Many of us daydream about being our own boss, but if you want to make it a reality, follow these guidelines.  

By Caitlin Pearce
Illustration by José Luis Merino

Why do you want go freelance?

Perhaps you’re ready to chart your own course. Or a more solitary work life better suits you. Maybe you want more time with your teen before they leave the nest. Or to take a Spin class on a random Tuesday. Or you desire a 60-second commute. 

Whatever the reason, freelancing can offer amazing perks, including autonomy, but there are inherent challenges too. It takes time to build a dependable client base and be able to charge market rate. You have to run yourself like a business, managing the day-to-day, figuring out pricing and planning for growth. Since it’s unlikely you’ll have coworkers, you’ll need a robust network to draw on for brainstorming, information sharing, business opportunities and emotional support.

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For further solidarity, find Facebook and LinkedIn groups in your field, or check out Freelancers Union’s free monthly SPARK meetups, held in 25 cities. In addition, connect with a fellow freelancer for when you need to talk, and explore coworking spaces like Impact Hub and WeWork. Getting involved with causes you care about is important too. Attend events with the goal of finding one or two people you click with—making genuine connections is more worthwhile than collecting business cards.

Are your skills truly marketable?

Freelance on the side first to test out the market for your skills, build a client base and gauge earnings. Focus on the value you provide. Specialized skills help you stand out from the competition. 

Successful freelancers are highly motivated to be at the top of their field. Be prepared to regularly retool and potentially cross-train in multiple skills to stay marketable. 

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Do you have the self-discipline?

Freelancing means meeting deadlines and keeping clients happy without a boss supervising you. In addition, you must allocate time for business building, including pitching, online marketing and developing long-term goals and strategies. You also want to establish a schedule and boundaries that differentiate work from home life. This is so important—otherwise work can start to feel like a 24/7 endeavor. Communicate your commitments to friends and family so they respect your time. And prioritize, prioritize, prioritize!

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Manage all this by setting lofty goals to inspire and motivate, but parse them out into achievable weekly actions, such as pitching a set number of new clients or refreshing your website by a specific date. Don’t shy away from setting personal and professional growth goals—learning new skills, attending industry events or simply exercising—and carve out the time to address them weekly. 

Your workspace should make you feel comfortable and productive. If you spend most of the day on your own, schedule in face-to-face interactions or even just a walk. Many freelancers have regular coffee groups that function as accountability  circles to ensure they’re on track to meet their goals.

Can you afford it?

Have at least several months’ expenses saved and a solid plan for generating income. As you budget, make sure to factor in your safety net, including health and liability insurance, as well as quarterly taxes. And plan for (unpaid) time off, because everyone needs a break!

Freelancers Union offers a range of benefits, including health, life, disability and liability insurance. Consider speaking with financial and legal advisors about incorporating and how to do it to ensure you’re on solid financial and legal footing.

About our expert

Caitlin Pearce is the executive editor of Freelancers Union.

About our expert

Photo courtesy of Caitlin Pearce

Caitlin Pearce is the executive director of Freelancers Union.