First Steps: Getting Started as a Freelancer

Insights and Advice from Current Entrepreneurs

Ever think about choosing when you work, where you work, and how you work? Curious about what it’s like to be a freelancer and want to learn more about how to get started? Women Who Code DC interviewed a few current female entrepreneurs: Eve Freeman, Erin Upton-Coulsich, Evan Taylor, and Becca Goodman about their experiences as freelancers.

There are many ways to get started in freelancing. For Becca and Evan, freelancing evolved organically as a result of requests from friends and acquaintances. Becca began her freelance career six years ago, when a boss had a side business and lost his in-house developer. “He eventually turned it over to me and I kept working on it,” she explains. Similarly, Evan became involved in freelancing through requests coming from her network.“I started when a lot of people in my network started asking me for advice on the same few topics in the space I was already working.”

It’s also possible to proactively seek freelance opportunities, as Eve Freeman did to get started.

“I used websites like rent-acoder and elance (now upwork) to find work. I don’t recommend them (at least, in my past experience), because often the rates are far lower than they should be. One place I do recommend is — I’ve had a very good experience there with short term clients (1–4 hours) at good rates.” — Eve

Eve also notes that it is important if you are currently a full-time employee, your employer must be amenable to freelancing. Some employers may have non-compete agreements in place, making it difficult to freelance without facing consequences.

Erin started gradually, “I took on a couple gigs for a year while I had a boring office job. Then I transitioned to a part-time job in the same industry and grew my client base for a year. Finally, I quit that job and went freelance full time — and signed on that part-time employer as my largest client (consider talking to your boss about this if they’d be open to it and you’re feeling indispensable). By then I had a portfolio and a solid client roster. I also had enough in my savings account that I was able to hold out for high-quality, high-paying gigs instead of desperately grabbing at whatever came my way just to pay the bills.”

Switching from being a full-time salaried employee to a full-time freelancer can take some time to adjust, as all the administrative aspects of being employed now are your responsibility. What considerations are important when making the switch?

“There is no HR…You are the CEO, CFO, CCO, CMO and COO unless you have the resources to outsource specific elements or department functions all together. It helps you develop a new awareness and distinct appreciation for all the “middlemen [or middlewomen]” of department processes.” — Evan

Becca and Erin highlight health care as a significant financial consideration when making the switch. “I would definitely look at health care and creating an LLC,” Becca says. Likewise, Erin suggests including the cost of health care in your freelance rate.

“Don’t be shy about telling clients that your hourly rate is (at least) twice what you made at your office job. That’s what you need to charge to pay the bills as a freelancer — no less” — Erin

“You won’t be living the high life just because you doubled your rate,” Erin explains. “There are plenty of nonbillable hours to consider — downtime between gigs, invoicing, writing proposals/calls/emails with new clients before you’re hired, etc. And you don’t get a paycheck when you take vacation or sick days. Employers expect to pay freelancers much higher hourly rates than what they pay their salaried employees anyway. A few low-paying, portfolio-padding jobs are fine when you’re starting out but don’t make a habit of it.”

In addition to health care, it’s worth looking into establishing a business structure, such as a DBA (Doing Business As), LLC (Limited Liability Corporation),or a Corporation (if you think you’ll need to hire other employees). In some cases, businesses might also require professional liability insurance. “Some larger corporate clients have requested that I maintain professional liability insurance (which has costed me about $75/month). I didn’t buy it until a client requested it though. Unless you’re making $10k+ on a single gig — or if your potential mistakes could cost the client a lot of time and money — I wouldn’t worry about legal stuff for the first few months when you’re getting started. Focus on marketing yourself and knocking each gig out of the park,” Erin explained.

Another requirement of self-employed work is taxes. As freelancers, you must file taxes on a quarterly basis since you do not have an employer filing taxes on your behalf and deducting it from your monthly paycheck.

“If you don’t, you can get burned at the end of the year.” — Becca, on filing quarterly taxes.

In some cases, it’s worth hiring an accountant to handle this, as Erin does. “Hire an accountant…overall, taxes are slightly higher because you have to pay for things an employer normally pays on your behalf — but those and other expenses are deductible (I’m not sure how that all works — that’s why I hire an accountant who’s worth every penny).” Whether you use an accountant or choose to file your own quarterly taxes, Erin assures us that it’s easy. “Don’t be scared of them. You don’t do a full return, you just send a little coupon along with your checks.”

