Four Things to Consider Before Going Freelance

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If you are dreaming of being your own boss, making your own schedule, and choosing your own clients, I’m here to tell you that it’s totally possible.

Freelancing is the future. The internet has made it possible to hire specialists on demand, and businesses are taking advantage of the wider talent pool to stay competitive. From the small business’ perspective, hiring a specialized freelancer is more cost efficient, easier, and yields better results than hiring a full-time generalist.

And from the freelancer’s perspective (...maybe I’m biased), freelancing provides the ultimate freedom of lifestyle, not to mention higher pay. Did someone say higher pay? Yes. Freelancers make an average of 17 percent more than their in-office counterparts.

Still, there are a lot of “what-ifs” that discourage talented people from going into business for themselves. Here are four things to consider before going freelance.

1. Is now the right time?

There is never going to be a perfect time to go freelance. You will never feel like you have enough money or like you are 100 percent ready to be a freelancer. You have to jump in and make it happen.

Getting some job experience won’t hurt. You can learn from your team, be challenged in new ways, and build relationships. But if your real dream is to work for yourself, don’t get stuck in a cycle of thinking one more promotion or one more company will be the key to your freelance success. That feeling won’t leave.

The truth is that leaving a steady 9-5 and paycheck is uncomfortable. You will have to fight through this discomfort to get what you want.

Keep this in mind: if you don’t try out freelancing, you will always wonder. There will always be another full-time job available.

2. Are you a specialist?

It’s tempting to be available for any and all work, but the secret of building your brand and business is to specialize. This will take you much further than being a generalist.

Think of it from the business’ perspective. If a company selling handmade organic soaps needs a content writer and uses Upwork to search for one, they are more likely to choose the writer specializing in writing about “Organic B2C content” than the writer specializing in “content writing.”

If this seems like it will narrow your potential clients, let me tell you, it will widen your potential revenue. Potential clients are more likely to have an urgency to hire you when they know you are the best at what you do.

There are several angles for you to specialize. You can choose to work with a specific type of client (“I work with female CEOs”), an industry (“I work with soap companies”), or a task (“I only do social media”).

An additional benefit to specializing is that it focuses your talent and promotional efforts. You will know exactly who you are looking for and the value you are offering them. You will get better at understanding and serving them. And when it comes to marketing, your specialized messages will reach further, rather than wider.

3. How will you handle your taxes?

Disclaimer: I am not an accountant, but both of my parents are. When I chose to go freelance, they helped me set up all my accounting from the beginning. I am so grateful. Thanks, Mom and Dad!

Knowing how to manage your books and how much to save from each paycheck will at least save you from getting in trouble, and at best, help you reach your financial goals.

The important part is to have an understanding, an accountant, and a plan to make sure your taxes are in line. I have seen a lot of friends run into problems with the IRS because they don’t plan accordingly for their taxes. This can put a big damper on things, and force you out of the freelance life very quickly. To avoid this issue, meet with an accountant at the beginning of your journey.

4.  Do you know your worth?

Remember when we talked about making money as a freelancer? That comes with a few conditions, starting with knowing your worth.

Your knowledge, time, and services are valuable. Make sure you are charging your clients what you deserve. Deciding on that number can be a little tricky. It’s a mistake to charge the same as you were paid by your employer. Your employer paid you a salary, and also took care of your office, equipment, software, marketing, accounting, vacations, holidays, healthcare, and more. Factor in these expenses when you calculate your rate.

If you are worried that people won’t pay you that much, you are looking at the wrong clients. You need to find customers that can afford your services. A little market research to see what others in the field are charging can point you in the right direction. See what specialties are charging higher rates and find your niche there.

And know that you can say “no.” It’s OK to set boundaries to protect the value of your time.

And one more thing—get started.

What’s more important than all of these tips is that you go for what you want. It won’t be perfect, and you will make a lot of mistakes, but you should be doing the work you actually want to do.

You don’t have quit your job to start. Today, you can start working on a website, research your market, meet with an accountant, or find your first client. These first baby steps can motivate you to make the leap to full-time freelancing.


Rebekah Epstein is the founder of fifteen media, a boutique PR firm specializing in media relations. While living in NYC, she worked at national magazines NYLON & Vogue, as well as fashion PR firm People’s Revolution. Working on both sides of the industry has given Rebekah a unique perspective on what works and what doesn’t.

She started fifteen media over seven years ago. Since then, She has worked with PR firms to get them more media placements for their clients (think: ghost publicist, similar to a ghostwriter), AND small businesses who need media placements to gain additional credibility and exposure.

Her clients have been featured in Forbes, Health, Refinery 29, Everyday Health, Men’s Health, etc.