14 Tips For Anyone Thinking of Freelancing

In 2008 I quit my job as research director at a technology company. I was burned out after four years of non-stop high-pressure work and didn’t know what I was going to do next. I decided to take a month off and not look for a job. What emerged in the six years since then was a solid career as a freelance writer, a completed master’s degree in writing and a life in which I have a lot more freedom than I ever envisioned as a full-time employee. But it wasn’t easy, and I made a lot of mistakes.

If you’re considering working for yourself as a contractor or freelancer and working from home, here are some things you should consider based on what I’ve learned.

1. Be Clear on Why You Want to Freelance

My original goal when I started freelancing was to write a book. The book turned into a graduate degree and a completed 230-page thesis. About a year after graduation my personal writing turned into drawing. Freelancing is a great way to have the freedom you want to pursue other things, whether that’s family, travel, a side project, or an artistic project. The more clear you are on what you want to do with your non-paid time, the easier it will be to focus on your paid work.

2. Use your Network and LinkedIn

I wouldn’t have been able to have a freelance career had I not put effort into building my network before I left the corporate world. When I was employed full-time I connected on LinkedIn with everyone I was connected to in real life, both inside and outside my job. If you work for a company of 150 people, that’s at least 100 connections. After every event I attended I diligently went through the cards I had collected and made connections on LinkedIn. I also wrote a few recommendations and was recommended in turn.

I wrote a summary on my LinkedIn page, used keywords and provided the same detail as on my resume under each of my positions. If you’re in any business remotely related to technology, LinkedIn is your lifeline. Complete your profile, upload a photo, and use keywords. While some clients I already knew, others were friends of friends and some came through blind searches for a specific skill set.

3. Schedule Work Time and Be Flexible

I’m the sort of person who can be entertained by herself all day, whether that’s making things, learning about new things, and yes, wasting time on the Internet. Many books on creativity will tell you to schedule your creative time. I found scheduling my work time to be a more effective strategy than scheduling my non-paid time. For someone like me who wants to be doing creative stuff 24/7, it’s better schedule my left-brain paid time so my right brain knows when it can come out to play. I’ve made the mistake of leaving art supplies on my desk and losing an entire afternoon to a drawing.

Every day is different. Based on my deadlines I wake up every day with a guesstimate of how many hours I will need to work. This allows me to gauge how much time I have to fit in other things, which could include making art, updating my website, working out, networking events or other appointments.

For big projects I gather information over time and then spend one or two days working non-stop, clearing my schedule of other appointments ahead of time. I would rather work till midnight a few days a month and have whole afternoons to devote to things that I find fun. When you are not bound to the world of 9-5, you are free to find out how YOU like to work, however eccentric that may be. It’s probably not 9-5.

4. Show Current Work Samples on Your Website

If LinkedIn is your “ad,” your website is your full brochure. Add samples or links and update your client list as soon as a project is completed. I’ve seen many freelancer websites that don’t show anything the person has done since 2010. Would you want to hire someone who doesn’t look like they’ve been working in the last 4 years? On the other hand, don’t be afraid to share samples of old work. One recent client hired me because they liked a report I wrote in 2009.

5. Set Boundaries with Your Friends

You may have friends and family members who want to hang out or call you to chat during the day, and it’s up to you to teach them how to contact you and not drop by without notice. If you let people push your boundaries on easy days, it will be hard to make them go away when you’re on a tight deadline. I made a habit of scheduling lunches, knowing that I have to eat anyway and I get tired of making lunches at home.

6. Pushing Back on Timing is OK

You are in charge of your schedule. Often clients want projects done immediately, and it’s your job set boundaries. I managed two new projects plus ongoing work for Simply Hired during a cross-country move. Both new clients were willing to work with me knowing that there was one week in which I would be unavailable. Be honest about your deadlines on other projects. Just as doctors have other patients in their schedule, potential clients know that you have other clients. If they want your services, they will work within your availability.

7. Know What You are Worth

If setting prices makes you uncomfortable, do some research. Talk to other freelancers and people who hire freelancers. I avoid giving quotes in writing. Discussing pricing in person or over the phone gives you the opportunity to negotiate. You will sense immediately if your price is too high. I prefer to bill by the project rather than the hour, since I don’t like keeping track of hours. Find out what works in your industry.

