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Why You Should Go Back to the Day Job

Tell regular jobbers that you work as a freelancer and you can see the envy in their eyes. They imagine you sitting on the beach with your laptop propped on your knees. They see you crawling out of bed while they’re still sitting in traffic, believe you take leisurely lunch breaks as they’re rushing back to their desks, and assume that you never have to argue with the boss.

If only. What day jobbers – and new freelancers too — fail to understand is that freelancing is work, and like any work, it comes with difficulties and frustrations, challenges which can, and sometimes even should, drive a freelancer back to the safety of the 9-5.

There are no figures that describe the numbers of people hanging up their lances and heading back to the office, but only around 48 percent of respondents in some surveys indicated that they would even consider telecommuting. A similar number said that they would like to stick to the day job but with flexible hours. Perhaps it’s no surprise then that despite the improvement in communications, the Bureau of Labor Statistics reports that the rate of self-employment has remained relatively steady at between 7-9 percent of the workforce since the 1970s.

Freelancing is Lonely

Perhaps the regular workers know something we don’t. Freelancing, after all, isn’t the same as retiring. For one, working for yourself can be anti-social. While wireless connections in cafes and libraries allow digital nomads to escape the home office, neither is a particularly social space.

The longest conversation you’re likely to have in a Starbucks is trying to explain how you’d like your green tea frapuccino.

It’s the need to speak to someone other than a barista that has led to the growth of co-working sites. But these can be expensive, typically charging from $25 a day to over $500 a month. That’s less than the cost of renting an office, but it’s a lot of money to buy new friends, even if you do end up liking most of them. A regular job would give you that social life for free.

Nor is there any guarantee that you would have anything in common with your fellow Jelly workers – except the lack of a regular paycheck.

Of course, for many freelancers, and wannabe freelancers, it’s precisely that financial instability that’s often the biggest anchor pulling them back to a cubicle. Dan Florio, a freelance developer, has talked of trying to build up enough savings to give him a three-month buffer if all of his clients disappeared at the same time.

“Even when I was just starting as a freelancer I didn’t have any trouble finding work so I doubt if I’ll ever come close to needing that much of a buffer but it certainly helps…” he says on his blog.

In practice, low income – and no income – tends to be the biggest concern at the beginning of a freelancing career. Over time, a growing portfolio makes new work easier to find, word-of-mouth brings in business for no extra effort, and regular clients give income levels at least a firm foundation with the occasional jobs topping up the rest.

The More You Do, The More You Earn

But even for established freelancers, the fear of losing everything never goes away, and that’s one of the reasons that the self-employed often have far worse bosses than those they fired. When you have no contract, no right to severance pay, no benefits and an awareness that plenty of other people could do the job almost as well – and that they’re no more than a website away – it’s hard to say no to a client even when their demands are unreasonable and your book is already looking fuller than you’d like.

And, of course, the more billable work you can squeeze into a month, the more money you can expect to take home at the end of it, a double-edged bonus. Without a plan and plenty of self-discipline, freelancers can easily find themselves working longer hours than they used to – and without many of the benefits of those long hours. After all, when a regular jobber stays late at the office, they’re looking for more than overtime. They expect their commitment to be noticed and rewarded with more responsibility, a grander title and higher pay overall. While income is most new freelancers’ first concern, established freelancers often find themselves wrestling with the question of “What next?” At least one developer has reported doing the same kinds of tasks after three years that he had been doing when he started. It was one of the reasons he cited for giving up freelancing.

And that’s perhaps the biggest reason that freelancing isn’t for everyone, and it’s the ultimate way to know whether it’s right for you.

You can replace the lost sociability with an active extra-curricular life, one filled with classes, sports, activities and new friends.

You can get your boss under control by placing firm limits on the time you stop working in the evenings, and steering clear of the computer at the weekends.

You can even learn to live with an unstable income with a bit of fiscal discipline and a base of regular clients whose repeat jobs pay the mortgage and fill the grocery cart.

But to freelance in the long term, you also need to know not just what you can do but what you’d like to do with your skills. You need to know where you want your career path to take you, and what you need to do to get there as you build experience and knowledge.

Freelancing might be the ultimate ambition for many workers but ambitious workers won’t just need to be driven and focused if they’re to achieve their goals. They also need to be their own career managers.

The alternative is to find a boss to do it for you.


  1. Ian Fernando Says:

    working at home is lonely esepcially if you have a whole house to your self. I find myself working at mcdonalds for a couple hours so I can sense that noise level.

  2. Ryan Yockey Says:

    Great post Alex.

    For me, I took to freelancing as soon as I was financially able to. I have to say after only a few months I started to think of the 'Whats Next?' question. I then started to build a sustainable business for myself after the six month mark. I knew sticking with freelancing forever was not going to achieve my personal goals. I think for most in this economy and freelancing, the goal is to figure out what you want in your career path/goals.

  3. Chris Says:

    "They imagine you sitting on the beach with your laptop propped on your knees. They see you crawling out of bed while they’re still sitting in traffic, believe you take leisurely lunch breaks as they’re rushing back to their desks, and assume that you never have to argue with the boss."

    I think your doing it wrong 🙂 I can sit on the beach and wake up when I want... It's just about management and delegation 🙂

  4. Jason Says:

    Fantastic article! I for one think there are some great resources making it easier every day http://www.freelanceswitch.com/the-business-of-freelancing/online-bookkeeping-for-freelancers-that-wont-cost-an-arm-and-a-leg/ (both the blog and the suggestions); the hardest part about freelance is trying to run the business of your business.

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