How I Learned to be My Own Boss

I come from a family of self-employed entrepreneurs.  I have witnessed their struggles over the years, but I’ve also seen the freedom that comes from setting your own rules, and working on your own terms.

For almost eight years I enjoyed a well-paying 9-to-5 job in the medical industry. And when I say enjoyed it, I actually did. I loved the stability. I loved knowing exactly how much my paycheck was going to be. I also loved leaving work at the end of the day and not having to think about it until I went back to the office.

But there was this nagging, itching feeling that I just couldn’t quell. There was something missing. Throughout the years I had dabbled in freelance writing on the side. The more I did it, the more it grew. As I began to enjoy the writer’s lifestyle, my interest in the office job began to wane.

Then I took the plunge that many people would deem crazy. I busted out of my comfortable box, waved goodbye to my well-oiled routine and quit my job to become a full-time freelance writer. It was glorious. I was my own boss and my creative juices were flowing. I had time to walk the dog, go to lunch with friends, clean the house, go shopping … and actually work and make money. That part took a second to figure out. With all the wonderful things that come with self-employment, there are some very real challenges. I certainly wouldn’t change a second of my journey so far, but there are a few things I could have prepared for that would have eased my transition, my stress level and my sanity.

The Importance of Savings

Believe it or not I didn’t venture into this all willy-nilly, with no planning. Common sense and advice from others had warned that I would need a little nest egg in order to avoid full-on financial panic. The feast or famine mentality of freelance work is certainly real in the beginning. Some months, clients were aplenty, and others I could hear the crickets chirping. Having a little cushion is not a luxury, it is a necessity.

The Office Is Always Looming

Not being chained to an office that you have to punch in and out of every day is liberating. One thing to keep in mind, however, is that your new office is now in your home. Days and weekends also have a way of blending together, and any free time has a way of pulling at your guilt strings and leading to longer hours than you would have normally spent in an office at your day job. Make it a comfortable space, because even though people may think you are sitting at home watching TV, the dirty little secret is you will be busting your butt, even if you are in the comfort of your pajamas.

Routine Is a Life Saver

And since we are talking about sleeping attire, I learned pretty quickly that motivation came much easier when I got up early, got dressed and prepared for my day just as I would with any office job. Lack of routine was a cause of extreme unproductivity for me. Develop a schedule that works for you, and stick to it. Dedicate certain hours to specific tasks. It will be much easier to enjoy free time if it’s not clouded with a to-do list with no direction.

Shut out (squirrel!) Distractions

The joys of working from home include finding time to do laundry, prep for dinner and go for a walk when you want, but those luxuries can quickly take up an entire day if you’re not careful. Remember, if you don’t put in the work, you won’t make much money.

Uncle Sam Is Unforgiving

The single most important lesson I have learned from my time as a freelancer is that nothing you make is taxed. Chances are you’ll probably underestimate how much you owe on untaxed income. If you’re living paycheck to paycheck when you start out, you could regret it at the end of the year. To help yourself out, make sure you’re saving a portion of your income from each paycheck you make to pay back when tax season comes around.

Once the kinks are ironed out, freelance work can be a beautiful thing. Just be prepared for a few bumps in the road along the way. Finding a balance that works for you is key to a productive and potentially lucrative career with freedom and flexibility.

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