How to Successfully Work with a Freelancer

Posted on Sunday, October 4th, 2015 1 Comment

How to Successfully Work with a Freelancer

I’ve been freelancing for about a year and a half. Before that I was self-employed, but working steadily for the same company. Now I work with a variety of people and companies, some of which are on long-term contracts, and others are project-by-project. I’ve also hired other freelancers, so I’ve experienced the relationship from the client’s side as well.

Overall, the majority of the work goes smoothly, but I’ve also learned some things that will help you successfully hire and work with a freelancer.


I’ll start with pricing because that’s probably on the top of any client’s mind. It’s important to have some understanding of how a freelancer sets her price.


Freelancers actually have a lot to pay for. Since they’re not employed on a W2, the government does not automatically deduct Social Security and other taxes from their pay. To make up for that, they have to pay self-employment tax. If you’ve ever employed someone, you know that you pay part of the taxes and the employee pays the other part. A freelancer pays all of it. On top of that, filing taxes becomes much more complicated with quarterly payments and it’s much more expensive to have your taxes done at the end of the year.

Health Insurance

Freelancers have to provide their own health insurance, and they don’t get a group discount like an employee does. Before the Affordable Care Act, I just didn’t have health insurance for many years because the cost was outrageous. Now I get health insurance through Covered California, with some assistance based on income.

Non-Paid Time

As a freelancer, not all of the work you do is actually paid for. Freelancers need to spend time finding jobs, writing proposals, preparing contracts, answering questions, managing finances, advertising, writing blog posts, updating social media profiles, etc. The cost of this time has to be made up for somehow.


Someone who is experienced in their field will likely charge more than someone who is just starting out. A freelancer with little experience might be willing to work for free, or for very cheap, just to build up a portfolio. (By the way, this isn’t the best approach – if you need portfolio items, try volunteering for a charity or non-profit instead of creating expectations of cheap prices.)

Life Situations

Some freelancers may be supporting two or three children. Others might live in an expensive city. As a client you might not be aware of these things, and it’s not your job to care, but they will be built into the freelancer’s pricing structure.

It’s a Whole Job

Some freelancers only do extra work on the side, to supplement their regular income, or just to earn some extra cash. Those folks will probably be willing to charge less because it’s not as important. But many are freelancing full time, which is essentially running a business.

You Get What You Pay For

There will always be someone who charges less for the same service. There will always be someone who charges more. You should consider the freelancer’s experience level and quality of work. You should also consider their personality and whether you get along with the person. You can think of it like hiring a lawyer or accountant. What would you think if a lawyer was willing to work for $9/hr? You would probably be skeptical of the quality of work you’d be receiving.

A Freelancer Is Not an Employee

There are a few reasons why it’s important to consciously make this distinction:

  • A freelancer is not only working with you, but also with any number of other people and handling multiple projects. A freelancer might not be able to take your call or answer your email right away, although she’ll do her best to get back to you quickly. Again, you can think of it like a lawyer or accountant – it’s helpful to schedule appointments for long discussions; for quick questions, send a text or email to find out when she’ll be available.
  • Since a freelancer doesn’t work in the same office as you, it’s easy to make assumptions. If you’re unsure about something, give her a call or send an email to get clarification. If you don’t, you’ll end up worrying and festering over something that might not even be an issue.
  • If you need a freelancer, that means you need someone to do some work that you can’t do yourself. You’re hiring an expert in her field who might have years of experience and can help guide you in the right direction as well as produce a deliverable. Again, think of a lawyer – if you need a lawyer, you need help with a specific topic that you don’t personally have knowledge on, and you need her advice.

Get Clear on What You Really Need

Some of the biggest problems can be avoided by clearly outlining your needs.

Would you rather be doing the work yourself? I actually had an entire project fall apart because the client wished she could do all the work herself, and ended up resenting the fact that she needed to go through me to get to the work done. If you want to hire a freelancer, you must recognize the fact that you need help with something, whether it’s because you don’t have the time, the knowledge, or the skill.

That doesn’t mean you have to give up all control, but it does mean that you won’t be doing everything. In fact, most projects will be collaborative endeavors, and you should also be prepared for that. Website development is a great example of this because most of the content is usually written/created by the website owner (the “about us” text, product descriptions, photos, etc.) The client and freelancer need to work together to create the best solution – the website structure and content have to work together.

The best situation is when the client has some solid ideas of what she wants, and then lets the freelancer create it. Another website development example would be: the client provides text, photos, graphics, and a mock-up design, while the freelancer takes care of the software and technical work. For writing projects, the best scenario I’ve been involved in is when the client provides a detailed outline of the piece to be written, and the freelancer does the writing. In both cases, minor edits can be done afterward, but the client should provide enough information upfront that no gigantic changes have to be made. When major changes are needed, the client is frustrated because of the delay, and the freelancer is frustrated because her income-over-time ratio probably just got cut in half.

Process and Deliverables

You should be aware of a few things regarding the materials that will be produced for you, whether it’s a website, written content, video, or otherwise. It’s also good to understand the general working process beforehand.


You should get a written proposal that outlines the work to be done, an estimated price, and estimated timeline. It should also tell you what you need to provide before the freelancer can get started. This can be useful if you’re shopping around, but it’s also important as a document to refer to if anyone has questions later on.


The best situation is to sign a contract for every project. This doesn’t always happen, especially if you have an existing working relationship with the client or freelancer. But expect it if you’re working with a new person. It’s mainly important as a way to spell out all details of the working relationship.


The work will usually be delivered in a preview or mock-up state first. For example, if you’ve hired an illustrator, she might provide you low-quality images with a watermark for you to approve. Once you pay for the work, she’ll send you the high-resolution version. For a website, the site might be developed on the freelancer’s own server until it’s finished, and then transferred over to your hosting account. Or, the freelancer might only give you the password once the project is paid for.


That being said, you shouldn’t allow a freelancer to completely control your assets. For example, you should have your own web hosting account. It will be necessary to allow a freelancer temporary access to get the work done, of course.


This is something that was a surprise to a few clients, and I even include it in my contracts. I reserve the right to post on my portfolio anything that I create. I must be able to show past examples of my work. This is a large part of the value of the work for me, because as a freelancer, I’m responsible for making sure I have new projects coming in.

Exceptions to this are:

  • If the product is intended for sale, and showing it on my own website would be a detriment to the client’s sales. In this case, I will create a blurred or “preview” version that only shows part of the product.
  • If the material contains sensitive information of any kind, I will not post it online. I will only show it to potential clients or employers privately, with your permission.

Improve Upon Past Experiences

One of the biggest things to keep in mind is that using a freelancer can be awesome. If you’re a small business, you can use a freelancer instead of hiring a whole employee, which should save you a lot of money. And if you find the right person, you’ll be getting access to someone with a ton of relevant experience that you can call on whenever you need help. If you’ve had a bad experience with a freelancer in the past, you can actually bring that up when talking to a new potential freelancer. Explain what went wrong, and how you’d prefer things to go. That will really help set up a better experience for both parties.

There are many other things that could be said about the client-freelancer relationship, but in this post I’ve focused on what I found to be less-than-common knowledge. I hope that this will shed some light on what it’s like to work with a freelancer and prevent potential problems. Please let me know if you have any questions!

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1 thought on “How to Successfully Work with a Freelancer”

  1. Great post, Bonnie. Clear, concise and oh so true. I know you to be a terrific freelancer and so I’d suggest to anyone reading that they give these learnings a good think. I know how you roll and it works. It’s clear you’ve been mindful along the way and have a lot to share. Thanks for doing so!

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