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8 Things You Should Know About Being Self-Employed as a Freelancer

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8 Things You Should Know About Being Self-Employed as a Freelancer

If you told me 10, 5, or even 2 years ago that I would be “self-employed” I would have told you that there was NO WAY that was for me. I mean… I have a family to support, I’m a practical person, and I like my benefits thank you very much.

And yet, here I am. A freelancer, a small business owner, a professional vagabond.

Being self-employed isn’t right for everyone, but I’m giving it a whirl anyway

How did I end up in this mess of happiness? Well, chasing a dream of course. But not exactly what you’d expect. After living in New York for many years, establishing a career, and starting a family, my dream was to get out of the city and live among nature. I craved an environmental change, and after years of putting this longing on hold my professional success became a secondary priority. I thought “I’m just gonna go, and then figure out the rest when I get there.” Smart huh? By some miracle I got my husband on board, and away we went, with our two kids and a finite amount of savings to western Massachusetts, where there are lots and lots of trees.

That was two months ago. Since then I’ve breathed a lot of fresh air, filled out all sorts of paperwork, gone to networking events, met great people, launched this website, and spent lots of time with my kids. I’ve also gradually begun to navigate the art of freelancing and man is there a lot to learn!

Here are 8 things you should know about being self-employed as a freelancer:

1. You still have to pay taxes.

Not only that but it’s way more complicated than filling out a simple w-2 for your employer and having them take care of the details. There’s a thing called “self-employment” tax and it’s basically 15% of whatever you earn right off the top, plus you have to fill out special forms when filing your taxes (schedule C), and depending on how your business is set up (sole proprietor, LLC, corporation) you might have to pay quarterly or the IRS will come after you. Just a heads up, it’s annoying, but figureoutable.

2. Networking is essential.

As a natural introvert this did not come easily to me at first, but the biggest challenge is always that first event where you literally don’t know a single person and have to risk awkwardness, exclusion, boredom, or rejection that’s the hardest. But that’s temporary. Once you get in there and meet a few people, follow up with them, and make yourself known, the domino effect kicks in and you find yourself gaining tons of resources and forming friendships, partnerships, and referral relationships before you know it.

3. You have to give and be of service before you get paid.

Of course income is important when you have bills to pay, but you should cushion yourself adequately before embarking on this journey so that you have the space to share your skills and talents freely and generously at first. Some professionals will say that you should never do things for free because you’ll get taken advantage of but I think that’s baloney. As long as you have some boundaries and don’t go spending 80 hours on some random project, sharing your expertise in a community hub without asking for anything in return will position you as a credible resource people will definitely remember. I call it planting the seed for future success.

4. Creativity is more accessible.

Sure there are some limitations depending on the scope of your projects or the needs of your clients, but in general there is much more room for creativity as a freelancer, in fact that’s what you’re getting paid for. Not being encumbered by office politics, pointless meetings, or outdated methods means you have more freedom to follow your instincts and color outside the lines, and that is F-U-N.

5. Work/life balance is still a challenge.

When office work ruled my life I daydreamed about working from home, setting my own hours, and spending more time with my kids. But since those things have been introduced to me as a freelancer (and I do appreciate them), new challenges have manifested that still make work/life balance hard. The boundaries between work and family are more blurred. Kids might barge in and interrupt work, you come up with ideas for client projects when you should be enjoying family time, and your schedule is a wacky mix of personal and professional. There is definitely more flexibility, but it still requires some juggling just like with any other job.

5. You’re responsible for your own professional growth.

There is no clear “ladder to success” when you’re on your own. You have to build the ladder yourself, adding each new step after taking the one before it and continually looking upwards to a clear blue sky of endless possibilities. Sometimes the freedom is exhilarating, and other times you wish someone else could just build the dang ladder for you. That means seeking out ways to enhance your expertise, determining who your role models are, digging deep to think about what you really want, mapping out a plan to get there, and asking for help when you need it.

6. This is a great time to do it.

I’ve spoken to entrepreneurs who started working independently 20 or 30 years ago, before there was internet and countless resources on how to pave your own professional way, now that is COURAGEOUS. They must have gotten all sorts of furrowed brows when they told people what they did. These days it seems like everyone is an entrepreneur in one way or another, and the number of books, blogs, apps, courses, motivational speakers, etc. to support you are infinite. Not only that but the economy is ready for it and if you’re good at what you do the chances for success are high.

7. Benefits… yeah, no.

Aside from the creativity, freedom, and fun previously mentioned, freelancers are generally lacking in the benefits department. Unlike with conventional employers you do not get paid vacation days or sick days, matching retirement savings, or getting to leave early for a doctors appointment while still earning your salary for that hour you’re not at your desk. If you don’t work, you don’t get paid. It’s a real bummer, but then again are those things worth the misery you endure if you hate your job? You just have to be smart about making up for these things when you set you rates and getting good at financial planning. Also keep in mind that being able to take a yoga class in the middle of the afternoon on a Tuesday or being there to hear a new joke your kid learned are pretty good benefits, too.

8. You don’t have to fit into a box.

What I’ve really enjoyed about freelancing is that I’m doing a variety of things that interest me and that makes work exciting. Being open to the needs of clients also means your experience and work scope can be stretched and challenged. I’m not just one thing, I wear many hats as a content creator, social media manager, photographer, researcher, designer, writer, and so much more. I work on projects relating to wellness, business, and even sports.  Rather than having a boss ignoring my opinion on things which aren’t in my job description I am my own boss with the freedom to pursue and express knowledge in a variety of ways.

Nothing here is meant to convince you either way whether freelancing or self-employment are right for you. It’s a career choice full of pros and cons just like anything else, but as one who is currently on the early side of navigating this path, I hope the above gives you something helpful to think about.

Are you self-employed, a business owner, or a freelancer? What has been your experience with this process?


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