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Why Freelancing Might Not Be For You

The following is a guest post from “Your Boss”, the creator and author of the blog What Your Boss Really Thinks, where she expresses her opinion and advice on career, job search, management issues and office life.  Your Boss created her site to help people to better understand their boss, give a direction and provide some guidelines on how to navigate life in the office.  Feel free to ask her about your office or career dilemma by submitting an Ask Your Boss form on her website.  She also offers resume review services that are worth checking out.  🙂

Freelancing Isn’t For Me

Sometimes I think about going rogue and doing stuff on my own. You know, stuff like writing, blogging and such. But then I take a step back and think about it. A lot of web sites and blogs encourage people to step outside of their office life and become freelancers. Nothing is wrong with it. Freelancing might open up great opportunities. The key word here is “might.” Not everyone can survive as a freelancer. Not everyone will.

I, personally, am not cut out to be a freelancer. For a few good reasons that I am going to list below. Those reasons apply not just to me. Over the years that I worked with people and observed them, I concluded that there are those who can embrace freelancing with all its risks and opportunities, and there are those who cannot.

You Are Not A Freelancer If

You like stability. I know that no one is guaranteed stability at any office or through a freelance contract. However, I believe that a regular 9 to 5 job provides more stability than any freelance contract can offer. At least, you know that a paycheck is coming. Your vacation time is paid. You even have insurance coverage and 401K employer matching contributions. Can you forgo all of this in the name of being your own boss? Not everyone can.

You like regular hours. People who are freelancers work long and odd hours. I like to have a routine. I like to know what I am doing next, where I am going to be and what the next project I am working on. Don’t tell me that freelancers have set regular hours too. Yes, they try to set regular hours, but tell me how many freelancers you know who actually work those hours?

You like flexibility. Freelancing does not equal freedom, and, in turn, it does not equal flexibility. Do not be naive and think that you will lounge in a hammock in your backyard. You will have a boss who will set your hours. Good news is you can choose who that boss will be. Bad news is that boss is not you. That boss is your clients.

You like the social aspect of your office life. I love dressing up and heading out the door. I love the feeling of anticipation of a busy work day. I crave social interaction that my office offers. I need to work with people and around people. Freelancing, depending on the type of work you are doing, can be a lonely business.

You want to get rich quick. Some of us watch others coming up with ideas, propelling these ideas to a profitable enterprise and think that “if they could do it, I can do it too.” Let’s be realistic and admit that no, you cannot do the same thing. First, you need to know what you are good at doing. Don’t just copy an idea, be really good at it! Second, borrowing the idea is fine, but developing it into something unique and profitable is a completely different endeavor. The overnight success stories are the results of a lot of hard work, sleepless nights and sometimes years of sweat.

You like to have real vacations. I know I do! If you are a freelancer, you can (pretty much) forget about having relaxing vacations, especially in the beginning of your freelance carrier.

You would rather have a long-term career as an employee. There are people who want to work for someone else.

You like “being a writer.” Really? If this is your reason to start freelancing, please do not say this out loud. To anyone

Do you think you are a freelancer? Or could be?

Crystal’s Comments:  I do agree that not everyone can be a freelancer sucessfully.  It takes a lot of personal motivation to make yourself wake up every day and do what needs to be done.  In my case, it takes a routine…one that I better follow or risk falling days behind.  But there is some flexibility in where I work, which is nice.  And there’s no commute, which kicks butt.  But I do know that self-employment and/or freelancing has its downsides.  We all need to find our happy spots.  🙂



FYI:  I worked at a dead end cubicle job from 2005-2011 for about $30,000 a year.  I went self-employed in July 2011 and make between $80,000-$100,000 through blogging, a rental home, and professional pet sitting.  If you’d like to start your own site (link to my free step-by-step guide), I highly suggest checking out Bluehost (my referral link with a nice discount for you).  I even have all of my favorite tools on a resource page - I hope they help you too. This all gives me the time to be with my aging family members, the flexibility to stay close with my friends and family, and it should help if we finally get pregnant too!  Please contact me any time at budgetingfunstuff*at*gmail*dot*com with questions or just to brainstorm! I’d love to help!
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10 thoughts on “Why Freelancing Might Not Be For You

  1. I agree with everything you said. I do some freelancing on the side and it’s all hard work. I’m working on diversifying and am starting something completely new (unrelated to blogging altogether) and am excited/nervous for it!

  2. I have to agree with what you mentioned in this article. Some people’s idea of working freelance is to gain more money, while taking things easy. I often encounter people who thought that way and eventually ended up finding the truth the hard way.

  3. I think I’m in love with Your Boss. I have wanted to freelance and write and blog… basically, I wanted to be like Crystal when I grew up. But everything you outline here is everything I need. Maybe that’s why I haven’t taken any big leaps yet. Thank you for this insight and reminding me that just because others are successful at it, does not mean I could be too. Great guest post, Crystal! I was a big fan of Your Boss before today, but this just hits one home!

  4. @Michelle – freelancing is hard work. I think one of the reasons is that people tend to work much harder for themselves than for someone else.

    @My Multiple Incomes – freelancing is not easy money. I do think it is a very common misconception.

    @SavvyFinancialLatina – I hope you will figure it out. Sometimes deciding what is good for you is not that easy. Hell, I think, it is more difficult than finding a job.

    @Mel – Thank you! You just made my day. It is always good to know I have fans.

  5. I have no desire to live the freelance lifestyle. That said, I’m taking six months off from work to travel this year and will be freelancing while on the road to keep funds coming in!

  6. I have found that I have a much stronger work ethic when people are watching me. Working by myself, whether it is paid or chores, I take all kinds of breaks, but when others are around and expecting me to be working, I tend to be the last one standing.

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