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The pros and cons of self-employment

The pros and cons of self-employment

But it’s also one of the hardest things I’ve ever done. It’s worth weighing up the pros and cons before you hand in your resignation.

The pros

One of the biggest perks of self-employment for me is that I get to work from home… in my pyjamas most of the time! That’s a huge advantage, particularly in cold weather. It also cuts out commuting time and costs, allowing you to work while other people are stuck like sardines on a sweaty train or bus.

Another huge advantage is that you basically get to pick your hours. You can work around the school run or other family or church commitments. You can take time out during the day to get chores done and work in the evenings or even in the middle of the night if you so wish!

Being your own boss can also be pretty glorious. You can decide what work to take on and how you want to complete it. There’s no one watching the clock or appraising your performance. The only person you can accuse of unfairness is yourself!

There is a real sense of satisfaction in knowing that you’ve built up a business from scratch and are able to make a living from it. You’ll need to be highly motivated to do so and it helps if you’re doing something you really love.

The cons

Starting out can be really hard-going. You may have the skills and experience to make a successful business, but do you have the right contacts? That will be key to making your business sustainable. I made sure I had secured some clients and a small regular income before I handed in my notice. However, it still took a good few years to get to the point where I was financially secure and able to turn down really boring and poorly paid assignments.

As a self-employed person you may feel like you never actually leave work, particularly if you work from home. It can be difficult to get physical and mental distance from ‘the office’ as you might with a traditional role. I didn’t take a holiday for years after I went self-employed and I still take my laptop away with me now if I manage to squeeze one in. Remember that you won’t get holiday, sick or maternity pay and there may not be anyone to pick up the pieces if you get sick or have to take time off.

You may also find that friends and family assume you don’t have a ‘proper’ job and that it’s fine to call on you during the day in a way that they wouldn’t if you worked outside the home. 

Some people find self-employment lonely. You could arrange an office share with other self-employed people. I have a friend who does this and they have a fun office set-up and often enjoy socialising together. Alternatively, you can focus on your social life outside work and make sure you build in time to meet friends outside work. Self-employment doesn’t have to be a lonely experience.

The dreaded tax return is another big con as far as I’m concerned. You’ll need to keep good records of earnings and expenses and make sure you fill in your tax return on time (by January 31 for the previous tax year) and pay whatever is owed by that date. You’ll need to set aside sufficient funds during the year to pay the bill. It may be worth hiring an accountant to do this for you, especially if you plan to take on staff. This should be a relatively low cost and may actually save you money as accountants know how to (legally) maximise your earnings and minimise you tax liabilities.

Making a decision

The cons I’ve listed here outweigh the pros in length, but that doesn’t mean you can’t make it work for you. If you’re looking for an easy nine-to-five life that you can just leave in the office at the end of the day, self-employment probably isn’t for you.


The key if you’re planning to go self-employed is to be prepared to work hard, to make vital connections and to be organised when it comes to handling invoices and tax returns. It may be worth talking to a careers coach before you decide, and government support may be available depending on your business sector.