The Pros and Cons of Going Self-Employed

Being a full-time freelancer isn't all Instagram-worthy coffee dates and working in pyjamas. Find out about the pros and cons of going self-employed

You’ve heard me talk before about the ups and downs of freelance life so today I thought it would be helpful to talk more about some of the pros and cons of going self-employed in more detail.

So shall we kick things off on a more positive note and take a look at some of the pros of self-employment first?

Flexibility to create your own schedule

Worked late into the evening and think you deserve a lie in? Fancy heading to the gym at lunch time to catch your favourite class? More productive in the morning and find yourself ready and raring to start the day at 6am?

All of these scenarios are perfectly possible whilst self-employed as you are the only one in charge of your daily schedule. This can be difficult to adapt to after years spent within a fairly rigid 9-5 office job but it’s one of the biggest perks so you need to learn how to take advantage of it! As a new business owner it can be extremely tempting to work every hour under the sun but I’ve found that creating a schedule and sticking to it can be really useful for helping you to remain motivated and avoid the dreaded procrastination.

Ability to take your work anywhere

Got your laptop? Got a Wi-Fi connection? Then you’re pretty much free to work from wherever you want! The image most people tend to have of self-employed folk is sat on a beach in Bali, sipping on a Pina Colada whilst knocking out an article or two but the ability to take your work anywhere doesn’t have to stretch to travelling half way around the world (especially as being self-employed = no paid holidays). It can be as simple as having the flexibility to travel back to my home town in the middle of the week to see my family and friends and avoiding the rush hour traffic on a Friday evening!

The growth of remote working over the past few years has meant that this flexible approach is definitely now an extremely attractive benefit of going self-employed and opens up a whole new world of opportunities instead of being chained to a desk 9-5, Monday to Friday.

Not having to answer to anyone

Working for yourself essentially means that you’re your own boss so you have the freedom to choose whether you’re going to be strict or give yourself a break once every so often! Business decisions that could take weeks or maybe even months to get signed off within a corporate company can be made a reality almost instantaneously when you’re the only one holding the reigns and that is an extremely empowering position to find yourself in.

Although there are many perks to not having a manager I’ve found that sometimes it can be easy to put certain tasks off as there’s no one to answer to when it comes to why you haven’t met a deadline. This is why you need to be super disciplined if you want to go self-employed, there won’t be anyone checking in to make sure you’re on track apart from maybe the client who you obviously want to impress and keep happy!

I’m not one to paint the picture that self-employed life is all about cute coffee shops and Instagrammable work dates so to level things out here are some of the cons I’ve found over the past six months about working for yourself.

Unpredictable income

Gone are the days of receiving a monthly wage slip and knowing off by heart the number that will appear in the bottom right hand corner, if you’re lucky like me then you’ll have a number of clients that you work for on a monthly basis but if not the unpredictable income can be an extremely difficult change to get used to.

After six months I think I’m just about starting to get to grips with my bookkeeping and have also managed to become a bit of a spreadsheet addict. Going self-employed has definitely meant I’ve had to get better at managing my money especially with the added pressure of currently being in the process of saving to buy a house (talk about doing everything at once)! I’ve found that I’m now much more meticulous with where my money is going, I have multiple bank accounts which allows me to split my income into several pots and one piece of advice I can’t stress enough is saving a portion of EVERY invoice to go towards your tax bill. No matter how much you might need those extra pennies you don’t want to find yourself into a sticky situation come January once your tax bill is due!


For me, this is without a doubt the biggest con and one that is extremely difficult to get used to when you come from an office job background. I’ve spoken before about the transition to working from home and ways to make sure you stay sane whilst spending so much time alone. My one piece of advice? Get out there and making some freelancing friends! Go to co-working spaces, join networks and communities, talk to other freelancers on Twitter, whatever it is make sure you’re not sat alone in your home office 24/7 as it can really start to take a tole on your mental health and leave you feeling like you can’t do your job to the best of your ability.

You’ll begin to miss the little, insignificant details about office life such as having a natter with your colleagues whilst making yourself a brew, heading to the local pub for lunch on a Friday afternoon and all of the various cakes and sweet treats that tend to appear when it’s any kind of special occasion. When you work from home you have to create these little interactions for yourself by getting out in the real world and meeting new people. I’ve honestly found this to be the most rewarding and beneficial part about going self-employed.

You’re a One Woman/Man Band

When you’re self-employed you are the only one responsible for bringing in paid work and the only one who can do the work so that’s a heck of a lot of responsibility on your shoulders. That is also one of the factors that makes taking time off so difficult; there’s no one to pick up the slack!

I haven’t actually been on a proper holiday since going self-employed but over the past couple of months I’ve taken a few long weekends off and even they take a lot of preparation and planning to make sure you’ve done the work up-front and got everything you might need to in place. Guilt-free sick days curled up under your duvet watching Disney films are also now somewhat a thing of the past but no matter how much work you have on and how much you might need the money it’s still SO important to look after yourself and take a day off when you need one to avoid burnout!

If you’re thinking about taking the leap into self-employment I hope this helped to give you a well-rounded view of what to expect and some of the difficulties you’re bound to face in the first few months!

Are you self-employed? What are the biggest pros and cons you’ve found about working for yourself?



Author: Jessica

I’m Jess, a twenty-six year old self diagnosed Instagram and brunch addict. Whilst browsing Jess Who expect to find a hint of relatable personal style, Pinterest-worthy interiors, drool-worthy food and all of the latest happenings in Nottingham!