5 important things to think about when you’re self-employed

Being self-employed is a double edged sword for me. On the one hand I love the flexibility it gives me; I can be around for school plays, sick days and to ferry in the inevitable forgotten PE kits, and it’s brilliant not to have to be forever letting Belle down because I can’t get time off work.


The flipside of this though is that it can be difficult to establish that elusive work life balance. To make up for the time I have off with family and home commitments, I often find myself fretting about work in the evenings and trying to get a head start on work emails over the weekend.

School holidays are tricky too. Unless we are actually away, I often find we spend day after day in a sort of limbo, where I’m working from home out of guilt at going into the office, but Belle is still left to her own devices. Taking proper holidays can be hard too – no one pays for your time off when you work for yourself and overcoming that feeling of losing out on valuable income puts the pressure on.

I’m about to embark on a new project, (which I plan to finish before the summer holidays), with Direct Line for Business. It’s going to cover not just the practicalities of self-employment, like business insurance, but also some of the emotional difficulties, as well the logistics of keeping everyone happy when you work for yourself.

As part of the project I’ll be hosting a Twitter chat and creating a video with one of Direct Line for Business’s experts, asking for their top tips to help successfully manage your own business. I’d love to know what issues you struggle with, and what advice or support you would find useful.

To kick things off, I’ve come up with five things to think about if you’re self-employed or are thinking about setting up your own business:

Where are you going to work?

I’ve done the whole lot – working at the kitchen table, loitering in Starbucks as well as casual and permanent office space. Although you might initially like the idea of being able to work in your pyjamas, the novelty quickly wears off if you’re a people person; it can get very lonely at home, especially if you’re tied to the house in the evenings too. Do you know any other freelancers who keen to share some office space? Are there any co-working spaces nearby that you could investigate?


Are you good with figures?

One of the things that puts a lot of people off running their own business is the thought of financial record keeping and tax returns. These don’t have to be complicated if your business is small – just make sure you keep records of everything. HMRC run workshops for new business owners that cover the basics and if you really don’t fancy it, consider employing an accountant; this will often save you more money than it costs as they will be able to help you manage your tax bill efficiently. Just make sure you’re not late, because overdue tax returns can cost a hefty sum.

What insurance do you need?

Speaking from personal experience, this is often something that business owners don’t think about, but it’s vital to protect your business. What would happen if someone came to your office or home, tripped on a cable and sued you? How about if you gave some social media advice that damaged the company’s reputation? Find out what you need and make sure you’re covered. (Direct Line for Business can help with this of course.)

What equipment do you need?

When you work as part of an office you get used to having things like a photocopier on tap, so setting up a home office can be pricey. Think carefully about what you actually need; don’t waste money for example on a top of the range printer if you only ever need to print black and white documents. Ask other business owners for tips and shop around for the best deals and don’t forget to keep your receipts.

business insurance

How many hours do you want to work?

And how much time off would you like? There is a tendency as a business owner to feel obliged to say yes to everything and take on as much work as possible, but this isn’t really necessary and kind of spoils the point of being self-employed. Instead, try to think about the bigger picture – how much do you need or want to earn annually? Factor in holidays – how much do you need to bring in every week or month to average out over the year? Have these broader targets in mind and you’ll feel much happier about taking time off as you’ll know it’s covered by the weeks you do work.

Do you have any questions about being self-employed that you’d like me to put to Direct Line for Business?

Are you unclear about the types of insurance your business needs? Maybe you want to work for yourself but are worried about financial record keeping? Perhaps you like some tips to help you work more efficiently and not get distracted by reading blogs??

Please leave your questions in the comments below and I will endeavour to find the answers!

Direct Line for Business insurance

Produced in partnership with Direct Line for Business. Image credit – coworking from rawpixel/shutterstock and office from bonninstudio/shutterstock



  1. 13 June, 2015 / 9:50 pm

    Typically I find that when I work from home for myself, the biggest issue is motivation. So I started this regime of comparing what I did while employed versus what I am doing while being self employed. Periodically checking and comparing the two helped me understand where I was weak as a self employed person, and that kicked me into gear reading more about what others do.

