The Born Freelancer’s love-hate relationship with freelancing

This series of posts by the Born Freelancer will share personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? Your input is welcome in the comments.

A friend of mine read my last blog and asked, “Why would anyone ever want to freelance?” Well…


My Top 10 Reasons to Love Freelancing

(1) I am my own boss

This is probably the number one reason for most of us. We get a sense of being in charge of our lives, even if we’re not. Sometimes it may feel like we have numerous bosses, but at the end of the day it’s still our choice, and that seems to be important. It’s my mandate (as decided by me) to do more or less exactly what I want to do, creating what I want to create, on an ongoing basis.

(2) I choose my own work hours

Admittedly we probably work longer than most people realize, but as long as we make our deadlines, which hours we pick are irrelevant. Are you an early riser? You could be finished before many of us begin. A late riser like me? You can work as late into the night as you wish.

(3) I choose where to work

Usually I work from home. Now, that has its own advantages and disadvantages. You do need discipline and a consistent routine, as well as a suitable work space. Given all that, what a joy it is not to have to commute every day to an ugly office during brutal rush hours, wasting a couple hours a day getting there and back. And there’s no putting up with loud talkers, overpowering perfume, “sick” offices, lousy lighting, poor heating/air conditioning, genres of music you hate, or objectionable body odours. Except your own, of course.

(4) I choose for whom I want to work

If an organization is incompatible with my own beliefs or philosophies there is no one with a gun pointed at my head forcing me to accept the gig. Conversely, I can choose to work for organizations or individuals whom I believe in and to whom feel I can make a meaningful contribution of my skills and experience.

(5) I wear many hats

As a freelancer I am also my own sales agent. And accountant. And press agent, and so on. I provide a variety of services (writing, production, announcing, teaching, etc.). It’s sometimes frustrating, sometimes exhausting, but it’s never dull.

(6) It has numerous tax advantages

Being self employed has special advantages when it comes to taxes. Best to check with your local tax office and read all their bumpf. My best tip: Keep all your receipts. And make it a habit to always, always ask for receipts. Anything that is definitively work-related potentially could be written off as a business expense.

(7) I’m never bored (and I get bored easily)

If I manufactured widgets that is all I could expect to do. As a freelancer, one week I may be covering a medical story. The next a political story. The next entertainment. Of course, I have my specialties and preferences, and some assignments I am much more proud of than others. But for those of us with low boredom thresholds, it is better than the latest attention-deficit medication.

(8) I meet new people all the time

Although far too much of my time is spent alone with a computer — not that there’s anything wrong with that! — on occasion you do need to venture out into the real world and interview subjects. Or meet your boss. Or a fellow freelancer. Although I have met one or two complete sociopaths in this business, I can count them on the fingers of one hand (okay, both hands and a foot). Most folk I encounter are interesting and have a great story to share (even if it’s not always the one I wanted for my assignment).

(9) I keep learning new things

I hear rumours that people actually pay to attend certain institutions to learn new things! To me one of the perks of freelancing is that with every assignment I learn something new. This keeps the gig interesting, but it’s also incredibly good for my mental health and overall well being. (Please see this previous post for details.)

(10) No office politics

When I have been parachuted into an office to work on site for more than a few weeks, the first thing I come to loathe is the office politics. The petty backstabbing that goes on in many offices can totally turn people off of the 9 to 5 existence. On television it is highly amusing. In real life, for some of us, not so much.

Now, in the interests of fair and objective reporting, here is the opposing point of view. Trust me, every freelancer is well aware of these too. In fact, depending upon how my day is going, it is often easier to remember this list than the previous one!

My Top 10 Reasons to Hate Freelancing

(1) No security of any kind

This is often a deal breaker for many novice freelancers. Emotionally, you are on your own, so you need to create your own totally job-independent support network that will carry on along side of any actual gigs. This way when the gigs end (and they all do eventually) your support network is still in place.

(2) No guaranteed income

This makes any semblance of what passes for normalcy these days in your life extremely difficult. If you don’t know how to save, if you don’t know how to budget, if you don’t know how to live within your means, it might be best to look for a 9-to-5 job.

(3) No employer loyalty

One day you are the Golden Boy or Girl. The next day you are dropped like a Blue Ray disc. They owe you no golden handshake nor any severance package. They rarely feel guilt. Even good employers forget the impact their decisions can have on your world. They conveniently assume you have endless other revenue streams when they drop you. (Just like they assume you have no other masters when they want work from you. You are theirs and theirs alone. Hint: While you are “golden,” it’s always best not to dissuade them from this delicate delusion.)