I don’t believe in working for free or below market rate. Therefore, I have never worked for free or below market rate. I’ve had plenty of people try to lowball me with hourly rates more appropriate for a new college graduate with little experience. In those cases, I politely point to my 20 years experience and graduate degree. Working for less than you are worth will only make you feel resentment toward the people you are working for.

8. Job Ads Are an Important Source of Information

Even though I have not looked seriously for a full-time job since starting freelancing, I still read job ads. Why? To keep abreast of changes in my industry and to find out which companies are hiring and might need freelance help. In the six years since I left my last office job a whole new field called content marketing has emerged. I read job descriptions on Simply Hired for positions of people that might end up hiring me, such as a director of content. It helps me get a sense of all the things they have on their plate and how I can add value as well as informing me of the latest buzzwords in the field.

9. Get Regular Clients

Freelancing doesn’t mean you have to leave the security of a regular paycheck. I wrote a report every quarter for one of my first clients. This covered my expenses for over a year. Now I have a regular client that covers most of my expenses. Regular clients provide consistency in your work and give you peace of mind from having to chase the next client win while you are working on a big project.

10. Save Money for Taxes

In the first few years I made the mistake of treating my income as I would a paycheck that already had taxes taken out. You will dread the month of April if you do this. I recommend hiring an accountant and making quarterly tax payments if you can. You will need to learn about what you can and can’t deduct, how to account for your home office space and how to account for your car and computer equipment. If you plan on hiring others, you may want to consider forming an LLC or other tax entity. I file as a sole proprietor.

11. Let Technology Help You

There are technology solutions to help you with just about every problem you can imagine: scheduling, project management, expenses and invoicing. Some of them are free. If not, they will give you a free trial. Research the ones that address your problems and pick one.

I use Mint to track my spending. It makes preparing taxes much simpler by allowing me to categorize tax deductible expenses, label checks and split transactions (e.g., buying both office supplies and personal items at Target) into tax deductible portions. I use Harvest  for time tracking and invoicing. I use Evernote to take notes on client phone calls, clip articles related to a project and keep track of my published work. One of my clients uses Wrike to manage projects for its freelance and in-house writers.

12. Read Contracts

After you submit a verbal or written proposal for a project, the client will send you a contract. You will submit a W-9 and most likely need to sign a Non-Disclosure Agreement (NDA). Most of the companies I have worked with have a standard contract that includes a non-compete agreement, with an “Exhibit” or “Statement of Work” on the last page with information about the project and the payment terms. Read everything, and don’t be afraid to ask questions. There are sometimes mistakes, and it’s your right to ask for the payment terms you want. For work based on a project fee, I usually ask for 50 percent upfront and 50 percent upon completion. Ongoing clients may ask that you submit your monthly invoice by a certain date each month.

13. Get a Contact in Accounting

During the contracting process you will likely be given an email address to accounts payable like, “AP@companyname.com”. I recommend sending an email to that address after getting started with a new client and making a personal connection to the person in accounting who answers it. There are a many things that can get in the way of you getting your money on time, and about all of them have happened to me.

During the contracting process, ask your client how they would like to be billed, how often they pay, and if they pay bills on time. I have a friend who works at a company for which vendors have shut off services due to non-payment of bills more than six months past due. Needless to say, it is hard for him to find contractors.

14. Plan to Receive Money in 30 Days by Mail

While I have heard of immediate payment terms and received it at times, this rarely happens. It seems no company likes to pay their bills early, and most want Net 30 terms. My one dream client pays invoices by direct deposit in about 10 days. Mostly though, I am obsessed with the mailbox.


Freelancing is possible for me because of the expertise and network I built up while working in the corporate world. The freedom I have now is the direct result of having “paid my dues” by working hard for many years. Depending on what you want to do, freelancing at an early stage in your career may not be the best choice. What I thought I wanted to at age 25 is different from what I was doing at age 35, and different from what I am now doing. The possibilities evolve as your assignments evolve, whether that’s at a full-time job or a unique freelance project.

The joy in a freelance life is the ability to set your own hours, work on a variety of projects and have the free time pursue your other interests. If you approach it with the attitude that you are better able to provide value to clients by having the freedom to work the way you want, you can have a successful freelance business.