    It’s interesting you bring up insurance, one area I completely didn’t think off, but if ever doing client work, I guess it’s an important factor.

  2. 14 June, 2015 / 5:31 pm

    I still need to sort out some business insurance, off to investigate! x

  3. 14 June, 2015 / 10:05 pm

    Completely get all you’re saying about the good and bad points. I find myself worrying a lot less when I’m self-employed though – I used to get so stressed about work things, but it’s so much better since I choose what I work on and workload. I would be interested in knowing about the insurance too, what you need etc.x

  4. 14 June, 2015 / 10:31 pm

    It’s all SO TRUE! Why do self employed people feel so guilty taking a microsecond off work?! The other day, after spotting that one of my emails had come through at 1.30am a client told me: ‘You shouldn’t work so late, you need to start working during the day instead’. Ummm, hello?! I start working at 9.30 every morning after the school run – I just don’t STOP working until 1.30am!!! xx

  5. 15 June, 2015 / 4:37 pm

    my main thing is not turning off or having set ‘work times’ I often feel like I never have an actual break from work. On the flip side I hated every job I had before i became self employed so there is defo more pro’s than cons! x

  6. 15 June, 2015 / 9:02 pm

    Great tips Jo. I’ve been self-employed for nearly five years now and I’m still learning as I go!

  7. Steve Holmes
    16 June, 2015 / 12:38 pm

    Some really good tips here. The finance is always a bit of a sticking point for me as I don’t know exactly what I need. If I’m a sole trader can I just do my tax return myself? If I wanted to employ a bookkeeper or accountant, where should I look?

  8. Helen
    16 June, 2015 / 12:39 pm

    I’ve been blogging for a little while now and started to earn a bit of money, but not enough to pat tax. Do I still need to register as self-employed?

  9. 16 June, 2015 / 1:46 pm

    Such a useful post for anyone considering the freelance life! xx

  10. 16 June, 2015 / 3:13 pm

    Great tips – especially the one about deciding how much to work. This is something we’re trying to achieve balance with right now as a couple since we’re both self-employed but I’m working less than I’d like and Laurence is working more than he’d like.

  11. 16 June, 2015 / 3:34 pm

    the one thing i find really hard is having ‘set’ work times. i often go through spells of no work at all, so when i get some i’ll sometimes go a bit overboard and overwork myself. whoops! being self employed always seems to be a work in progress, doesn’t it?

  12. Jonny
    16 June, 2015 / 4:13 pm

    I have a couple of questions – will being self-employed stop me getting a mortgage? Is there any insurance I can take out in case I get ill?

  13. Abigail M
    16 June, 2015 / 5:25 pm

    I found this really useful but it still feels like a scary step, and expensive too. If I work for myself from home, what’s the worst that could happen in terms of not having insurance? Could someone really sue me?

  14. 16 June, 2015 / 11:42 pm

    This is a great post Jo and these are really good points to bring up and consider when working freelance and self-employed. I sort of fell into it and wish I had done more research on the business side of things like getting insurance and doing tax returns but have learnt a long the way, now I just need a place to work again as the baby has taken my office space

    Laura x

  15. 3 July, 2015 / 5:41 am

    Hey Jo – It’s so important to know your numbers and be good with figures… something I’ve struggled with! Cheers :)

  16. 16 July, 2015 / 10:54 pm

    So useful. I am finding my work picking up – and I am a novice to all this as I have always been employed by companies. I need to sort out my tax and get some of this investigated. Thanks for the tips :) Jess x

  17. 30 May, 2016 / 1:32 pm

    Thanks for sharing. Guess I’ll have to up my ante when it comes to financial and well as insurance issues. I need the most assistance with those. I enjoyed the article.

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