(4) No paid holidays and no sick days

You take a holiday when there is no work. That’s your holiday! Even then you learn to keep an eye out for stories, inspiration, and subjects. If you travel for pleasure, you learn to always work in a meeting or 10 with prospective employers or old employers who have gone cold. And if you’re sick and can’t work, good luck. You’d better have something socked away for a rainy day.

(5) No paid healthcare

Related to (4) above. I’ve written about this in a previous post. There is no personal asset more precious to freelancers than their health. To me it is a priority before almost all others. And like most things in life, you only miss it when it’s gone.

(6) No easy 9 to 5 hours

I don’t doubt that some folk work very hard in 9-to-5 settings. But I’ve watched many of them and have on occasion wished for the comfort of their set hours. When they go home, they’re usually done for the day or for the weekend. For a freelancer, we are never “finished” until the assignment is over. And then we’re already working on the next assignment as well as chasing after the next few after that. A freelancer’s day is never really “over.”

(7) No office camaraderie

Despite my comments earlier about office politics, the flip side of that is the built-in social life in an office. We are social creatures after all. It’s not natural to be forever holed up in a small room on your own, typing away and staring at an illuminated screen. This is partly why Facebook users exist in such overwhelming numbers. But in offices you also have the option of relating to real people in real life. Trust me, if you’ve never tried it, it can be way better than even Facebook with Skype!

(8) Hard on family, friends

We have chosen this lifestyle, but others near and dear to us often have had it imposed upon them or entered into it without fully understanding its hardships. There is no better reason for leaving the freelancing world, IMHO, than the negative impact it can have on family. The inconsistency, the insecurity, the financial irregularity, and the often obsessive attention it demands can hurt all but the most solid relationships. It requires tolerance, understanding, and great patience from your partner and/or family. If you are lucky enough to find yourself surrounded by such empathetic people, consider yourself successful beyond your wildest dreams.

Friends can find it extremely difficult to accept that the lunch you set up last week is going to have to be moved three months down the road while you sort out your current assignment. As with family, don’t take friends for granted and do whatever you can to keep in touch. And when you do find true friends ready to stick with you throughout upturns and downturns in your career, recognize them (along with family) as the irreplaceable gatekeepers of your sanity.

(9) No phoning it in

You have to knock a ball out of the park every time. Often a freelancer is called in to relief pitch for regular staff or to provide that extra “zing” that regular staff are too exhausted to give. This means not only providing content as good as any staff member, it usually means providing extra value — something better than any staff could hope to muster. Unfair to expect every time? Sure, but that’s what will get you a return gig. I call it my motivation.

(10) Lack of prestige

Let’s face it, many 9 to 5 folks view freelancers as not much better than casual labourers. I’ve been to parties and talked about the interesting people I’ve met and the pleasure I get from the gig. The response about half the time? “Freelance, huh? Couldn’t you get a real job”? So you must learn to live with it. Whether it is out of ignorance or jealousy, that is how much of the rest of the world may view us and our work. We can take great comfort, however, in knowing that when it does all come together, there is no lifestyle sweeter. And when it doesn’t work quite as planned, well, at least we have something to look forward to returning to when things get better again.

Posted on July 11, 2011 at 10:36 am by editor · · Tagged with: ,

2 Responses

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  1. Written by Suzanne Boles
    on July 11, 2011 at 10:50 am
    Reply · Permalink

    I love freelancing for all the reasons you list. They outweigh any negatives for me.

  2. Written by Ian Harvey
    on July 20, 2011 at 12:55 pm
    Reply · Permalink

    All lof the above, though most people I meet or know soon realize that with nearly 30 years as a staffer and in the corporate world my decision to go freelance seven years ago was a personal choice, not a decision forced on me.
    That said I came close to taking a staff job but quit after eight days….eight days of commuting, sitting at a desk and doing the same thing – print production – was a cure for freelancer fear…I stuck around for three months to help them find someone to replace me…but I’ve never looked back.
    You’d have to offer me $120,000 a year and up to entice me to look at a “job” with a single employer.
    What I really like about freelancing is that you can fire your clients!!!
    My pet peeve? Friends who think that because you work at home for yourself that you can take off for the afternoon to go drinking with them, play PS2 in their basement for hours in the middle of the week or that they can drop by anytime and yak.

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