I’ve been successfully self-employed for a year — here are 9 things I wish I’d known before starting

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Creative Nina/Shutterstock

  • Being self-employed will present you with many challenges and some distinct advantages.
  • Here, author Jamie Friedlander details 9 things she wishes she’d known before she started being self-employed as a writer.

In January, I received an unsettling phone call late at night. The magazine I worked as the features editor for was shutting down. The entire staff was laid off. My immediate emotions were shock and sadness. But I also knew this could happen when working in such a volatile industry.

At 28, I was still at the beginning of my career. I envisioned becoming a full-time freelance writer one day, but I always thought I’d wait until I had more years behind me. But jobs were sparse, and freelancing would allow me to take control of my future. I decided to do it.

Now 12 months in, I can say it was the best professional decision I’ve ever made. I’m making significantly more money than I did when I was traditionally employed, not to mention I have more free time, the flexibility to travel whenever I want, and the comfort of knowing I’m in charge of my own future.

In the past year, I’ve learned a handful of things I wish I’d known before I became self-employed as a freelancer.


1. Ride the motivation tide.

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Strelka Institute/Flickr

When I first started my business, I was often given the advice that I should try to stick to a 9-to-5 schedule as closely as possible. After many sleepy Monday mornings and unproductive Friday afternoons, I learned that what’s more important is working when I’m motivated. I can get more done in a 6-hour motivational stretch than I ever could in a 12-hour day when I’m just not feeling it.


2. Don’t be afraid to ask where your money is.

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Ray_LAC/Flickr

It can feel awkward to follow up on an invoice that’s overdue. This is especially true if you’re new to the game. Will they not want to work with me again because they find my following up annoying? Am I being too persistent? I’ve learned you should never feel uncomfortable asking for money you’re due. After all, you’d question a paycheck that didn’t arrive on time at work, right?


3. Don’t pigeonhole yourself.

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GaudiLab/Shutterstock

My identity as a writer is and always has been formed around health. Most of my writing is medical in nature, and health journalism is what I’m most passionate about. Every time I took an assignment that didn’t fit under this umbrella, I would feel anxious – as though I was abandoning my niche.

But I’ve learned it’s important to have a breath of fresh air every now and then. After days on end full of health writing, it’s often nice to have a break to write about hyperlocal news or personal finance. In fact, I’ve carved a second niche for myself in personal finance all because I was willing to explore new topics.


4. Continually set new goals.

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Strelka/Flickr

When I started my freelancing business in January, I set a benchmark for how much money I’d like to make in my first year. I made this amount by July. Once I hit my goal, I was ecstatic. But shortly thereafter, I felt like I’d lost all motivation to work.

I’ve since discovered that when I’m approaching whatever current goal I’ve been working toward, I need to set new goals. (For example, I’m approaching my 2018 goals, and am in the process of setting my January 2019 and 2019 overall goals.) This ensures I’m constantly striving to be the best at what I do and not getting lazy once I’ve hit a goal.


5. Negotiate, negotiate, negotiate.

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Strelka Institute/Flickr/Attribution License

Don’t be afraid to negotiate a freelance rate that seems too low. As the old saying goes, you’ll never know if you don’t ask. Most times, a rate will stay the same, but every so often, there will be a little wiggle room.


6. Don’t feel like you have to do it all.

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iStock / Getty Images Plus

I hate – with a capital H – transcribing. There’s nothing I dislike more as a freelance writer. About six months into freelancing, I learned that my week was much more productive if I simply outsourced this one task. If there are one or two elements of your business you despise, don’t be afraid to hire someone else to do them.


7. Remember: You get to take vacations, too.

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De Visu/Shutterstock

Because I set my own schedule, I often struggle to take time off. I remind myself that I can take personal days or vacations just like everyone else. It took many months for me to not feel guilty about taking time off, and it’s something I continually struggle with.


8. Don’t feel like you need to get dressed for work.

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Creative Nina/Shutterstock

Whenever I told people I was a freelancer, many would mention a sage piece of advice they’d heard at some point: Always get dressed as if you’re going to the office.

I’m here to say I’ve never once gotten dressed. I roll out of bed, make a pot of coffee and head over to my computer, still in my pajamas with my curly hair messily piled atop my head. I made double what I projected this year, so I’d say getting dressed is kind of overrated.


9. Don’t worry about what other people think.

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Gleb Leonov/Strelka Institute for Media and Design/Flickr

Since I’ve become a full-time freelancer, I’ve been skeptically asked what I do for work, and whether I work at all. At first, I felt insecure about this, as my job as a magazine editor was so intertwined with my identity. I’ve learned that it doesn’t matter what others think. I’m making a living doing something I love, so who cares what others think?