Freelancers speaking frankly: Part I – why people leave employment

Not long after going freelance, I had the idea to interview a bunch of other freelancers; specifically, people like me who’d left employed roles to set up on their own.

On a purely selfish basis, I was keen to hear from people 10 steps ahead of me about what had worked for them, and what hadn’t. My own little freelancing crystal ball, if you will.

I also wanted to unearth information to share with other freelancers, or people thinking of going freelance.

By its nature, self-employment is a solitary pursuit. Most people are left to figure it out on their own using a combination of Google, their mum’s friend who happens to be a tax accountant, and good old-fashioned trial and error.

A certain degree of figuring it out on your own is fine, but wouldn’t life be a lot easier if we were all a bit more candid about what we were going through?

This is what I’ve tried to provide a snapshot of here. A no-filter glimpse into the world of 17 employees-turned-freelancers from around the world.

Specifically, I wanted to know:

• What was it about employment that wasn’t working for them anymore
• Why they ultimately decided to go freelance
• What their biggest headaches are around freelancing
• What solutions they’ve found to tackle these
• What their ambitions are for the next 12 months

The findings were so rich that I’ve opted to split this into two blogs – I’ll publish part 2 next week.

For now, are you keen to hear the unvarnished truth?

I thought so. Let’s go.

Top reasons people want to quit employment

• Boredom
• Stress & overwork
• Politics & culture
• Poor pay and/or pay prospects  

If I could sum this up in one word, it would be stifling.

Everyone I spoke to felt that employment had been blocking them in some way.

Some talked about their job becoming increasingly narrow and monotonous, and a longing to broaden out and learn new things. Others had become increasingly distanced from the work they loved, as they rose through the ranks of seniority, and were now spending most of their time managing and politicking. They longed to be more hands-on again, and see the direct impact of their actions.

Many people were sick of the stress. It’s one thing to be anxious about a path you’ve chosen, or even built; it’s quite another to be losing sleep over things you’ve been ordered to do, but deep down, don’t care much about. People spoke of having had enough of being on the frontline; things that seemed acceptable – fun, even – in their younger years were now just a grinding chore: the evening events, the constant commuting and travelling, the never-ending sucking up to potential clients.  

Office politics was a problem for many. People from big corporations had good resources, such as training and decent HR support, but change happened at snail’s pace, such was the internal bureaucracy and need to involve an army of stakeholders. Meanwhile, people at smaller organisations were told there was no money for professional development, and would find themselves pulled between different roles, or constantly fire-fighting.

And of course, many people spoke to me about money.

Seeing how much the company was making – and how little, comparatively, they got to take home. Pay rises barely keeping up with inflation. Low-paying industries which made you feel bad about wanting money, as if the job itself was enough of a reward (this is common in the arts, the industry I came from).

Top reasons people decide to go freelance

• Freedom           
• Money
• Security             
• Growth
• Loved ones       
• Practical reasons           
• Heart-led reasons

This was when I got to see my interviewees come alive. Shoulders relaxed and smiles broadened.

Freedom was by far and away the single biggest reason people gave for making the leap. I guess this makes sense, as it’s the opposite of feeling stifled. People talked about the desire to be their own boss, structure their days as they saw fit, and work from a location of their choosing. They wanted to create their own rules rather than play by someone else’s.

“Waking up and not commuting!” yelled one of my interviewees joyfully, before going on to tell me how happy it makes her to start every day having a leisurely coffee with her boyfriend. Lots of us got a taste of this way of life during the work-from-home period of the pandemic, and it’s fair to say that many don’t want to let it go.

Fluidity and flexibility were also words that came up a lot – the power to decide: ‘No, I don’t feel like starting work at 9am today’ or ‘I want to go and stay with my mum for a while – just because’. Not impossible when you’re employed, but often harder.

Money was a big driver too.

“It’s where the real money is” stated one of my interviewees, matter-of-factly. Despite the well-documented difficulties of starting your own business, the truth is undeniable – you don’t define your worth when you’re employed. The person paying your salary does. As a self-employed person, you get to choose how much you charge. There’s no ceiling and there’s no rulebook. No-one’s saying it’s easy, but the sky really is the limit, and that in itself is thrilling.

A few of my interviewees spoke about wanting more career security. Eh? What could be more secure than being part of a company with a pension, sick pay, parental leave, medical insurance, union support and all the rest? Well, you only have to look back at the last two sad years to see how many employees were left high and dry by their employers in a time of global crisis. For many people this was a wake-up call – rather than looking to a large entity to sustain them, they’ve concluded that their biggest source of security is their own skillset and ability to generate work.

For some of the people I spoke to, their move to working for themselves was driven by a burning desire to grow. This was certainly my own experience – I didn’t particularly want more money but boy, was I desperate to spread my wings and learn some new stuff.

The decision to go freelance isn’t always made just with ourselves in mind. Sometimes it’s directly related to the people we love, and such was the case for a few people I spoke to. One had given birth to her first child and was simply looking for a way to spend more time with him. Another told me that his wife’s career had gone stratospheric, and that someone needed to be at home to look after their son while she was travelling. I personally love seeing my husband and pets at home every day – I don’t want to go back to a routine where I only check in with them post-8pm, grumpy and tired.

Then there are eminently practical reasons – less sexy but equally valid.

Some people were made redundant, and freelancing was their best next move. Others simply couldn’t find any companies or organisations that inspired them enough to want to apply (I loved the person that told me this – what a brilliantly high set of standards). One person had already built a side-hustle in freelancing, so thought it made sense to turn it into a full-time gig. Sadly, one woman told me that companies in her country don’t count freelancing as work experience – so she couldn’t land an employed role even if she wanted to.

Lastly, there are what I call heart-led reasons.

One person spoke of the deep calling he felt to become a coach, and the sense of true alignment he now has. An events producer told me of the sheer joy she feels being able to move from one creative project to another, choosing the ones that really speak to her, infusing them with her personal passions and seeking out like-minded collaborators.

For some there's a mysterious, almost spiritual quality – a sense of destiny calling. It's a path you simply can't turn your back on, even if you can't fully explain why.

Next time, I’ll cover some of the biggest challenges freelancers face, as well as the solutions they’ve come up with to deal with them.

In the meantime, I’d love to know whether any of the above insights resonate with you.

If you’re a freelancer reading this, why did you leave the safety of your employed role? And anticipating next week's blog, what are the biggest obstacles you face on day-to-day basis?

Till next week,

Fabienne

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