After making the decision to start a freelance career and sorting through the administrative details, we asked our entrepreneurs how to begin marketing as a freelancer. Word of mouth was an obvious starter. “Start with word of mouth (it’s free),” Evan suggests. “Then once you can explain precisely and concisely what you do, why you’re better than anyone else and what you can deliver if someone hires you; you can take your show on the road.” Meetups, networking events, and small intimate events in your target market’s community serve as a great starting point for bringing awareness to your services and specialties.

For Eve, this worked particularly well.

“I have sort of a niche expertise with the Neo4j work I do, people have seen my contributions and classes and talks. I will say that going to meetups, organizing meetups, giving talks, and doing open source work has done wonders for my career in general, as well as my freelance marketing.” — Eve

Another option for marketing is social media. Facebook and Linkedin are great platforms for finding potential clients. “Facebook is a good one for me too; both with Facebook advertising, and in various Facebook groups,” Becca explains. “I have advertised my services and in one case offered free work to a raffle winner and then got more business from there.”

Erin also agrees that Facebook is a valuable place to gain clients.

“Let everyone and their sister know you’re available for hire — now is not the time to be shy! After I announced my freelance transition on Facebook, I got a few gigs right away from long-lost friends I never would have expected to need my services.” — Erin

Likewise, Linkedin can connect freelancers with recruiters who know of opportunities. On Linkedin, Erin recommends changing your title to include the word ‘freelance’ plus other keywords people will use to find you. The more specific, the better. For example, switching your title from ‘Freelance Proposal Writer’ to ‘Freelance Proposal Writer for U.S. Government Contractors’ will get you more attention from the clients you are hoping to attract. “Befriend strangers on LinkedIn who will hire you — recruiters, agencies, other freelancers with clients who will need your services…the first Ruby on Rails gig I got came from a freelance web designer via LinkedIn, which made me realize I need to befriend more freelance designers, who like to have a few developer contacts in their roster,” says Erin.

Getting started in freelancing may seem intimidating, but as Eve, Evan, Erin, and Becca have shown, it’s not impossible. Keep an eye out for the second part in this two-part series, where we discuss managing client relations, additional resources for freelancers, and other aspects of freelancing.

About the Interviewees

Eve Freeman, CTO of Emerging Technology @ Information Analysis Inc.

Eve Freeman

Eve Freeman is currently the CTO of Emerging Technology at Information Analysis Incorporated in Fairfax, VA. She has done a variety of freelancing activities, from rent-a-coder (since changed to vworker, then absorbed by, to Spanish->English translation. Most of her freelancing work these days is consulting on database technology (primarily Neo4j) and golang.

Evan Taylor, Tech-Savvy Writer, Designer & Agile Project Manager

Evan Taylor

Evan Taylor is a tech-savvy communicator & stakeholder advocate with a penchant for service, storytelling, education and economic empowerment. She thinks like a creative, implements like a project manager and measures like a data scientist. Evan is committed to creating equity in entrepreneurship and education across cultural, socio-economical and racial difference. She is dedicated to life-long learning, technical understanding and has a passion for purposeful entrepreneurship and building sustainable communities.

Erin Upton-Cosulich, Web Developer | Copyeditor | Social Media Consultant

Erin Upton-Cosulich

Erin has a master’s degree in creative writing and started building simple websites in 2011. While freelancing full-time as a writer/editor/front-end developer over the past three years, she taught herself Ruby on Rails and currently works as a freelance Ruby on Rails developer.

Becca Goodman, IT Specialist @ Fish and Wildlife Service

Becca Goodman

Becca is an IT Specialist/Software Engineer working for Fish and Wildlife Service. Becca has over 10 years of experience in web and software development. Becca likes to stay busy and has a freelance business that is pretty active (second full time gig). Becca just recently had a daughter (4-months) who joins her fur brother (pug) in the family. In her non-existent spare time, she run marathons and gives her husband a hard time.

Additional Resources

31 Days to Start Freelancing

Tools for Freelancers

Credit: Banner Photo by

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