30 Key Questions to Ask Yourself before Going Self-Employed

Over the past few decades, self-employment has grown dramatically. In the UK, there are an estimated 4.8 million self-employed people (around 15% of the population), and that figure continues to rise. In legal terms, “self-employed” covers sole traders, limited company business owners, and contract-based independent workers. In simple terms, many self-employed people consider themselves “freelancers”. In short, self-employed people are their own boss.

If that sounds like your cup of tea, what do you need to consider before quitting your job and taking the plunge into the freelance world? Here you’ll find a list of questions to ask yourself before going self-employed…

#1 Is it right for me?

The first question to ask yourself is whether self-employment is right for you personally.

  • Does it suit your personality, skills, lifestyle, and career goals?
  • Are you self-sufficient, independent, disciplined, and self-motivated?
  • Are you happy as a lone worker?
  • Would you enjoy permanently working from home or a co-working space?
  • Do you want to carve your own path or climb the corporate ladder?

Freelancing is a very different way of working compared to being an employee, so it has to be right for you.

#2 Can I manage it?

The second consideration is whether you can manage freelance projects.

As a freelancer, nobody will do any of these things for you, so you have to be able to manage all of these aspects yourself.

#3 Can I afford it?

The third area to consider is finances, since freelancers often don’t earn a regular, stable income.

  • Do you have a start-up pot of savings to cover the beginning of your freelance journey when you have no clients?
  • Do you have back-up savings to cover an unstable income?
  • Do you have extreme emergency savings to cover lack of earnings?
  • Are you confident managing your own money, chasing up clients to pay invoices, and keeping track of your business expenses?
  • Are you happy paying your own pension and setting aside money to cover sick leave, holiday, and taxes?
  • Are you happy to pay for an accountant and outsource other tasks if need be?

Being able to manage your money is vital as a freelancer, since you can’t rely on a standard salary and monthly payday.

#4 Do I have a support network?

This is an area that not everybody considers, but freelancers need support just as much as employees do.

  • Do your family and friends support your plan to become a freelancer and understand the unusual hours you might keep?
  • Do you have people you can regularly meet up with to get out of the house?
  • Do you have people you can talk to about your work and bounce ideas off?
  • Is there someone you can talk to if you’re having a tough time?
  • Are you happy building a freelance network?
  • Do you have someone who can support you and pay the bills if need be?
  • Will you be lonely working from home?

Freelancing can be lonely and isolating without a support network, so this is vital.

#5 Is it the right time?

Freelancing can be tough, especially when you’re starting out, so it’s important to have consider whether now is the ideal time for you to become self-employed.

  • Could you take on a part-time employed job as well as freelancing for some guaranteed income?
  • Could you take a career break from your employed job to start freelancing, then go back to it if your freelance venture doesn’t work out?
  • Can you build up your freelance business as a side hustle until you’re ready to take the plunge?
  • Have you tried freelancing to see whether you like it?
  • Are you ready to start being your own boss?

If now isn’t the right time, then you can always dabble in freelancing to see whether you enjoy it, then build up gradually until it is the right time.

Empower yourself!

Of course, these aren’t the only areas to consider and the only questions to ask yourself, but they do give you a good basis to start from. These questions might make freelancing seem scary, but being your own boss is empowering, freeing, and exciting—giving you freedom and control over your own life, time, and goals. If you want to become self-employed, you can work on improving in these main areas until you feel confident taking the plunge to become your own boss.


Any questions to add? Did this list help you? Comment below or get in touch.

And stay tuned for more freelance tips and insights every Monday, Wednesday, and Friday on A Freelance Life!

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