Wouldn’t it be great to wake up knowing you could start your day when you wanted to? Haven’t we all seen ‘those people’ working on their laptops in Starbucks slurping on their cappuccinos, looking rather chilled. They’re dressed for comfort rather than for work. They’re their own boss; calling the shots and dictating their own hours. Are you ever a little envious? Especially when you consider your own vigorous line of work. Perhaps you have started to think more seriously about quitting your job to go freelance. Well for those that are, then we’ve devised 5 things to consider if you are.


  1. It’s lonely.

A lot of people don’t factor in that having no human contact all day might get lonely, but it does. There is no one to nip out for a coffee with, no after work drinks with the team and no real social interaction all day long. You don’t have anyone you can bounce an idea off instantly with or even to ask someone for their general opinion on something. This lack of social correspondence can leave you at times feeling a tad vacant and a bit disheartened. Office environments are good for spurring on creativity and whilst the idea of doing ‘your own thing’ may be appealing initially, will you still feel the same in 6 months time or will you be ripping out your hair?



  1. Be prepared to chase

You’ve done the work, you’ve sent your invoice and then you dutifully wait for your money that you rightfully earned to enter your account. Then you wait some more. A little bit more and then even some more. You send the initial polite emails, which will soon be replaced by a phone call, followed by perhaps a slightly sterner phone call. I mean you have bills to pay, a holiday to book and you have to chip in to pay for the new washing machine. You need that money. Those that owe the money will be full of apologies, making promises that they will do it first thing in the morning but you have to remind them they are at least 20 mornings behind the payment. Chasing is draining. You put the new washing machine on hold…



  1. Be prepared to work your arse off.

Whilst a lot of your friends may believe you spend all your day drinking coffee, tapping off at 3pm they couldn’t be more wrong. You can guarantee you will work far harder than you did in your last job because at the end of the day the person responsible for getting yourself paid is you. As a result of this, you will find yourself working all day, a lot of nights and over your much-deserved weekends. You will have clients but you will always be trying to obtain new clients. That means a lot of networking via email, LinkedIn, freelancing sites or over the phone. You will find a lot of the time you are in work mode, as a result of your clients calling you at various anti social times of the day and night, but you do it (graciously) because you’re your own boss and brand.



  1. You have to do your own taxes

Ah the joys of taxes! Just because you now work for yourself you are not exempt from paying the dastardly things, but what’s worse is you now have to organize paying them without the cushy aid of your previous job. We would highly recommend getting an accountant who specializes in freelancers and small business. It will save you from getting hit with a big penalty fine for not doing them properly.



  1. Be confident in your own abilities

You have to be confident that you can do it. The 4 points previous to this can get overwhelming. You have to trust that you can get over the day or days of self-doubt (which can be frequent) if things aren’t going as accordingly as you had hoped. You have to trust yourself that you can make it work and that you will consistently work at being your own boss. That means early starts and late finishes and some long weekends. You have to be prepared that whilst those first initial months will be the hardest, that you can pull it together and make it work…


This article isn’t meant to scare you, rather prepare you before you pack in your job to live the life of a freelancer. Don’t be fooled into believing that the life of a freelancer is a glamorous one; it’s a consistent hard graft, which for a while can seem slightly unrewarding. BUT once you get to the stage of freelancing that see’s you have a steady income and a loyal client base (and you’ve cracked the issue of sorting your taxes) you will enjoy the perks of being your own boss significantly more than the position you held working for someone else.


Best of luck


Twenty Mile Club