Freelance 101: How to Start Working in a Creative Field

I’ve worked in creative industries for a decade. Primarily as a fashion designer. In that time I’ve worked for companies big and small. I’ve been employed full-time by a single company, I’ve been a freelancer, and I’ve started my own business. For as many wonderful people I have met, there are plenty who have tried (and sometimes succeeded!) in taking advantage of my eagerness or naivety. My experience has been hard won, and I’ve been able to come as far as I have because of the knowledge shared with me by mentors along the way. Today I’m going to pay it forward by sharing some of that knowledge with you. I hope you take these lessons and apply them proactively in your own work-life if you choose to pursue a career in a creative field.


Whether you’re in the running for a full-time position or meeting a new potential client, conducting a thorough interview is key. You’re starting a new relationship with someone. You are both vetting each other to make sure this is going to be mutually beneficial. You should both be putting your best foot forward. Your potential client or employer will likely never treat you with more care than they do in that meeting. If you’re already noticing red and orange flags, know that those will likely only get more intense with time. 

When I interview for a position these are some of my go-to questions:

“Why is this position available?”

“How long have you (hiring manager) been employed here? Who is the longest serving employee (besides the owner)? What is the average time someone stays with your company?”

“What does a typical day with your team look like? How often do you come in early/stay late?”

I always research the company I’m meeting with ahead of time and try to find the answers to these questions on my own. I use sites like LinkedIn, Glassdoor, and Who Pays Knitters, to find out what general sentiments are, who they have worked with in the past, and if there are any major events in the company history I didn’t know about. 

If I’m working with a magazine, I’ll reach  out to contributors from past issues and ask about their experience. I’ve found that a kind email is usually well received and people are happy to share, even with relative strangers.

Portfolio and Sample Work

If you are primarily offering a service, such as designing, tech editing, or marketing, you usually have a portfolio of past work and a client list to show as proof of your skill. If you are still building up your book, you may be asked to do a small sample project. If the requested sample project will require more than an hour or two to complete, or involves creating entirely new bodies of work “as if you worked for [company],” I would highly suggest you rethink if this is the kind of place you want to work for. Asking for free labor under the guise of a test is a common exploitation tactic used by unscrupulous companies.

How to create a good portfolio could be its own post. But the basic idea is that you should assemble your best work showcasing the skills and style your client or employer is interested in. I have around 6 basic variations on my portfolio, and depending on who I’m meeting, I will edit them further as needed.

As someone with an extensive body of work to show, when I get asked to do a sample project, I typically push back by asking a question like “what do you think was missing from my presentation?” Chances are I have something I can show to ease any lingering fears about my skills. I may also offer to work for a day if the company will pay me a day-rate or hourly wage.

Spec Work

This is work that is done in advance with the hope that the client picks it. Any magazine submission you’ve done are an example of spec work. You should only send spec work to places you trust, and you should never trust someone who tries to lay claim to your work without compensation. Want to hear a funny joke? I once read submission guidelines for a publication that said they may keep my proposal for consideration for up to a year and not to shop it around during that time! The audacity! It’s pretty rare for me to submit a design to more than one publication at all, and if I do, it’s usually months after the first publication has finalized its assortment. But if you haven’t signed a contract or been paid, your work belongs to you and you can do with it as you please.

Trust is Everything

If your manager or client doesn’t trust you, your relationship is doomed to fail. Business is a relationship just like any other. Whether platonic or romantic, without trust, you have nothing.

Build trust by being prompt in your email replies, detail oriented in your correspondence, meeting promised deadlines, and paying for goods and services on time.

Setting Boundaries

If you’re working as a freelancer, it’s a great idea to have some sort of onboarding document for clients to let them know what to expect when working with you. Maybe you don’t answer text or emails after a certain time, or IG DM’s are off-limits for official inquiries. 

I know you’re enthusiastic about working in a job you love, but you need to be realistic about what you can offer to prevent burnout. I would advise against offering anything unlimited like a “happiness guarantee” where you don’t charge the client until they’re completely satisfied. It will probably work out most of the time, but there’s always a few bad apples out there, eager to eat up your time.


Contracts are a formal, legal method of boundary setting. Contracts are not inherently good or bad. They’re meant to establish responsibilities and protect all parties that enter into them. 

When things are good, you probably feel like you don’t need a contract. Your trust in your partner is enough. But contracts are most useful when things have gone wrong, and it can be hard to foresee when or how that might happen before it’s too late. 

At the bare minimum a contract should outline the steps necessary to complete the project, define compensation, give a timeline for completion of work, payment schedule, and include details on how to handle ending the working relationship early, including any penalties. 

Always read a contract through in its entirety before signing and keep a copy for your own records. If there’s anything you find questionable, ask about it before you sign. You can always ask for things to be removed or added, even if you’ve been given a “standard” contract.

If you’re feeling over your head, most states have Volunteer Lawyers for the Arts foundations that offer heavily discounted or free legal advice. You typically contact the organization for a free consultation where you explain your needs and financial situation, then, for a small donation/membership fee they will connect you with representation.

Parting Ways

Quitting is underrated. Quitting things that don’t serve you opens you up to new, better opportunities in the future. 

Obviously you hope to leave every client satisfied and singing your praises, but sometimes things just don’t work out. Maybe your working styles just don’t mesh, or there are trust issues, or maybe you just aren’t in a place where you can complete a project like you thought. There’s nothing wrong with ending a business relationship if it’s not working. 

Take a moment to consider your options and decide the best course of action. It’s always preferable to find a way to withdraw gracefully when possible. Do you know someone who could take over and finish the job? Recommend them!

Sometimes you find yourself in a truly bad situation and grace isn’t an option. If you find yourself in a toxic or abusive work environment, you need to formulate an exit plan as soon as possible. The daily stress can be extremely detrimental to your mental and physical health and it can take years to fully recover from the experience. No job is worth that.

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