, competitive analysis), IA, UX, branding (voice & tone, brand guides), social media, responsive content, content management systems, analytics. The list goes on. I’m sure I’ve missed something, and I’m sure others can find reasons to disagree with the things I’ve included. My point is that you need a fairly comprehensive view of the web.

It’s also extremely important that you specialize in one area. This helps you market yourself and know which opportunities to pursue, and it helps the people assembling project teams know how to place you. You need to figure out what types of projects you want to work on (do you prefer large scale redesigns? Social media campaigns? Blogging?) and what your role will be on those projects (are you a great writer? Planner? Team leader?)

Finally, I’d say don’t worry about knowing everything. The web changes too quickly to keep up with. It’s impossible to know everything you need to. So do your best to stay on top of trends and major changes to the web, devote time and energy to professional development (I suggest subscribing to The Moz Top 10), go to conferences and industry meetups (more on that in a moment), and then trust that you’ll learn new skills as you need to.

4. Get out there and meet people.

Because we work on the web, it’s easy to forget how important real life relationships are. But so many opportunities have come my way because I met somebody who has a project for me, or recommends me to somebody who does. Plus, it’s a lot of fun meeting other people in the industry, if for no other reason than to commiserate on shared experiences.

I highly recommend going to conferences as often as you can. These are usually a great way to learn new skills, stay ahead of the curve, and get to know your peers. Conferences can get expensive, so it’s a good idea to set aside a yearly conference budget when you start making money (consider it a business expense). In the Twin Cities, MinneWebCon is an excellent, affordable option at the University of Minnesota, while Confab is the (more expensive) gold standard.

The Twin Cities also has a Content Strategy Meetup Group that gets together once a month (give or take). The group typically hosts a speaker or panel that presents on a content strategy topic, followed by time for Q&A.

Minneapolis agency Spyder Trap periodically hosts events they call Digital Way Finder. They cover a range of industry topics, trends, projects, etc. These are great for sharing ideas and meeting people who work in agency settings. As a bonus, food and beer is usually included in the price of admission.

Finally, a few thoughts on social media. Most of the industry is on Twitter. So you should have a handle. Admittedly, I’m not very good at Twitter. Tweeting just hasn’t become habitual, or ingrained in my process, or something I think to do on a regular basis.

I think that’s okay. You don’t need to be the most prolific tweeter. You just have to be present. On the other hand, I’ve had good luck connecting with clients through LinkedIn and I make a concerted effort to do something on LinkedIn at least every other day. Again, being present is key, so find what works for you and try to be consistent.

5. Partner with (the right) recruiters.

I’ve worked with a few different recruiters since I started freelancing. Some of them are really great partners. They take the time to learn about my skills and strengths. They understand the types of projects I’m looking for. They work hard to send me assignments that align with those strengths and interests. They follow up and check in on a regular basis. They’re good people who I enjoy talking to.

And then I’ve had less fulfilling recruiter relationships, without naming names or getting too specific.

I would just say this — working with recruiters can be rewarding and profitable. They can help you get projects you’d never get on your own. They help manage business processes like negotiations, scheduling, and invoicing. They can be your biggest advocates.

Find a recruiting agency or two that you trust, that works on the types of projects you want, and that invests back in you as a partner. And if the relationship isn’t working, don’t be afraid to cut ties.

6. Learn some business basics.

As I mentioned earlier, when you become a freelancer you become your own business. So you need to learn some business basics. For me, this has been one of the biggest challenges and I’m still working on developing my business acumen.

First, you need to decide if you want to form an LLC, or if you want to be a sole proprietor (there’s also a thing called an s-corp that I won’t get into). With an LLC, your personal assets and business assets are considered separate, which can be important in the case of a lawsuit. LLCs need to be registered, which costs money.

I’m a sole proprietor for the time being, which means I’m the sole owner and operator of the business. As a sole proprietor, I’m responsible for filing taxes and paying estimated taxes once a quarter (you’ll be penalized if you fail to pay estimated taxes). I’m also personally responsible if I were ever to lose a lawsuit, so I have my own business insurance (it costs something like $10/month).  

For most projects, you’ll either be paid on a W2 or a 1099. Typically a W2 if you’re working through a recruiter, and a 1099 if you got the project on your own as an independent contractor. The big difference? Money you’re paid on a W2 is already taxed, while money you’re paid on a 1099 isn’t taxed (so you need to withhold and pay your own taxes). I’ve seen people get burned by this. Expect to pay about 35% of whatever you make on 1099s in taxes. As a general rule, I set aside 40% of every 1099 paycheck for taxes, and roll the extra into my business account for business expenses (computers, conferences, office chairs, etc). I also put at least 10% of whatever I make in W2 paychecks into my business account.

When it comes time to file your taxes, I’d suggest working with a CPA (unless you really enjoy that sort of thing). They can help you get deductions you never knew existed and help you avoid mistakes. When I estimated how long it’d take me to do my own taxes, and how much I charge an hour, the cost was well worth it.

You’ll also want to come up with templates and processes for proposals, contracts, and invoices. In proposals and contracts, make sure you’re explicit and detailed in what you’re agreeing to, processes, timelines, payment schedules, liabilities and disclaimers, etc. Those documents are the promise for both you and your client and, like I mentioned earlier, your reputation is on the line. Your first proposal will take you an obscene amount of time to put together, but it gets easier as you solidify a template.

7. Be kind.

Nobody likes working with jerks.


There you have it — my best advice for people getting started as freelancers. Obviously more could be said about the freelancing life. I just hope this is a helpful start. Best of luck to anyone setting out on their own!