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Posted by on Sep 11, 2012 in General Advice, Guest Posts, Personal Freelance Experiences, Productivity, Running a Business | 4 comments

The “Mental” Side of Freelancing: Staying Organized, Serious, and Positive

There are a million awesome things about freelancing. You are your own boss. You set your hours. If the weather’s nice, you can stop and take the dog out for a jaunt in the park. You get to do what you love, every day, and nobody else takes credit for your hard work. Having built your own business gives you an incredible feeling of accomplishment.

It’s not all butterflies and roses and three-hour lunch breaks, though. I’ve found that some of the biggest—and least expected—challenges I face as a freelancer have been problems of perspective, of priorities, of wondering if this really is a legitimate career. In other words, the “mental” side of freelancing.

Below are three things I’ve struggled with, along with some solutions that work for me. If you have anything to add, either a problem or a solution, please leave a comment!

You start the day with good intentions, but suddenly it’s mid-afternoon and you’ve spent seven hours surfing the Internet looking for ideas for a small future project and still haven’t started on the estimate you said you’d send to a client by the end of the day.

Even if you manage to stay away from cat videos on YouTube, it’s easy to be distracted by work that seems more interesting, or to get sidetracked by e-mails that arrive in the middle of whatever you’re supposed to be working on. I’ve found that two things help. One: plan your day ahead of time. Most evenings, I sit down with my list of things to do and Google Calendar, decide what my priorities are, and mark out which chunks of the next day’s time will be devoted to what. I give myself an hour every morning for catching up on email, social media, RSS feeds, and job postings. Then I might schedule four hours of time for Project X, followed by a lunch break, followed by three hours of time for researching Project Y. Two: Come up with a reliable way to keep track of what you need to do. I highly recommend David Allen’s Getting Things Done system. He emphasizes getting your to-do list out of your head and on to paper (or a computer screen). That way you won’t forget anything, you won’t have to do things right as you think of them, and you’ll free up a lot more of your brain power for what really matters—your creative work.

Friends and relatives listen kindly to your description of your freshly-launched freelance career, then ask when you’re going to get a “real” job.

You know what you do is legitimate, but the way you talk about it might help Uncle Ed take it more seriously. Be proud. Go ahead and call it “my business”—it IS your business. At the start of my freelance career it was easy (and exciting) for me to say “I’m a freelancer,” but then I realized that to a lot of people, that’s code for “I’m between jobs” or “I work as a hobby on my little artist thing while my significant other pays the rent.” I changed my tune and started telling people “I run my own editing business.” Try mentioning your growing client list or your newest marketing effort instead of flaunting the fact that you get to work in your pajamas every day. Some people will just never get it, but for others, framing it as a business and using business-y words will help them understand how serious it is. Either way you’ll probably benefit—as I did—from the thrill and the confidence boost you feel every time the words “my business” come out of your mouth.

The slow times get you down.

Especially at the beginning, work does not come to a freelancer regularly. One week will be overwhelming, and the next will be heart-breakingly slow. I didn’t know I had the capacity to be so emotional about my work until I realized that a day without a paid project could bring me nearly to tears. I was wasting time! Nobody wanted me! I would never edit again! No, none of those things were true, but it was hard to accept that there would be times when I wasn’t actively earning money. My advice? Learn to embrace those times and use them productively. Get in touch with potential clients or former ones you haven’t heard from in a while. Research some ideas you’ve been meaning to explore. Think of a way to diversify your business—not in ten directions at once, but maybe by adding one more service, or one more area of expertise. Invest in your education, whether that means watching more videos or finally reading about how self-employment taxes work. If all else fails, give yourself permission to take a break. You worked crazy hours on last week’s projects, and you deserve some time to walk in the park or grab a sandwich in a cafe.

This is a guest post written by Emily Albarillo, the proud owner of EA Editorial, an editing and proofreading business based in Brooklyn, New York.


  1. This is all very nice, but how do I break my addiction to the New York Times? I go to their on-line edition many times per day, and am continually distracted by reading articles on how Romney “really understands” the middle class, or how his wife’s ownership of ten dressage horses does not mean she is any different from plain folks. Do you have any helpful hints for my problem? I write lists about the ten journal articles I am supposed to write per day, but somehow, I never quite achieve my goals. You seem like a very organized person — can you help me increase my personal impact factor by spending less time with the NYT?

    Uncle Bill

    • Hi Bill –
      Sounds like a tough case. You might want to consider the extreme approach of pulling the plug on your internet.
      Best of luck,

  2. Great advice, despite being a great lifestyle, there are plenty of challenges and it’s not always easy keeping focused on the task at hand. Emails are probably the biggest distraction of all. How did you find starting up as a freelancer? Was the career choice a difficult one?

  3. Very inspiring look behind the scenes of a freelancer! I was doing some freelance work myself but found it challenging to justify it in front of people who would not see it as a real work.
    Thanks for putting this into perspective!

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