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The Freelance Fallacy: 5 Major CONS Of Having No Boss

Increased flexibility in working hours gives an illusion of freedom but with great freedom comes great responsibility and I, for one, am out.


It is pretty widely accepted at this point that the millennial generation is throwing out the rulebook in terms of career track. It is estimated that by 2020 half of the workforce in America will be freelance. This is largely being met with a kind of begrudging, jealous tone by older generations who’ve put in decades at the same desk.

Technological advances mean the landscape of work has altered dramatically in the last five years. Companies are beginning to see the advantages of allowing employees to work off-site – after all, even just on just a nuts and bolts level there are savings to be made from not having to provide four walls and heating for your staff. So while the bosses are getting on board and the new generation is on board, why am I most definitely not on board? I’ve been freelance for the last few years and it is with huge relief that I am now reentering the 9-5 rat race. I always seem to be slightly out of step with my peers. I don’t understand the obsession with sharpie brows, I secretly LOVE diet coke, I took my husband’s name and I litch only just discovered London Grammar. Plus after three years of bitching and pitching, I am done with working for myself. Here’s why:

Con #1: The Freelancer Fear Of Saying No

You think you will have more freedom when you work for yourself. You imagine you can control your workload, taking things down a notch for example in the Summer months, or clearing the decks to take a month off for some Winter sun in January but actually, I found the total opposite to be true. I was always terrified of turning down work and becoming known as the ‘no’ person, and so I found I was in a near-constant state of being vaguely overworked.

Con #2: The Work You Don’t Get Paid For

Pitching is a full-time job when you are freelance and it is impossible to quantify how much time you spend on this unpaid stage of a job, but let me tell you it feels like a lot.

Con #3: You Don’t Have Working Hours, So All Your Hours Become Working Hours

It is 4am and I am nursing an infant. I am also typing on my phone because I am afraid to let any spare second of potential work time slip away. This, of course, could well be a symptom of my personality rather than a problem with freelancing specifically but I think that the flexibility of freelance can be to your good or to your own detriment. Freelancing can be a great lifestyle as long as it doesn’t completely become your lifestyle. I found the boundary between work time and non-work time to be completely non-existent; I literally worked in my bed most days. At the height of the freelancing, I would sit down to watch TV in the evening and it was also a complete given that I would be working on some project or other at the same time.

Con #4: Your Boss Is The WORST

Sure you may not have a regular, sits-in-the-glass-office-judging-KPIs type of boss but you actually have a far worse, even more inescapable boss: You. This is a boss that you don’t leave in the evenings and at the weekends and for many freelancers the work-life balance actually becomes MORE elusive after switching to freelance work.

Con #5: The Goddamn Paperwork

If you are the kind of person who can keep on top of deadlines, expenses, proof of tax deductibles, invoices and where you left the bloody accountant’s number then you will perhaps be better at this element of freelancing that I was. If, however, you are the type of person who’s ‘long finger’ is crowded with half-done jobs, who owes about 60 quid in fines to the library because you have an inability to return books on time and whose filing system is affectionately referred to as the ‘Drawer of Terror’ then this side of freelancing will be a major challenge. Every time I remember the fact that I won’t have to self-assess this year, my stomach does a giddy swoop similar to went I first started dating my husband – it’s that level of sheer delight.

Do you do the freelance thing? Feel free to share any words of wisdom in the comments…

Main image via @phoebesoup

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