Written by Dotty Winters


Everything You Always Wanted To Know About Self-Employment (But Were Afraid To Ask)

From boss-less lounging to lucrative cupcakes, Dotty Winters tackles the top five myths about self-employment.

Illustration by Claire Jones

I’ve ever been great at dealing with authority – check with my parents if you don’t believe me. When I was around 13 I had a lengthy chat with a good friend about what we wanted from our careers. After an afternoon of debate we agreed to three major aspirations:

•To drink black coffee
•To wear trouser suits
•To have a PA

I say she was a good friend, although a truly good friend would have warned me straight away what a terrible look trouser suits are for me. Nonetheless my career has involved all of those things and none of them made me happy (one of them gave me palpitations).

After years of swanning around other people’s businesses in my trouser suit, I eventually found my way into self-employment – the natural home of people who go through life convinced they can do things better than other people. So now I have a business and get to spend my working life not wearing trouser suits while helping other people to grow their own escape route business.

It’s a route that more and more of us are choosing. But it can be hard to get good information to inform your decision to move to self-employment. So here are the Top Five Myths that you need to understand before you decide to take the plunge.

Before you embark on self-employment, ask yourself one question: just how much do you really enjoy eating lentils?

1. You won’t have a boss
For many people the biggest appeal of being self-employed is that you no longer have to answer to your boss. After years of biting your tongue, laughing at appalling jokes and daydreaming about crushing laxatives into their cuppa the idea of being boss-less can certainly feel appealing. However, any successful self-employment venture is going to require customers or clients: and without the buffer provided by a boss or organisation they quickly become your boss. Until you are in a position to pick and choose the clients you work with (which, depending on the success of your venture and the size of your mortgage, can take years) you may find you’ve swapped one demanding idiot for several demanding idiots who all expect your immediate attention.

2. You can choose the hours you work
On the face of things this statement is literally true; you can choose the hours you work. Except of course:
• You’ll probably have to be available during the regular working hours of your clients or customers.
• If you work internationally your availability may need to stretch several time zones.
• If you do any sort of face-to-face delivery of a service or performance, that will need to be delivered at a time to suit your customers.
• You’ll need to fit in all the hours it takes to do your job; most business owners who are self-employed work significantly longer hours than employees.
• You’ll also need to find time to do all the admin, tax returns and paperwork associated with your self-employment.
• You probably won’t have allocated days off or holidays.

3. You can make a living doing what you love
You might be able to make a living doing what you love; lots of people do. But loving doing something will not guarantee:
• That you are good enough at it to make a living doing it. If you ask your friends and family they will all tell you that you are good enough to do it as a job, but they may not be bona fide business experts and we’ve all seen people on telly whose families told them they could sing.
• That it’s profitable. Cupcakes may be tons of fun, but if you’re making a profit of 40p per cake you will need to sell a massive number per day to feed the wine habit you will inevitably develop as a result of the daily grind of trying to sell cupcakes.
• That there is a market. Those crochet glasses cases are simply darling, honestly they are. But seriously?

4. You’ll make more money than you would in employment
Nope. Some do, many more don’t, and even the very best often have to wait months, if not years, before they can afford to pay themselves a decent salary. Before you embark on self-employment, ask yourself one question: just how much do you really enjoy eating lentils?

5. It will improve your future job prospects
You’re a self-starter, you have gumption and you’ve filled that potentially blank space on your CV with your own exciting venture. But to an employer you are a bloody liability. All too often your potential employer will see only three options:
• You’ve failed as an entrepreneur. This is hardly a ringing endorsement.
• Your self-employment has hit a hitch; you’re only looking for a job to tide you over then you’ll be off.
• You are a great entrepreneur and therefore utterly unmanageable and you’ll probably be after their job within a few days.

I’m a huge fan of self-employment. Personally I wouldn’t go back – I like not having to wear trouser suits too much. But I do think it’s a world that it’s best to enter with your eyes wide open. Good luck, whatever you decide.

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Written by Dotty Winters

Nascent stand-up, fan of fancy words, purveyor of occasional wrongness, haphazard but enthusiastic parent, science-fan, apprentice-feminist.