Freelance Career Checklist


When you start freelancing, it’s like embarking on a new adventure. You start with gusto and begin to trek up the mountain but as you make some headway, you realize there is so much more to learn and more mountains to climb.

It can leave you feeling a little overwhelmed. When I get emails from complete strangers asking for advice on their careers, it’s a very humbling experience, because I feel as though I’m still stuck at the bottom of the mountain myself.

Recently I received an email from a reader asking for advice on how to start her freelance career. Her story is a little different from most because this was not her first career choice. She had been an educator for 10 years and was laid off in 2008. Gathering her courage and will power to never give up, she went back to school and is now well on her way into a web design program.

So I thought about the things I did within the first 6 months of graduating and the things I SHOULD have done to really become established and ready to handle clients. Some of these may seem obvious, but they are worth repeating.

1) The Portfolio


How many projects should you show?
The answer is going to be depend on two things: What industry you are in and where you are in your career. For example, in my graphic design program I had to have between 9 and 11 projects to graduate. Other majors like game art are only expected to have maybe 4 or 5 projects because each project takes longer to create.

The second part of that is where you are in your career. If you are just starting out, you may be wondering whether you should take the general approach or the specialist approach. I took the general approach and it has served me well up to a point. I used to get inquiries about all kinds of design projects, which was a great way to learn as I went. One woman had her own skin care line and asked me where I go the blue bottles for my own skin care line concept. I had to explain to her that it was a student project and that I hand tinted those bottles myself, most of them coming from the goodwill. Since then I have taken that project off my portfolio because I realized I didn’t want to do package design, and though I love that project, it opened the door for a lot of people looking for a service I’m not interested in providing.

I now fully embrace the digital world and focus on branding, marketing, and web design, leaving behind print, publication, and package design.

What about the descriptions?
Another semi-important piece of your portfolio is your descriptions.  I say semi-important because a lot of people choose to skip reading and just look at the imagery. Even though most people skip over it, you still should write them. I hate seeing a portfolio project with no information and I’m sure art directors and hiring managers do too. People want to know how you think, why you made the decisions you did, and so on. Leave out “this assignment was to…” and just skip ahead to

“[Company Name] is…. and they needed help with [ insert design problem ]. The solution was [insert your concept and strategy]. The final design was to [insert your final project  with a few key design decisions].

It’s 2014, why don’t you have a website yet?!
Not only are the projects themselves important, but having your own portfolio website is a MUST. When I graduated, most of my fellow classmates spent 90% of their time on their print portfolios and 10% on their websites. In my opinion, print portfolios become obsolete in the first 6 months of graduating. I haven’t used mine nor even opened it in over 2 years.

Spend more time and money on a good branded website, and a digital portfolio that you can email or show on a tablet than a printed one.

Most designers have 3 pages tops on their websites: portfolio, contact, and about. This is great if you want to get hired by an agency or in-house and work full time. You’re speaking directly to creatives and all they need to see is your work, a little about you and how to contact you. Freelancing websites are different. Your website isn’t just a place to house your work, it’s your business. You have to sell yourself not as an individual looking to be hired, but more as a business owner with services, price rates, and so on.

One tip that came out of the How Interactive Design Conference: Have some sort of introductory message on the homepage; something welcoming. A lot of people start with “hello. I’m [name], and I like to [insert design role].” Immediately your user will feel welcomed, will know your name and what you do. Check out mine here.

Website Tools for the non-developer:

WordPress -I use this because its easy to update and it doesnt look like a templated site. You can read more about my thought process on designing my own freelance site using WordPress here.

I should mention that there are three ways of using wordpress:

  • The first option is completely free. You sign up at, create an account, pick a template and boom, you can start creating posts. This is best for blogs, not portfolios. The “free” templates are very limiting and often kind of ugly. You also don’t have a unique website name. It can’t be “”, but instead is “”. It gives it away that you’re using a free site which isn’t very professional.
  • The Second option is to pay the small fee and get a custom domain name. You have a few more template options to choose from but they still might not fit your needs for a portfolio. 
  • The third and best option requires a little web developer know-how: If you go to, you download the wordpress file, upload it via ftp to your own web host and then go through the installation instructions, you will have your self hosted wordpress site. The benefits of this method are more control. You can buy better themes that fit your need or make your own and hire a developer to program it for you, like I did. This option is not for a beginner, but if you want the utmost control over your portfolio, then this is the best option for you.

Cargo Collective – a clean portfolio option for those not comfortable with code. I believe you choose a template and maybe a font/link colors and that’s it. I’m not sure if this is free or paid.

Behance – One of the most popular portfolio site for creatives. The plus is that its super easy and has SOME customization, the downside is that its a template so you can’t go changing the layout. Also, your page is just one of many. It’s easy for someone to click off to someone elses portfolio.

