From W-2 Employee to 1099 Tax Form Flaunting Entrepreneur

By Angela Tague, Contributor, on March 23, 2018

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I understand the struggle. Your mind races with the possibility of starting your own business. Freedom. Full creative control. There’s too many ideas flowing in; you can’t fall asleep. Mental plans are mounting. But, the practical side of your brain hits the brakes and wonders if your business can generate a viable income. Every entrepreneur faces the fear of making the leap from a W2 employee to a 1099 tax form wielding independent contractor.

During the summer of 2009, I faced those fears head-on. I made lists of pros and cons, talked with my colleagues and had deep discussions with my husband. The decision to leave a full-time newspaper career to dig into writing on a freelance basis didn’t come without hesitation — and hours upon hours of research.

What Were My Fears?

The primary thing holding you back from making the leap is probably your fear of the unknown. When I was evaluating my possible transition from employee to self-employed, I had several concerns, both tangible and emotional.

On the practical side, I wondered about insurance, the process of paying taxes and if I’d make enough money to replace my previous income. On a personal level, I worried about what my friends and family would think about me leaving a “good job,” and if I could handle the time and energy needed to grow a business from the ground up. Does any of this sound familiar?

Now, I’m eight years into a full-time freelance career, and I can confidently say there’s a way to make every single thing work out if you do the research and have patience.

Thankfully, there are a variety of resources available to you on…

How to get insurance as a freelancer:

How to start your own business:

How to fill out a 1099 tax form:

Fear is fueled by not knowing what the outcome of a decision or situation will be. So, take the reins. Make a list of your concerns and address each one with complete honesty. You’re not the first person to start a business, so there’s a pretty good chance someone like you has faced similar fears and offered advice (like this post) online, in a book at the local library or in a workshop at a nearby college. Dig in.

What Gave Me Stability?

Every entrepreneur’s path includes stretches of success, detours of learning and roadblocks of concern. So, we navigate.

My path to freelancing started out part time. I was working full time as a photojournalist at my hometown newspaper when a magazine’s art director called the newsroom. He asked if any of the photographers wanted a side gig photographing kids making crafts for a scrapbook magazine. The photo editor handed me the phone, and I was bit by the freelance bug.

That assignment was back in 1998, and I’ve taken on side gigs ever since. I never contemplated making these one-off projects a full-time career until I realized the freedom and empowerment that awaited me. When I left my last employer in 2009, I gained the ability to earn more income, work hours that better suited my needs and do a job that allowed me to educate others on topics I’m passionate about.

During this transition, I was fortunate to have enough stability in my life to make the leap. I started out still working a part-time job that offered me a health insurance package. When I got married, I transitioned to my husband’s benefit plan. I also had an incredibly supportive best friend by my side who always had words of inspiration and admiration to fuel my fire.

Luckily, I had the energy to spend my weekends at the local community college learning about business structures and tax liabilities. I had so many notes and handouts that I started a business learning binder to keep it all organized. I also knew I was choosing a career with very little upfront investment. As a writer, I work from a home office on my desktop computer or at the library on my laptop. My annual expenses include some office equipment, parking fees, conference reimbursements, software, apps and business cards.

Think It Over

As you think through your business plan, ask yourself: Can you start out part time? Can you get by with minimal capital or supplies? Can you create a timeline of progress where you gradually build your business and its needs? Can you identify a support system both personally at home and professionally in the community? All of these considerations will give you stability as you move forward with your decision.

Above all: Listen to your intuition. If you feel a burning passion for a career transition, you have your answer. Take ample time to plan a successful launch, then dig in 100 percent and never look back. Welcome to Generation 1099.

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