How to know if you should quit your 9-5 and go freelance.


“The death of 9-5” is a phrase many in the media have used to describe how the labour markets in the UK are changing. The rise of those working for themselves or freelancing has been attributed to “the gig market”. One of the largest freelance marketplaces in the UK, People Per Hour, reported an increase of 64 per cent in the number of UK freelancers using their platform between 2012 and 2015. Forecasts by PwC (reported by the BBC) show that, by 2020, global online marketplaces that fuel the gig economy could be worth around £43 billion.

Image Credit: Andrew Neel Unsplash

Image Credit: Andrew Neel Unsplash


It seems everyone is at it!

My husband left his admin job 17 years ago with 3 months of savings and formed a web agency. It is still going – although he has since started another digital company with two friends. I became self-employed 2 years ago when the need to have flexible work to fit around my children was paramount to our family’s wellbeing. My husband and I both work from home (albeit in different rooms to avoid winding each other up!). We have the flexibility to go to school events or book an appointment with the financial advisor whenever we like. More importantly, we have control over our careers and the option to start or shut things down as our needs and opportunities change.

It is true that we have had to sacrifice the security of a job and the income that goes with a salaried role. But for us and so many of our friends, the freedom to self-style our lives that freelancing gives us is worth the cost.

The Multi-hyphen Life

Emma Gannon’s new book The Multi Hyphen Method speaks of this growing rise in the flexibility of our thinking about jobs. She says, “We should be taught the skills that allow us to look at a landscape and see how it will change and grow, and predict our own moves… We should be less hung up on job titles and hierarchy and instead focus on what we can do and how much value it brings.”

I have a clutch of friends who are also carving out their own “multi-hyphen” lives as freelancers or small-business owners. Elle and Ben run a car hire firm and then built an eco house. They now give tours and speak about passive energy while supplying local shops with micro greens and eggs from their veg patch. Beth discovered that the wedding stylist market was saturated with consultants so she did a deal with a local farmer that allows her to run weddings for 5 months of the year from his barn. Her partner Stu runs the bar and is a freelance gardener. Hatti and Luke combine a supper club in their lounge with marketing for other entrepreneurs. Amy is a freelance seamstress while her husband Paul runs a digital start-up for students. They are about to turn their house into an Airbnb let.

Image Credit: Danielle Marroquin Unsplash

Image Credit: Danielle Marroquin Unsplash

Image Credit: Unsplash

Image Credit: Unsplash

Image credit: Oliver Pacas Unsplash

Image credit: Oliver Pacas Unsplash

Image credit: Unsplash

Image credit: Unsplash


Very few of these roles came from following the traditional employment routes. The work emerged from a combination of interest, opportunity and taking some risks.

For some, their freelance job begins as a hobby. For some, they take skills they have learned in traditional roles and go solo. Still others have a good idea and make a go of it.

Age-old Principles

These two principles form the basis of thinking about work in a gig-market age:

  • What are my interests? What do enjoy doing and have a natural flare for?

  • How can I serve others with my time and talents?

Maybe you are thinking through the options you have for freelance work. But how do you know if your basket-weaving classes could turn into freelance work or if it should stay as a hobby to make the occasional basket gift for Grandma?

The key is in your ability to be flexible in your thinking.

Blurring the lines around the categories of hobby, job, vocation, role and work give scope for creativity. Ask yourself if anyone would find your services useful. Offer to help a friend with a skill that you have developed as a hobby or interest. Become interested in what others are doing in your area of expertise. Register with a website that allows you to advertise your skills in a freelance listing: (link), or are good places to start.

In a conversation with a friend today, she shared with me about how she was changing her thinking about her start-up catering business. The idea (similar to the now-famous Tom’s strategy) had been to sponsor a meal for a homeless person with every meal that was bought through her supper club. Lots of hard work and trial-and-error later, they had their first few bookings. Sarah told me how one of these events was hosted in a venue that also served hot meals to the community. She had been reflecting on whether the current focus on catering was, in fact, the best way to achieve her dream of providing food for the homeless and creating great experiences around food for her clients. She was thinking flexibly enough to blur the boundaries between a hobby and a job so the two were almost interchangeable. I’m not sure which way she will take her passion for food but as she places the importance on finding fulfilment in her skill and serving others with it, she will enjoy a multi-hyphen life.

Image credit: Garrett Sears Unsplash

Image credit: Garrett Sears Unsplash


How do I know what is right for me?

Being willing to blur the definitions between life and work is the kind of flexible thinking that will enable a single-income, 9-5 life to transition into a multi-hyphen life with lots of opportunity for fulfilment and diversity.
The question, “Should I quit my 9-5 and go freelance?’ becomes too rigid a way to think about work. Try asking yourself these questions instead:

  • How many ways can you think differently about what you do?

  • How far can you pursue an interest in model vehicles or sugarcraft or antique books?

  • What are the opportunities you have to use your skills to help others around you?

Spend some time reflecting on the core principles of interest and service. Getting a coach to help you explore what this could look like for you is one way to ensure you do the right kind of thinking.

However you decide to express your multi-hyphen approach to working, I hope you find fulfilment and meaning while paying the rent. I hope you can define work on your own terms and make life work for you.

If you are looking for coaching that helps you move from a job into the freelance/self-employed world then our Ideation to Creation coaching package is perfect.

1 to 1 coaching with Naomi over 4 sessions that explores at your pace what drivers there are inside you for work and how those best get expressed.

For a more in depth (and hilarious) look at the psychology behind choosing a career path read Wait But Why