Muse – I have reservations about even mentioning muse, but I wanted to let you know there is a website building software that acts like indesign but spits out code when you export. I could go on a rant about how muse is still not the best solution, and I think most developers would agree. It can be really finicky and limiting to work with. It isn’t good for any sites that need to be updated regularly like blogs or e-commerce, but it may suit your needs for a portfolio. To watch free tutorials, visit adobe tv.

Key Take Aways:

  • Go general at first (so that you can try your hand at different things), then slowly become a specialist.
  • Show enough projects to give a range of skills and styles.
  • Look to others in your field both at your level and higher for cues on how many projects to show and what to show.
  • Showing process is good, but I choose to showcase it in my blog instead of on the project page. You can also offer up a downloadable pdf of your process.
  • Write professional descriptions even though most people wont read them. Find a format that you like and stick with it.
  • Spend 65% on your website and 35% on your printed portfolio. I say to hell with print portfolios, but most schools still require one to graduate.

2) Get Active in Your Industry

When I was a student at AICA-SF, I participated in a lot of school functions. I became a peer mentor, a club president and a tutor, but none of these things had much of an impact on my career. The best thing I ever did was join AIGA as a student. Not only did it allow me to go to a bunch of events, but I became a student liaison for my school, which meant I attended monthly board meetings and promoted AIGA to students. When I graduated, my position evolved into Associate Volunteer Coordinator. My job was to make sure volunteers ran all the AIGA-SF events smoothly. During this time I met a ton of really great people, which expanded my network and gave me more opportunities for work.

Getting involved and going to industry events, whether they are big conferences, or just a one day event exposes you to so many passionate people. Those are the people you want to network with, collaborate with, and receive advice from because they are the ones that are continuing conversations about the industry and are more likely to find work because they are actively seeking new opportunities.

I can’t speak enough on how important it is to join a group and participate. You have to do both. If that wasn’t enough incentive, here’s more reasons to join a group.

Groups you can join:
Graphic Artists Guild (GAG)
Linked in Groups
Meetup Groups
Freelancer’s Union

Conferences you can go to:
UX thursdays – Cheap one day conference about UX design put on by the brilliant Jared Spool
Moxie Con – One of the most inspiring mini conferences I’ve ever been to. Read about it here.
HOW Conference – this is the big one. It’s actually a series of conferences: Die-line, Managers Conference, Freelancers Conference, and just How Design conference. There’s also the Interactive How Conference – which is next week in Chicago! Lucky me!
AIGA Design Week: A jam packed week of design events all over your city. AIGA makes the plans with local agencies and businesses but lets them run their own events. You can go to as many as you want. Some are free and some cost money to get into. The events range from design talks, studio tours, parties and speakers. Check out your local AIGA chapter to get involved.

One day events:
Creative Mornings – A great monthly event held in different cities around the world. One morning each month, creatives gather for networking and coffee along with an inspirational speaker. It only lasts for a few hours so that people can get back to work.

Webinars:These days you can find a webinar about anything. The beautiful part? You don’t have to leave your couch.
Graphic Artist Guild Webinars Page
Adobe Webinars
AIGA webinars
HOW webinars

3) Get “Legit”

  • DO set up a seperate business checking account.  Two years into freelancing and my CPA wanted to wring my neck for not having a business account. It makes taxes so much easier when you have all the money from your business going in and out of one account. Do it early, and save yourself a head ache.
  • DO get a CPA: It isn’t as expensive as it would seem and they are worth every penny because they help you write off every possible thing they can and keep you from owing a ton of money. Rule of thumb30% of everything you earn as a freelancer goes to self -employment taxes (OUCH! Right?) The last thing you want at the end of the year is a nasty “you owe $15,000” from the IRS. Luckily here in Chicago we have a really great CPA company that specializes in taxes for creatives called Rockstar CPA.
  • DO Register your trade mark : People think that because they are small fries starting out that they can get away with not registering their trademark. It’s a really uncomfortable area for most people who aren’t in law because we have no idea what to do and lets face it, the is not the easiest place to navigate. There are reasons why you want to do your homework first before choosing a company name. If it’s just your name, like LorettaMay Design, it’s probably ok. But if you were to make up a fake name like “creatively driven”, you would want to check that the domain name is free AND the trademark is free. Here’s some more info on trademarks and to check the availability of trademarks, go to USPTO.GOV
  • DO (eventually) get a business license and tax ID: I was told by my accountant that you really don’t need a business license until you’re forced into it. When does this happen? When you’re applying for a business loan, when you want business insurance, when you want to work with a high profile client that will only work with an insured business. Starting out I didn’t need any of these things, so I haven’t yet gotten one. Not the best practice, but I haven’t needed to YET. If you like doing things by the books, then get a business license and tax ID number so that you don’t have to use your social security on everything.
  • DO hire a law professional to draft up your licensing agreements. The last place you want to be in is in court because your client didn’t pay or is trying to sue you for whatever reason. Protect yourself and get someone to write a general license agreement drafted up. For more information on what to put in it, check out my post Art of: Licensing Agreements.
  • DO invest in invoicing software: Starting out I used to create all my invoices and estimates in indesign. I had a template that I would just update, but 2.5 years in, I realized this system is TERRIBLE. For starters, I didn’t start my invoicing # at 001, but rather used the first few letters of the client + a number, but it was all over the place. Second, I had no invoicing storage system. I kept them in my client folders and often lost them when I really needed them. I didn’t keep record of them paying me either. Come taxes time, i would spend hours looking at my bank account statements for the whole year trying to figure out how much I had made that year.
  • Do yourself a favor and research a good estimate and invoicing software and just buy it. It will pay for itself just by saving you time alone. Here’s one resource of many.

Lastly, check out the Graphic Artists Guild hand book for more information on trade marks, taxes, etc. and Success By Design for  everything you need to know about the business side of freelancing or starting your own agency.

4) Join Job Agencies

When I first started out people told me to work with recruitment companies like Creative Circle or Aquent because it gets you a ton of experience fast and it did.

  • Recruiters are great because they are extra hands helping you find temporary/permanent work.
  • They provide great “in’s” into companies that only hire through agencies and are otherwise impossible to get into from the outside.
  • There are some rules that accompany their services.
  • It comes at a price. You get less money than you would be promised if you got in on your own. Ask them how much they charge on top of your rate first.
  • It’s ok to use more than one agency at once, but be transparent with them. They frown on “double dipping”. If your resume has been sent by one agency to Company A, tell the other agency so that they don’t look like fools to the “client”.
  • They are great support for those large “hard to reach” companies, but you should also keep looking on your own.

Here is more information on working with recruitment agencies here.

5) Never Stop Learning

As soon as you graduate, the last thing you want to think about is going back to school, but you will soon realize that the industry is changing faster than we can plan for. Learning doesn’t have to be time-consuming or expensive, there are plenty of free, cheap, or subscription based options out there and you can find one that suits your schedule.

Girl develop it – a workshop for girls who want to learn code.
Skill share -This has become my favorite learning site. The classes are quick, cheap and really digestible. You can learn anything from wire framing to fashion design. – My best advice for anyone who really needs to learn a new skill or software. This subscription based educational video site covers everything from business to content management systems and more.
adobe tv – This is free for all and super helpful when you are trying to learn the newest features of the adobe programs.
blog shop – Want to learn to set up a blog and create amazing content? This traveling workshop is for you. Not only do you get to learn from some really business savvy ladies, but you get to meet a bunch of amazing people who are passionate about blogging. You establish a network of bloggers and thus, increase your following ten fold. Sign up quickly, because the spots are limited and they go really fast.
HOW university – a little more pricey than the other online options but these classes are put on by industry professionals that have a ton of experience in their fields. The lessons are often very comprehensive and worth every penny.

6) Make Personal Projects


I learned quickly that if I wanted to get hired for a job I had little to no professional experience for, I needed to create personal projects. As long as your portfolio doesn’t have over 50% personal projects, I believe there’s nothing wrong with including a few that demonstrate what you’re passionate about.

That’s why I designed my very own theme for Creatively Driven. With that I’ve learned a ton about blog design that I am excited to share with you soon.

7) Be social media savvy + blog

It’s surprising to me how many of my friends will spend the time checking in on 4 square (isn’t that app dead yet?) or posting images on instagram, but they don’t see the value in twitter as a marketing tool.

A really easy way to follow current trends is to just follow some really great designers or agencies. They tweet news, interesting articles and new projects all the time. If you tweet about industry related material, like-minded people will follow you and BOOM. You have a soap box. It’s a tiny one, but you’ve got a following. You can enhance that soap box by blogging about your industry, your inspirations or maybe a completely different hobby that influences your work. All of the social media and blogging platforms are tools that you should use together to drive your brand and get more freelance clients. And don’t forget facebook! Create a page for your company and add news and updates about your company and take those inspiring articles you found from twitter and emails and whatever and post them to your professional page. Here’s more info on facebook marketing.

 Keep in mind that I didn’t have all of these things in place at once.

If your head is swimming right now and you feel completely overwhelmed, take a breather and relax. It’s important to call out that I didn’t have all of these things in place at once. I didn’t even have them all within my first year. But  now that you know the tools, you can set goals each month toward one or two of them and within a year you will be amazed how muchf you get done. Your business (like your website) is a living, growing entity and must be fed on a regular basis. It’s a full-time job acquiring clients, updating your blog/website, and going to industry events. Not one of these things is effective on its own. It’s the sum of all of them put together.

The main take away for me was this: if you want to be a freelancer, simply doing good work isn’t enough. You need to be active in your community, you need to spend ample time marketing yourself across social media platforms, and you need to BE a brand, not just one person.

If you want to be a freelancer, simply doing good work isn’t enough. You need to be active in your community, you need to spend ample time marketing yourself across social media platforms, and you need to BE a brand, not just one person.

I sincerely hope this helped anyone who is a little lost on how to get started as a freelancer. Do reach out if you have any questions!

** please remember that this is advice and any questions about legal issues or tax laws are best addressed to a professional**

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